tert-Butyl 3-formylbenzoate

Name: tert-Butyl 3-formylbenzoate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 247186-56-7
Cat. No. CS-0154845
Purity≥95%
MDL No.MFCD02180885

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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 247186-56-7

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General Information

CAS No. 247186-56-7
Cat. No. CS-0154845
Purity ≥95%
MDL No. MFCD02180885
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₄O₃
Molecular Weight 206.24
Synonym(s) None
SMILES CC(C)(C)OC(=O)C1=CC=CC(=C1)C=O

Description

tert-Butyl 3-formylbenzoate features a para-formyl group positioned ortho to a sterically hindered tert-butyl ester, enabling selective functionalization in complex synthesis. The electron-deficient aldehyde facilitates nucleophilic additions and condensation reactions under mild conditions, while the bulky ester group enhances solubility and reduces unwanted side reactions. This combination delivers robust reactivity with improved handling stability.

Application

tert-Butyl 3-formylbenzoate serves as a versatile synthetic intermediate for the construction of functionalized aromatic scaffolds. The ortho-formyl group enables direct electrophilic functionalization, while the tert-butyl ester provides steric protection and facilitates selective deprotection under mild acidic conditions. This combination offers excellent stability, compatibility with diverse reaction conditions, and ease of purification—making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  69038-74-0
- 68-12-2
- ~31%
- In-stock
  
  247186-56-7
References
- Kende, Andrew S.; Zhong, Min Synthetic Communications, 1999 , vol. 29, # 19 p. 3401 - 3407
Route2
- In-stock
  
  71432-55-8
- In-stock
  
  619-21-6
- ~%
- In-stock
  
  247186-56-7
References
- Maruoka, Hiroshi; Muto, Tsuyoshi; Tanaka, Taisaku; Imajo, Seiichi; Tomimori, Yoshiaki; Fukuda, Yoshiaki; Nakatsuka, Takashi Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 12 p. 3435 - 3439

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 3-formylbenzoate

CAS No. 247186-56-7

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