tert-Butyl 4-chlorophenylcarbamate

Name: tert-Butyl 4-chlorophenylcarbamate
Brand: ChemScene
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CAS No. 18437-66-6
Cat. No. CS-M0552
Purity≥98%
MDL No.MFCD00816772

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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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tert-Butyl 4-chlorophenylcarbamate|CS-M0552

Structure of 18437-66-6

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General Information

CAS No. 18437-66-6
Cat. No. CS-M0552
Purity ≥98%
MDL No. MFCD00816772
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₄ClNO₂
Molecular Weight 227.69
Synonym(s) tert-butyl N-(4-chlorophenyl)carbamate
SMILES O=C(OC(C)(C)C)NC1=CC=C(Cl)C=C1

Description

tert-Butyl 4-chlorophenylcarbamate serves as a robust protecting group for primary amines, offering stability under basic conditions and facilitating straightforward deprotection. The para-chlorophenyl moiety enhances solubility in organic solvents, while the tert-butyl carbamate fragment ensures compatibility with diverse synthetic workflows. This derivative integrates cleanly into peptide synthesis and small-molecule drug discovery.

Application

tert-Butyl 4-chlorophenylcarbamate serves as a stable, bench-ready carbamate protecting group for primary amines, enabling selective amidation and coupling reactions in peptide and heterocycle synthesis. Its chlorine substituent enhances electrophilic reactivity in palladium-catalyzed cross-coupling processes, facilitating efficient C–N bond formation. The tert-butyl moiety ensures straightforward deprotection under mild acidic conditions, preserving sensitive functional groups.

Synthesis

Route1
- In-stock
  
  24424-99-5
- 106-47-8
- ~99%
- In-stock
  
  18437-66-6
References
- Chankeshwara, Sunay V.; Chakraborti, Asit K. Tetrahedron Letters, 2006 , vol. 47, # 7 p. 1087 - 1091
Route2
- In-stock
  
  106-39-8
- In-stock
  
  4248-19-5
- ~95%
- In-stock
  
  18437-66-6
References
- Isley, Nicholas A.; Dobarco, Sebastian; Lipshutz, Bruce H. Green Chemistry, 2014 , vol. 16, # 3 p. 1480 - 1488
Route3
- 3296-05-7
- In-stock
  
  24424-99-5
- ~85%
- In-stock
  
  18437-66-6
References
- Chandrasekhar; Narsihmulu Tetrahedron Letters, 2000 , vol. 41, # 41 p. 7969 - 7972

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-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 38.33
LogP 3.687
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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tert-Butyl 4-chlorophenylcarbamate

CAS No. 18437-66-6

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