2-({[(tert-butoxy)carbonyl]amino}oxy)acetic acid

• ChemBase ID: 38470
• Molecular Formular: C7H13NO5
• Molecular Mass: 191.18182
• Monoisotopic Mass: 191.07937252
• SMILES: C(ONC(=O)OC(C)(C)C)C(=O)O
• Canonical SMILES: O=C(OC(C)(C)C)NOCC(=O)O
• InChI: InChI=1S/C7H13NO5/c1-7(2,3)13-6(11)8-12-4-5(9)10/h4H2,1-3H3,(H,8,11)(H,9,10)
• InChIKey: QBXODCKYUZNZCY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({[(tert-butoxy)carbonyl]amino}oxy)acetic acid
• IUPAC Traditional name: {[(tert-butoxycarbonyl)amino]oxy}acetic acid
• Synonyms: 2-[[[(1,1-Dimethylethoxy)carbonyl]amino]oxy]acetic Acid; 2-((tert-Butoxycarbonyl)aminooxy)acetic Acid; [[N-(tert-Butoxycarbonyl)amino]oxy]acetic Acid; t-Boc-aminooxyacetic Acid; N-Boc-(carboxymethoxy)amine; (Boc-aminooxy)acetic acid; Boc-3-(aminooxy)acetic acid; N-Boc-(羧基甲氧基)胺; (Boc-氨氧基)乙酸

Database IDs

• CAS Number: 42989-85-5
• MDL Number: MFCD01632027
• Beilstein Number: 6137646
• PubChem SID: 24849020; 161001777
• PubChem CID: 2755974

CALCULATED PROPERTIES

• Acid pKa: 3.7500207
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.2547671
• LogD (pH = 7.4): -2.7901661
• Log P: 0.49572477
• Molar Refractivity: 42.2266 cm^3
• Polarizability: 16.949965 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~115 °C (dec.)

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (T)
• Linear Formula: (CH3)3CO2CNHOCH2CO2H

DETAILS

Sigma Aldrich - 15035

Other Notes
Employed to introduce a hydroxylamine moiety into peptides; reaction with an aldehyde to an oxime.1,2
Packaging
1 g in poly tube
5 g in poly bottle

Toronto Research Chemicals - B200750

A Boc-protected bifunctional linking reagent.

REFERENCES

• Jimenez-Castells, C., et al.: Bioorg. Med. Chem. Lett., 17, 5155 (2007)
• Carmona, S., et al.: Mol. Pharm., 6, 706 (2007)
• Nagahori, N., et al.: Biochem., 48, 583 (2007)