Diethylcarbamoyl chloride

Base Information

• Chemical Name: Diethylcarbamoyl chloride
• CAS No.: 88-10-8
• Molecular Formula: C5H10ClNO
• Molecular Weight: 135.594
• Hs Code.: Oral rat LD50: 2700 mg/kg
• European Community (EC) Number: 201-798-5
• NSC Number: 512306,223067
• UN Number: 1993
• UNII: 5RIV1U6H5W
• DSSTox Substance ID: DTXSID0052598
• Nikkaji Number: J33.934B
• Wikidata: Q26840750
• ChEMBL ID: CHEMBL3559788
• Mol file: 88-10-8.mol

Synonyms:diethylcarbamoyl chloride

Chemical Property of Diethylcarbamoyl chloride

Chemical Property:

• Appearance/Colour: clear yellow to brownish liquid
• Vapor Pressure: 0.678mmHg at 25°C
• Melting Point: -32 °C(lit.)
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 186 °C at 760 mmHg
• PKA: -1.85±0.70(Predicted)
• Flash Point: 75 °C
• PSA: 20.31000
• Density: 1.069 g/cm³
• LogP: 1.68700
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Water Solubility.: HYDROLYSIS
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 135.0450916
• Heavy Atom Count: 8
• Complexity: 80.5

Purity/Quality:

99% ^*data from raw suppliers

Diethylcarbamoyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/22-36/37/38-40
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: CCN(CC)C(=O)Cl
• Uses: It is used in the production of pharma ingredients. It is a reagent in the synthesis of S-Methyl-N,N-diethylthiocarbamate Sulfoxide, which is an oxygenated metabolite of Disulfiram (Antabuse) that is capable of in vitro inactivation of liver mitochondrial aldehyde dehydrogenase.

Technology Process of Diethylcarbamoyl chloride

There total 24 articles about Diethylcarbamoyl chloride 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: 90.3%

disulfiram (97-77-8) → N,N-diethylcarbamyl chloride (88-10-8)

Guidance literature:

disulfiram; With chlorine; In dichloromethane; at 24 - 26 ℃; for 7h; Cooling with ice;

With water; sodium hydrogencarbonate; In dichloromethane; Cooling with ice;

DOI:10.1080/00397910903537331

Reference yield: 88.6%

chloro(chlorosulfanyl)methanone (2757-23-5) + diethylamine (109-89-7) → N,N-diethylcarbamyl chloride (88-10-8)

Guidance literature:

chloro(chlorosulfanyl)methanone; diethylamine; In dichloromethane; at 40 ℃; Inert atmosphere;

With chlorine; In dichloromethane; at 20 ℃;

DOI:10.1139/V10-138

Reference yield: 73.2%

bis(trichloromethyl) carbonate (32315-10-9) + diethylamine (109-89-7) → N,N-diethylcarbamyl chloride (88-10-8)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at -10 ℃;

DOI:10.1007/s11164-012-1003-1

upstream raw materials:

2-(diethylamino)-2-oxoacetic acid

phosgene

diethylamine

N,N-diethylthiocarbamoyl chloride

Downstream raw materials:

2-methyl-aziridine-1-carboxylic acid diethylamide

4-methyl-hexahydro-[1,4]diazepine-1-carboxylic acid diethylamide

N,N-diethyl-2-phenyl-malonamic acid

diethyl-carbamic acid-(4-chloro-3-methyl-phenyl ester)

Refernces

(Z)-1-Nitro-3-hexene as (Z)-3-Hexen-1-yl d¹-Reagent: Synthesis of (Z)-5-Octen-2-one and (Z)-1,8-Undecadien-5-one

10.1055/s-1986-31802

The research focuses on the development of a new synthetic procedure for the preparation of (Z)-5-octen-2-one and (Z)-1,8-undecadien-5-one using (Z)-1-nitro-3-hexene as a key reagent, which corresponds to the (Z)-3-hexen-1-yl d'-synthon. These compounds are important intermediates in the synthesis of (Z)-jasmolone and (Z)-jasmone, natural products with insecticidal and perfumery applications. The study concludes that the target molecules can be obtained in high purity through simple procedures, with an overall yield of 39% and 33% for (Z)-5-octen-2-one and (Z)-1,8-undecadien-5-one, respectively, and chemical purities above 98% as confirmed by gas chromatography analysis.