Benzyl bis(2-chloroethyl)carbamate

Name: Benzyl bis(2-chloroethyl)carbamate
Brand: ChemScene
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CAS No. 72791-76-5
Cat. No. CS-0156246
Purity≥95%
MDL No.MFCD06858694

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Benzyl bis(2-chloroethyl)carbamate|CS-0156246

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General Information

CAS No. 72791-76-5
Cat. No. CS-0156246
Purity ≥95%
MDL No. MFCD06858694
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₅Cl₂NO₂
Molecular Weight 276.16
Synonym(s) Carbamic acid, N,N-bis(2-chloroethyl)-, phenylmethyl ester
SMILES C1=CC=C(C=C1)COC(=O)N(CCCl)CCCl

Description

Benzyl bis(2-chloroethyl)carbamate is a moisture-tolerant, bench-stable carbamate reagent featuring two chloroethyl groups that facilitate efficient alkylation under mild conditions. This compound integrates readily into synthetic sequences requiring selective nitrogen functionalization, offering high reactivity with nucleophiles while maintaining stability during storage and handling.

Application

Benzyl bis(2-chloroethyl)carbamate serves as a stable, bench-friendly carbamoylating agent for the selective introduction of urea linkages in peptide synthesis and medicinal chemistry. Its dual chloroethyl groups enable efficient intramolecular cyclization to form oxazolidinone intermediates, facilitating controlled release of active species. The compound exhibits excellent functional group tolerance and simplifies purification due to its crystalline nature, making it well-suited for scalable synthetic workflows.

Synthesis

Route1
- In-stock
  
  821-48-7
- 501-53-1
- ~97%
- In-stock
  
  72791-76-5
References
- Lin, Weimin; Gupta, Anuradha; Kim, Kyung Hee; Mendel, David; Miller, Marvin J. Organic Letters, 2009 , vol. 11, # 2 p. 449 - 452
Route2
- 501-53-1
- In-stock
  
  334-22-5
- ~61%
- In-stock
  
  72791-76-5
References
- Park, Woul Seong; Jun, Mi Ae; Shin, Mi Sik; Kwon, Sung Wook; Kang, Seung Kyu; Kim, Ki Young; Dal Rhee, Sang; Bae, Myung Ae; Narsaiah, Banda; Lee, Duck Hyung; Cheon, Hyae Gyeong; Ahn, Jin Hee; Kim, Sung Soo Journal of Fluorine Chemistry, 2009 , vol. 130, # 11 p. 1001 - 1010

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

TPSA 29.54
LogP 3.1028
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Benzyl bis(2-chloroethyl)carbamate

CAS No. 72791-76-5

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