tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate

Name: tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate
Brand: ChemScene
Availability: InStock
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CAS No. 330794-35-9
Cat. No. CS-0116442
Purity≥96%
MDL No.MFCD06409942

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tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate|CS-0116442

Structure of 330794-35-9

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General Information

CAS No. 330794-35-9
Cat. No. CS-0116442
Purity ≥96%
MDL No. MFCD06409942
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₈BNO₄
Molecular Weight 333.23
Synonym(s) tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate
SMILES O=C(OC(C)(C)C)NCC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1

Description

This boronate ester features a tert-butyl carbamate-protected amine tethered to a para-substituted benzyl group, enabling stable coupling in Suzuki-Miyaura reactions. The tetramethyl-dioxaborolane moiety delivers high functional group tolerance and compatibility with diverse reaction conditions. Designed for efficient incorporation into complex molecular architectures, this reagent streamlines access to biaryl and arylalkyl scaffolds in medicinal chemistry and materials synthesis.

Application

tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The boryl group enables efficient C–C bond formation under mild conditions, while the tert-butyl carbamate protects the primary amine and enhances stability during storage and handling. Its compatibility with diverse functional groups and ease of purification make it ideal for constructing complex aromatic scaffolds in medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  138500-88-6
- ~97%
- In-stock
  
  330794-35-9
References
- JANSSEN PHARMACEUTICA N.V.; ADDEX PHARMACEUTICALS S.A. Patent: WO2007/104783 A2, 2007 ; Location in patent: Page/Page column 53 ; WO 2007/104783 A2
Route2
- In-stock
  
  68819-84-1
- In-stock
  
  73183-34-3
- ~82%
- In-stock
  
  330794-35-9
References
- Howgego, Joshua D.; Butts, Craig P.; Crump, Matthew P.; Davis, Anthony P. Chemical Communications, 2013 , vol. 49, # 30 p. 3110 - 3112
Route3
- 861359-74-2
- In-stock
  
  24424-99-5
- In-stock
  
  26177-44-6
- In-stock
  
  73183-34-3
- ~80%
- In-stock
  
  330794-35-9
References
- Hirst, Gavin C.; Calderwood, David; Munschauer, Rainer; Arnold, Lee D.; Johnston, David N.; Rafferty, Paul Patent: US2003/153752 A1, 2003 ;

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 56.79
LogP 3.0105
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate

CAS No. 330794-35-9

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