1,2-Bis(bromomethyl)benzene

Base Information

• Chemical Name: 1,2-Bis(bromomethyl)benzene
• CAS No.: 91-13-4
• Molecular Formula: C8H8Br2
• Molecular Weight: 263.96
• Hs Code.: 29036990
• European Community (EC) Number: 202-042-7
• NSC Number: 3986
• UNII: 9FRJ55E5UL
• DSSTox Substance ID: DTXSID2059019
• Nikkaji Number: J31.713F
• Wikipedia: Xylylene_dibromide
• Wikidata: Q27272501
• Mol file: 91-13-4.mol

Synonyms:alpha,alpha'-dibromoxylene

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

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 91-94 °C(lit.)
• Refractive Index: 1.6113 (estimate)
• Boiling Point: 272.6 °C at 760 mmHg
• Flash Point: 133.6 °C
• PSA: 0.00000
• Density: 1.778 g/cm³
• LogP: 3.47640
• Storage Temp.: Store below +30°C.
• Water Solubility.: soluble, hydrolyses
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 263.89723
• Heavy Atom Count: 10
• Complexity: 81.3

Purity/Quality:

99% ^*data from raw suppliers

1,2-Bis(bromomethyl)benzene ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CBr)CBr
• Uses: 1,2-Bis(bromomethyl)benzene is used in the synthesis of isothioureas involved in the inhibition of human nitric oxide synthases. Also used in the synthesis of tridentate carbene ligands.

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

There total 14 articles about 1,2-Bis(bromomethyl)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: 99.0%

phthalyl alcohol (612-14-6) → α,α'-dibromo-o-xylene (91-13-4)

Guidance literature:

With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at -78 - 20 ℃; for 12h; chemoselective reaction; Darkness;

DOI:10.1055/s-0034-1380132

Reference yield: 90.0%

o-xylene (95-47-6) → α,α'-dibromo-o-xylene (91-13-4)

Guidance literature:

With N-Bromosuccinimide; HZSM-5 (SiO₂/Al₂O₃ = 40); In tetrachloromethane; Heating;

DOI:10.1016/0040-4039(94)88224-X

Reference yield: 80.0%

o-xylene (95-47-6) → 2-methylbenzyl bromide (89-92-9) + α,α'-dibromo-o-xylene (91-13-4)

Guidance literature:

With hydrogen bromide; dihydrogen peroxide; In water; at 20 ℃; Irradiation;

DOI:10.1016/j.tetlet.2006.07.109

upstream raw materials:

o-xylene

2-phenoxymethyl-benzyl alcohol

2-methylbenzyl bromide

α,α-dibromo-o-xylene

Downstream raw materials:

1,1'-bis(pyridinium)-1,2-phenyldimethylene dibromide

3,3'-dihydroxy-1,1'-o-xylylene-bis-pyridinium; dibromide

4,5,4',5'-tetrahydro-1H,1'H-2,2'-(o-phenylene-bis-methylsulfanyl)-bis-imidazole

2,3,4,5,6,7-hexahydro-spiro[azepine-1,2'-isoindolinium]; bromide

Refernces

• 1、 Kurtay, Gülbin,Soganci, Tugba,Sarikavak, Kübra,Ak, Metin,Güllü, Mustafa. "Synthesis and electrochemical characterization of a new benzodioxocine-fused poly(: N -methylpyrrole) derivative: A joint experimental and DFT study". . p. 18929 - 18941. Retrieved 2020.
• 2、 Welker, Armin,Kersten, Christian,Müller, Christin,Madhugiri, Ramakanth,Zimmer, Collin,Müller, Patrick,Zimmermann, Robert,Hammerschmidt, Stefan,Maus, Hannah,Ziebuhr, John,Sotriffer, Christoph,Schirmeister, Tanja. "Structure-Activity Relationships of Benzamides and Isoindolines Designed as SARS-CoV Protease Inhibitors Effective against SARS-CoV-2". supporting information. p. 340 - 354. Retrieved 2020/10/19.
• 3、 -. "Novel bridged tetradentate fourth subgroup metal complex as well as preparation method and application thereof (by machine translation)". Paragraph 0223-0226; 0228; 0229-0231. . Retrieved 2020/10/14.