Bromobenzene

Base Information

• Chemical Name: Bromobenzene
• CAS No.: 108-86-1
• Molecular Formula: C6H5Br
• Molecular Weight: 157.01
• Hs Code.: 2903 99 80
• European Community (EC) Number: 203-623-8
• ICSC Number: 1016
• NSC Number: 6529
• UN Number: 2514
• UNII: CO4D5J547L
• DSSTox Substance ID: DTXSID5024637
• Nikkaji Number: J2.867C
• Wikipedia: Bromobenzene
• Wikidata: Q410597
• Metabolomics Workbench ID: 53022
• ChEMBL ID: CHEMBL16068
• Mol file: 108-86-1.mol

Synonyms:bromobenzene;bromobenzene, 14C-labeled

Chemical Property of Bromobenzene

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 10 mm Hg ( 40 °C)
• Melting Point: -31 °C
• Refractive Index: n20/D 1.559(lit.)
• Boiling Point: 154.219 °C at 760 mmHg
• Flash Point: 51.111 °C
• PSA: 0.00000
• Density: 1.486 g/cm³
• LogP: 2.44910
• Storage Temp.: 2-8°C
• Solubility.: Miscible with diethyl ether, alcohol, carbon tetrachloride, chlo
• Water Solubility.: insoluble.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 155.95746
• Heavy Atom Count: 7
• Complexity: 46.1
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

1-Bromobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N,F,T
• Statements: 10-38-51/53-39/23/24/25-23/24/25
• Safety Statements: 61-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Brominated Solvents
• Canonical SMILES: C1=CC=C(C=C1)Br
• 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: The substance is irritating to the skin. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. The substance may cause effects on the nervous system.
• Effects of Long Term Exposure: The substance may have effects on the liver and kidneys. This may result in impaired functions.
• Physical properties: Mobile, clear, colorless to pale yellow liquid with an aromatic odor. The reported odor threshold is 4.6 ppm (Mateson, 1955). Insoluble in water, soluble in benzene, alcohol, ether, chlorobenzene and other organic solvents. It is irritating to the skin and anesthetic to the nerves. Its toxicity is stronger than chlorobenzene. Inhalation of its vapors can cause anemia and damage the liver.
• Uses: Bromobenzene is a colorless, flammable liquid with a density greater than water and with an aromatic odor. It is synthesized by the reaction of bromide with benzene in the presence of iron powder. It is used for organic synthesis, particularly in the production of the intermediate phenylmagnesium bromide. Bromobenzene is an additive to motor oils and used as a crystallizing solvent. It is used as an ingredient in the manufacture of phencyclidine, a recreational drug.

Technology Process of Bromobenzene

There total 539 articles about Bromobenzene 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: 34.0%

cis-bicyclo<2.2.0>hexane (186-04-9,72033-85-3) → bromobenzene (108-86-1,52753-63-6) + 4-bromocyclohexene (3540-84-9) + trans-1,4-dibromocyclohexane (13618-83-2) + cis-1,4-dibromocyclohexane (16661-99-7) + cis-1-bromobicyclo<2.2.0>hexane (113555-32-1) + exo-2-bromobicyclo<2.2.0>hexane (113555-33-2)

Guidance literature:

With N-bromobis(trimethylsilyl)amine; at 75 ℃; Product distribution; different reagent and temperature;

DOI:10.1039/c39870001252

Reference yield: 10.0%

1.4-dibromobenzene (106-37-6) + phenylboronic acid (98-80-6) → bromobenzene (108-86-1,52753-63-6) + 4-bromo-1,1'-biphenyl (92-66-0) + [1,1';4',1'']terphenyl (92-94-4,94363-13-0)

Guidance literature:

With (2,4-dibenzyl-2,4-dihydro-3H-1,2,4-triazol-3-ylidene)(dibromo)(pyridine)palladium; tetrabutylammomium bromide; In N,N-dimethyl-formamide; isopropyl alcohol; at 80 ℃; for 2h; Reagent/catalyst; Inert atmosphere;

DOI:10.1007/s11172-018-2040-8

Reference yield:

diethyl ether (60-29-7,927820-24-4) + phenyllithium (591-51-5) + 1,1-dibromomethane (74-95-3) → bromobenzene (108-86-1,52753-63-6) + benzyl bromide (100-39-0) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7)

Guidance literature:

zuletzt bei Raumtemperatur;

upstream raw materials:

diphenylbromonium hexafluorophosphate

benzene

diethyl ether

ethyl 2-bromo-3-oxo-3-phenylpropionate

Downstream raw materials:

8β-chloro-4,5α-epoxy-3-methoxy-17-methyl-morphin-6-ene

4,4'-dibromobibenzyl

3-phenylpyridine

p-phenylpyridine

Refernces

• 1、 Soroka, Miroslaw,Goldeman, Waldemar,Malysa, Piotr,Stochaj, Monika. "Comments on a Conversion of Epoxides to Halohydrins with Elemental Halogen Catalyzed by Phenylhydrazine: Tandem Electrophilic Halogenation of Aromatic Compounds and Epoxide Ring Opening to Halohydrins". . p. 2341 - 2344. Retrieved 2003.
• 2、 Robertson, Peter K. J.,Eggins, Brian R.. "Photoelectrochemistry with Quinone Radical Anions-Photoassisted Reduction of Halobenzenes and Carbonyl Compounds". . p. 1829 - 1832. Retrieved 1994.
• 3、 Roy, Amy H.,Hartwig, John F.. "Directly Observed Reductive Elimination of Aryl Halides from Monomeric Arylpalladium(II) Halide Complexes". . p. 13944 - 13945. Retrieved 2003.
• 4、 Lambert, Joseph B.,Boch, Richard J.,Larson, Eric G.. "Effects of Solvent and Additives on the Rearrangement Pathway of the Seyferth Reaction". . p. 3054 - 3059. Retrieved 1985.
• 5、 Egashira, Naoyoshi,Takenga, Jun,Hori, Fumikai. "The Addition Reaction of Benzynes Generated Electrochemically from Dihalobenzenes with Tertiary Amines". . p. 2671 - 2673. Retrieved 1987.
• 6、 Hashimoto, Ji-Ichiro,Segawa, Katsunori,Itoh, Hiroki,Sakuragi, Hirochika. "Generation, structure, and reactivity of o-iodobenzoyloxyl radicals. Pulsed laser photolysis of 1-(o-halobenzoyloxy)-2-pyridones". . p. 362 - 363. Retrieved 2000.
• 7、 Shi, Shen Yi,Kong, Ai Guo,Zhao, Xin Hua,Ding, Han Ming,Yang, Fan,Shan, Yong Kui. "Nucleophilic substitution of hydrogen in naphthalene by chloride (Cl -) in ionic liquids". . p. 147 - 150. Retrieved 2011.
• 8、 Su, Kuan-Jen,Mieusset, Jean-Luc,Arion, Vladimir B.,Brecker, Lothar,Brinker, Udo H.. "Cope rearrangement versus a novel tandem retro-diels-alder-diels-alder reaction with role reversal". . p. 113 - 115. Retrieved 2007.
• 9、 Guan, Liangyu,Holl, Maxwell Gargiulo,Pitts, Cody Ross,Struble, Mark D.,Siegler, Maxime A.,Lectka, Thomas. "Through-Space Activation Can Override Substituent Effects in Electrophilic Aromatic Substitution". . p. 14913 - 14916. Retrieved 2017.
• 10、 Beringer et al.. "-". . p. 141,143. Retrieved 1956.