1,3-Bis(2-chloroethyl)urea

Base Information

• Chemical Name: 1,3-Bis(2-chloroethyl)urea
• CAS No.: 2214-72-4
• Molecular Formula: C5H10Cl2N2O
• Molecular Weight: 185.053
• Hs Code.: 2924190002
• European Community (EC) Number: 811-761-0
• NSC Number: 36198
• UNII: 67617YV44S
• DSSTox Substance ID: DTXSID40176672
• Nikkaji Number: J600.103C
• Wikidata: Q27264067
• ChEMBL ID: CHEMBL1331
• Mol file: 2214-72-4.mol

Synonyms:1,3-Bis(2-chloroethyl)urea;2214-72-4;Urea, N,N'-bis(2-chloroethyl)-;N,N'-Bis(2-chloroethyl)urea;Urea, 1,3-bis(2-chloroethyl)-;NSC-36198;67617YV44S;N,N'-bis-(2-Chloroethyl)urea;C5H10Cl2N2O;UNII-67617YV44S;NSC 36198;PARENT UREA;AI3-08682;CHEMBL1331;Urea,3-bis(2-chloroethyl)-;N,N-Bis-(2-chloroethyl)urea;Urea,N'-bis(2-chloroethyl)-;SCHEMBL7579999;DTXSID40176672;N,N'-Bis(2-chloroethyl)urea #;NSC36198;MFCD00068573;AKOS002666604;AB89862;AM806154;AS-59501;LOMUSTINE IMPURITY A [EP IMPURITY];CARMUSTINE IMPURITY A [EP IMPURITY];CS-0158327;FT-0629409;EN300-172613;W10366;Q27264067;Z1198149941;Urea, 1,3-bis(2-chloroethyl)- (6CI,7CI,8CI)

Chemical Property of 1,3-Bis(2-chloroethyl)urea

Chemical Property:

• Melting Point: 128-129 °C
• Boiling Point: 358.2 °C at 760 mmHg
• PKA: 12.99±0.46(Predicted)
• Flash Point: 170.4 °C
• PSA: 41.13000
• Density: 1.245 g/cm³
• LogP: 1.54500
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 184.0170183
• Heavy Atom Count: 10
• Complexity: 89.6

Purity/Quality:

98.5%, ^*data from raw suppliers

1,3-Bis(2-chloroethyl)urea ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCl)NC(=O)NCCCl
• Uses: 1,3-Bis(2-chloroethyl)urea is an impurity in the synthesis of Carmustine (C183875), an alkylating and carbamoylating nitrosourea compound. It interacts with DNA, RNA and proteins causing DNA interstrand cross linking which is cytotoxic and leads to apoptotic cell death.

Technology Process of 1,3-Bis(2-chloroethyl)urea

There total 9 articles about 1,3-Bis(2-chloroethyl)urea 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: 87.2%

N-(2-chloroethyl)-1H-imidazole-1-carboxamide + 2-chloroethanamine hydrochloride (870-24-6) → 1,3-bis(2-chloroethyl)urea (2214-72-4)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 40 ℃; for 4h; Reagent/catalyst; Time; Temperature;

Reference yield: 82.0%

2-chloroethyl isothiocyanate (1943-83-5) + chloroethylamine (689-98-5) → 1,3-bis(2-chloroethyl)urea (2214-72-4)

Guidance literature:

In dichloromethane; 1) 0 deg C, 20 min; 2) room temperature, 18 h;

DOI:10.1002/jps.2600780811

Reference yield: 61.5%

di(succinimido) carbonate (74124-79-1) + 2-chloroethanamine hydrochloride (870-24-6) → 1,3-bis(2-chloroethyl)urea (2214-72-4) + N-(2-chloroethyl)carbamic acid N'-hydroxysuccinimide ester (80354-45-6)

Guidance literature:

With triethylamine; In acetonitrile; Ambient temperature;

DOI:10.1016/S0040-4039(00)85958-4

upstream raw materials:

ethyleneimine

phosgene

2-chloroethyl isothiocyanate

di(succinimido) carbonate

Downstream raw materials:

1,3-bis(2-chloroethyl)-1-nitrosourea

N,N'-Bis-<2-iod-ethyl>-harnstoff

2-<(2-chloroethyl)amino>-2-oxazoline hydrochloride

2-<(2'-chloroethyl)imino>-3-nitroso-2-oxazolidine

Refernces

• 1、 Crawshaw,Mason. "-". . p. 3971. Retrieved 1965.
• 2、 -. "Method for preparing high-purity carmustine". Paragraph 0062-0063; 0065. . Retrieved 2020/04/17.
• 3、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF 1,3-BIS(2-CHLOROETHYL)-1-NITROSOUREA". Page/Page column 9; 10. . Retrieved 2017/09/27.