tert-Butyl 2-hydroxyacetate

Name: tert-Butyl 2-hydroxyacetate
Brand: ChemScene
Availability: InStock
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CAS No. 50595-15-8
Cat. No. CS-W003086
Purity≥96%
MDL No.MFCD03452739

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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+
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General Information

CAS No. 50595-15-8
Cat. No. CS-W003086
Purity ≥96%
MDL No. MFCD03452739
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₁₂O₃
Molecular Weight 132.16
Synonym(s) tert-Butyl Hydroxyacetate
SMILES OCC(=O)OC(C)(C)C

Description

tert-Butyl 2-hydroxyacetate features a masked hydroxyacetyl group, enabling controlled delivery of reactive intermediates in synthetic sequences. This bench-stable, moisture-tolerant ester integrates readily into complex molecule assembly, particularly in peptide and natural product synthesis where selective functionalization is critical.

Application

tert-Butyl 2-hydroxyacetate serves as a stable, bench-friendly synthon for the introduction of α-hydroxyacetyl units in synthetic sequences. It functions as a protected form of hydroxyacetic acid, enabling selective functionalization under mild conditions. The tert-butyl ester group provides excellent stability and facilitates straightforward deprotection via acid-catalyzed cleavage. Its compatibility with diverse reaction types—including nucleophilic substitutions and metal-mediated transformations—makes it a valuable building block in the construction of complex molecules and heterocyclic scaffolds.

Synthesis

Route1
- 5292-43-3
- ~%
- In-stock
  
  50595-15-8
References
- Jurayj, Jurjus; Cushman, Mark Tetrahedron, 1992 , vol. 48, # 40 p. 8601 - 8614
Route2
- 145641-58-3
- ~95%
- In-stock
  
  50595-15-8
References
- Jurayj, Jurjus; Cushman, Mark Tetrahedron, 1992 , vol. 48, # 40 p. 8601 - 8614
Route3
- 5292-43-3
- ~9%
- In-stock
  
  50595-15-8
- 18598-93-1
References
- Scardovi, Noemi; Casalini, Andrea; Peri, Francesca; Righi, Paolo Organic Letters, 2002 , vol. 4, # 6 p. 965 - 968

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS02
Signal Word : Warning	UN#: 1993
Class : 3	Packing Group : Ⅲ
Hazard Statements : H226
Precautionary Statements : P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

Quality Control

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Computational Chemistry Data

TPSA 46.53
LogP 0.3204
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boc

Building Blocks Functional Group Alcohol

Building Blocks Functional Group Ester

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tert-Butyl 2-hydroxyacetate

CAS No. 50595-15-8

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