tert-Butyl 2-(hydroxymethyl)azetidine-1-carboxylate

Name: tert-Butyl 2-(hydroxymethyl)azetidine-1-carboxylate
Brand: ChemScene
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CAS No. 174346-82-8
Cat. No. CS-0048457
Purity≥97%
MDL No.MFCD03790936

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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 2-(hydroxymethyl)azetidine-1-carboxylate|CS-0048457

Structure of 174346-82-8

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General Information

CAS No. 174346-82-8
Cat. No. CS-0048457
Purity ≥97%
MDL No. MFCD03790936
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₇NO₃
Molecular Weight 187.24
Synonym(s) [1-(TERT-BUTOXYCARBONYL)AZETIDIN-2-YL]METHANOL
SMILES CC(C)(C)OC(=O)N1CCC1CO

Description

tert-Butyl 2-(hydroxymethyl)azetidine-1-carboxylate delivers a strained azetidine core functionalized with a hydroxymethyl group, enabling direct incorporation into bioactive scaffolds. The tert-butyl ester provides stability and convenient deprotection under mild acidic conditions. This compound serves as a key intermediate in the synthesis of pharmacologically active molecules requiring precise stereocontrol and metabolic stability.

Application

tert-Butyl 2-(hydroxymethyl)azetidine-1-carboxylate serves as a versatile building block in medicinal chemistry, enabling the efficient construction of azetidine-containing scaffolds. The hydroxymethyl group facilitates downstream functionalization via oxidation, protection, or coupling reactions, while the tert-butyl ester offers excellent bench stability and ease of removal under mild acidic conditions. Its compatibility with diverse reaction conditions makes it a practical choice for synthesizing bioactive molecules and peptide mimetics.

Synthesis

Route1
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  31247-34-4
- In-stock
  
  24424-99-5
- ~%
- In-stock
  
  174346-82-8
References
- Evans, Gary B.; Furneaux, Richard H.; Greatrex, Ben; Murkin, Andrew S.; Schramm, Vern L.; Tyler, Peter C. Journal of Medicinal Chemistry, 2008 , vol. 51, # 4 p. 948 - 956
Route2
- In-stock
  
  255882-72-5
- ~%
- In-stock
  
  174346-82-8
References
- US2003/229226 A1, ; Page 19 ;

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

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Computational Chemistry Data

TPSA 49.77
LogP 0.9881
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Alcohol

Building Blocks Skeleton Aliphatic heterocycle compounds Azetidine compounds

Key Words

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tert-Butyl 2-(hydroxymethyl)azetidine-1-carboxylate

CAS No. 174346-82-8

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