Methyl 4-bromobenzoate

Base Information

• Chemical Name: Methyl 4-bromobenzoate
• CAS No.: 619-42-1
• Molecular Formula: C8H7BrO2
• Molecular Weight: 215.046
• Hs Code.: 29163990
• European Community (EC) Number: 210-596-6
• NSC Number: 9392
• UNII: UB1YSJ5XAR
• DSSTox Substance ID: DTXSID7060702
• Nikkaji Number: J96.122A
• Wikidata: Q27290993
• Mol file: 619-42-1.mol

Synonyms:Methyl 4-bromobenzoate;619-42-1;Benzoic acid, 4-bromo-, methyl ester;METHYL P-BROMOBENZOATE;4-Bromobenzoic Acid Methyl Ester;p-Bromobenzoic acid, methyl ester;Benzoic acid, p-bromo-, methyl ester;UB1YSJ5XAR;UNII-UB1YSJ5XAR;p-Bromobenzoic acid methyl ester;4-Bromo-benzoic acid methyl ester;NSC 9392;NSC-9392;EINECS 210-596-6;MFCD00013531;4-(Methoxycarbonyl)bromobenzene-2,3,5,6-d4;1643577-32-5;methyl-4-Bromobenzoate;Methyl p-bromo benzoate;methyl 4-bromo-benzoate;Maybridge3_003726;SCHEMBL7623;Methyl 4-bromobenzoate, 99%;4-bromobenzoicacid methyl ester;F3095-4305;DTXSID7060702;NSC9392;4-bromo benzoic acid methyl ester;4-Bromobenzoic acid, methyl ester;HMS1441J08;4-METHOXYCARBONYLPHENYL BROMIDE;AKOS002264647;CCG-252688;CS-W004846;GS-3045;4-METHOXYCARBONYL-1-BROMOBENZENE;IDI1_015113;AC-19470;SY001702;1-BROMO-4-(METHOXYCARBONYL)BENZENE;4-bromo-phenyl carboxylic acid methyl ester;A8567;AM20060697;B0556;FT-0617866;4-BROMOBENZOIC ACID METHYL ESTER [MI];EN300-44164;A833495;AE-848/01025045;W-105074;Q27290993;Z19682625

Chemical Property of Methyl 4-bromobenzoate

Chemical Property:

• Appearance/Colour: White crystals or crystalline powder
• Vapor Pressure: 0.0111mmHg at 25°C
• Melting Point: 77-81 °C(lit.)
• Refractive Index: 1.549
• Boiling Point: 262.2 °C at 760 mmHg
• Flash Point: 112.4 °C
• PSA: 26.30000
• Density: 1.498 g/cm³
• LogP: 2.23570
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 213.96294
• Heavy Atom Count: 11
• Complexity: 139

Purity/Quality:

99% ^*data from raw suppliers

4-BromobenzoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: COC(=O)C1=CC=C(C=C1)Br
• Uses: 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. 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. 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.

Technology Process of Methyl 4-bromobenzoate

There total 109 articles about Methyl 4-bromobenzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-Bromobenzoic acid (586-76-5) → 4-methoxycarbonylphenyl bromide (619-42-1)

Guidance literature:

With sulfuric acid; In methanol; for 16h; Reflux;

DOI:10.1002/ejic.201801118

Reference yield: 99.0%

methanol (67-56-1) + 4-bromobenzenemethanol (873-75-6) → 4-methoxycarbonylphenyl bromide (619-42-1)

Guidance literature:

With oxygen; potassium carbonate; at 60 ℃; for 20h; under 750.075 Torr;

DOI:10.1039/c6ra27073e

Reference yield: 98.0%

4-methoxycarbonylphenylboronic acid (99768-12-4) → 4-methoxycarbonylphenyl bromide (619-42-1)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at 80 ℃; for 12h;

DOI:10.1039/c6ra25666j

upstream raw materials:

methanol

Ethyl 4-bromobenzoate

4-Bromobenzoic acid

4-chlorobenzoyl chloride

Downstream raw materials:

1-(4-bromophenyl)-2-(pyridin-2-yl)ethanone

Ethyl 4-bromobenzoate

methyl 4-(4-phenoxyphenoxy)benzoate

methyl 4-phenoxybenzoate

Refernces

Palladium-catalyzed intermolecular α-arylation of zinc amide enolates under mild conditions

10.1021/ja056076i

The study presents a novel method for the intermolecular R-arylation and vinylation of amides through palladium-catalyzed coupling of aryl and vinyl bromides with zinc enolates of amides. The researchers developed reactions using three different types of zinc enolates, achieving high yields with a variety of bromoarenes, including those with functional groups such as cyano, nitro, ester, keto, fluoro, hydroxyl, or amino. The use of zinc enolates, as opposed to alkali metal enolates, significantly expands the scope of amide arylation by allowing reactions at room temperature or 70 °C and by tolerating a broader range of functional groups. The study also introduces the use of morpholine amides, which are precursors to ketones and aldehydes, in the arylation process. The reactions were facilitated by catalysts bearing hindered pentaphenylferrocenyl di-tert-butylphosphine (Q-phos) or the highly reactive, dimeric Pd(I) complex {[P(t-Bu)3]PdBr}2, offering a mild and efficient approach to synthesize R-aryl carbonyl compounds, which are prevalent in pharmaceuticals and biologically active compounds.

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