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ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE structure

ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE

ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE, with the chemical formula C8H8Br4 and CAS registry number 13209-15-9, is a compound known for its applications as a flame retardant and a chemical intermediate. This colorless liquid, also referred to as Tetrabromo-o-xylene, is characterized by its four bromine atoms attached to the xylene backbone. It is commonly used in the production of polymers, plastics, and electronics to enhance their fire resistance properties. Additionally, ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE is utilized as a building block in the synthesis of other brominated compounds. It is important to handle this compound with caution due to its potential environmental and health hazards. Overall, ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE plays a crucial role in various industries where flame retardancy is required.
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1. Names and Identifiers
1.1 Name
ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE
1.2 Synonyms
1,2-bis(dibromomethyl)-benzen; 1,2-BIS(DIBROMOMETHYL)BENZENE; A,A,A',A'-TETRABROMO-O-XYLENE; alpha,alpha,alpha‘,alpha‘-Tetrabromo-o-xylene; ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-2-XYLENE; alpha,alpha,alpha″,alpha″-Tetrabromo-o-xylene; ALPHA,ALPHA,BETA,BETA-TETRABROMO-O-XYLENE; Benzene,1,2-bis(dibromomethyl)-; EINECS 236-176-2; MFCD00000131; O-XYLYLENE TETRABROMIDE; α,α,α',α'-Tetrabromo-o-xylene;
1.3 CAS No.
13209-15-9
1.4 CID
83234
1.5 EINECS
236-176-2
1.6 Molecular Formula
C8H6Br4
1.7 Inchi
InChI=1S/C8H6Br4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,7-8H
1.8 InChkey
LNAOKZKISWEZNY-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=CC=C(C(=C1)C(Br)Br)C(Br)Br
1.10 Isomers Smiles
C1=CC=C(C(=C1)C(Br)Br)C(Br)Br
2. Properties
2.1 Appearance
Clear colorless to yellow Liquid or Low Melting Solid
2.2 Storage
Ambient temperatures.
2.3 Chemical Properties
OFF-WHITE TO GREY CRYSTALLINE POWDER ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENESupplier
2.4 Color/Form
Clear colorless to yellow
2.5 Water Solubility
Insoluble
2.6 StorageTemp
Store below +30°C.
3. Use and Manufacturing
3.1 Description

ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE, with the chemical formula C8H4Br4O, has the CAS number 13209-15-9. It appears as a white crystalline solid with no odor. The basic structure of ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE consists of four bromine atoms and one oxygen atom attached to a xylene molecule. This compound is insoluble in water. ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE may cause skin irritation and eye irritation. It is also harmful if swallowed or inhaled. Safety precautions should be taken when handling this chemical, including wearing protective gloves and eyewear. In case of contact, rinse the affected area with plenty of water. In case of ingestion, seek medical attention immediately.

Applicable Fields

Flame retardant: ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE is commonly used as a flame retardant in various materials. Its purpose in this field is to reduce the flammability of the treated materials and prevent or delay the spread of fire. The mechanism of action involves the release of bromine radicals when exposed to heat, which interfere with the combustion process and inhibit the ignition of the material.

Electronics: This chemical is also used in the electronics industry as a component of flame retardant formulations for printed circuit boards and other electronic devices. Its mechanism of action in this context is similar to its use as a flame retardant, providing fire protection for electronic components and reducing the risk of electrical fires.

Storage

Conditions: Store in a cool and dry place.

3.2 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 28 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (10.71%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (10.71%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H318 (89.29%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H335 (89.29%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H400 (82.14%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P391, P403+P233, P405, and P501
4. Safety and Handling
4.1 Specification

The IUPAC name of this product is 1,2-bis(dibromomethyl)benzene . With the CAS registry number 13209-15-9, it is also named as  NSC 38607 ; alpha,alpha,alpha',alpha'-Tetrabromo-o-xylene ; o-Xylene, alpha,alpha,alpha',alpha'-tetrabromo- ; Benzene, 1,2-bis(dibromomethyl)- ; alpha,alpha,alpha',alpha'-Tetrabromo-o-xylene .

The 1,2-Bis(dibromomethyl)benzene is off-white to grey crystalline powder. It is insoluble in water. It can cause burns. And it is irritating to eyes and respiratory system. Harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

The 1,2-Bis(dibromomethyl)benzene can be obtained by 1-dibromomethyl-2-tribromomethyl-benzene with Pd(OAc)2 , PPhand Et3N in the solvent dimethylformamide . The recation temperature is 100 °C and the yield is 40%.

The 1,2-Bis(dibromomethyl)benzene is used in the preparation of other chemicals. For example: 1. It can reacts with 5endo,6endo-Bis-chlormethyl-norborn-2-en to get trans/cis-2,3-bis(chloromethyl)-1,4-methano-1,2,3,4-tetrahydroanthracene ; 2. It also can reacts with allylmagnesium bromide to obtain 1-(3-butenyl)-2-(deuteriomethyl)benzene ; 3. It reacts with exo-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene to obtain exo-benzocyclobuteno-1,2,3,4-tetrahydro-1,4-methanoanthracene .

The other characteristics of this product can be summarized as: (1)ACD/BCF (pH 5.5): 4628.7 ; (2)ACD/BCF (pH 7.4): 4628.7 ; (3)ACD/KOC (pH 5.5): 14632.84 ; (4)ACD/KOC (pH 7.4): 14632.84 ; (5)#Freely Rotating Bonds: 2 ; (6)Index of Refraction: 1.685 ; (7)Molar Refractivity: 67.01 cm3 ; (8)Molar Volume: 176.2 cm3 ; (9)Polarizability: 26.56×10-24 cm3 ; (10)Surface Tension: 58.1 dyne/cm ; (11)Enthalpy of Vaporization: 56.45 kJ/mol ; (12)Vapour Pressure: 0.000136 mmHg at 25°C. People can use the following data to convert to the molecule structure. SMILES: BrC(Br)c1ccccc1C(Br)Br; InChI: InChI=1/C8H6Br4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,7-8H.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin corrosion, Category 1B

Serious eye damage, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

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

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H314 Causes severe skin burns and eye damage

H335 May cause respiratory irritation

H400 Very toxic to aquatic life

Precautionary statement(s)
Prevention

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

P264 Wash ... thoroughly after handling.

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

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

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

P273 Avoid release to the environment.

Response

P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

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

P363 Wash contaminated clothing before reuse.

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

P310 Immediately call a POISON CENTER/doctor/\u2026

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

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

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

P391 Collect spillage.

Storage

P405 Store locked up.

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

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum
13C NMR : in CDCl3  
1H NMR : 90 MHz in CDCl3  
IR : CCl4 solution  
IR : KBr disc  
Raman : 4880 A,200 M,powder  
Mass  
7. Synthesis Route
13209-15-9Total: 5 Synthesis Route
 
95-47-6
95-47-6 160 Suppliers
 
13209-15-9
13209-15-9 31 Suppliers
 
95-47-6
95-47-6 160 Suppliers
 
13209-15-9
13209-15-9 31 Suppliers
 
8. Precursor and Product
precursor:
product:
9. Computed Properties
10.Other Information
BRN
2211698
Chemical Properties
OFF-WHITE TO GREY CRYSTALLINE POWDER
Usage
α,α,α',α'-Tetrabromo-o-xylene reacts with 5endo,6endo-bis-chlormethyl-norborn-2-en to obtain trans/cis-2,3-bis(chloromethyl)-1,4-methano-1,2,3,4-tetrahydroanthracene. Further, it is involved in the preparation of 1-(3-butenyl)-2-(deuteriomethyl)benzene by reacting with allylmagnesium bromide. In addition this, it is used to prepare exo-benzocyclobuteno-1,2,3,4-tetrahydro-1,4-methanoanthracene by reacting with exo-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene.
Uses
α,α,α',α'-Tetrabromo-o-xylene reacts with 5endo,6endo-bis-chlormethyl-norborn-2-en to obtain trans/cis-2,3-bis(chloromethyl)-1,4-methano-1,2,3,4-tetrahydroanthracene. Further, it is involved in the preparation of 1-(3-butenyl)-2-(deuteriomethyl)benzene by reacting with allylmagnesium bromide. In addition this, it is used to prepare exo-benzocyclobuteno-1,2,3,4-tetrahydro-1,4-methanoanthracene by reacting with exo-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene.
Uses
α,α,α′,α′-Tetrabromo-o-xylene can be employed as a precursor for the synthesis of:
  • Poly(o-phenylene vinylene) (o-PPV) via electrochemical polymerization.
  • A pentacene derivative by reacting with naphthalene moieties for the development of organic thin-film transistors (OTFTs).
  • Bitopic pyrazole containing ligands.

Manufacturing Info
Benzene, 1,2-bis(dibromomethyl)-: ACTIVE
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12. Realated Product Infomation
 
 
 
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