tert-Butyl allylcarbamate

Name: tert-Butyl allylcarbamate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

SDS

CAS No. 78888-18-3
Cat. No. CS-W007444
Purity≥96%
MDL No.MFCD00191870

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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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Structure of 78888-18-3

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General Information

CAS No. 78888-18-3
Cat. No. CS-W007444
Purity ≥96%
MDL No. MFCD00191870
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₅NO₂
Molecular Weight 157.21
Synonym(s) tert-butyl prop-2-en-1-ylcarbamate
SMILES CC(C)(OC(NCC=C)=O)C

Description

tert-Butyl allylcarbamate serves as a stable, bench-friendly protecting group for primary amines, enabling selective functionalization in complex synthesis. The allyl moiety permits orthogonal deprotection via palladium-catalyzed cleavage, while the tert-butyl carbamate offers robust stability under basic and mildly acidic conditions. This combination facilitates efficient peptide coupling and late-stage derivatization workflows.

Application

tert-Butyl allylcarbamate serves as a robust, bench-stable amine protecting group that enables efficient N-allylation in peptide synthesis and heterocycle construction. Its orthogonal cleavage under mild hydrogenolysis or acid conditions facilitates selective deprotection in complex molecules. The allyl moiety further supports transition-metal-catalyzed transformations, including palladium-mediated coupling reactions, enhancing its utility in diversification workflows.

Synthesis

Route1
- In-stock
  
  92136-39-5
- ~63%
- In-stock
  
  78888-18-3
References
- Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K. Patent: US2005/43347 A1, 2005 ; Location in patent: Page/Page column 67-68 ; US 20050043347 A1
Route2
- In-stock
  
  24424-99-5
- 107-11-9
- ~99%
- In-stock
  
  78888-18-3
References
- Tayama, Eiji; Sugai, Sayaka Tetrahedron Letters, 2007 , vol. 48, # 35 p. 6163 - 6166
Route3
- 41840-28-2
- 107-11-9
- ~86%
- In-stock
  
  78888-18-3
References
- Takeda Chemical Industries, Ltd. Patent: EP278621 B1, 1991 ;

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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SDS
COA

Computational Chemistry Data

TPSA 38.33
LogP 1.6971
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 2

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Other Classifications

Building Blocks Functional Group Boc

Building Blocks Functional Group Amine

Building Blocks Functional Group Olefins

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tert-Butyl allylcarbamate

CAS No. 78888-18-3

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Synthesis

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References

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