Methylcarbamoyl chloride
Methylcarbamic chloride · n-methylaminoformyl chloride · N-Methylchloroformamide · METHYLCARBAMOYLCHLORIDE · methylamineylformylchloro · METHYLAMINOFORMYL CHLORIDE · Carbamic chloride, methyl- · N-Methylcarbamoyl chloride
Identifiers & Physical Properties
| CAS No. | 6452-47-7 |
|---|---|
| Molecular formula | C2H4ClNO |
| Average molar mass | 93.51 g/mol |
| Monoisotopic mass | 92.99814143 g/mol |
| SMILES | CNC(=O)Cl |
| InChIKey | GRRYSIXDUIAUGY-UHFFFAOYSA-N |
| PubChem CID | 80931 |
| EC No. | 229-253-7 |
| DTXSID | DTXSID60214787 |
Chemical & Physical Properties
| XLogP | 0.6 |
|---|---|
| Topological polar surface area | 29.1 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 5 |
| Formal charge | 0 |
| Complexity | 44.9 |
| Melting point | 45°C |
| Boiling point | 93°C (dec.) |
| Density | 1.185±0.06 g/cm3(Predicted) |
| Storage conditions | under inert gas (nitrogen or Argon) at 2-8°C |
| Solubility | Acetonitrile, Chloroform (Slightly), DMSO |
| pKa (acidity coefficient) | 10.67±0.46(Predicted) |
| Physical state | 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 | 6452-47-7(CAS DataBase Reference) |
| UNSPSC Code | 12352200 |
| NACRES | NA.21 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302 |
| GHS precautionary statements | P264-P270-P301+P312-P501 |
| Hazard symbols | Xn |
| Risk statements (R) | 22 |
| Water hazard class (WGK) | WGK 3 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Acute Tox. 4 Oral |
Safety & Regulations
| GHS classification | WarningH302 (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 Classes and Categories | Acute Tox. 4 (100%) |
| Water hazard class (WGK) | WGK 3 |
| Risk statements (R) | 22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302 |
| Hazard class | Acute Tox. 4 Oral |
| GHS precautionary statements | P264-P270-P301+P312-P501 |
Applications & Uses
Description
Methylcarbamoyl 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.
Uses
Methylaminoformyl 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.
Uses
Methylcarbamoyl 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 & Synthesis
Preparation
Methylaminoformyl 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].