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Benzyl bromide

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CAS:100-39-0
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CAS:100-39-0
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Benzyl bromide manufacturers

  • Benzyl bromide
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  • 2024-01-08
  • CAS:100-39-0
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  • Purity: 99%
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  • Benzyl bromide
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  • 2023-12-26
  • CAS:100-39-0
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  • Benzyl bromide
  • Benzyl bromide pictures
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  • 2023-07-27
  • CAS:100-39-0
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Benzyl bromide Basic information
Product Name:Benzyl bromide
Synonyms:(bromomethyl)-benzen;ai3-15300;alpha-bromo-toluen;Bromophenylmethane;ALPHA-BROMOPHENYLMETHANE;A-BROMOTOLUENE;BENZYL BROMIDE;N-BENZYL BROMIDE
CAS:100-39-0
MF:C7H7Br
MW:171.03
EINECS:202-847-3
Product Categories:Reagents for Oligosaccharide Synthesis;Aryl;Building Blocks;C7;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks;Benzyl;Biochemistry;Aromatic Halides (substituted);Organics;Pharmaceutical Intermediates;1;K00001;top
Mol File:100-39-0.mol
Benzyl bromide Structure
Benzyl bromide Chemical Properties
Melting point -3 °C
Boiling point 198-199 °C(lit.)
density 1.44 g/mL at 20 °C
vapor density 5.8 (vs air)
vapor pressure 0.5 hPa (20 °C)
refractive index n20/D 1.575(lit.)
Fp 188 °F
storage temp. Store below +30°C.
solubility Miscible with benzene, carbon tetrachloride, ethanol and ether.
form Liquid
color Clear colorless to yellow
OdorVery sharp, pungent, like tear gas.
Sensitive Moisture Sensitive/Light Sensitive
Merck 14,1128
BRN 385801
Dielectric constant5.1(20℃)
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKeyAGEZXYOZHKGVCM-UHFFFAOYSA-N
CAS DataBase Reference100-39-0(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, (bromomethyl)-(100-39-0)
EPA Substance Registry SystemBenzyl bromide (100-39-0)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 39-2
RIDADR UN 1737 6.1/PG 2
WGK Germany 2
RTECS XS7965000
9-19-21
TSCA Yes
HS Code 2903 99 80
HazardClass 6.1
PackingGroup II
Hazardous Substances Data100-39-0(Hazardous Substances Data)
Toxicitydns-esc 1300 mmol/L ZKKOBW 92,177,78
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Benzyl bromide Usage And Synthesis
DescriptionBenzyl bromide is a combustible, colorless toyellow liquid with a pleasant odor. Molecularweight=171.05;Specific gravity (H2O:1) =1.438; Boilingpoint= 198℃; Freezing/Melting point =-4.0℃;Flashpoint =79℃ (cc). Hazard Identification (based on NFPA-704 M Rating System): Health 3, Flammability 2,Reactivity 1. Insoluble in water (slowly decomposes).
Chemical PropertiesBenzyl bromide is an aromatic compound in which the benzene ring substituted with a bromomethyl group, and is produced by the reaction of toluene with bromine in the presence of an oxidizing agent. It is a combustible, colorless to yellow liquid with a pleasant odor. insoluble in water and easily soluble in most organic solvents. Has a strong tearing effect and unpleasant pungent odor, minimum irritant concentration of 4 mg/m3, intolerable concentration of 50-60 mg/m3.
UsesMaking foaming and frothing agents, organic synthesis.
UsesBenzyl 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.
DefinitionChEBI: Benzyl bromide is a member of the class of benzyl bromides that is toluene substituted on the alpha-carbon with bromine. It has a role as a lachrymator.
PreparationBenzyl bromide is synthesized by toluene bromination. Toluene heated to 50°C, add bromine reaction, the reaction temperature of 75-80°C, reaction 6h, fractional distillation at atmospheric pressure to remove the fraction before 140°C, and then distillation under reduced pressure, collect 112-114°C(2.0kPa) fraction, to get benzyl bromide.
ApplicationBenzyl bromide is an aromatic halide that is mainly used as a protecting agent for protecting hydroxy group of alcohols via O-benzylation reaction. It has been used as an initiator in the synthesis of poly(styrene-b-methylmethacrylate) copolymers by atom transfer radical polymerization. It can undergo Menschutkin reaction with 1, 2-dimethylimidazole to form 3-benzyl-1, 2-dimethylimidazolium bromide.
Synthesis Reference(s)Journal of the American Chemical Society, 95, p. 3412, 1973 DOI: 10.1021/ja00791a072
Tetrahedron Letters, 29, p. 707, 1988 DOI: 10.1016/S0040-4039(00)80190-2
The Journal of Organic Chemistry, 51, p. 929, 1986 DOI: 10.1021/jo00356a032
General DescriptionBenzyl bromide appears as a colorless liquid with an agreeable odor. Toxic by inhalation and by skin absorption. It is slightly soluble in water and denser than water (density 1.44 g / cm3 (Aldrich)). A lachrymator. Corrosive to metals and tissue.
Air & Water ReactionsSensitive to exposure to light and moisture. Slightly soluble in water.
Reactivity ProfileBenzyl bromide reacts with water, alcohols, common metals (except nickel and lead), bases, amines and oxidizing agents. . Benzyl bromide stored over activated 4A molecular sieve burst a bottle due to condensation-polymerization reaction with generation of HBr gas, [Chem. Eng. News, 1979, 57(12), 74].
HazardHighly toxic. Corrosive to skin and tissue. A lachrymator.
Health HazardInhalation causes irritation of nose and throat; severe exposure may cause pulmonary edema. Vapors cause severe eye irritation; liquid can burn eyes. Skin contact causes irritation. Ingestion causes irritation of mouth and stomach.
Chemical ReactivityReactivity with Water Reacts slowly generating hydrogen bromide (hydrobromic acid); Reactivity with Common Materials: Decomposes rapidly in the presence of all common metals except nickel and lead, liberating heat and hydrogen bromide; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Rinse with sodium bicarbonate or lime solution; Polymerization: Polymerizes with evolution of heat and hydrogen bromide when in presence with all common metals except nickel and lead; Inhibitor of Polymerization: None.
Safety ProfileIntensely irritating and corrosiveto skin, eyes, and mucous membranes. Large doses causecentral nervous system depression. Mutation datareported. Reaction with molecular sieve produces toxichydrogen bromide gas.
Potential ExposureIt is used as a chemical intermediate; in organic syntheses; as a foaming and frothing agent.
First aidIf this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seekmedical attention immediately. If this chemical contactsthe skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attentionimmediately. If this chemical has been inhaled, removefrom exposure, begin rescue breathing (using universalprecautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transferpromptly to a medical facility. When this chemical hasbeen swallowed, get medical attention. If victim is conscious,administer water or milk. Do not induce vomiting.Medical observation is recommended for 24 48 h afterbreathing overexposure, as pulmonary edema may bedelayed. As first aid for pulmonary edema, a doctor orauthorized paramedic may consider administering a corticosteroid spray
storageColor Code—Blue: Health Hazard/Poison: Storein a secure poison location. Color Code—White: Corrosiveor Contact Hazard; Store separately in a corrosion-resistantlocation. Store in tightly closed containers in a cool, wellventilated area away from water and other incompatiblematerials listed above.
ShippingUN1737 Benzyl Bromide, Hazard class: 6.1; Labels: 6.1—Poisonous materials, 8—Corrosive material.
Purification MethodsWash benzyl chloride with conc H2SO4 (CARE), water, 10% Na2CO3 or NaHCO3 solution, and again with water. Dry it with CaCl2, Na2CO3 or MgSO4 and fractionally distil it in the dark, under reduced pressure. It has also been thoroughly degassed at 10-6 mm and redistilled in the dark. This gives material with max (MeCN): 226nm ( 8200) [Mohammed & Kosower J Am Chem Soc 93 2709 1971]. [Beilstein 5 IV 829.] Handle in a fume cupboard, extremely LACHRYMATORY.
IncompatibilitiesMay form explosive mixture with air. Contact with water forms hydrogen bromide and benzyl alcohol. Incompatible with strong oxidizers, bases, magnesium. Attacks metals, except nickel and lead, in the presence of moisture.
Waste DisposalPour into vermiculite, sodium bicarbonate, or a sand-soda ash mixture and transfer to paper boxes, then to an open incinerator. Alternatively, mix Benzyl Bromide 417 with flammable solvent and spray into incinerator equipped with after burner and alkali scrubber.
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