Benzyl bromide

Not to be confused with Bromotoluene.

Benzyl bromide[1] | Skeletal structure of the benzyl bromide molecule | 3D structure of the benzyl bromide molecule

|

Names
Preferred IUPAC name

(Bromomethyl)benzene

Other names

α-Bromotoluene
Benzyl bromide

Identifiers

CAS Number

* 100-39-0 Y

3D model (JSmol)

* Interactive image
* Interactive image

ChEBI |

* CHEBI:59858 Y

ChEMBL |

* ChEMBL1085946 Y

ChemSpider |

* 13851576 Y

ECHA InfoCard | 100.002.589

IUPHAR/BPS

* 6294

PubChem CID

* 7498

UNII |

* XR75BS721D N

CompTox Dashboard (EPA)

* DTXSID8024658

InChI

* InChI=1S/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2 Y

Key: AGEZXYOZHKGVCM-UHFFFAOYSA-N Y

* InChI=1/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2

Key: AGEZXYOZHKGVCM-UHFFFAOYAM

SMILES

* BrCc1ccccc1

* c1ccc(cc1)CBr

Properties

Chemical formula

| C7H7Br
Molar mass | 171.037 g·mol−1
Appearance  | Colorless liquid
Odor | Sharp and pungent
Density | 1.438 g/cm3
Melting point | −3.9 °C (25.0 °F; 269.2 K)
Boiling point | 201 °C (394 °F; 474 K)
Solubility | organic solvents
log P | 2.92[2]

Refractive index (nD)

| 1.5752
Hazards
GHS labelling:

Pictograms

Flash point | 70 °C (158 °F; 343 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

Chemical compound

Benzyl bromide is an organic compound with the formula C6H5CH2Br. The molecule consists of a benzene ring substituted with a bromomethyl group. It is a colorless liquid with lachrymatory properties. The compound is a reagent for introducing benzyl groups.[3][4]

## Synthesis and structure[edit]

Benzyl bromide can be synthesized by the bromination of toluene under conditions suitable for a free radical halogenation:

The structure has been examined by electron diffraction.[5]

## Applications[edit]

Benzyl bromide is used in organic synthesis for the introduction of the benzyl groups when the less expensive benzyl chloride is insufficiently reactive.[6] [7] Benzylations are often achieved in the presence of catalytic amounts of sodium iodide, which generates the more reactive benzyl iodide in situ.[3] In some cases, benzyl serves as protecting group for alcohols and carboxylic acids.[8]

## Safety[edit]

Benzyl bromide is a strong lachrymator and is also intensely irritating to skin and mucous membranes. Because of these properties, it has been used in chemical warfare, both in combat and in training due to its irritating yet non-lethal nature.

## See also[edit]

* Benzyl chloride
* Benzyl fluoride
* Benzyl iodide

## References[edit]

1. ^ Merck Index (11th ed.). p. 1142.
2. ^ "Benzyl bromide_msds".
3. ^ a b William E. Bauta (2001). "Benzyl Bromide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb047. ISBN 0-471-93623-5.
4. ^ "Benzyl bromide". Sigma Aldrich. sigmaaldrich.com. Retrieved 8 June 2017.
5. ^ Vilkov, L. V.; Sadova, N. I. (March 1976). "Electron diffraction study on the molecular structure of benzyl chloride and benzyl bromide in the vapour phase". Journal of Molecular Structure. 31 (1): 131–142. Bibcode:1976JMoSt..31..131S. doi:10.1016/0022-2860(76)80124-X.
6. ^ Andrew G. Myers; Bryant H. Yang (2000). "Synthesis and Diastereoselective Alkylation of Pseudoephenedrine Amides". Org. Synth. 77: 22. doi:10.15227/orgsyn.077.0022.
7. ^ Harry Heaney; Steven V. Ley (1974). "1-Benzylindole". Org. Synth. 54: 58. doi:10.15227/orgsyn.054.0058.
8. ^ "Benzyl bromide". chemicalbook.com. Retrieved 8 June 2017.

* v
* t
* e

* Agents used in chemical warfare
* incapacitation
* riot control

Blood agents|

* Cyanogen
* Cyanogen bromide
* Cyanogen chloride (CK)
* Hydrogen cyanide (AC)
* Arsine
* Cacodyl cyanide
* Cacodyl oxide
* Hydrogen sulfide
* Phosphine
* Carbon monoxide
* Phosphorus trifluoride
* Methyl cyanoformate
* Iron pentacarbonyl
* Nickel tetracarbonyl
* 2,3,7,8-Tetrachlorodibenzodioxin
* Glycolonitrile
* Lactonitrile
* Acetone cyanohydrin
* Stibine
* Chloral cyanohydrin

Blister agents|

| Arsenicals|

* Ethyldichloroarsine (ED)
* Methyldichloroarsine (MD)
* Phenyldichloroarsine (PD)
* Lewisite (L)
* Lewisite 2 (L2)
* Lewisite 3 (L3)

|

Sulfur mustards|

* Levinstein mustard (EA-229)
* T
* Q
* CEES

Nitrogen mustards|

* HN1
* HN2
* HN3
* TL-301

Nettle agents|

* Phosgene oxime (CX)

Other|

* KB-16
* Dibutylchloromethyltin chloride
* Selenium oxychloride

Nerve agents|

| G-agents|

* Tabun (GA)
* Sarin (GB)
* Chlorosarin (ClGB)
* Thiosarin (SGB)
* Soman (GD)
* Chlorosoman (ClGD)
* Ethylsarin (GE)
* GH
* Cyclosarin (GF)
* GP
* Fluorotabun
* EA-1356
* EA-4352
* Crotylsarin

|

V-agents|

* EA-2192
* EA-3148
* VE
* VG
* VM
* VP
* VR
* VS
* VX
* EA-1763
* Chinese VX
* V-sub x (GD-7)

GV agents|

* GV (EA-5365)

Novichok agents|

* A-208
* A-232
* A-234
* A-242
* A-262
* C01-A035
* C01-A039
* C01-A042

Carbamates|

* Dimethylcarbamoyl fluoride
* EA-3887
* EA-3887A
* EA-3966
* EA-3990
* EA-4056
* T-1123
* T-1152
* T-1194
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
* TL-599
* TL-1238
* TL-1299
* TL-1317
* Miotine (AR-28/T-1843)
* 3152 CT
* 4-686-293-01 (Agent 1-10)

Other|

* Diisopropyl fluorophosphate
* Dicyclohexyl phosphorofluoridate
* EA-2012
* EA-2054
* EA-2098
* EA-2613
* 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
* Neopentylene fluorophosphate
* Selenophos
* Phospholine
* R-16661
* Ro 3-0422
* Methanesulfonyl fluoride
* Dimefox (TL-792)
* MSPI

Precursors|

* Acetonitrile
* AT
* ATO
* AlP
* A.P.C. complex
* Chlorosarin
* Chlorosoman
* Cyclohexanol
* 1,8-Dibromooctane
* N,N-Diisopropylaminoethanol (KB)
* EA-1250
* DIHP
* ZS
* DEHP
* EA-1224
* Dimethylamidophosphoric dichloride
* Dimethylamidophosphoric dicyanide
* DMHP
* Ethylphosphonoselenoic dichloride
* Formaldoxime
* Nital
* 4-Hydroxycoumarin
* Isopropyl alcohol (TB)
* Methyldichlorophosphine (SW)
* Methylphosphonyl difluoride (difluoro) (DF)
* Methylphosphonyl dichloride (dichloro)
* Nitromethane
* OPA mixture
* Phosphoryl chloride
* Phosphorus pentachloride
* Phosphorus trichloride (TH)
* Pinacolone
* Pinacolyl alcohol
* Phenacyl chloride
* QL
* 2,4,5-Trichlorophenol
* 3,3,5-Trimethylcyclohexanol
* Triethyl phosphite
* Trimethyl phosphite
* TC
* TG

Neurotoxins|

* Anatoxin-a
* Saxitoxin (TZ)
* Bungarotoxin
* Botulinum toxin (BTX)
* Tetanospasmin (TeNT)
* Ryanodine
* Ciguatoxin (CTX)
* Guanitoxin (GTX)
* Chlorophenylsilatrane
* Palytoxin (PTX)
* Maitotoxin (MTX)
* Tetrodotoxin
* Aconitine
* Brevetoxin (PbTX)
* Strychnine
* Antillatoxin (ATX)
* Tetraethyllead
* Dimethylmercury
* HN1 hydrochloride
* HN2 hydrochloride
* HN3 hydrochloride
* A-8564
* Picrotoxin
* Sulfuryl fluoride
* Tremorine
* Oxotremorine
* Batrachotoxin
* Tetramethylenedisulfotetramine (TETS)
* Bicyclic phosphates
* IPTBO
* TBPO
* TBPS
* Cloflubicyne
* Trimethylolpropane phosphite
* Domoic acid

Pulmonary/
choking agents|

* Chlorine
* Bromine
* Phosgene (CG)
* Fluorine
* Perfluoroisobutene
* Chloropicrin (PS)
* Dimethyl(trifluoromethylthio)arsine
* Diphosgene (DP)
* Disulfur decafluoride (Z)
* Acrolein
* Ethyl bromoacetate
* Perchloromethyl mercaptan
* Phenylcarbylamine chloride
* Tetranitromethane
* Tetrachlorodinitroethane
* Chlorine trifluoride
* Perchloryl fluoride
* Cadmium oxide
* Cadmium chloride
* Mercuric chloride
* Selenium dioxide
* Selenoyl fluoride
* Trifluoronitrosomethane
* Trichloronitrosomethane
* Nitric oxide
* Nitrogen dioxide
* Dinitrogen tetroxide
* Sulfur dioxide
* Phosphorus trichloride
* Methyl isocyanate
* Ethenone
* Methyl vinyl ketone
* Trifluoroacetyl chloride
* Salcomine
* Fluomine
* Uranium hexafluoride
* Diborane
* Green Cross

Vomiting agents|

* Adamsite (DM)
* Chloropicrin
* Litharge-glycerine
* Diphenylchlorarsine
* Diphenylcyanoarsine
* Cacodyl cyanide
* o-Dianisidine

Incapacitating
agents|

* BZ (CS-4030)
* Apomorphine
* Butyrophenone
* EA-4941 (CS-4640)
* Etorphine
* EA-2092
* CS-4297
* Etoxadrol
* Dimethylheptylpyran (DMHP)
* EA-2148
* EA-3167
* EA-3443
* Pethidine
* EA-3580
* Ibogaine
* EA-3834
* Kolokol-1
* LSD-25
* PAVA spray
* Psilocybin
* Sleeping gas
* Carfentanil
* JB-318
* JB-336
* CS-27349
* CAR-226,086
* CAR-301,060
* CAR-302,196
* CAR-302,282
* CAR-302,668
* Benperidol
* Desflurane
* Enflurane
* Bufotenin
* Isoflurane
* Halothane
* Sevoflurane
* Pentazocine
* Procarbazine
* Fluphenazine
* Chlorpromazine

Lachrymatory
agents|

* Xylyl bromide
* Pepper spray (OC)
* Mace (spray)
* CN
* CS
* CR
* CNS
* Benzyl chloride
* Benzyl bromide
* Benzyl iodide
* Bromobenzyl cyanide
* Thiophosgene
* Chloroacetone
* Bromoacetone
* Bromomethyl ethyl ketone
* Acrolein
* Phenacyl bromide
* Chloroacetophenone oxime
* Ethyl bromoacetate
* Ethyl iodoacetate
* Iodoacetone
* Allyl isothiocyanate
* Hexamethylene diisocyanate
* Crotonaldehyde

Malodorant agents|

* Thioacetone
* Allicin
* Skatole
* Cadaverine
* Putrescine

Cornea-clouding agents|

* Lewisite
* CX
* KB-16
* Methyl cyanoacrylate
* N-Methylmorpholine
* Allyl alcohol
* Osmium tetroxide
* Acrolein

Biological toxins|

* Abrin
* Aconitine
* Cyclopiazonic acid
* Histrionicotoxins
* Aflatoxins
* Anatoxin-a
* Batrachotoxin
* Botulinum toxin
* Brevetoxin
* Ciguatoxin
* Domoic acid
* Enterotoxin type B
* Grayanotoxin
* Guanitoxin
* Maitotoxin
* Modeccin
* Palytoxin
* Ricin
* Saxitoxin
* Shiga toxin
* T-2 mycotoxin
* Tetanospasmin
* Tetrodotoxin
* Volkensin
* Veratridine

Other|

* Methyl fluoroacetate
* Napalm (variants and mixtures)
* Fluoroethyl fluoroacetate
* Depleted uranium
* post-combustion uranium oxides
* Plutonium and its compounds
* Polonium
* White phosphorus

* List of chemical warfare agents
* CB military symbol

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