Methyl 4-bromobenzoate Chemical Properties

Melting point:

77-81 °C (lit.)

Boiling point:

252.95°C (rough estimate)

Density 

1,689 g/cm³

refractive index 

1.5500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Crystals or Crystalline Powder

color 

White

Water Solubility 

Insoluble in water.

Merck 

14,1408

BRN 

2045132

InChI

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

InChIKey

HANNIMAAZKBBRE-UHFFFAOYSA-N

SMILES

COC(=O)c1ccc(Br)cc1

CAS DataBase Reference

619-42-1(CAS DataBase Reference)

NIST Chemistry Reference

4-Bromobenzoic acid methyl ester(619-42-1)

EPA Substance Registry System

Benzoic acid, 4-bromo-, methyl ester (619-42-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-24/25

WGK Germany 

3

TSCA 

TSCA listed

HS Code 

29163990

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:Methyl 4-bromobenzoate
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
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Methyl 4-bromobenzoate Usage And Synthesis

Chemical Properties

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Uses

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.

Uses

Methyl 4-bromobenzoate is a halogenated benzoate used as a reagent in organic synthesis. It can be used to stimulate microbial dechlorination of PCBs. By condensing methyl 4-bromobenzoate with 3-buten-1-ol, 4-(4-methylphenyl)butanal can be obtained.

Application

Methyl 4-bromobenzoate may be used in the following syntheses:

1. Methyl 4-(2-pyridyl)benzoate by cross coupling reaction with lithium 2-pyridyltriolborate.
2. Methyl 4-imidazo[1,2-a]pyridin-3-ylbenzoate by ligand-free Pd(OAc)2 catalyzed reaction with Imidazo[1,2-a]pyridine.
3. 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′.

Synthesis

To a 25 mL reaction flask were sequentially added magnets, 1 mmol 1-bromo-4-(methoxymethyl)benzene (214 mg), 15 mg20 mol% AgI/BiVO4 composite and 2 mL of water, equipped with a 28 cm diameter oxygen sphere, and a 16 W white light lamp 10 cm to the right of the reaction vial, the reaction system was irradiated by a 16 W white light lamp, the reaction system was reacted under the irradiation of 16 for 15 . h, the reaction solution was extracted, the combined organic layers were washed three times with saturated brine, dried with anhydrous sodium sulfate, desolvated under reduced pressure, and the residue was processed by column chromatography (ethyl acetate/petroleum ether=1:10) to give methyl p-bromobenzoate in 88% yield (188.7 mg).

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.]

Methyl 4-bromobenzoate(619-42-1)Related Product Information

• METHYL THIOPHENE-2-CARBOXYLATE
• Methyl 2-bromo-2-methylpropionate
• Methylparaben
• Kresoxim-methyl
• 4-Bromobenzoic acid
• 4-Aminobenzoic acid
• Bensulfuron methyl
• Methyl bromoacetate
• Methyl benzoate
• Methyl acetate
• Methyl 4-cyanobenzoate
• Benzoic acid
• Methyl acrylate
• Methyl 4-(bromomethyl)benzoate
• 4-Bromomethylbenzoic acid
• 4-Nitrophenylacetic acid
• Thiophanate-methyl
• 4-Nitrophenyl chloroformate