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

Description

Methyl 4-bromobenzoate is a halogenated benzoate compound that serves as a versatile reagent in organic synthesis. It is characterized by the presence of a bromine atom attached to a benzene ring, with a methyl ester group attached to the carboxylic acid. This unique structure allows it to participate in various chemical reactions and be used in the synthesis of different compounds.

Uses

Used in Organic Synthesis:
Methyl 4-bromobenzoate is used as a reagent in organic synthesis for the preparation of various compounds. Its bromine atom can be replaced by other functional groups, making it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Environmental Applications:
Methyl 4-bromobenzoate is used to stimulate microbial dechlorination of polychlorinated biphenyls (PCBs). PCBs are a group of toxic, persistent environmental pollutants that pose a significant risk to human health and the environment. By promoting the dechlorination process, Methyl 4-bromobenzoate helps in the bioremediation of contaminated sites.
Used in Cancer Therapy:
Methyl 4-bromobenzoate is used in the preparation of stable radioiodinating reagents to label monoclonal antibodies for radiotherapy of cancer. Radiolabeled antibodies can specifically target cancer cells, allowing for targeted radiation therapy with minimal damage to healthy tissues.
Used in Pharmaceutical Synthesis:
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 analogs, which are employed as antifolates. Antifolates are a class of drugs that inhibit the synthesis of folic acid, an essential nutrient for cell growth and replication, and are used in the treatment of various cancers.
Used in Cross-Coupling Reactions:
Methyl 4-bromobenzoate is used in cross-coupling reactions to synthesize various derivatives, such as methyl 4-tri-n-butylstannylbenzoate, methyl 4-(2-pyridyl)benzoate, and methyl 4-imidazo[1,2-a]pyridin-3-ylbenzoate. These reactions involve the formation of carbon-carbon bonds and are essential for the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals.

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

• 6018-41-3 methyl coumalate 
• 13852-14-7 trichlorosilylacetylene 
• 75-16-1 methylmagnesium bromide 
• 67-56-1 methanol 
• 98386-16-4 (4-Brombenzoyloxy)essigsaeure 
• 57699-28-2 methyl 4-bromophenylglyoxalate 
• 14633-95-5 triphenylphosphonium cyclopropylide 
• 106-38-7 para-bromotoluene 
• 106-37-6 1.4-dibromobenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 873-75-6 4-bromobenzenemethanol 
• 865-33-8 potassium methanolate 
• 1122-91-4 4-bromo-benzaldehyde 
• 586-76-5 4-Bromobenzoic acid 

Downstream Products

• 17595-86-7 methyl 4-(2-thienyl)benzoate 
• 197172-67-1 N-(4-methoxycarbonylphenyl)-n-hexylamine 
• 98061-21-3 4-pyridin-2-yl-benzoic acid methyl ester 
• 103094-70-8 methyl 4-(4-oxopentyl)benzoate 
• 489434-12-0 4-(1-Butoxy-vinyl)-benzoic acid methyl ester 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 619-45-4 4-methoxycarbonyl aniline 
• 4526-07-2 1,4-bis(trimethylsilyl)-1,3-butadiyne 
• 75867-41-3 4-trimethylsilanylethynyl-benzoic acid methyl ester 
• 219320-15-7 methyl 4-[(tert-butoxycarbonyl)methyl]benzoate 
• 49742-56-5 methyl 4-(4-tolyl)benzoate 
• 56158-11-3 methyl 4-((dimethyl(oxo)-λ⁶-sulfaneylidene)amino)benzoate 
• 23676-05-3 4-morpholin-4-yl-benzoic acid methyl ester 
• 99-75-2 4-methyl-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.