(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}propanoic acid

• ChemBase ID: 39519
• Molecular Formular: C9H17NO4
• Molecular Mass: 203.23558
• Monoisotopic Mass: 203.11575803
• SMILES: N([C@@H](C)C(=O)O)(C)C(=O)OC(C)(C)C
• Canonical SMILES: C[C@H](N(C(=O)OC(C)(C)C)C)C(=O)O
• InChI: InChI=1S/C9H17NO4/c1-6(7(11)12)10(5)8(13)14-9(2,3)4/h6H,1-5H3,(H,11,12)/t6-/m0/s1
• InChIKey: VLHQXRIIQSTJCQ-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}propanoic acid
• IUPAC Traditional name: (2S)-2-[(tert-butoxycarbonyl)(methyl)amino]propanoic acid
• Synonyms: N-[(1,1-Dimethylethoxy)carbonyl]-N-methyl-L-alanine; (S)-2-[(tert-Butoxycarbonyl)(methyl)amino]propanoic Acid; N-Methyl-N-(tert-butyloxycarbonyl)alanine; N-tert-Butoxycarbonyl-N-methylalanine; Boc-N-methyl-L-alanine; Boc-N-Me-Ala-OH; Boc-Nalpha-methyl-L-alanine; Boc-N-Me-Ala-OH; N-tert-Butoxycarbonyl-N-methyl-L-alanine; N-Boc-N-methyl-L-alanine; Boc-N-methyl-L-alanine; Boc-N-Me-Ala-OH; Boc-N-甲基-L-丙氨酸; Boc-N-甲基-L-丙氨酸

Database IDs

• CAS Number: 16948-16-6
• MDL Number: MFCD00037242
• Beilstein Number: 2366513
• PubChem SID: 161002826; 24849537
• PubChem CID: 7009590

CALCULATED PROPERTIES

• Acid pKa: 4.06867
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.3066129
• LogD (pH = 7.4): -1.9813066
• Log P: 1.1370622
• Molar Refractivity: 50.267 cm^3
• Polarizability: 19.816086 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 88-92°C; 88-92°C
• Optical Rotation: [α]20/D -30±1°, c = 1% in ethanol; -31 (c=1 in ethanol)

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (TLC); 95+%; 98%
• Empirical Formula (Hill Notation): C9H17NO4

DETAILS

Sigma Aldrich - 15549

Packaging
1 g in poly tube
5 g in poly bottle

Toronto Research Chemicals - B656955

Used in peptide synthesis.

REFERENCES

• Flohr, S., et al.: Chem. Eur. J., 5, 669 (1999)
• Kadereit, D., et al.: ChemBioChem., 1, 144 (1999)
• Volkert, M., et al.: Biol. Chem., 382, 1133 (1999)