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Nerve Agent Precursors: Pinacolone and Pinacolyl Alcohol

CA Index Name
3,3-dimethyl butan-2-ol 3,3-dimethyl butan-2-one
CAS Registry Number
464-07-3 75-97-8
EINECS Number
207-347-9 200-920-4
RTECS Number
EL2276000 EL7700000
UN Transport Code
1987 1325
ICSC Number
none none
CWC Schedule 2B

 

Warning symbols
Flammable Irritating

 

Synonyms
Pinacolone Pinacolyl alcohol
  • 1,1,1-trimethylacetone
  • 1,1-dimethylethyl methyl ketone
  • 2,2-dimethyl-3-butanone
  • 3,3-dimethyl-2-butanone
  • Methyl tert-butyl ketone
  • Methyl-t-butylketone
  • Pinacolin
  • Pinacoline
  • tert-Butyl methyl ketone
  • (±)-3,3-dimethyl-2-butanol
  • (±)-Pinacolyl alcohol
  • 2,2-dimethyl-3-butanol
  • 3,3-dimethyl-2-butanol
  • tert-Butyl-methylcarbinol

 

CHEMICAL AND PHYSICAL PROPERTIES

 

  Pinacolyl alcohol Pinacolone
Structure
Appearance
Clear liquid with alcoholic odor Clear liquid with camphor or mint odor
Molecular
Formula
C6H14O C6H12O
Molecular
Weight
102.2 102.2
Melting
Point
5.45°C -52.5°C
Boiling
Point
120°C 106°C
Liquid
Density
0.835 0.723
Vapor
Density
3.52 -
Vapor pressure 1.7 kPa at 25°C 4.2 kPa at 25°C
Flammable

 

NFPA Hazard Ratings
 
FIRE

HEALTH

REACTIVITY

SPECIAL

Pinacolyl alcohol 3 1 0 *
Pinacolone 4 1 0 *

Also refer to 2000 Emergency Response Guidebook (ERG2000) Guide 127.

 


Initial Isolation and Protective Action Distances

No specific recommendations

Health Hazards

Irritating by skin contact, inhalation, and ingestion although it may take some time for effects to become evident. Large quantities can have effects on the central nervous system, suffocation and cyanosis in the case of skin contact. Both are extremely flammable.

Risk and Safety Phrases.

Pinacolyl alcohol Pinacolone
  • R10 - Flammable
  • S16 - Keep away from source of ignition - No smoking
  • S23 - Do not breathe fumes
  • S24/25 - Avoid contact with skin and eyes
  • R11 - Highly flammable
  • R22 -Harmful if swallowed
  • S16 - Keep away from source of ignition - No smoking
  • S20/21 - When using, do not eat, drink or smoke

INDUSTRIAL/COMMERCIAL USES

Pinacolone is the more important of the two in industrial chemistry. Its primary use is in the synthesis of triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin.It is also the immediate precursor for pinacolyl alcohol.

 

COMMENTS

Pinacolyl alcohol is used in the preparation of the nerve agent soman. The immediate synthesis is by the reduction of pinacolone. Pinacolone can be made by several routes. The simplest, or at least the one using the most unobtrusive starting materials, is by a well-characterized reaction known as the pinacol rearrangement. This involves acetone as the only reactant in the presence of an acid catalyst. Acetone is a high production volume chemical with worldwide annual production of 1 million tons. Other routes use more exotic starting materials that would be more telling indicators of their intent. The other significant commercial route is by the reaction of tert-butanol and formaldehyde.

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