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472654

Sigma-Aldrich

N-Boc-2-aminoacetaldehyde

95%

Synonym(s):
tert-Butyl N-(2-oxoethyl)carbamate
Linear Formula:
HCOCH2NHCO2C(CH3)3
CAS Number:
Molecular Weight:
159.18
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

refractive index

n20/D 1.455 (lit.)

storage temp.

−20°C

SMILES string

CC(C)(C)OC(=O)NCC=O

InChI

1S/C7H13NO3/c1-7(2,3)11-6(10)8-4-5-9/h5H,4H2,1-3H3,(H,8,10)

InChI key

ACNRTYKOPZDRCO-UHFFFAOYSA-N

Gene Information

human ... CTSK(1513)

Related Categories

General description

N-Boc-2-aminoacetaldehyde is an organic building block. It reacts with Horner-Wadsworth-Emmons (HWE) reagent to afford γ-aminobutyric acid (GABA)-derived α-keto amide/ester units.

Application

A building block in the synthesis of a protected pyrroloproline.
N-Boc-2-aminoacetaldehyde may be employed in the following:
  • As a starting reagent in the total synthesis of (+)-negamycin.
  • Synthesis of (E)-ethyl 4-((tert-butoxycarbonyl)amino)but-2-enoate.
  • Synthesis of 2,2′-bipyridine.
α-Methylenation of this amino aldehyde proceeds in a quick and efficient manner using a recently reported protocol involving formaldehyde and catalysis by either pyrrolidine proprionic acid or the dipeptide L-Pro-β-Ala.
Also used in a three-component synthesis of pyrrolidines involving 1,3-dipolar cycloaddition.

Packaging

1, 5, 25 g in glass bottle

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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