CHLOROMETHYL BENZOATE Chemical Properties

Boiling point:

114-115 °C(Press: 8 Torr)

Density 

1.229±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

liquid

color 

Colourless

EPA Substance Registry System

Chloromethyl benzoate (5335-05-7)

Safety Information

HS Code 

2916399090

CHLOROMETHYL BENZOATE Usage And Synthesis

Synthesis

The general procedure for the synthesis of chloromethyl benzoate from formaldehyde and benzoyl chloride was as follows: paraformaldehyde (4.5 g) was mixed with a catalytic amount of zinc chloride at 0°C. Subsequently, benzoyl chloride (0.142 mol, 20 g) was added slowly and dropwise over a period of 1 hour. The reaction mixture was gradually warmed up to room temperature, then heated to 55 °C and maintained at this temperature for 10 h of reaction. The progress of the reaction was monitored by thin layer chromatography (TLC, silica gel plate, unfolding agent ratio 5:95 ethyl acetate/hexane). If the TLC showed that there were still raw materials unreacted, 1 g of paraformaldehyde was added additionally. After continuing the reaction with stirring at 55 °C for 10 h, the reaction mixture was cooled and purified by fast column chromatography (500 g silica gel, eluent a solvent mixture of 2% ethyl acetate and 98% hexane). The solvent was evaporated under vacuum, taking care that the temperature of the water bath of the rotary evaporator did not exceed 35 °C to avoid loss of product due to low boiling point. Finally 11.82 g (49% yield) of the target product chloromethyl benzoate was obtained as a clear oil. The mass spectrum (electrospray positive ion mode, ES+) showed m/e 171 (M+H).

References

[1] Russian Journal of Organic Chemistry, 2013, vol. 49, # 2, p. 198 - 203
[2] Zh. Org. Khim., 2013, vol. 49, # 2, p. 210 - 214,5
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 3, p. 771 - 778
[4] Synthetic Communications, 1995, vol. 25, # 18, p. 2739 - 2749
[5] Patent: WO2004/92189, 2004, A1. Location in patent: Page 26

CHLOROMETHYL BENZOATE(5335-05-7)Related Product Information

• 3-Chlorophthalide
• Chloromethyl acetate
• Benzyl chloromethyl ether
• Chloromethyl ethyl ether
• 2-Amino-5-chloromethyl benzoate
• METHYL 4-(CHLOROMETHYL)BENZOATE,METHYL P-(CHLOROMETHYL)BENZOATE
• 4-(Chloromethyl)benzoate,ETHYL P-(CHLOROMETHYL)BENZOATE,ETHYL 4-(CHLOROMETHYL)BENZOATE
• ETHYL 3-(CHLOROMETHYL)BENZOATE,ETHYL M-(CHLOROMETHYL)BENZOATE
• 3,4-DICHLOROISOCOUMARIN
• tert-Butyl 4-(chloromethyl)benzoate
• METHYL (2-CHLOROMETHYL)BENZOATE,METHYL O-(CHLOROMETHYL)BENZOATE
• ETHYL O-(CHLOROMETHYL)BENZOATE
• METHYL M-(CHLOROMETHYL)BENZOATE
• CHLOROMETHYL BENZOATE
• 2,4-DIFLUOROPHENYL 4-(CHLOROMETHYL)BENZOATE
• tert-Butyl 2-(chloromethyl)benzoate
• 2-CHLORO-4-FLUOROPHENYL 4-(CHLOROMETHYL)BENZOATE, TECH
• PHENYL 3-(CHLOROMETHYL)BENZOATE, TECH