Trichloronitrosomethane

Trichloronitrosomethane
Names

Other names TL-358
Identifiers
CAS Number	3711-49-7
3D model (JSmol)	Interactive image
ChemSpider	69724
PubChem CID	77305
CompTox Dashboard (EPA)	DTXSID80190610
InChI InChI=1S/CCl3NO/c2-1(3,4)5-6 Key: WXWITNRAXGTELB-UHFFFAOYSA-N
SMILES C(N=O)(Cl)(Cl)Cl
Properties
Chemical formula	CCl₃NO
Molar mass	148.37 g·mol⁻¹
Appearance	Deep blue liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Trichloronitrosomethane is a chlorinated nitrosoalkane. It is a deep blue liquid with powerful lachrymatory effects.^[1]

Synthesis

Trichloronitrosomethane can be produced with following methods:^[1]^[2]

Oxidation of trichloromethylsulfinic acid with nitric acid.
Reaction of sodium trichloromethylsulfinate with sodium nitrite and sodium nitrate or potassium nitrate in sulfuric acid.
Pyrolysis of trichloroacethydroxamic acid.

Chemistry

Trichloronitrosomethane is an unstable substance. It slowly decomposes into nitrosyl chloride, nitrogen oxides, and chloropicrin over time.^[1]

Trichloronitrosomethane can be reduced to phosgene oxime by hydrogen sulfide.^[1]

References

^ ^a ^b ^c ^d Sartori, Mario (1939). The War Gases (PDF).
^ Sutcliffe, H. (September 1965). "The Synthesis of Trichloronitrosomethane". The Journal of Organic Chemistry. 30 (9): 3221–3222. doi:10.1021/jo01020a516.

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