Phosgene oxime

Base Information

• Chemical Name: Phosgene oxime
• CAS No.: 1794-86-1
• Molecular Formula: CH Cl2 N O
• Molecular Weight: 113.931
• UNII: G45S3149SQ
• DSSTox Substance ID: DTXSID9075292
• Nikkaji Number: J156.553B
• Wikipedia: Phosgene_oxime
• Wikidata: Q3241634
• NCI Thesaurus Code: C163689
• Mol file: 1794-86-1.mol

Synonyms:dichloroformossina;dichloroformoxine;dichlorophormoxine

Chemical Property of Phosgene oxime

Chemical Property:

• Vapor Pressure: 0.201mmHg at 25°C
• Melting Point: 39-40 °C
• Boiling Point: 185.1°C at 760 mmHg
• PKA: 7.70±0.11(Predicted)
• Flash Point: 65.7°C
• PSA: 32.59000
• Density: 1.66g/cm³
• LogP: 1.20920
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 112.9435190
• Heavy Atom Count: 5
• Complexity: 47.6

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Chemical Weapons
• Canonical SMILES: C(=NO)(Cl)Cl
• Description: Phosgene oxime is a colourless solid or yellowish-brown liquid with a disagreeable penetrating odour. Pure phosgene oxime is a colourless, crystalline solid; the munitions grade compound is a yellowish-brown liquid. Phosgene oxime is soluble in water and organic solvents, but hydrolyses rapidly, and especially in the presence of alkali. Chemically similar to but more reactive than an amide. Incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. It is also incompatible with strongly oxidising acids, peroxides, and hydroperoxides. Phosgene oxime is a very severe blistering agent. Both the liquid and the solid can give off vapours at ambient temperatures. Phosgene oxime was developed as a potential chemical warfare agent but has never been known to be used on the battlefield. Phosgene oxime (CX) is an urticant or nettle agent causing instant intolerable pain, erythema, wheals, and urticaria. It is very corrosive, capable of causing extensive tissue damage. Phosgene oxime was first produced by the Germans in 1929 as a possible warfare agent. The mechanism of action is not fully understood but the lesions produced in the skin are similar to those caused by a strong acid. Phosgene oxime will penetrate ordinary clothing and surgical gear.
• Uses: There are no commercial or beneficial uses of phosgene oxime. It was developed and produced solely as a chemical warfare agent, but has never been used on the battlefield.

Technology Process of Phosgene oxime

There total 22 articles about Phosgene oxime which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

Chloronitroacetyl chloride (85915-53-3) → dichloroformoxime (1794-86-1)

Guidance literature:

With urea; In diethyl ether; for 0.5h; Heating; further reagents (C₆H₁₁NH)2CO, (MeNH)2CO, thiourea, (PhNH)2CO;

DOI:10.1007/BF00954248

Reference yield: 16.8%

stannane (7440-31-5) + chloropicrin (76-06-2) → dichloroformoxime (1794-86-1)

Guidance literature:

With tin; In acetonitrile;

Reference yield:

trichloronitrosomethane (3711-49-7) → dichloroformoxime (1794-86-1)

Guidance literature:

With hydrogenchloride; diethyl ether; tin(ll) chloride;

upstream raw materials:

trichloronitrosomethane

bromodichloronitrosomethane

chloropicrin

dichloro-dinitro-methane

Downstream raw materials:

dichloro-dinitro-methane

triaminoguanidine hydrochloride

3-chloro-isoxazole

(3-chloro-isoxazol-5-yl)-methanol

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF PYROXASULFONE". Page/Page column 21. . Retrieved 2020/12/11.
• 2、 Orth, Ronald,Boettcher, Thomas,Sieber, Stephan A.. "The biological targets of acivicin inspired 3-chloro- and 3-bromodihydroisoxazole scaffolds". supporting information; experimental part. p. 8475 - 8477. Retrieved 2011/02/24.