tert-butyl N-hydroxycarbamate

• ChemBase ID: 63641
• Molecular Formular: C5H11NO3
• Molecular Mass: 133.14574
• Monoisotopic Mass: 133.07389322
• SMILES: O(C(C)(C)C)C(=O)NO
• Canonical SMILES: ONC(=O)OC(C)(C)C
• InChI: InChI=1S/C5H11NO3/c1-5(2,3)9-4(7)6-8/h8H,1-3H3,(H,6,7)
• InChIKey: DRDVJQOGFWAVLH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-hydroxycarbamate
• IUPAC Traditional name: tert-butyl N-hydroxycarbamate
• Synonyms: tert-Butyl N-hydroxycarbamate; N-Boc-hydroxylamine; N-(tert-Butoxycarbonyl)hydroxylamine; tert-Butyl N-hydroxycarbamate; N-tert-Butoxycarbonylhydroxylamine; N-叔丁氧羰基羟胺; N-羟基氨基甲酸叔丁酯; N-Boc-羟基胺

Database IDs

• CAS Number: 36016-38-3
• EC Number: 252-836-2
• MDL Number: MFCD00002107
• Beilstein Number: 1756546
• PubChem SID: 24879088; 162029380; 24853547
• PubChem CID: 97534

CALCULATED PROPERTIES

• Acid pKa: 8.455683
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.6393041
• LogD (pH = 7.4): 0.60348445
• Log P: 0.6397807
• Molar Refractivity: 31.6597 cm^3
• Polarizability: 12.556731 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 53 - 55°C; 53-55 °C; 53-55 °C(lit.); 55-58°C
• Hydrophobicity(logP): 0.368

Safety Information

• Storage Warning: IRRITANT; Moisture Sensitive
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: >95%; ≥98%; ≥98.0% (N); 95%; 98%; 98+%
• Grade: purum
• Linear Formula: (CH3)3COCONHOH

DETAILS

Sigma Aldrich - 226157

Packaging
1, 5 g in glass bottle
Application
Preparation of azridines via cycloaddition of azides with nitroso Diels-Alder adducts.1
Reagent for the synthesis of hydroxylamine derivatives, t-butyl-N-(acyloxy)carbamates, and N,O-diacylated N-hydroxyarylsulfonamides.

Sigma Aldrich - 55005

Other Notes
Reagent for the synthesis of α-aminoxy acids 1,2; intermediate for the preparation of hydroxamic acids 3; mild oxidation of hydroxamic acids to acyl nitroso compds. and CA 4

REFERENCES

• Precursor of O-substituted hydroxylamines, including the unstable O-acyl and O-sulfonylhydroxylamines which, having a good leaving group on nitrogen, are powerful aminating agents: J. Am. Chem. Soc.,82, 3133 (1960); Tetrahedron, 29, 1063 (1973); Synthesis, 140 (1972). For a review of O-mesitylenesulfonylhydroxylamine and related compounds, see: Synthesis, 1 (1977).