CHLOROMETHYL BENZOATE

CHLOROMETHYL BENZOATE Property

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

HS Code 

2916399090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

CHLOROMETHYL BENZOATE Chemical Properties,Usage,Production

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