N,N-Bis(2-chloroethyl)carbamoyl Chloride

Base Information

• Chemical Name: N,N-Bis(2-chloroethyl)carbamoyl Chloride
• CAS No.: 2998-56-3
• Molecular Formula: C5H8 Cl3 N O
• Molecular Weight: 204.484
• European Community (EC) Number: 221-075-8
• NSC Number: 73023
• DSSTox Substance ID: DTXSID40184075
• Nikkaji Number: J205.288A
• Wikidata: Q72444634
• Mol file: 2998-56-3.mol

Synonyms:N,N-Bis(2-chloroethyl)carbamoyl Chloride;2998-56-3;Bis(2-chloroethyl)carbamic chloride;Bis(2-chloroethyl)carbamoyl chloride;Carbamic chloride, bis(2-chloroethyl)-;EINECS 221-075-8;TL 460;BRN 1765484;Carbamoyl chloride, bis(2-chloroethyl)-;C5H8Cl3NO;Bis(2-chloroethyl)carbamic acid chloride;SCHEMBL571432;C5-H8-Cl3-N-O;2-Aminonicotinic acid hydrazide;DTXSID40184075;NSC73023;MFCD00144974;NSC 73023;NSC-73023;AKOS015899386;chloro(1-chloroethyl)carbamic chloride;N,N-di(2-chloroethyl)carbamic chloride;AS-50280;LS-50718;N-chloroformyl-bis-(beta-chloroethyl)-amine;B1451;FT-0629407;O11700;Bis(2-chloroethyl)carbamic chloride, AldrichCPR;EN300-1612252;A853769

Chemical Property of N,N-Bis(2-chloroethyl)carbamoyl Chloride

Chemical Property:

• Appearance/Colour: Colorless transparent liquid
• Melting Point: 114-128 °C / 400-533Pa
• Refractive Index: 1.5060-1.5100
• Boiling Point: 125°C 3mm
• PKA: -2.30±0.70(Predicted)
• Flash Point: 129.3 °C
• PSA: 20.31000
• Density: 1,4 g/cm³
• LogP: 2.12480
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 202.967147
• Heavy Atom Count: 10
• Complexity: 103

Purity/Quality:

98% ^*data from raw suppliers

N,N-Bis(2-chloroethyl)carbamoyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 34-43-25
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCl)N(CCCl)C(=O)Cl
• General Description: **N,N-Bis(2-chloroethyl)carbamoyl chloride** is a reactive intermediate used in the synthesis of chloroethyl-substituted ureas and imidazolidinones. It participates in intramolecular condensation reactions, such as forming 1,3-bis(2-chloroethyl)-2-imidazolidinone when reacted with bis(2-chloroethyl)amine, demonstrating its tendency to undergo rearrangement under thermal conditions. Additionally, it reacts with amines like diethylamine or pyrrolidine to yield substituted imidazolidinones, highlighting its utility in heterocyclic synthesis. Its reactivity in aqueous solutions leads to hydrolysis products, further underscoring its versatility in chemical transformations.

Technology Process of N,N-Bis(2-chloroethyl)carbamoyl Chloride

There total 6 articles about N,N-Bis(2-chloroethyl)carbamoyl 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: 85.0%

bis(trichloromethyl) carbonate (32315-10-9) + N,N-bis(chloro-2-ethyl)amine (334-22-5) → N,N-bis-(2-chloroethyl)carbamoyl chloride (2998-56-3)

Guidance literature:

With pyridine; at 20 ℃; for 72h;

Reference yield: 28.1%

bis(trichloromethyl) carbonate (32315-10-9) + bis-(2-chloroethyl)amine hydrochloride (821-48-7) → N,N-bis-(2-chloroethyl)carbamoyl chloride (2998-56-3)

Guidance literature:

With pyridine; triethylamine; In dichloromethane;

DOI:10.1002/anie.201910014

Reference yield:

N,N-bis(chloro-2-ethyl)amine (334-22-5) → N,N-bis-(2-chloroethyl)carbamoyl chloride (2998-56-3) + estradiol-3-N-bis-(β-chloroethyl)-carbamate

Guidance literature:

In benzene;

upstream raw materials:

phosgene

N,N-bis(chloro-2-ethyl)amine

bis-(2-chloroethyl)amine hydrochloride

trichloromethyl chloroformate

Downstream raw materials:

bis-(2-chloro-ethyl)-carbamic acid methyl ester

Bis-(2-chloro-ethyl)-carbamic acid 4-[(E)-2-{4-[bis-(2-chloro-ethyl)-carbamoyloxy]-phenyl}-1-eth-(Z)-ylidene-but-2-enyl]-phenyl ester

N,N-Bis-<2-chloraethyl>-carbamoyl-L-phenylalanin-aethylester

C₂₅H₂₁Cl₂NO₆

Refernces

Intramolecular Condensation Reactions of 1,1,3,3-Tetrakis(2-chloroethyl)urea

10.1021/jo00828a075

The study investigates the intramolecular condensation reactions of 1,1,3,3-tetrakis(2-chloroethyl)urea (Ia). The researchers prepared Ia by reacting bis(2-chloroethyl)carbamoyl chloride with bis(2-chloroethyl)amine in refluxing benzene. Upon distillation, Ia unexpectedly transformed into 1,3-bis(2-chloroethyl)-2-imidazolidinone (IIa), indicating a rearrangement from a tetrasubstituted urea to an imidazolidinone structure. This transformation was further explored through alternative syntheses and reactions with other reagents. For instance, bis(2-chloroethyl)carbamoyl chloride was reacted with diethylamine to produce 1-(2-chloroethyl)-3-ethyl-2-imidazolidinone (IIc), and with pyrrolidine to yield 1-(4-chlorobutyl)-3-(2-chloroethyl)-2-imidazolidinone (IId). Additionally, the study examined the behavior of Ia in aqueous solution, where it underwent hydrolysis to form bis(2-[(2-chloroethyl)amino]ethyl) carbonate (V). The study provides insights into the reactivity and transformation pathways of these chloroethyl-containing ureas and imidazolidinones under different conditions.