Sarin

Sarin

Names
Preferred IUPAC name (RS)-Propan-2-yl methylphosphonofluoridate
Other names (RS)-O-Isopropyl methylphosphonofluoridate; IMPF; GB; 2-(Fluoro-methylphosphoryl)oxypropane; Phosphonofluoridic acid, P-methyl-, 1-methylethyl ester
Identifiers
CAS Number	107-44-8 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:75701 N
ChEMBL	ChEMBL509554 Y
ChemSpider	7583 Y
PubChem	7871
UNII	B4XG72QGFM N
InChI InChI=1S/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3 Y Key: DYAHQFWOVKZOOW-UHFFFAOYSA-N Y InChI=1/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3 InChI=1/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3 Key: DYAHQFWOVKZOOW-UHFFFAOYAY
SMILES FP(=O)(OC(C)C)C
Properties
Chemical formula	C4H10FO2P
Molar mass	140.09 g·mol−1
Appearance	Clear colorless liquid
Odor	Odorless in pure form. Impure sarin can smell like mustard or burned rubber.
Density	1.0887 g/cm3 (25 °C) 1.102 g/cm3 (20 °C)
Melting point	−56 °C (−69 °F; 217 K)
Boiling point	158 °C (316 °F; 431 K)
Solubility in water	Miscible
log P	0.30
Hazards
Main hazards	It is a lethal cholinergic agent.
Safety data sheet	Lethal Nerve Agent Sarin (GB)
EU classification (DSD)	Extremely Toxic (T+)
NFPA 704	1 4 0
Lethal dose or concentration (LD, LC):
LD50 (median dose)	550 ug/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Sarin, or GB (G-series, 'B'), is a colorless, odorless liquid, used as a chemical weapon owing to its extreme potency as a nerve agent. It is generally considered a weapon of mass destruction. Production and stockpiling of sarin was outlawed as of April 1997 by the Chemical Weapons Convention of 1993, and it is classified as a Schedule 1 substance. In June 1994, the UN Special Commission on Iraqi disarmament destroyed the nerve agent sarin under Security Council resolution 687 (1991) concerning the disposal of Iraq's weapons of mass destruction.

Sarin is an organophosphorus compound with the formula (CH₃)₂CHO]CH₃P(O)F. It can be lethal even at very low concentrations, where death can occur within one to ten minutes after direct inhalation of a lethal dose, due to suffocation from lung muscle paralysis, unless some antidotes, typically atropine and an oxime, such as pralidoxime, are quickly administered. People who absorb a non-lethal dose, but do not receive immediate medical treatment, may suffer permanent neurological damage.

Sarin is a chiral molecule because it has four chemically distinct substituents attached to the tetrahedral phosphorus center. The S_P form (the (–) optical isomer) is the more active enantiomer due to its greater binding affinity to acetylcholinesterase. The P-F bond is easily broken by nucleophilic agents, such as water and hydroxide. At high pH, sarin decomposes rapidly to nontoxic phosphonic acid derivatives.