Methyl 3-(bromomethyl)benzoate Chemical Properties

Melting point:

46-47 °C(lit.)

Boiling point:

112-114 °C3 mm Hg(lit.)

Density 

1,47 g/cm³

Flash point:

115°C/0.8mm

storage temp. 

2-8°C

form 

Crystals or Crystalline Powder

color 

White

Water Solubility 

Slightly soluble in water.

BRN 

638569

InChI

InChI=1S/C9H9BrO2/c1-12-9(11)8-4-2-3-7(5-8)6-10/h2-5H,6H2,1H3

InChIKey

YUHSMQQNPRLEEJ-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=CC(CBr)=C1

CAS DataBase Reference

1129-28-8(CAS DataBase Reference)

NIST Chemistry Reference

Methyl 3-bromomethylbenzoate(1129-28-8)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

22-34-43

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

2

F 

19

Hazard Note 

Irritant/Corrosive

HazardClass 

8

PackingGroup 

III

HS Code 

29163990

MSDS

• Language:English Provider:Methyl 3-(bromomethyl)benzoate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Methyl 3-(bromomethyl)benzoate Usage And Synthesis

Chemical Properties

white crystalline powder or crystals

Uses

Methyl 3-(bromomethyl)benzoate is used in organic synthesis of other chemicals.

Synthesis

General procedure for the synthesis of methyl 3-bromomethylbenzoate from methyl m-methylbenzoate: 30 mL of carbon tetrachloride (CCl4) and 7.9 g of methyl m-methylbenzoate were added to a dry 100 mL three-necked flask, and after dissolution, 0.23 g of AIBN (azobisisobutyronitrile) and 9.36 g of NBS (N-bromosuccinimide) were sequentially added in three additions (with an interval of about 2-3 hours). The reaction system was heated to 70°C and the color of the reaction solution was observed to change gradually from yellow to orange and finally to white. The reaction was monitored by TLC (eluent: cyclohexane/ethyl acetate = 5:1) until the reaction was almost complete. At the end of the reaction, the resulting succinimide and unreacted N-bromosuccinimide were removed by filtration. The filtrate was rotary evaporated to give 11.5 g of a yellow oily product, methyl 3-bromomethylbenzoate, in 95% yield.

References

[1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 14, p. 2506 - 2511
[2] Patent: CN106146413, 2016, A. Location in patent: Paragraph 0027; 0028
[3] European Journal of Medicinal Chemistry, 2009, vol. 44, # 1, p. 7 - 17
[4] Molecules, 2016, vol. 21, # 12,
[5] Patent: WO2018/169777, 2018, A1. Location in patent: Paragraph 0227

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