ethyl 2-{[(tert-butoxy)carbonyl]amino}-2-oxoacetate

• ChemBase ID: 152235
• Molecular Formular: C9H15NO5
• Molecular Mass: 217.2191
• Monoisotopic Mass: 217.09502259
• SMILES: CCOC(=O)C(=O)NC(=O)OC(C)(C)C
• Canonical SMILES: CCOC(=O)C(=O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C9H15NO5/c1-5-14-7(12)6(11)10-8(13)15-9(2,3)4/h5H2,1-4H3,(H,10,11,13)
• InChIKey: DSDQWJVXMDHQLK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-{[(tert-butoxy)carbonyl]amino}-2-oxoacetate
• IUPAC Traditional name: ethyl 2-[(tert-butoxycarbonyl)amino]-2-oxoacetate
• Synonyms: Ethyl N-Boc-oxamidate; tert-Butoxycarbonylamino-oxo-acetic acid ethyl ester; N-Boc-草酰胺酸乙酯

Database IDs

• CAS Number: 216959-34-1
• MDL Number: MFCD01631201
• Beilstein Number: 8201747
• PubChem SID: 162246380; 24850446
• PubChem CID: 2733665

CALCULATED PROPERTIES

• Acid pKa: 5.4020963
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.98062646
• LogD (pH = 7.4): -0.34566727
• Log P: 1.3272003
• Molar Refractivity: 50.7736 cm^3
• Polarizability: 20.204498 Å^3
• Polar Surface Area: 81.7 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Refractive Index: n20/D 1.449

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0%; 97%
• Empirical Formula (Hill Notation): C9H15NO5

DETAILS

Sigma Aldrich - 17346

Other Notes
Reagent for transforming alcohols into BOC-protected amines by Mitsunobu reaction (PPh3/DEAD); prim and sec alcohols (inversion of configuration) give good yields1
Packaging
5 g in glass bottle