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Hydroxylamine hydrochloride structure

Hydroxylamine hydrochloride
Hydroxylamine hydrochloride, with the chemical formula NH2OH·HCl and CAS registry number 5470-11-1, is a compound commonly used in chemical reactions and industrial processes. It is a white crystalline solid that is highly soluble in water. Hydroxylamine hydrochloride is known for its ability to undergo various reactions, including reduction, oxidation, and condensation reactions. It is often used as a reducing agent in organic synthesis and as a stabilizer in photographic developing solutions. Additionally, it finds applications in the production of pharmaceuticals, dyes, and rubber chemicals. Hydroxylamine hydrochloride is a versatile compound that plays a crucial role in many chemical processes.
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1. Names and Identifiers
1.1 Name
Hydroxylamine hydrochloride
1.2 Synonyms
Ammonium, hydroxy-, chloride (1:1); EINECS 226-798-2; hydroxyaminehydrochloride; hydroxylamine,hydrochloride; hydroxylaminechloride; hydroxylaminechloride(1:1); HydroxyLamine-Hydrochioride; Hydroxylammonium chloride; HYDROXYLAMMONIUM CHLORIDE REAGENT (ACS), LOW MERCURY; MFCD00051089; OXAMMONIUM HCL; OXAMMONIUM HYDROCHLORIDE;
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1.3 CAS No.
5470-11-1
1.4 CID
443297
1.5 EINECS
226-798-2
1.6 Molecular Formula
ClH4NO
1.7 Inchi
InChI=1S/ClH.H3NO/c;1-2/h1H;2H,1H2
1.8 InChkey
WTDHULULXKLSOZ-UHFFFAOYSA-N
1.9 Canonical Smiles
NO.Cl
1.10 Isomers Smiles
NO.Cl
2. Properties
2.1 Solubility
470g/l
2.2 Appearance
Colorless or off-white crystalline solid
2.3 Storage
Hygroscopic. Ambient temperatures.
2.4 Chemical Properties
White crystals
2.5 Color/Form
White to off-white
2.6 Contact Allergens
Hydroxylamine and its salts are used in variousbranches of industry, as reducing agents in color filmdevelopers or as reagents in laboratories.
2.7 PH
2.5-3.5 (25℃, 50mg/mL in H2O)
2.8 Water Solubility
560 g/L (20 oC)
2.9 Stability
Substances to be avoided include strong oxidizing agents. Heating above 115 C may cause explosion; do not store above 65C. Moisture and air sensitive.
2.10 StorageTemp
Store at +15°C to +25°C.
3. Use and Manufacturing
3.1 Description

Hydroxylamine hydrochloride, with the chemical formula NH2OH·HCl, has the CAS number 5470-11-1. It appears as a white crystalline solid with a strong ammonia-like odor. The basic structure of hydroxylamine hydrochloride consists of a hydroxylamine molecule bonded to a hydrogen chloride molecule. This compound is highly soluble in water. Hydroxylamine hydrochloride is a strong reducing agent and can react violently with oxidizing agents. It is also corrosive to metals and may cause severe skin burns and eye damage. Ingestion or inhalation of hydroxylamine hydrochloride can cause serious health effects and should be avoided. It is important to handle this chemical with caution and use appropriate protective measures.

Applicable Fields

Chemical synthesis: Hydroxylamine hydrochloride is commonly used in chemical synthesis as a reducing agent. Its purpose in this field involves its ability to donate electrons and facilitate the reduction of other compounds. The mechanism of action in chemical synthesis involves the transfer of electrons from hydroxylamine hydrochloride to the target compound, resulting in a reduction reaction.

Photography: This compound is also used in the field of photography. Its purpose in this context involves its ability to act as a developer, converting exposed silver halide crystals into metallic silver. The mechanism of action in photography involves the reduction of silver ions by hydroxylamine hydrochloride, leading to the formation of metallic silver.

Storage

Conditions: Store in a cool and dry place.

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3.2 General Description
Colorless or off-white crystalline solid. pH (0.1 molar aqueous solution) 3.4. pH (0.2 molar aqueous solution) 3.2.
3.3 Purification Methods
Crystallise the salt from aqueous75% ethanol or boiling methanol, and dry it under vacuum over CaSO4 or P2O5. It has also been dissolved in a minimum of water and saturated with HCl; after three such crystallisations, it is dried under a vacuum over CaCl2 and NaOH. Its solubility at 20o is 85% in H2O, 6% in EtOH and 12% in MeOH. [Hurd Inorg Synth I 87 1939, Semon in Org Synth Coll Vol I 318 1941.] Hydroxylamine hydrochloride Preparation Products And Raw materials Raw materials
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3.4 Usage
Organic synthesis, photographic developer,medicine, controlled reduction reactions, nondiscoloring short-stopper for synthetic rubbers, antioxidant for fatty acids.
4. Safety and Handling
4.1 Fire Hazard
Flash point data for Hydroxylamine hydrochloride are not available; however, Hydroxylamine hydrochloride is probably combustible.
4.2 Report

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

4.3 Safety

Poison by intraperitoneal and subcutaneous routes. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits very toxic fumes of HCl and NOx.
Safety Information of Hydroxylamine hydrochloride (CAS NO.5470-11-1):
Hazard Codes:?HarmfulXn,DangerousN
Risk Statements: 22-36/38-43-48/22-50?
R22:Harmful if swallowed.?
R36/38:Irritating to eyes and skin.?
R43:May cause sensitization by skin contact.?
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed.?
R50:Very toxic to aquatic organisms.
Safety Statements: 22-24-37-61?
S22:Do not breathe dust.?
S24:Avoid contact with skin.?
S37:Wear suitable gloves.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 2923 8/PG 2
WGK Germany: 3
RTECS: NC3675000
F: 21
HazardClass: 8
PackingGroup: III

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4.4 Sensitive
Hygroscopic
4.5 Specification

?Hydroxylamine hydrochloride (CAS NO.5470-11-1), its Synonyms are Hydroxyamine hydrochloride ; Hydroxyammonium chloride ; Hydroxylamine chloride ; Hydroxylamine chloride (1:1) ; Hydroxylamine-1-hydrochloride ; Hydroxylammonium chloride ; Oxammonium hydrochloride .

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4.6 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo subcutaneous 70mg/kg (70mg/kg) ? "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
mouse LD50 intraperitoneal 10mg/kg (10mg/kg) ? National Technical Information Service. Vol. AD277-689,
mouse LD50 oral 408mg/kg (408mg/kg) ? Acta Pharmacologica et Toxicologica. Vol. 6, Pg. 285, 1950.
mouse LD50 subcutaneous 125mg/kg (125mg/kg) ? Acta Biologica et Medica Germanica. Vol. 21, Pg. 635, 1968.
rat LD50 oral 141mg/kg (141mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD National Technical Information Service. Vol. OTS0555279,

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Corrosive to metals, Category 1

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Skin sensitization, Category 1

Carcinogenicity, Category 2

Specific target organ toxicity \u2013 repeated exposure, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H290 May be corrosive to metals

H302 Harmful if swallowed

H312 Harmful in contact with skin

H315 Causes skin irritation

H319 Causes serious eye irritation

H317 May cause an allergic skin reaction

H351 Suspected of causing cancer

H400 Very toxic to aquatic life
Precautionary statement(s)
Prevention

P234 Keep only in original packaging.

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

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

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

P272 Contaminated work clothing should not be allowed out of the workplace.

P201 Obtain special instructions before use.

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

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

P273 Avoid release to the environment.

Response

P390 Absorb spillage to prevent material damage.

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

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

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

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

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

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

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.

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

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

P314 Get medical advice/attention if you feel unwell.

P391 Collect spillage.

Storage

P406 Store in a corrosion resistant/...container with a resistant inner liner.

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
IR : KBr disc  
IR : nujol mull  
7. Synthesis Route
5470-11-1Total: 22 Synthesis Route
 
75-52-5
75-52-5
 
5470-11-1
5470-11-1 397 Suppliers
 
79-24-3
79-24-3
 
5470-11-1
5470-11-1 397 Suppliers
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8. Precursor and Product
precursor:
79-46-9
79-46-9
7632-00-0
7632-00-0
51060-05-0
51060-05-0
108-03-2
108-03-2
7758-09-0
7758-09-0
3021-39-4
3021-39-4
product:
1121-47-7
1121-47-7
7803-49-8
7803-49-8
3848-36-0
3848-36-0
89-73-6
89-73-6
23451-95-8
23451-95-8
932-90-1
932-90-1
6134-79-8
6134-79-8
7340-09-2
7340-09-2
73472-94-3
73472-94-3
9. Computed Properties
10.Other Information
Usage
Hydroxylamine hydrochloride is a monomoamine oxidase inhibitor. It is used to prepare oximes and hydroxmic acids in organic synthesis. It acts as a copolymerization inhibitor. It can be used to remove bromine and polybromide from a solution during extraction of lignin from lignocellulosic biomass. It is key starting material for the preparation of pharmaceuticals and agrochemicals. It plays a vital role in rubber and plastic industries as an antioxidant, a vulcanization accelerator and a radical scavenger. It is also used as a color stabilizer and emulsion additive in color films.
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Merck
14,4828
BRN
3539763
Description
Hydroxylamine hydrochloride is a reducing agent that is routinely used for the deacetylation of SATA to form free sulfhydryls (Figure 1), for cleavage of protein cross‐linkers that contain carbonyl groups (i.e. EGS) and for mutagenesis of plasmid DNA.
Generation of free sulfhydryls with SATA and hydroxylamine.
Hydroxylamine converts aldehydes and ketones (carbonyls) to their oxime derivative in weak bases, therefore cross‐linkers and other compounds with carbonyl groups are cleavable with Hydroxylamine hydrochloride.
SATA and SATP are modification reagents that add a sulfhydryl group to primary amines on biomolecules. The initial modification results in the addition of an acetyl‐protected sulfur enabling storage of the biomolecule. To generate a free sulfhydryl the biomolecule is treated with hydroxylamine to remove the protecting acetyl group (see figure).
EGS and sulfo‐EGS are homobifunctional, succinimidyl ester, amine reactive crosslinkers that are resistant to cleavage by denaturants used in SDS‐PAGE conditions, but may be cleaved with hydroxylamine.
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Chemical Properties
White crystals
Physical properties
Colorless monoclinic crystals; hygroscopic; decomposes slowly in moist air;density 1.67 g/cm3at 17°C; melts at 151°C (decomposes); highly soluble inwater (84g/100g at 20°C); soluble in lower alcohols and glycols; pH of 0.1molar solution 3.4.
Uses
Organic synthesis, photographic developer, medicine, controlled reduction reactions, nondiscoloring short-stopper for synthetic rubbers, antioxidant for fatty acids.
Uses
Hydroxylammonium-chloride is a reducing agent in photography; in synthetic and analytical chemistry; as an antioxidant for fatty acids and soaps; in textiles; in medicine; controlled reduction reactions; non-discoloring short stoppers for synthetic rubbers; reagent for enzyme reactivation; powerful reducing agent; converts aldehydes and ketones to oximes and acid chlorides to hydroxamic acids; catalyst, swelling agent, and copolymerization inhibitor in polymerization processes; in floor lacquers and as an antioxidant for fatty acids and soaps.
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Preparation
Hydroxylamine hydrochloride is prepared by electrolytic reduction ofammonium chloride.
Biotechnological Applications
Hydroxylamine hydrochloride is a strong reducing agent that is useful in biochemical crosslinking applications, including the deacetylation of SATA and chemical cleavage of EGS and Sulfo-EGS. Hydroxylamine converts carbonyl compounds (aldehydes and ketones) to their oxime derivatives in the presence of a weak base. Therefore, crosslinkers and other compounds that contain a carbonyl within their structure are cleavable with hydroxylamine?HCl.
EGS  and its water-soluble analog, Sulfo-EGS, are homobifunctional, succinimidyl ester, amine-reactive crosslinkers useful for covalent stabilization of polypeptide multimers and protein:protein interactions. Unlike disulfidecontaining crosslinkers, EGS and Sulfo-EGS will not cleave by reducing SDS-PAGE conditions but may be cleaved when necessary with hydroxylamine.
SATA  and SATP are modification reagents for addition of sulfhydryl groups to proteins and other molecules containing primary amines. Such sulfhydryl addition is an important step in one popular method for preparing protein conjugates such as antibodies with horseradish peroxidase enzyme. The initial modification results in addition of an acetyl-protected sulfur, enabling storage of the modified protein; to make the sulfur available as a sulhydryl group (-SH) for the final conjugation reaction, hydroxylamine is used to remove the protecting acetyl group.
Hydroxylamine?HCl is more stable to oxidation than the free base form of hydroxylamine; nevertheless, always prepare hydroxylamine solutions immediately before use and store the product desiccated. Hydroxylamine?HCl is soluble in polar solvents such as water, ethanol, methanol, glycerol and propylene glycol.
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General Description
Colorless or off-white crystalline solid. pH (0.1 molar aqueous solution) 3.4. pH (0.2 molar aqueous solution) 3.2.
Air & Water Reactions
Hygroscopic. Sensitive to prolonged exposure to air. Water soluble. Reacts slowly with water.
Reactivity Profile
A powerful reducing agent. Reacts with bases and oxidizing agents.
Hazard
Toxic by ingestion, strong irritant to tissue.
Fire Hazard
Flash point data for Hydroxylamine hydrochloride are not available; however, Hydroxylamine hydrochloride is probably combustible.
Biochem/physiol Actions
MAO inhibitor; inhibits platelet aggregation.
Contact allergens
Hydroxylamine and its salts are used in various branches of industry, as reducing agents in color film developers or as reagents in laboratories.
Purification Methods
Crystallise the salt from aqueous75% ethanol or boiling methanol, and dry it under vacuum over CaSO4 or P2O5. It has also been dissolved in a minimum of water and saturated with HCl; after three such crystallisations, it is dried under a vacuum over CaCl2 and NaOH. Its solubility at 20o is 85% in H2O, 6% in EtOH and 12% in MeOH. [Hurd Inorg Synth I 87 1939, Semon in Org Synth Coll Vol I 318 1941.]
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Description
Hydroxylamine hydrochloride is an inorganic substance, a colorless crystalline, easily deliquescence, white chemical substance, mainly used as a reducing agent and an imaging agent, used in the preparation of oximes in organic synthesis, and also used in the synthesis of anticancer drugs (hydroxylamine hydrochloride). urea), sulfonamides (trimoxazole) and pesticides (methomyl). It has strong hygroscopicity and will decompose when it is damped above 151℃. At 17°C, 83.8g can be dissolved in 100g of water. This product is highly toxic and irritating to the skin. The production equipment should be sealed to prevent running, running, dripping and leaking, and operators should wear protective equipment. When splashed on the skin, rinse with plenty of water.
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Preparation
Sodium nitrite synthesis method (oximation method) Add water to the reaction kettle, add sodium nitrite under stirring, add sodium metabisulfite in stages, and then acidify with sulfuric acid. The acidified material is sent to the hydrolysis kettle, acetone is added, neutralized with liquid caustic soda, and the neutralized liquid is distilled to obtain acetone oxime. Acetone oxime and hydrochloric acid are added to the salt-forming kettle for reaction to generate hydroxylamine hydrochloride and acetone. Acetone is recovered and used; hydroxylamine hydrochloride is concentrated, crystallized by cooling, centrifuged and dried to obtain the finished product. Raw material consumption quota: sodium nitrite (95%) 1970kg/t, sodium metabisulfite (64% as SO2) 5418kg/t, acetone (98%) 1175kg/t. 2. Nitromethane method Nitromethane reacts with hydrochloric acid and water to obtain hydroxylamine hydrochloride. According to HGB3044-76, the hydroxylamine hydrochloride product is white crystal, the content of the second-grade product is ≥98.5, and the content of the third-grade product is ≥97%. Raw material consumption quota: nitromethane 1200kg/t, hydrochloric acid (30%) 1500kg/t. Or by the action of nitromethane with hydrochloric acid and water to obtain hydroxylamine hydrochloride.
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Flammability and Explosibility
Notclassified
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12. Related Questions
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13. Realated Product Infomation
 
1. Names and Identifiers
2. Properties
3. Use and Manufacturing
4. Safety and Handling
5. Msds
6. NMR Spectrum
7. Synthesis Route
8. Precursor and Product
9. Computational chemical data
10. Other Information
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12. Related Questions
13. Realated Product Infomation
 
 
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