tert-Butyl 4-formylbenzoate

CAS No. 65874-27-3
Cat. No. CS-W007267
Molecule weight206.24
Purity≥96%
MDL No.MFCD01111994

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Structure of 65874-27-3

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General Information

CAS No. 65874-27-3
Cat. No. CS-W007267
Purity ≥96%
MDL No. MFCD01111994
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₄O₃
Molecular Weight 206.24
Synonym(s) 4-Formylbenzoic Acid tert-Butyl Ester
SMILES O=C(OC(C)(C)C)C1=CC=C(C=O)C=C1

Description

tert-Butyl 4-formylbenzoate features a para-formyl group flanked by a sterically hindered tert-butyl ester, enabling stable incorporation into complex synthetic sequences. This electron-deficient aromatic aldehyde facilitates efficient coupling reactions and serves as a key intermediate in the construction of functionalized biaryl systems under mild conditions.

Application

tert-Butyl 4-formylbenzoate serves as a versatile synthetic intermediate for the construction of aromatic aldehydes and heterocyclic scaffolds. The formyl group enables efficient transformations via nucleophilic addition, oxime formation, or reductive amination, while the tert-butyl ester provides stability and ease of purification. Its compatibility with standard functional group manipulations facilitates downstream derivatization in medicinal chemistry and materials synthesis.

Synthesis

Route1
- In-stock
  
  619-66-9
- In-stock
  
  36805-97-7
- ~81%
- In-stock
  
  65874-27-3
References
- Zimmerman, Sommer S.; Khatri, Alpa; Garnier-Amblard, Ethel C.; Mullasseril, Praseeda; Kurtkaya, Natalie L.; Gyoneva, Stefka; Hansen, Kasper B.; Traynelis, Stephen F.; Liotta, Dennis C. Journal of Medicinal Chemistry, 2014 , vol. 57, # 6 p. 2334 - 2356
Route2
- In-stock
  
  24424-99-5
- In-stock
  
  619-66-9
- ~51%
- In-stock
  
  65874-27-3
References
- Hishikawa, Kazuhiro; Nakagawa, Hidehiko; Furuta, Toshiaki; Fukuhara, Kiyoshi; Tsumoto, Hiroki; et al. Journal of the American Chemical Society, 2009 , vol. 131, p. 7488 - 7489
Route3
- In-stock
  
  24424-99-5
- In-stock
  
  619-66-9
- 75-65-0
- ~%
- In-stock
  
  65874-27-3
References
- RIGEL PHARMACEUTICALS, INC. Patent: WO2005/97760 A1, 2005 ; Location in patent: Page/Page column 65; 17/24 ;

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 43.37
LogP 2.4544
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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tert-Butyl 4-formylbenzoate

CAS No. 65874-27-3

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