Benzyl bromide

Base Information

• Chemical Name: Benzyl bromide
• CAS No.: 100-39-0
• Deprecated CAS: 1401918-81-7
• Molecular Formula: C7H7Br
• Molecular Weight: 171.037
• Hs Code.: 2903 99 80
• ICSC Number: 1225
• NSC Number: 8041
• UN Number: 1737
• UNII: XR75BS721D
• DSSTox Substance ID: DTXSID8024658
• Nikkaji Number: J3.230A
• Wikipedia: Benzyl_bromide
• Wikidata: Q416113
• Pharos Ligand ID: P9WFW7R79TH4
• Metabolomics Workbench ID: 60824
• ChEMBL ID: CHEMBL1085946
• Mol file: 100-39-0.mol

Synonyms:benzyl bromide

Chemical Property of Benzyl bromide

Chemical Property:

• Appearance/Colour: clear light amber liquid
• Vapor Pressure: 0.506mmHg at 25°C
• Melting Point: -3 ºC
• Refractive Index: n20/D 1.575(lit.)
• Boiling Point: 198.499 ºC at 760 mmHg
• Flash Point: 86.667 ºC
• PSA: 0.00000
• Density: 1.438 g/cm³
• LogP: 2.58150
• Storage Temp.: Store at RT.
• Sensitive.: Moisture Sensitive/Light Sensi
• Solubility.: Miscible with benzene, carbon tetrachloride, ethanol and ether.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 169.97311
• Heavy Atom Count: 8
• Complexity: 55.4
• Transport DOT Label: Poison Corrosive

Purity/Quality:

99% ^*data from raw suppliers

Benzyl bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 39-2

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: C1=CC=C(C=C1)CBr
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: Lachrymation. The substance is severely irritating to the eyes, skin, respiratory tract and gastrointestinal tract.
• Uses: Making foaming and frothing agents, organic synthesis. Benzyl bromide is widely useful in organic synthesis as a benzyl protecting group for alcohols and carboxylic acids. It is used in the preparation of foaming and frothing agents, quaternary ammonium compounds, peniclins, photographic chemicals, synthetic resins, dyes and plasticizers and esters. It is also involved in the synthesis of (E)-(2-Iodovinyl)benzene by reacting it with diiodomethane.

Technology Process of Benzyl bromide

There total 390 articles about Benzyl bromide 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:

1,2-propylene cyclic carbonate (108-32-7) + N-Bromosuccinimide (128-08-5) + chloranil (118-75-2) + toluene (108-88-3,15644-74-3,16713-13-6) → para-bromotoluene (106-38-7) + 2-methylphenyl bromide (95-46-5) + benzyl bromide (100-39-0)

Guidance literature:

at 100 ℃; Product distribution;

DOI:10.1021/ja01549a053

Reference yield:

1,2-propylene cyclic carbonate (108-32-7) + N-Bromosuccinimide (128-08-5) + toluene (108-88-3,15644-74-3,16713-13-6) + dibenzoyl peroxide (94-36-0) → para-bromotoluene (106-38-7) + 2-methylphenyl bromide (95-46-5) + benzyl bromide (100-39-0)

Guidance literature:

at 100 ℃; Product distribution;

DOI:10.1021/ja01549a053

Reference yield:

1,2-propylene cyclic carbonate (108-32-7) + N-Bromosuccinimide (128-08-5) + toluene (108-88-3,15644-74-3,16713-13-6) → para-bromotoluene (106-38-7) + 2-methylphenyl bromide (95-46-5) + benzyl bromide (100-39-0)

Guidance literature:

at 100 ℃; Product distribution;

DOI:10.1021/ja01549a053

upstream raw materials:

1,2-propylene cyclic carbonate

N-Bromosuccinimide

chloranil

toluene

Downstream raw materials:

N-benzyl-2-(2-hydroxyethyl)piperidine

2-benzyloxymethylfuran

1-benzyl-4-methyl-quinolinium; iodide

2-(benzylthio)-4-phenylthiazole

Refernces

• 1、 Mattes, Henri,Benezra, Claude. "REACTIVITY OF t-BUTYLDIMETHYLSILYL ETHERS : A FACILE CONVERSION INTO BROMIDE". . p. 1697 - 1698. Retrieved 1987.
• 2、 Wang, Ten-Tsai,Chang, Chyi-Huang,Huang, Ting-Chia. "Kinetics of the nucleophilic substitution of benzyltributylammonium bromide with allyl, butyl, and benzyl chlorides and with benzyl acetate and benzyl ether". . p. 615 - 626. Retrieved 1996.
• 3、 Chuchani, Gabriel,Dominguez, Rosa M.. "Kinetics of the gas-phase elimination of α-bromophenylacetic acid under maximum inhibition". . p. 725 - 728. Retrieved 1999.
• 4、 Krafft, Grant A.,Siddall, Thomas L.. "STEREOSPECIFIC DISPLACEMENT OF SULFUR FROM CHIRAL CENTERS. ACTIVATION VIA THIAPHOSPHONIUM SALTS.". . p. 4867 - 4870. Retrieved 1985.
• 5、 Mupparapu, Nagaraju,Lin, Yu-Hsin Cindy,Kim, Tae Ho,Elshahawi, Sherif I.. "Regiospecific Synthesis of Calcium-Independent Daptomycin Antibiotics using a Chemoenzymatic Method". . p. 4176 - 4182. Retrieved 2021.
• 6、 Offermann,Voegtle. "-". . p. 272. Retrieved 1977.
• 7、 Podgorsek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej. "Association of fluorous "phase-vanishing" method with visible-light activation in benzylic bromination by bromine". . p. 483 - 488. Retrieved 2006.
• 8、 Sharma, Priti,Sasson, Yoel. "Facile continuous process for gas phase halogen exchange over supported alkyl phosphonium salts". . p. 2824 - 2828. Retrieved 2018.
• 9、 Yang, Yaqi,Ye, Zihang,Zhang, Xu,Zhou, Yipeng,Ma, Xiantao,Cao, Hongen,Li, Huan,Yu, Lei,Xu, Qing. "Efficient dehydrative alkylation of thiols with alcohols catalyzed by alkyl halides". . p. 9638 - 9642. Retrieved 2017.
• 10、 Rahman, Md. Taifur,Kamata, Naoya,Matsubara, Hiroshi,Ryu, Ilhyong. "Quadraphasic phase-vanishing method: Application to bromination reactions that produce acidic by-products". . p. 2664 - 2666. Retrieved 2005.