Methylcarbamoyl chloride (HCID 80931)

Names & identifiers

Preferred name: Methylcarbamoyl chloride
IUPAC: N-methylcarbamoyl chloride
English name: Methylaminoformyl chloride
Molecular formula: C2H4ClNO
Molecular weight: 93.51

Names & synonyms

6452-47-7Methylcarbamoyl chlorideEINECS 229-253-7NSC 133003DTXSID60214787RefChem:158151DTXCID90137278229-253-7Methylaminoformyl chlorideN-methylcarbamoyl chloridemethylcarbamic chlorideMethylcarbamoylchloride

Show more names

N-MethylchloroformamidemethylamineylformylchloroN-(Chloroformyl)methylamineMethylcarbamic acid chloride

Carbamic chloride, methyl-N-Methylaminoformyl chlorideMethylcarbamic Chloride; N-Methylcarbamoyl Chloride; NSC 133003methylcarbamicchloridemethylcarbamyl chlorideMethylaminoformylchlorideethylaminoformyl chlorideN-Methylcarbamic chloride

Database identifiers

CAS: 6452-47-7
PubChem CID: 80931
DTXSID: DTXSID60214787
EC Number: 229-253-7
Nikkaji: J23.393E

Properties

Computed structural properties

XLogP: 0.6
Topological polar surface area: 29.1 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 0
Heavy atoms: 5
Formal charge: 0
Complexity: 44.9

Physicochemical properties

Melting point: 45 °C · 45°C
Boiling point: 93 °C · 93°C (dec.)
Density: 1.185 · 1.185±0.06 g/cm3(Predicted)
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
solubility: Acetonitrile, Chloroform (Slightly), DMSO
pka: 10.67 · 10.67±0.46(Predicted)
form: Solid
color: White to Off-White
Stability: Air Sensitive, Hygroscopic, Moisture Sensitive, Volatile
InChI: InChI=1S/C2H4ClNO/c1-4-2(3)5/h1H3,(H,4,5)
InChIKey: GRRYSIXDUIAUGY-UHFFFAOYSA-N
SMILES: C(Cl)(=O)NC
CAS DataBase Reference: 6452 · 6452-47-7(CAS DataBase Reference)
UNSPSC Code: 12352200 · 12352200
NACRES: 21 · NA.21
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 · P264-P270-P301+P312-P501
Hazard Codes: Xn
Risk Statements: 22 · 22
WGK Germany: 3 · WGK 3
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 Oral · Acute Tox. 4 Oral

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

wgk: WGK 3
risk_code: 22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Hazard Classifications: Acute Tox. 4 Oral
Precautionary statements: P264-P270-P301+P312-P501

Chemistry & industry

Applications · 3 items

DescriptionMethylcarbamoyl Chloride is used as a reagent in the synthesis of acylprolinamides as a new class of peptide deformylase inhibitors with in vivo antibacterial activity. Methylcarbamoyl Chloride is also used as a reagent in the synthesis of carbamate derivatives as potential dual-binding site acetylcholinesterase inhibitors. The decomposition tail gas hydrogen chloride of Methylaminoformyl chloride is also useful during the cartap synthesis.

UsesMethylaminoformyl chloride can be widely used as an intermediate of carbamate insecticides such as Zhongdingwei, carbofuran, isoprocarb, methomyl, chlorhexidine and carbaryl. Methylaminoformyl chloride is also used as a reagent in the synthesis of carbamate derivatives as potential dual-binding site acetylcholinesterase inhibitors. The decomposition tail gas hydrogen chloride of Methylaminoformyl chloride is also useful during the cartap synthesis.

UsesMethylcarbamoyl Chloride is used as a reagent in the synthesis of acylprolinamides as a new class of peptide deformylase inhibitors with in vivo antibacterial activity. Methylcarbamoyl Chloride is also used as a reagent in the synthesis of carbamate derivatives as potential dual-binding site acetylcholinesterase inhibitors.

Preparation methods · 1 item

PreparationMethylaminoformyl chloride is prepared by reacting methylamine with phosgene. Reaction equation: CH3NH2+COCl2→CH3NHCOCl. A 40% aqueous solution of methylamine is vaporized, and after drying, it is combined with phosgene at a ratio of 1:1.3 (methanol), methylamine at 4 m3/h, and phosgene at a rate of 8.6 m3/h (content 60%-70%). Preheating into the preheater, the preheating temperature of methylamine is controlled at 220-260°C, and the phosgene is controlled at 200-240°C. The preheated two gases enter the test tube and are synthesized at 280-300°C to obtain gaseous methaqualyl chloride. Then, carbon tetrachloride (or chlorobenzene solution) is circulated and absorbed at 0-20°C to obtain a solution of about 10% of carbamoyl chloride (or chlorobenzene), or cooled to a liquid product after 35-40°C or lower[2,3].