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 
• 586-76-5 4-Bromobenzoic acid 
• 1515-88-4 1-bromo-4-methoxymethylbenzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 124-41-4 sodium methylate 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 
• 74-88-4 methyl iodide 
• 616-38-6 carbonic acid dimethyl ester 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 201230-82-2 carbon monoxide 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 17104-98-2 1-(4-bromophenyl)-2-nitroethanol 
• 14367-97-6 1-(4-bromophenyl)-2-nitro-1-ethanone 

Downstream Products

• 5798-75-4 Ethyl 4-bromobenzoate 
• 70812-97-4 (Z)-3-(p-Bromphenyl)-2-penten 
• 70812-98-5 (E)-1-bromo-4-(pent-2-en-3-yl)benzene 
• 123910-87-2 methyl 4-(5-hydroxypent-1-yn-1-yl)benzoate 
• 89510-60-1 all-trans-1--4-phenyl-1,3-butadiene 
• 119984-87-1 methyl 4-((4-aminophenyl)ethynyl)benzoate 
• 135043-10-6 4-(4-Methylsulfanyl-phenylethynyl)-benzoic acid methyl ester 
• 89510-80-5 4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-benzoic acid methyl ester 
• 57466-23-6 4-Methoxy-3,5-bis<4-(methoxycarbonyl)phenoxy>benzoesaeure-methylester 
• 118799-06-7 5-Hydroxy-4-methoxy-3-<4-(methoxycarbonyl)phenoxy>benzoesaeure-methylester 
• 118798-99-5 4,5-Dimethoxy-3-<4-(methoxycarbonyl)phenoxy>benzoesaeure-methylester 
• 101110-74-1 methyl 4-(5'-formyl-2'-methoxyphenoxy)benzoate 
• 78303-11-4 methyl 4-(3'-methylphenoxy)benzoate 
• 1129-35-7 4-cyanobenzoic 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.

Preparation method of methyl benzoate compound

A preparation method of a methyl benzoate compound comprises the step that the methyl benzoate compound is prepared by carrying out esterification reaction on a benzoic acid compound and methyl alcohol under the catalysis of dihalogen hydantoin, and the molar ratio of the benzoic acid compound to the dihalogen hydantoin to the methyl alcohol is 1: (0.01-0.4): (2-30). According to the preparation method, the methyl benzoate compound can be efficiently prepared under mild conditions, the operation is safe, no acid waste liquid exists, meanwhile, raw materials are easy to obtain, and the production cost is low.

Creative Construction of a Series of Chiral 3D Indium-Organic Frameworks with a umy Topology

Using 2,2′-R2-biphenyl-4,4′-dicarboxylic acid to bind with a cis-[InO4(μ2-OH)2] octahedron, three novel chiral 3D indium-organic frameworks, [In(μ2-OH)L] [1, L1, R = N(CH3)2; 2, L2, R = OCH3; 3, L3, R = CH3], have been hydrothermally synthesized without chiral reagents. Crystal structure analyses reveal that 1-3 show an unprecedented 4-connected umy topology with the Schl?fli symbol (42·64). 1 exhibits high water stability and good sorption selectivity of CO2 over N2, while 3 displays high C2H2, C2H4, and C2H6 uptake capacity at 273 K.