1,2-Bis(dibromomethyl)benzene

Base Information

• Chemical Name: 1,2-Bis(dibromomethyl)benzene
• CAS No.: 13209-15-9
• Molecular Formula: C8H6Br4
• Molecular Weight: 421.752
• Hs Code.: 29039990
• European Community (EC) Number: 236-176-2
• NSC Number: 38607
• UNII: 3WG2H68VX4
• DSSTox Substance ID: DTXSID7022255
• Nikkaji Number: J31.710A
• Wikidata: Q27258135
• Mol file: 13209-15-9.mol

Synonyms:1,2-Bis(dibromomethyl)benzene;13209-15-9;alpha,alpha,alpha',alpha'-Tetrabromo-o-xylene;Benzene, 1,2-bis(dibromomethyl)-;a,a,a',a'-tetrabromo-o-xylene;EINECS 236-176-2;NSC 38607;UNII-3WG2H68VX4;Alpha,alpha,alpha,alpha-tetrabromo-o-xylene;3WG2H68VX4;o-Xylene, alpha,alpha,alpha',alpha'-tetrabromo-;NSC-38607;o-Xylene, .alpha.,.alpha.,.alpha.',.alpha.'-tetrabromo-;o-Xylylene Tetrabromide;NSC38607;SCHEMBL655520;Benzene,2-bis(dibromomethyl)-;DTXSID7022255;MFCD00000131;AKOS003404887;BS-43776;LS-184959;FT-0606305;T0052;.alpha.,.alpha.',.alpha.'-Tetrabromo-o-xylene;o-Xylene,.alpha.,.alpha.',.alpha.'-tetrabromo-;.alpha.,.alpha.,.beta.,.beta.-Tetrabromo-o-xylene;alpha,alpha,alpha',alpha'-Tetrabromo-o-xylene, 97%;Q-102053;Q27258135;.alpha.,.alpha.,.alpha.',.alpha.'-Tetrabromo-o-xylene;.alpha.,.alpha.,.alpha.1,.alpha.1-Tetrabromo-o-xylene;alpha , alpha , alpha ', alpha '-Tetrabromo-o-xylene;1,2-bis(dibromomethyl)-benzen;Benzene,1,2-bis(dibromomethyl)-

Chemical Property of 1,2-Bis(dibromomethyl)benzene

Chemical Property:

• Appearance/Colour: off-white to grey crystalline powder
• Melting Point: 114-116 ºC
• Refractive Index: 1.7040 (estimate)
• Boiling Point: 343.9 °C at 760 mmHg
• Flash Point: 157.8 °C
• PSA: 0.00000
• Density: 2.392 g/cm³
• LogP: 5.26340
• Storage Temp.: Store below +30°C.
• Water Solubility.: Insoluble
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 421.71620
• Heavy Atom Count: 12
• Complexity: 119

Purity/Quality:

98%,99%, ^*data from raw suppliers

α,α,α',α'-Tetrabromo-o-xylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-36/37-20/21/22
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: C1=CC=C(C(=C1)C(Br)Br)C(Br)Br
• 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. 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.

Technology Process of 1,2-Bis(dibromomethyl)benzene

There total 6 articles about 1,2-Bis(dibromomethyl)benzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 42.0%

o-xylene (95-47-6) → 1,2-bis(dibromomethyl)benzene (13209-15-9) + 1-(dibromomethyl)-2-(tribromomethyl)benzene (95110-95-5)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In dichloromethane; for 19h; Irradiation;

DOI:10.1246/bcsj.67.1113

Reference yield: 40.0%

1-(dibromomethyl)-2-(tribromomethyl)benzene (95110-95-5) → 1,2-bis(dibromomethyl)benzene (13209-15-9)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1055/s-1995-3878

Reference yield:

o-xylene (95-47-6) → 1,2-bis(dibromomethyl)benzene (13209-15-9)

Guidance literature:

With bromine; at 120 - 170 ℃; Irradiation;

upstream raw materials:

o-xylene

1-chloromethyl-2-methylbenzene

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

bromine

Downstream raw materials:

2-phenyl-1H-benzo[f]isoindole-1,3(2H)-dione

5,12-naphthacenequinone

2,3-Naphthalimide

1,2-bis-diacetoxymethyl-benzene

Refernces

• 1、 de Souza, Thalita F.M.,Ribeiro, Anderson O.. "The impact of the extended π-conjugation in photophysical, photochemical and aggregation behavior of new phthalocyanine–naphthalocyanine hybrids". . p. 1 - 7. Retrieved 2017.
• 2、 Mataka,Liu,Tashiro. "Palladium(0) complex-catalyzed debrominative coupling of (tribromomethyl)- and (dibromomethyl)benzenes to diarylacetylenes and 1,2-diarylethenes". . p. 133 - 135. Retrieved 2007/10/02.