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1,2-Bis(dibromomethyl)benzene

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Name

1,2-Bis(dibromomethyl)benzene

EINECS 236-176-2
CAS No. 13209-15-9 Density 2.392 g/cm3
PSA 0.00000 LogP 5.26340
Solubility Insoluble in water Melting Point 114-116 ºC
Formula C8H6Br4 Boiling Point 343.9 °C at 760 mmHg
Molecular Weight 421.752 Flash Point 157.8 °C
Transport Information UN 3261 Appearance off-white to grey crystalline powder
Safety 26-36/37/39-45 Risk Codes 34-36/37-20/21/22
Molecular Structure Molecular Structure of 13209-15-9 (ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE) Hazard Symbols CorrosiveC
Synonyms

o-Xylene, a,a,a',a'-tetrabromo- (6CI,8CI);1,2-Bis(dibromomethyl)benzene;NSC 38607;a,a,a',a'-Tetrabromo-o-xylene;

Article Data 13

1,2-Bis(dibromomethyl)benzene Synthetic route

95-47-6

o-xylene

A

13209-15-9

1,2-bis(dibromomethyl)benzene

B

95110-95-5

1-(dibromomethyl)-2-(tribromomethyl)benzene

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane for 19h; Irradiation;A 72%
B 6%
With N-Bromosuccinimide for 19h;A 38%
B 42%
95110-95-5

1-(dibromomethyl)-2-(tribromomethyl)benzene

13209-15-9

1,2-bis(dibromomethyl)benzene

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 100℃;40%
95-47-6

o-xylene

13209-15-9

1,2-bis(dibromomethyl)benzene

Conditions
ConditionsYield
With bromine at 120 - 170℃; Irradiation;
With bromine at 140℃;
With bromine im Sonnenlicht;
552-45-4

1-chloromethyl-2-methylbenzene

13209-15-9

1,2-bis(dibromomethyl)benzene

Conditions
ConditionsYield
With bromine at 140 - 160℃; Irradiation;
7726-95-6

bromine

552-45-4

1-chloromethyl-2-methylbenzene

A

13209-15-9

1,2-bis(dibromomethyl)benzene

B

2-chlorobromomethyl-1-dibromomethyl-benzene

2-chlorobromomethyl-1-dibromomethyl-benzene

Conditions
ConditionsYield
at 140 - 160℃; Irradiation;
13209-15-9

1,2-bis(dibromomethyl)benzene

764-42-1

1,2-Dicyanoethylene

22856-30-0

2,3-dicyanonaphthalene

Conditions
ConditionsYield
With sodium iodide In N,N-dimethyl-formamide at 75 - 80℃; for 8h;97%
With sodium iodide In N,N-dimethyl-formamide at 75℃; for 7h;88%
With sodium iodide In N,N-dimethyl-formamide at 75℃; for 5.5h;78%
13209-15-9

1,2-bis(dibromomethyl)benzene

phenylmagnesium bromide

713-36-0

2-benzyltoluene

Conditions
ConditionsYield
Stage #1: phenylmagnesium bromide With manganese(ll) chloride In tetrahydrofuran Metallation;
Stage #2: 1,2-bis(dibromomethyl)benzene In tetrahydrofuran at 0℃; for 2.5h; Substitution;
Stage #3: With water Substitution;
92%
13209-15-9

1,2-bis(dibromomethyl)benzene

phenylmagnesium bromide

716-78-9

1-benzyl-2-(deuteriomethyl)benzene

Conditions
ConditionsYield
Stage #1: phenylmagnesium bromide With manganese(ll) chloride In tetrahydrofuran Metallation;
Stage #2: 1,2-bis(dibromomethyl)benzene In tetrahydrofuran at 0℃; for 2.5h; Substitution;
Stage #3: With water-d2 Substitution;
92%
13209-15-9

1,2-bis(dibromomethyl)benzene

643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
Stage #1: 1,2-bis(dibromomethyl)benzene With sulfuric acid
Stage #2: With water; sodium hydrogencarbonate Product distribution / selectivity;
91%
With sulfuric acid Product distribution / selectivity;79%
With sulfuric acid
13209-15-9

1,2-bis(dibromomethyl)benzene

106-51-4

p-benzoquinone

3029-32-1

6,13-pentacenequinone

Conditions
ConditionsYield
With sodium iodide In N,N-dimethyl-formamide at 120℃;91%
With sodium iodide In N,N-dimethyl-formamide at 120℃; Inert atmosphere;91%
Stage #1: p-benzoquinone With sodium iodide In N,N-dimethyl-formamide at 70℃; Inert atmosphere;
Stage #2: 1,2-bis(dibromomethyl)benzene In N,N-dimethyl-formamide at 70℃; for 18h; Diels-Alder Cycloaddition; Inert atmosphere;
28%

1,2-Bis(dibromomethyl)benzene 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.

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