472654

N-Boc-2-aminoacetaldehyde

95%

• Synonym(s): tert-Butyl N-(2-oxoethyl)carbamate
• Linear Formula: HCOCH₂NHCO₂C(CH₃)₃
• CAS Number: 89711-08-0
• Molecular Weight: 159.18
• MDL number: MFCD01321273
• UNSPSC Code: 12352100
• PubChem Substance ID: 24870815
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: 95%
• refractive index: n20/D 1.455 (lit.)
• functional group: aldehyde; amine
• 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)

Description

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

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.

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.

A building block in the synthesis of a protected pyrroloproline.

Safety Information

• Storage Class Code: 11 - 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