Fluoroethyl fluoroacetate

2-Fluoroethyl fluoroacetate
Names

Preferred IUPAC name 2-Fluoroethyl fluoroacetate
Other names TL-855
Identifiers
CAS Number	459-99-4
3D model (JSmol)	Interactive image
ChemSpider	9598
PubChem CID	9992
UNII	NR4H23SR3Q^Y
CompTox Dashboard (EPA)	DTXSID20196651
InChI InChI=1S/C4H6F2O2/c5-1-2-8-4(7)3-6/h1-3H2 Key: ZIJVALRYXQXDOL-UHFFFAOYSA-N
SMILES C(CF)OC(=O)CF
Properties
Chemical formula	FCH₂CO₂CH₂CH₂F
Molar mass	124.087 g·mol⁻¹
Appearance	Liquid
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Extremely toxic
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	8500 ug/kg (mouse, subcutaneous)^[1]
LD_Lo (lowest published)	1 mg/kg (oral, rats)^[2]
LC₅₀ (median concentration)	150 mg/m3, 10M (rat, inhalation) 450 ug/m3 (mouse, inhalation) 50 mg/m3 (rabbit, inhalation) 70 mg/m3, 10M (guinea pig, inhalation) ^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Fluoroethyl fluoroacetate, or more accurately 2-fluoroethyl fluoroacetate, is an organic compound with the chemical formula FCH₂CO₂CH₂CH₂F. It is the fluoroacetate ester of 2-fluoroethanol, or in other words, the 2-fluoroethyl ester of fluoroacetic acid. 2-Fluoroethyl fluoroacetate is two times more toxic than methyl fluoroacetate.^[3]

References

^ ^a ^b https://pubchem.ncbi.nlm.nih.gov/compound/2-Fluoroethyl-fluoroacetate
^ Kitano, Hisao; Fukui, Ken-ichi; Nozu, Ryuzaburo; Osaka, Taichiro (1955). "(85) Some Reactions of Monofluoroacetic Acid Derivatives". The Journal of the Society of Chemical Industry, Japan (in Japanese). 58 (3): 224–226. doi:10.1246/nikkashi1898.58.224.
^ Saunders, B. C.; Stacey, G. J. (1949). "196. Toxic fluorine compounds containing the C–F link. Part IV. (a) 2-Fluoroethyl fluoroacetate and allied compounds. (b) 2 : 2′-Difluorodiethyl ethylene dithioglycol ether". J. Chem. Soc.: 916–919. doi:10.1039/JR9490000916.

Blood agents

Blister agents

Arsenicals	Ethyldichloroarsine (ED) Methyldichloroarsine (MD) Phenyldichloroarsine (PD) Lewisite (L) Lewisite 2 (L2) Lewisite 3 (L3)
Sulfur mustards	Levinstein mustard (EA-229) T Q CEES
Nitrogen mustards	HN1 HN2 HN3 TL-301
Nettle agents	Phosgene oxime (CX)
Other	KB-16 Dibutylchloromethyltin chloride Selenium oxychloride

Nerve agents

G-agents	Tabun (GA) Sarin (GB) Chlorosarin (ClGB) Thiosarin (SGB) Soman (GD) Chlorosoman (ClGD) Ethylsarin (GE) GH Cyclosarin (GF) GP Fluorotabun EA-1356 EA-4352 Crotylsarin
V-agents	EA-2192 EA-3148 VE VG VM VP VR VS VX EA-1763 Chinese VX V-sub x (GD-7)
GV agents	GV (EA-5365)
Novichok agents	A-208 A-232 A-234 A-242 A-262 C01-A035 C01-A039 C01-A042
Carbamates	Dimethylcarbamoyl fluoride EA-3887 EA-3887A EA-3966 EA-3990 EA-4056 T-1123 T-1152 T-1194 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) TL-599 TL-1238 TL-1299 TL-1317 Miotine (AR-28/T-1843) 3152 CT 4-686-293-01 (Agent 1-10)
Other	Diisopropyl fluorophosphate Dicyclohexyl phosphorofluoridate EA-2012 EA-2054 EA-2098 EA-2613 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Neopentylene fluorophosphate Selenophos Phospholine R-16661 Ro 3-0422 Methanesulfonyl fluoride Dimefox (TL-792) MSPI
Precursors	Acetonitrile AT ATO AlP A.P.C. complex Chlorosarin Chlorosoman Cyclohexanol 1,8-Dibromooctane N,N-Diisopropylaminoethanol (KB) EA-1250 DIHP ZS DEHP EA-1224 Dimethylamidophosphoric dichloride Dimethylamidophosphoric dicyanide DMHP Ethylphosphonoselenoic dichloride Formaldoxime Nital 4-Hydroxycoumarin Isopropyl alcohol (TB) Methyldichlorophosphine (SW) Methylphosphonyl difluoride (difluoro) (DF) Methylphosphonyl dichloride (dichloro) Nitromethane OPA mixture Phosphoryl chloride Phosphorus pentachloride Phosphorus trichloride (TH) Pinacolone Pinacolyl alcohol Phenacyl chloride QL 2,4,5-Trichlorophenol 3,3,5-Trimethylcyclohexanol Triethyl phosphite Trimethyl phosphite TC TG

Neurotoxins

Anatoxin-a
Saxitoxin (TZ)
Bungarotoxin
Botulinum toxin (BTX)
Tetanospasmin (TeNT)
Ryanodine
Ciguatoxin (CTX)
Guanitoxin (GTX)
Chlorophenylsilatrane
Palytoxin (PTX)
Maitotoxin (MTX)
Tetrodotoxin
Aconitine
Brevetoxin (PbTX)
Strychnine
Antillatoxin (ATX)
Tetraethyllead
Dimethylmercury
HN1 hydrochloride
HN2 hydrochloride
HN3 hydrochloride
A-8564
Picrotoxin
Sulfuryl fluoride
Tremorine
Oxotremorine
Batrachotoxin
Tetramethylenedisulfotetramine (TETS)
Bicyclic phosphates
- IPTBO
- TBPO
- TBPS
Cloflubicyne
Trimethylolpropane phosphite
Domoic acid

Pulmonary/
choking agents

Vomiting agents

Incapacitating
agents

Lachrymatory
agents

Malodorant agents

Cornea-clouding agents

Biological toxins

Other

Methyl fluoroacetate
Napalm (variants and mixtures)
Fluoroethyl fluoroacetate
Depleted uranium
- post-combustion uranium oxides
Plutonium and its compounds
Polonium
White phosphorus

v t e Convulsants
GABA receptor antagonists	Bicuculline Bicyclic phosphates (TBPS, TBPO, IPTBO) BIDN Chlorophenylsilatrane Cicutoxin Cloflubicyne Coriamyrtin Dihydropicrotoxinin DMCM EBOB Endosulfan FG-7142 Fipronil Flurothyl Gabazine Oenanthotoxin Pentylenetetrazol Phenylsilatrane Picrotoxin p-CN-TBOB p-NCS-TBOB RDX TBOB Tetramethylenedisulfotetramine Thujone Trimethylolpropane phosphite Tutin
GABA synthesis inhibitors	3-Mercaptopropionic acid 4-Deoxypyridoxine Allylglycine Crimidine Decaborane Ginkgotoxin Isoniazid Pentaborane Thiocarbohydrazide Toxopyrimidine
Glycine receptor antagonists	Coriamyrtin Dendrobine Picrotoxin Strychnine Tutin
Glutamate receptor agonists	AMPA Domoic acid Kainic acid NMDA Quisqualic acid Tetrazolylglycine
Convulsant barbiturates	CHEB DMBB McN-481
Other	2,2,3,3-Tetrafluoropropyl trifluoromethyl ether Bromocamphor Camphor FAZ-4 Fluoroethyl fluoroacetate MC-2973 Methionine sulfoximine Methyl fluoroacetate Nitrocyclohexane Thebaine

v t e Derivatives of fluoroacetic acid and 2-fluoroethanol
Fluoroacetate salts	Aluminum fluoroacetate Ammonium fluoroacetate Barium fluoroacetate Cadmium fluoroacetate Calcium fluoroacetate Cupric fluoroacetate Potassium fluoroacetate Sodium fluoroacetate Thallous fluoroacetate Triethyllead fluoroacetate
Fluoroacetate esters	Allyl fluoroacetate Butyl fluoroacetate Cetyl fluoroacetate Cholesteryl fluoroacetate Ethyl fluoroacetate 2-Ethylhexyl fluoroacetate Fluoroacetylcholine Fluoroaspirin Fluoroethyl fluoroacetate Isopropyl fluoroacetate Methyl fluoroacetate Methylene bis(fluoroacetate) Phenyl fluoroacetate Propyl fluoroacetate
Fluoroethyl esters	Bis(2-fluoroethyl) carbonate Bis(2-fluoroethyl) hydrogen phosphite Bis(2-fluoroethyl) phosphorofluoridate Bis(2-fluoroethyl) sulfate Bis(2-fluoroethyl) sulfite Fluenetil Fluoroethyl acetate Fluoroethyl chloroacetate Fluoroethyl chloroformate Fluoroethyl chlorosulfonate Fluoroethyl fluoroacetate Fluoroethyl nitrite Fluoroethyl trichloroacetate Tetrakis(2-fluoroethyl) orthosilicate TL-790 TL-821 Tris(2-fluoroethyl) arsenite Tris(2-fluoroethyl) borate Tris(2-fluoroethyl) phosphite Tris(2-fluoroethyl) orthoformate
Fluoroacetamides	Fluoroacetamide Fluoroacetanilide Nissol
Other	Bis(2-fluoroethyl)ether 2-chloroethyl fluorothioacetate Fluoroacetic anhydride Fluoroacetyl chloride Fluoroacetyl fluoride