619-42-1

Basic information

• Product Name: Methyl 4-bromobenzoate
• Synonyms: RARECHEM AL BF 0075;BRBSME;METHYL P-BROMOBENZOATE;METHYL 4-BROMOBENZOATE;4-BROMOBENZOIC ACID METHYL ESTER;4-bromo-benzoicacimethylester;Benzoic acid, 4-bromo-, methyl ester;Benzoic acid, p-bromo-, methyl ester
• CAS NO: 619-42-1
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.04
• EINECS: 210-596-6
• Product Categories: Aromatic Esters;Acids & Esters;Bromine Compounds;C8 to C9;Carbonyl Compounds;Esters;Pyridines
• Mol File: 619-42-1.mol
• Article Data: 241

Chemical Properties

• Melting Point: 77-81 °C(lit.)
• Boiling Point: 252.95°C (rough estimate)
• Flash Point: 112.4 °C
• Appearance: White/Crystals or Crystalline Powder
• Density: 1,689 g/cm3
• Vapor Pressure: 0.0111mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: Insoluble in water.
• Merck: 14,1408
• BRN: 2045132
• CAS DataBase Reference: Methyl 4-bromobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-bromobenzoate(619-42-1)
• EPA Substance Registry System: Methyl 4-bromobenzoate(619-42-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 619-42-1(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALS OR CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 619-42-1 differently. You can refer to the following data:
1. Methyl 4-bromobenzoate is halogenated benzoate used as a reagent in organic synthesis. Methyl 4-bromobenzoate can be used to stimulate microbial dechlorination of PCBs. It is also used in the preparation of stable radioiodinating reagent to label monoclonal antibodies for radiotherapy of cancer.
2. Methyl 4-bromobenzoate is used as a starting material in the synthesis of three-carbon-bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine and methyl 4-tri-n-butylstannylbenzoate. It is also used to stimulate microbial dechlorination of polychlorinated biphenyls. Further, it is used in the preparation of stable radioiodinating reagent to label monoclonal antibodies for radiotherapy of cancer.
3. Methyl 4-bromobenzoate may be used in the following syntheses:Three-carbon-bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine analogs, employed as antifolates. Methyl 4-tri-n-butylstannylbenzoate.Methyl 4-(2-pyridyl)benzoate by cross coupling reaction with lithium 2-pyridyltriolborate.Methyl 4-imidazo[1,2-a]pyridin-3-ylbenzoate by ligand-free Pd(OAc)2 catalyzed reaction with Imidazo[1,2-a]pyridine.Methyl (E)-4-[3-(2-methoxycarbonylvinyl)-thiophen-2-yl]acrylate by reacting with methyl (E)-3-(thiophen-3-y)lacrylate.

General Description

Methyl 4-bromobenzoate is a para-substituted aryl bromide. Mol-ecules of methyl 4-bromobenzoate are almost planar. The compound is isostructural with methyl 4-iodo-benzoate. The Zeeman effect on the N.Q.R. (nuclear quadrupole resonance) of methyl 4-bromobenzoate on single crystals, has been investigated by the ′geometric method′.

Purification Methods

Crystallise the ester from MeOH. EtOH (m 81o, also 80.5o, 79.5o) or *C6H6/pet ether (m 78-79o). [Beilstein 9 H 352, 9 III 1405, 9 IV 1017.]

InChI:InChI=1/C8H7BrO2/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5H,1H3

Upstream product

• 67-56-1 methanol 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 586-76-5 4-Bromobenzoic acid 
• 586-75-4 4-chlorobenzoyl chloride 
• 201230-82-2 carbon monoxide 
• 106-37-6 1.4-dibromobenzene 
• 108-86-1 bromobenzene 
• 57031-51-3 Methyl-tert.-butylperoxyoxalat 
• 186581-53-3 diazomethane 
• 106-38-7 para-bromotoluene 
• 36695-16-6 2-(4-bromobenzoyloxy)acetophenone 
• 25062-46-8 4-bromobenzaldehyde oxime 
• 24856-58-4 1,1-dimethoxy-1-(4-bromophenyl)methane 
• 32158-85-3 N-(4-Bromobenzyoyl)-2,2-dimethylaziridine 

Downstream Products

• 72053-00-0 1-(4-bromophenyl)-2-(pyridin-2-yl)ethanone 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 99113-99-2 methyl 4-(4-phenoxyphenoxy)benzoate 
• 21218-94-0 methyl 4-phenoxybenzoate 
• 61623-62-9 1-(p-bromophenyl)-1,1-diphenylcarbinol 
• 845790-83-2 (4-bromo-phenyl)-bis-(4-chloro-phenyl)-methanol 
• 698-67-9 p-bromobenzamide 
• 1836-27-7 4-bromo-N-hydroxybenzamide 
• 14908-44-2 1-(4-bromobenzoyl)-2,2-dimethylhydrazine 
• 70812-97-4 (Z)-3-(p-Bromphenyl)-2-penten 
• 70812-98-5 (E)-1-bromo-4-(pent-2-en-3-yl)benzene 
• 53355-25-2 methyl 4-(2-furanyl)benzoate 
• 17595-86-7 methyl 4-(2-thienyl)benzoate 
• 93-58-3 benzoic acid methyl ester 

Relevant articles and documents

The tremulanes, a new group of sesquiterpenes from the aspen rotting fungus Phellinus tremulae

A series of new sesquiterpenes, the tremulanes, possessing a previously unreported substituted perhydroazulene carbon skeleton, has been isolated from liquid cultures of the aspen (Populus tremuloides) rotting fungus Phellinus tremulae. The structures were determined by NMR techniques (1H- 1H COSY, HMQC, and HMBC) and other physical methods including, in the case of tremulenolide A (6), X-ray crystallography. The chemical correlation of tremulenediol A (10) with tremulenolide A (6) is described as is the correlation of tremulenedial (8) with tremulenediol B (11). The absolute configuration of the compounds is assigned by application of the olefin octant rule to the allylic alcohol tremulenediol A (10). These new sesquiterpenes do not obey the biogenetic isoprene rule and it is suggested that they may not be derived from farnesyl pyrophosphate.

Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids

The chlorination of aromatic carboxylic acids with SOCl2 has been effectively performed by reacting with a Br?nsted acid as the catalyst. Based on this discovery, an efficient catalytic method that is cheaper than traditional catalytic methods was developed. 20 substrates were chlorinated offering excellent yields in a short reaction time. And the SOCl2/Br?nsted acid system has been used in a larger scale preparative reaction. A dual activation mechanism was proposed to prove the irreplaceable system of SOCl2/Br?nsted acid.

Efficient aerobic oxidation of alcohols to esters by acidified carbon nitride photocatalysts

Photocatalytic aerobic oxidation of alcohols for the direct synthesis of esters has received significant attention in recent years, but the relatively low efficiency and selectivity under visible light irradiation is the main challenge for their practical applications. Here, surface acidic sites were imparted onto metal-free heterogeneous photocatalysts by the protonation of carbon nitride (HMCN) to promote the activity for the esterification reaction through further adsorption and activation of the intermediate aldehyde. The activation of the substrate could be remarkably modulated through tuning the acidic sites on the surface of the photocatalyst, leading to a controllable reactivity of the catalytic reaction. The one-pot process for the direct aerobic oxidative esterification of alcohol exhibits high efficiency and selectivity under mild and additive-free conditions and the apparent quantum yield (AQY) of the photocatalytic esterification reaction is 0.41% at 420 nm. Moreover, a scalable photocatalytic process by the merging of a continuous flow system with the heterogeneous HMCN photocatalyst is demonstrated, combining high catalytic efficiency and stability at ambient temperatures and being promising for larger-scale applications.