tert-butyl N-(2-oxoethyl)carbamate

• ChemBase ID: 145229
• Molecular Formular: C7H13NO3
• Molecular Mass: 159.18302
• Monoisotopic Mass: 159.08954328
• SMILES: CC(C)(C)OC(=O)NCC=O
• Canonical SMILES: O=CCNC(=O)OC(C)(C)C
• InChI: InChI=1S/C7H13NO3/c1-7(2,3)11-6(10)8-4-5-9/h5H,4H2,1-3H3,(H,8,10)
• InChIKey: ACNRTYKOPZDRCO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-(2-oxoethyl)carbamate
• IUPAC Traditional name: tert-butyl N-(2-oxoethyl)carbamate
• Synonyms: Carbamic acid, N-(2-oxoethyl)-, 1,1-dimethylethyl ester; tert-Butyl N-(2-oxoethyl)carbamate; N-Boc-2-aminoacetaldehyde; N-(2-氧代乙基)氨基甲酸叔丁酯; N-Boc-2-氨基乙醛

Database IDs

• CAS Number: 89711-08-0
• MDL Number: MFCD01321273
• PubChem SID: 24870815; 162239439
• PubChem CID: 4247255

CALCULATED PROPERTIES

• Acid pKa: 13.910411
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.18600558
• LogD (pH = 7.4): 0.18600546
• Log P: 0.18600558
• Molar Refractivity: 39.951 cm^3
• Polarizability: 15.661511 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 113 °C; 235.4 °F
• Refractive Index: n20/D 1.455(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CTSK(1513)

Product Information

• Purity: 95%; min 96%
• Linear Formula: HCOCH2NHCO2C(CH3)3

DETAILS

Sigma Aldrich - 472654

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.1Also used in a three-component synthesis of pyrrolidines involving 1,3-dipolar cycloaddition.2
A building block in the synthesis of a protected pyrroloproline.
Packaging
1, 5 g in glass bottle