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 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 
• 36695-16-6 2-(4-bromobenzoyloxy)acetophenone 
• 25062-46-8 4-bromobenzaldehyde oxime 
• 24856-58-4 1,1-dimethoxy-1-(4-bromophenyl)methane 

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.

Oxidative esterification of alcohols by a single-side organically decorated Anderson-type chrome-based catalyst

The direct esterification of alcohols with non-noble metal-based catalytic systems faces great challenges. Here, we report a new chrome-based catalyst stabilized by a single pentaerythritol decorated Anderson-type polyoxometalate, [N(C4H9)4]3[CrMo6O18(OH)3C{(OCH2)3CH2OH}], which can realize the efficient transformation from alcohols to esters by H2O2oxidation in good yields and high selectivity without extra organic ligands. A variety of alcohols with different functionalities including some natural products and pharmaceutical intermediates are tolerated in this system. The chrome-based catalyst can be recycled several times and still keep the original configuration and catalytic activity. We also propose a reasonable catalytic mechanism and prove the potential for industrial applications.

Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics

Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.