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Nerve Agent Precursors: Benzilic acid and Methyl Benzilate

CA Index Name
Benzene acetic acid, alpha-hydroxy-alpha-phenyl Benzene acetic acid, alpha-hydroxy-alpha-phenyl, methyl ester
CAS Registry Number
76-93-7 76-89-1
RTECS Number
DD2064000 none
EINECS Number
200-993-2 200-991-1
UN Transport Code
none none
ICSC Number
none none
CWC Schedule 2B

 

Synonyms
Benzilic acid Methyl benzilate
  • alpha,alpha,-diphenyl-alpha-hydroxyacetic acid
  • alpha,alpha-diphenylglycolic acid
  • alpha-hydroxydiphenyl acetic acid
  • 2,2-diphenyl-2-hydroxyacetic acid
  • 2-hydroxy-2,2-diphenylacetic acid
  • Diphenyl glycolic acid
  • Hydroxydiphenyl acetic acid
  • Benzilic acid, methyl ester
  • Methyl alpha-hydroxydiphenyl acetate
  • Methyl alpha-phenylmandelate
  • Methyl-2-hydroxy-2,2-diphenylacetate
  • Methyl diphenylglycolate
  • Methyl hydroxydiphenylacetate

CHEMICAL AND PHYSICAL PROPERTIES

Structural Formula

 

  Benzilic acid Methyl benzilate
Structure
Appearance White powder White powder
Molecular
Formula
C14H12O3 C15H14O3
Molecular
Weight
228 242.3
Melting
Point
150-152°C 73-76°C
Boiling
Point
180°C 187°C (reduced pressure)
Liquid
Density
n/a n/a
Vapor
Density
n/a n/a
Vapor pressure n/a n/a
Not flammable

 

NFPA Hazard Ratings
FIRE
*
HEALTH
*
REACTIVITY
*

SPECIAL
*

Also refer to 2000 Emergency Response Guidebook (ERG2000) Guide: no specific reference.

 


Initial Isolation and Protective Action Distances

No specific recommendation

Health Hazards

Benzilic acid and methyl benzilate are considered harmful and dangerous if swallowed. They are not completely characterized in terms of their toxicologies but reasonable care: use of protective clothing and eyewear and thorough washing after use, are recommended. Like many other small organic compounds, the fumes given off by burning may be dangerous.

Risk and Safety Phrases.

Benzilic acid Methyl benzilate
  • R22 - Harmful if swallowed 
  • S23 - Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer)
  • S24/25 - Avoid contact with skin and eyes
  • S28 -After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
  • S36/37 - Wear suitable protective clothing and gloves
  • S45 - If swallowed, seek medical advice immediately and show this container or label
  • S22- Do not breathe dust
  • S24/25 - Avoid contact with skin and eyes

INDUSTRIAL/COMMERCIAL USES

Benzilic acid and methyl benzilate have a limited number of uses. Their main use is in the manufacture of glycollate pharmaceuticals including Clidinium, Dilantin, and Flutropium. These are used as antagonists of the muscarinic acetylcholine receptors.

 

COMMENTS

The chemical weapons use of these compounds is in the manufactured of the incapacitating agent BZ. Benzilic acid is manufactured in small quantities for the preparation of a small number of pharmaceuticals and is described as a fine or specialty chemical (or more informally as a boutique chemical.) In addition to regulation under the Chemical Weapons Convention, benzilic acid and methyl benzilate are also monitored by law enforcement communities because of their use in the manufacture in hallucinogenic drugs. Synthesis of benzilic acid is unfortunately fairly straightforward, if a little incestuous, and uses benzaldehyde as a relatively inexpensive starting material. Benzaldehyde is a major aroma component of almond oil and is used artificial almond flavorings. It is about 100-fold cheaper than benzilic acid. Benzaldehyde first of all reacts with itself (a dimerization) to form benzil. Benzil can then undergo a rearrangement reaction, the benzil-benzilic acid rearrangement, to form benzilic acid. The reaction is historically interesting because it was the first demonstrated case of a rearrangement. Methyl benzilate can be prepared by the reaction of benzilic acid and methanol.

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