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1-Bromopropane structure

1-Bromopropane
  • CAS：106-94-5
  • MW:122.99200
  • MF：C3H7Br
1-bromopropane was used primarily as a solvent for fats, waxes or resins and as an intermediate in the synthesis of other compounds including pharmaceuticals, insecticides, quaternary ammonium compounds, flavors and fragrances in generally well-controlled, closed processes. 1-Bromopropane is now used as a solvent cleaner in vapor and immersion cleaning and degreasing operations for optics, electronics and metals and as a solvent in industries that use spray-applied adhesives. Its use as a solvent substitute for ozone-depleting chlorofluorohydrocarbons (freons) or suspect carcinogens (e.g., trichloroethylene, methylene chloride) has prompted the dry cleaning industry to view it as a replacement for perchloroethylene (“perc”), especially in states that are proposing to ban the use of the latter chemical in dry cleaning.1-Bromopropane is one of several chemicals included in the Environmental Protection Agency’s Significant New Alternatives Policy (SNAP) that has been approved as a substitute for ozone-depleting solvents currently in use in certain applications. Specifically, 1-bromopropane has been approved as an acceptable substitute for CFC-113 (1,1,2-Trichloro1,2,2-trifluoroethane, Freon 113) and methyl chloroform (1,1,1-trichloroethane) in non-aerosol electronics, metal and precision cleaning. View more+
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1. Names and Identifiers
1.1 Name
1-Bromopropane
1.2 Synonyms
1,3-Br-propane; 1-BROMO PROPANE; 1-Bromopropan; 1-bromo-propan; 1-Bromo-propane; 1-BROMOPROPANE FOR SYNTHESIS; 1-BROMOPROPANE, REAGENT (1 LT PVC); 1-Brompropan; 1-propyl bromide; bromo propane; Bromopropane; Bromopropane, 1-; Brompropan; EINECS 203-445-0; MFCD00000254; n-C3H7Br; n-propyl; n-Propyl Bromide; n-propylbromide; N-PROPYLBROMIDE(BROMOPROPANE); Propane, 1-bromo-; propane, bromo-; PROPYL BROMIDE; Propylbromid; UNII-Y9746DNE68;
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1.3 CAS No.
106-94-5
1.4 CID
7840
1.5 EINECS
203-445-0
1.6 Molecular Formula
C3H7Br
1.7 Inchi
InChI=1S/C3H7Br/c1-2-3-4/h2-3H2,1H3
1.8 InChkey
CYNYIHKIEHGYOZ-UHFFFAOYSA-N
1.9 Canonical Smiles
CCCBr
1.10 Isomers Smiles
CCCBr
2. Properties
2.1 Vapour pressure
4.3 (vs air)
2.2 Solubility
2.5 g/L (20 oC)
2.3 Viscosity
Viscosity is a measure of a fluid's resistance to flow. It describes the internal friction of a moving fluid.
2.4 VaporDensity
4.3 (vs air)
2.5 AnalyticLaboratory Methods
Method: NIOSH 2552, Issue 1; Procedure: gas chromatography with flame ionization detector; Analyte: 1-bromopropane;; Matrix: air; Detection Limit: 1.0 ug/sample.
2.6 Appearance
1-bromopropane appears as a colorless liquid. Slightly denser than water and slightly soluble in water. Flash point below 75°F. When heated to high temperatures may emit toxic fumes.
2.7 AutoIgnition
490°C
2.8 Storage
Light Sensitive. Ambient temperatures.
2.9 Color/Form
COLORLESS LIQUID WHEN FRESH
Colorless liquid
2.10 Decomposition
When heated to decomposition it emits toxic fumes of /hydrogen bromide;/.
2.11 Heat of Combustion
-1.89X10+9 J/kmol (est)
2.12 Odor
Sweet odor
2.13 Physical
1-BROMOPROPANE; is a colorless liquid. Slightly denser than water; and slightly soluble in water;. Flash point below 75°F. When heated to high temperatures may emit toxic fumes.
2.14 Water Solubility
Solubility in water, g/100ml at 20°C: 0.25
2.15 Spectral Properties
Index of refraction: 1.4341 at 20 deg C/D
IR: 11352 (Sadtler Research Laboratories Prism Collection)
NMR: 1892 (Sadtler Research Laboratories Spectral Collection)
MASS: 31730 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 494 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
RAMAN: 341 (Sadtler Research Laboratories Raman Collection)
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2.16 Stability
Stability Flammable - note low flash point. Incompatible with strong oxidizing agents, strong bases.
2.17 StorageTemp
Store below +30°C.
3. Use and Manufacturing
3.1 Definition
ChEBI: A bromoalkane that is propane carrying a bromo substituent at position 1.
3.2 Description
1-Bromopropane (CAS 106-94-5) is a colorless liquid with a sweet odor. Its basic structure consists of a propane molecule with a bromine atom attached to one of the carbon atoms. This chemical is sparingly soluble in water, but it can mix well with organic solvents.

Physically, 1-Bromopropane is a clear liquid with a density of 1.35 grams per milliliter. It has a boiling point of 71 degrees Celsius and a melting point of -110 degrees Celsius. The chemical properties of 1-Bromopropane include its reactivity with nucleophiles, making it useful in various chemical reactions.

Applicable Fields
Industrial Cleaning: 1-Bromopropane is commonly used as a solvent in industrial cleaning products. Its mechanism of action involves its ability to dissolve and remove oils, greases, and other contaminants from surfaces.

Chemical Synthesis: This chemical is also utilized in chemical synthesis processes. It can act as a reactant or a solvent in reactions that involve the substitution or addition of functional groups.

Storage Conditions
Store in a cool, dry place.
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3.3 GHS Classification
Signal: Danger
GHS Hazard Statements
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
H315: Causes skin irritation [Warning Skin corrosion/irritation]
H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H336: May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure; Narcotic effects]
H360FD: May damage fertility; May damage the unborn child [Danger Reproductive toxicity]
H373 **: Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

Precautionary Statement Codes
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P281, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501
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3.4 Methods of Manufacturing
Treatment of the parent hydroxyl; compound with a bromide; and sulfuric acid;, as in the preparation of methyl bromide;. If the parent compound is unstable toward sulfuric acid;, hydrobromic acid; is passed in and alkyl bromide is flashed over from the hot mixture. The product is condensed, neutralized, and fractionated. In modifications of these procedures, bromine; may be used along with a reducing agent such as sulfur;, sulfur dioxide;, phosphorus;, or sodium borohydride;.
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3.5 Purification Methods
Likely contaminants include n-propyl alcohol and isopropyl bromide. The simplest purification procedure uses drying with MgSO4 or CaCl2 (with or without a preliminary wash of the bromide with aqueous NaHCO3, then water), followed by fractional distillation away from bright light. Chien and Willard [J Am Chem Soc 79 4872 1957] bubbled a stream of oxygen containing 5% ozone through n-propyl bromide for 1hour, then shook it with 3% hydrogen peroxide solution, neutralised it with aqueous Na2CO3, washed it with distilled water and dried it. This was followed by vigorous stirring with 95% H2SO4 until fresh acid did not discolour within 12hours. The propyl bromide was separated, neutralised, washed, dried with MgSO4 and fractionally distilled. The centre cut was stored in the dark. Instead of ozone, Schuler and McCauley [J Am Chem Soc 79 821 1957] added bromine and stored it for 4 weeks, the bromine then being extracted with aqueous NaHSO3 before the sulfuric acid treatment was applied and finally distilled. Further purification is by preparative gas chromatography on a column packed with 30% SE-30 (General Electric ethylsilicone rubber) on 42/60 Chromosorb P at 150o and 40psi, using helium. [Chu J Phys Chem 41 226 1964, Beilstein 1 IV 205.]
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3.6 Usage
1-bromopropane was used primarily as a solvent for fats, waxes or resins and as an intermediate in the synthesis of other compounds including pharmaceuticals, insecticides, quaternary ammonium compounds, flavors and fragrances in generally well-controlled, closed processes. 1-Bromopropane is now used as a solvent cleaner in vapor and immersion cleaning and degreasing operations for optics, electronics and metals and as a solvent in industries that use spray-applied adhesives. Its use as a solvent substitute for ozone-depleting chlorofluorohydrocarbons (freons) or suspect carcinogens (e.g., trichloroethylene, methylene chloride) has prompted the dry cleaning industry to view it as a replacement for perchloroethylene (“perc”), especially in states that are proposing to ban the use of the latter chemical in dry cleaning.1-Bromopropane is one of several chemicals included in the Environmental Protection Agency’s Significant New Alternatives Policy (SNAP) that has been approved as a substitute for ozone-depleting solvents currently in use in certain applications. Specifically, 1-bromopropane has been approved as an acceptable substitute for CFC-113 (1,1,2-Trichloro1,2,2-trifluoroethane, Freon 113) and methyl chloroform (1,1,1-trichloroethane) in non-aerosol electronics, metal and precision cleaning.
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4. Safety and Handling
4.1 Octanol/Water Partition Coefficient
log Kow = 2.10
4.2 Other Preventative Measures
Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.
/If inhalted/: /Get/ fresh air, rest. Refer for medical attention. /If contacted with skin/: Remove contaminated clothes. Rinse skin with plenty of water or shower. /If contacted with eyes/: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. /If ingested/: Rinse mouth.
/Use/ ventilation, local exhaust, or breathing protection. /Wear/ protective gloves and safety spectacles. Do not eat, drink, or smoke during work.
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4.3 Cleanup Methods
Environmental considerations: Land Spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.
Environmental considerations: Water Spill: Use natural barriers or oil spill control booms to limit spill travel. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
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4.4 DisposalMethods
Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT wash away into sewer. Personal protection: filter respirator for organic gases and vapours.
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
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4.5 DOT Emergency Guidelines
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Bromopropanes/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Bromopropanes/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Bromopropanes/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Bromopropanes/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Evacuation: Large spill: Consider initial downwind evacuation for at least 300 meters (1000 feet). Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Bromopropanes/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire: Caution: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or alcohol-resistant foam. Do not use dry chemical extinguishers to control fires involving nitromethane or nitroethane. Large fires: Water spray, fog or alcohol-resistant foam. Do not use straight streams. Move containers from fire area if you can do it without risk. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. /Bromopropanes/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces. /Bromopropanes/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Bromopropanes/
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4.6 Fire Fighting Procedures
If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. Cool all affected containers with flooding quantities of water. Do not extinguish fire unless flow can be stopped. Keep run-off water out of sewers and water sources.
To fight fire, use water, foam, CO2, or dry chemical.
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4.7 FirePotential
Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire.
Dangerous fire hazard when heated or exposed to flame or oxidizers.
4.8 Safety Profile
Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by inhalation. Experimental reproductive effects. Mutation data reported. Dangerous fire hazard when heated or exposed to flame or oxidizers. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Br-. See also BROMIDES.
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4.9 Incompatibilities
Strong oxidants; strong bases 1-Bromopropane Preparation Products And Raw materials Raw materials
4.10 Protective Equipment and Clothing
The substance is irritating to the eyes and the respiratory tract.
4.11 Report

Related alkyl halides Ethyl bromide:isopropyl bromide;n-propyl chloride

4.12 Skin, Eye, and Respiratory Irritations
The substance is irritating to the eyes and the respiratory tract.
4.13 Safety

Hazard Codes: F,T
Risk Statements: 60-11-36/37/38-48/20-63-67
60:? May impair fertility?
11:? Highly Flammable?
36/37/38:? Irritating to eyes, respiratory system and skin?
48/20:? Harmful: danger of serious damage to health by prolonged exposure through inhalation?
63:? Possible risk of harm to the unborn child?
67:? Vapors may cause drowsiness and dizziness?
Safety Statements: 53-45
53:? Avoid exposure - obtain special instruction before use?
45:? In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)?
RIDADR: UN 2344 3/PG 2
WGK Germany: 2
F: 8: Photosensitive.
HazardClass: 3
PackingGroup: II
HS Code: 29033036

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4.14 Specification

?n-Propyl bromide , its cas register number is 106-94-5. It also can be called 1-Bromopropane ;? Propyl bromide ; Propane, 1-bromo- . It is?a colourless liquid. It has quite a potent smell.

4.15 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 2530mg/kg (2530mg/kg) ? "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 102, 1982.
rat LC50 inhalation 253gm/m3/30M (253000mg/m3) ? Fiziologicheski Aktivnye Veshchestva. Physiologically Active Substances. Vol. 7, Pg. 35, 1975.
rat LD50 intraperitoneal 2950mg/kg (2950mg/kg) ? "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 102, 1982.
rat LDLo oral 4gm/kg (4000mg/kg) ? Mutation Research. Vol. 101, Pg. 321, 1982.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 2

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

Specific target organ toxicity \u2013 single exposure, Category 3

Specific target organ toxicity \u2013 repeated exposure, Category 2

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H225 Highly flammable liquid and vapour

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation

H336 May cause drowsiness or dizziness

H360FD

Precautionary statement(s)
Prevention

P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.

P233 Keep container tightly closed.

P240 Ground and bond container and receiving equipment.

P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment.

P242 Use non-sparking tools.

P243 Take action to prevent static discharges.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P264 Wash ... thoroughly after handling.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

Response

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P370+P378 In case of fire: Use ... to extinguish.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P314 Get medical advice/attention if you feel unwell.

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P403+P235 Store in a well-ventilated place. Keep cool.

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
Mass spectrum (electron ionization)  
7. Synthesis Route
106-94-5Total: 60 Synthesis Route
 
71-23-8
71-23-8 248 Suppliers
 
106-94-5
106-94-5 67 Suppliers
 
78-77-3
78-77-3 142 Suppliers
 
106-94-5
106-94-5 67 Suppliers
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8. Precursor and Product
precursor:
75-26-3
75-26-3
107-08-4
107-08-4
78-77-3
78-77-3
102-69-2
102-69-2
71-23-8
71-23-8
540-54-5
540-54-5
74-98-6
74-98-6
product:
75-26-3
75-26-3
96-11-7
96-11-7
937-61-1
937-61-1
74-96-4
74-96-4
78-75-1
78-75-1
107-08-4
107-08-4
628-91-1
628-91-1
107-03-9
107-03-9
540-54-5
540-54-5
107-10-8
107-10-8
9. Computed Properties
10.Other Information
Usage
1-Bromopropane is used as a solvent for adhesives, degreasing plastics and optics. It is used in the production of asphalt, synthetic fiber and aerosols. It is employed for cleaning the metal surfaces, electronic circuit boards, and multi-layered OLEDs (Organic Light Emitting Diodes). It serves to replace perchloroethylene as a dry cleaning solvent.
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Merck
14,7845
BRN
505936
Chemical Properties
1-Bromopropane(1-BP), also known as n-propyl bromide, is a colourless to pale yellow liquid with a strong, characteristic sweet odour. It is soluble in some organic solvents and slightly soluble in water. 1-BP is a highly flammable liquid with flash point of 220℃. Its vapor is also flammable.
1-Bromopropane
1-Bromopropane is a solvent that is used in degreasing, dry cleaning, spray adhesives,aerosol solvents and resins and is primarily used as a chemical intermediate in the production of pesticides, quaternary ammonium compounds, flavours and fragrances, and pharmaceuticals in closed processes (NTP, 2013). In the mid-to-late 1990s, 1-bromopropane was introduced as a non-toxic, fast-drying solvent that does not leave surface residue for cleaning metals, plastics, and optical, electrical and electronic components (NTP, 2011; NIOSH, 2013). It was marketed as a substitute solvent for ozone-depleting and other solvents such as trichloroethylene, tetrachloroethylene (perchloroethylene) and methylene chloride. 1-Bromopropane is used for vapour degreasing and immersion cleaning, liquid and spray adhesive applications, fabric dry cleaning, and aerosol spray products (Blando et al., 2010; NTP, 2013).
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Uses
1-bromopropane was used primarily as a solvent for fats, waxes or resins and as an intermediate in the synthesis of other compounds including pharmaceuticals, insecticides, quaternary ammonium compounds, flavors and fragrances in generally well-controlled, closed processes. 1-Bromopropane is now used as a solvent cleaner in vapor and immersion cleaning and degreasing operations for optics, electronics and metals and as a solvent in industries that use spray-applied adhesives. Its use as a solvent substitute for ozone-depleting chlorofluorohydrocarbons (freons) or suspect carcinogens (e.g., trichloroethylene, methylene chloride) has prompted the dry cleaning industry to view it as a replacement for perchloroethylene (“perc”), especially in states that are proposing to ban the use of the latter chemical in dry cleaning.
1-Bromopropane is one of several chemicals included in the Environmental Protection Agency’s Significant New Alternatives Policy (SNAP) that has been approved as a substitute for ozone-depleting solvents currently in use in certain applications. Specifically, 1-bromopropane has been approved as an acceptable substitute for CFC-113 (1,1,2-Trichloro1,2,2-trifluoroethane, Freon 113) and methyl chloroform (1,1,1-trichloroethane) in non-aerosol electronics, metal and precision cleaning.
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Uses
1-Bromopropane has been used in spray glue and as a degreaser in the United States. 1-Bromopropane is an experimental reprotoxicant in both males and females and shows dose-dependent neurotoxicity; there is limited evidence of these effects in exposed workers.
Preparation
1-Bromopropane can be synthesized by reacting n-propyl alcohol (n-propanol) with excess hydrobromic acid. Water formed as a by-product is quickly removed from the resulting crude product before purification to give the final product. A modification of this reaction procedure involves using bromine with a reducing agent such as sulfur, sulfur dioxide, phosphorus or sodium borohydride. The overall reaction with hydrobromic acid is depicted below.
n-C3H7OH + HBr => n-C3H7Br + H2O
The prefix n (or normal) refers to a “straight chain” hydrocarbon component as opposed to a branched hydrocarbon component, such as the isopropyl group in isopropyl alcohol (i-propyl alcohol or i-propanol) where the hydroxyl (?OH) group is attached to the middle carbon.
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Definition
ChEBI: A bromoalkane that is propane carrying a bromo substituent at position 1.
Application
1-Bromopropane is used as a component of various models of binary mixtures, prepared to study their properties such as viscosity and refractive index.
It can be used as an alkylating reagent:
For the functionalization of seleno-substituted imidazo[1,2-α]pyridine derivatives.
For the synthesis of 1,4-dihydroxy-2-propoxy anthraquinone derivatives.
It can also be used as a reactant:
For the synthesis of Berberine-benzimidazole derivatives.
For the synthesis of alkyl aryl ketones via carbonylative Barbier-Negishi coupling with aryl iodides.
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General Description
A colorless liquid. Slightly denser than water and slightly soluble in water. Flash point below 75°F. When heated to high temperatures may emit toxic fumes.
Air & Water Reactions
Highly flammable. Slightly soluble in water.
Reactivity Profile
Halogenated aliphatic compounds, such as 2-BROMOPROPANE, are moderately or very reactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Low molecular weight haloalkanes are highly flammable and can react with some metals to form dangerous products. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. Emits toxic fumes of bromine when burned.
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Hazard
1-Bromopropane is classified as a Category 2 flammable liquid. It has an autoignition temperature of 914 degrees F and a flash point of less than 72 degrees F. Although a specific upper explosive (flammability) limit has not been determined, it has a lower explosive limit of 4.6 percent by volume in air. 1-Bromopropane decomposes when burned to emit hydrogen bromide (HBr) gas.
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Health Hazard
Occupational exposure to 1-bromopropane occurs primarily through inhalation and skin contact, although exposure through ingestion and the eyes are other possible routes. Short-term exposure to the chemical can result in irritation of the eyes, nose, throat or respiratory tract.
Chronic (long-term) exposure to 1-bromopropane can adversely affect peripheral nerves and the central nervous system. Symptoms that have been reported include joint pain or leg weakness and pain leading to difficulty standing and walking; muscle twitching or numbness, tingling and prickling in the hands or feet, loss of vibration sense; and anxiety, apathy, insomnia, and difficulties with concentration and memory.
Other health effects that may also occur include dermatitis, nausea and vomiting, diarrhea, difficulty in swallowing, disruption or failure of menstruation, urinary difficulties, anemia or low hematocrit (red blood cell count), liver damage, and lung disease.
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Safety Profile
Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by inhalation. Experimental reproductive effects. Mutation data reported. Dangerous fire hazard when heated or exposed to flame or oxidizers. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Br-. See also BROMIDES.
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Purification Methods
Likely contaminants include n-propyl alcohol and isopropyl bromide. The simplest purification procedure uses drying with MgSO4 or CaCl2 (with or without a preliminary wash of the bromide with aqueous NaHCO3, then water), followed by fractional distillation away from bright light. Chien and Willard [J Am Chem Soc 79 4872 1957] bubbled a stream of oxygen containing 5% ozone through n-propyl bromide for 1hour, then shook it with 3% hydrogen peroxide solution, neutralised it with aqueous Na2CO3, washed it with distilled water and dried it. This was followed by vigorous stirring with 95% H2SO4 until fresh acid did not discolour within 12hours. The propyl bromide was separated, neutralised, washed, dried with MgSO4 and fractionally distilled. The centre cut was stored in the dark. Instead of ozone, Schuler and McCauley [J Am Chem Soc 79 821 1957] added bromine and stored it for 4 weeks, the bromine then being extracted with aqueous NaHSO3 before the sulfuric acid treatment was applied and finally distilled. Further purification is by preparative gas chromatography on a column packed with 30% SE-30 (General Electric ethylsilicone rubber) on 42/60 Chromosorb P at 150o and 40psi, using helium. [Chu J Phys Chem 41 226 1964, Beilstein 1 IV 205.]
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Incompatibilities
Strong oxidants; strong bases
Storage features
Fireproof. Separated from strong oxidants and strong bases.
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12. Related Questions
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