591-17-3

Basic information

• Product Name: 3-Bromotoluene
• Synonyms: 1-Brom-3-methylbenzol;1-bromo-3-methyl-benzen;3-bromo-toluen;3-Bromtoluol;3-Methyl-1-bromobenzene;3-Methylbromobenzene;3-Methyl-bromobenzene;3-Methylphenylbromide
• CAS NO: 591-17-3
• Molecular Formula: C₇H₇Br
• Molecular Weight: 171.03
• EINECS: 209-702-3
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Halogen toluene;Miscellaneous;Bromine Compounds;Aryl;C7;Halogenated Hydrocarbons;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks;alkyl bromide
• Mol File: 591-17-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: -40 °C
• Boiling Point: 183.7 °C(lit.)
• Flash Point: 140 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.41 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.12mmHg at 25°C
• Refractive Index: n20/D 1.552(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 0.05g/l
• Water Solubility: insoluble
• Merck: 14,1439
• BRN: 1903633
• CAS DataBase Reference: 3-Bromotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromotoluene(591-17-3)
• EPA Substance Registry System: 3-Bromotoluene(591-17-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: XS7965400
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 591-17-3(Hazardous Substances Data)

Usage

Chemical Properties

colorless to light yellow liquid. Insoluble in water, soluble in ethanol and ether.

Uses

3-Bromotoluene was used in the precise determination of bromine isotope ratio in organic compounds by MC-ICPMS ( Multicollector-Inductively Coupled Plasma Mass Spectrometer). It undergoes palladium-catalyzed cyanation reaction in the presence of K4[Fe(CN)6] as the cyanide surrogate. It also undergoes palladium-catalyzed reaction with alkynyltriarylborates to yield trisubstituted alkenylboranes.

Application

3-Bromotoluene is used as a solvent (for fats, waxes or resins, and as a medium for carrying out reactions) and as a chemical intermediate.

Preparation

Synthesis of 3-Bromotoluene: It is derived from 3-bromo-4-aminotoluene by diazotization and reduction. The mixture of 95% ethanol, concentrated sulfuric acid and 3-bromo-4-aminotoluene was stirred and cooled to 10°C, and sodium nitrite solution was added to keep the reaction temperature not exceeding 10°C. After adding, continue stirring for 20min. Add the copper powder washed with ether, heat carefully, stop heating after the reaction starts, nitrogen will be released violently, and acetaldehyde will be formed. Then steam distillation is carried out until no oily substance evaporates. Separate the organic phase from the distillate and wash with 10% sodium hydroxide, water, concentrated sulfuric acid, and 5% sodium carbonate solution in sequence. Dry with anhydrous calcium chloride, filter, distill, collect 180-183 ℃ (99.75kPa) fractions to obtain colorless pure 3-bromotoluene with a yield of over 50%.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 1, p. 133, 1941The Journal of Organic Chemistry, 57, p. 3772, 1992 DOI: 10.1021/jo00040a010

General Description

3-Bromotoluene is an electron-rich aryl bromide. It participates in the Heck reaction. 3-Bromotoluene undergoes palladium-catalyzed cyanation reaction in the presence of K4[Fe(CN)6] as the cyanide surrogate. It undergoes palladium-catalysed reaction with alkynyltriarylborates to yield trisubstituted alkenylboranes.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

3-Bromotoluene is incompatible with strong oxidizing agents.

Fire Hazard

3-Bromotoluene is combustible.

Upstream product

• 106-41-2 4-bromo-phenol 
• 108-88-3 toluene 
• 118-79-6 2,4,6-tribromophenol 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 139-02-6 sodium phenoxide 
• 823-78-9 meta-bromobenzyl bromide 
• 1422-76-0 3-methylbenzenediazonium tetrafluoroborate 
• 15852-73-0 (3-Bromophenyl)methanol 
• 637-04-7 (3-methylphenyl)hydrazine hydrochloride 
• 103-89-9 4-Methylacetanilide 
• 63468-48-4 5-bromo-toluene-2-diazonium 
• 71-43-2 benzene 
• 53926-63-9 3-bromo-toluene-4-diazonium 

Downstream Products

• 823-78-9 meta-bromobenzyl bromide 
• 108-88-3 toluene 
• 106-44-5 p-cresol 
• 108-39-4 3-methyl-phenol 
• 95-48-7 ortho-cresol 
• 80814-74-0 3-methyl-3'-(trifluoromethyl)diphenylamine 
• 130713-28-9 tetra-m-tolyl-arsonium; iodide 
• 13865-48-0 3-methylphenyl phenyl sulfide 
• 140380-82-1 1-methoxy-2-m-tolyloxy-benzene 
• 82721-04-8 1-(4-methoxyphenoxy)-3-methylbenzene 
• 96028-10-3 1-(4-chlorophenoxy)-3-methylbenzene 
• 3132-99-8 m-bromobenzoic aldehyde 
• 612-75-9 3,3'-dimethyl-biphenyl 
• 71838-16-9 3-bromo-4-iodotoluene 

Relevant articles and documents

Alkali Metal Adducts of an Iron(0) Complex and Their Synergistic FLP-Type Activation of Aliphatic C-X Bonds

We report the formation and full characterization of weak adducts between Li+ and Na+ cations and a neutral iron(0) complex, [Fe(CO)3(PMe3)2] (1), supported by weakly coordinating [BArF20] anions, [1·M][BArF20] (M = Li, Na). The adducts are found to synergistically activate aliphatic C-X bonds (X = F, Cl, Br, I, OMs, OTf), leading to the formation of iron(II) organyl compounds of the type [FeR(CO)3(PMe3)2][BArF20], of which several were isolated and fully characterized. Stoichiometric reactions with the resulting iron(II) organyl compounds show that this system can be utilized for homocoupling and cross-coupling reactions and the formation of new C-E bonds (E = C, H, O, N, S). Further, we utilize [1·M][BArF20] as a catalyst in a simple hydrodehalogenation reaction under mild conditions to showcase its potential use in catalytic reactions. Finally, the mechanism of activation is probed using DFT and kinetic experiments that reveal that the alkali metal and iron(0) center cooperate to cleave C-X via a mechanism closely related to intramolecular FLP activation.

Nanolayered cobalt-molybdenum sulphides (Co-Mo-S) catalyse borrowing hydrogen C-S bond formation reactions of thiols or H2S with alcohols

Nanolayered cobalt-molybdenum sulphide (Co-Mo-S) materials have been established as excellent catalysts for C-S bond construction. These catalysts allow for the preparation of a broad range of thioethers in good to excellent yields from structurally diverse thiols and readily available primary as well as secondary alcohols. Chemoselectivity in the presence of sensitive groups such as double bonds, nitriles, carboxylic esters and halogens has been demonstrated. It is also shown that the reaction takes place through a hydrogen-autotransfer (borrowing hydrogen) mechanism that involves Co-Mo-S-mediated dehydrogenation and hydrogenation reactions. A novel catalytic protocol based on the thioetherification of alcohols with hydrogen sulphide (H2S) to furnish symmetrical thioethers has also been developed using these earth-abundant metal-based sulphide catalysts.

Hydro-dediazoniation of diazonium salts using trichlorosilane: New cleavage conditions for the T1 traceless linker

An efficient, selective cleavage of triazenes and in situ hydro- dediazoniation of the intermediately formed diazonium salts with trichlorosilane (HSiCl3) in liquid as well on solid phase is reported. Starting from anilines, attachment to solid support and subsequent cleavage gives rise to the corresponding unsubstituted arenes. This cleavage reagent is compatible with various functionalities (esters, amides, nitro groups, halides, aliphatic double and triple bonds). (C) 2000 Elsevier Science Ltd.