(2R)-2-amino-3,3-dimethylbutanoic acid

• ChemBase ID: 69899
• Molecular Formular: C6H13NO2
• Molecular Mass: 131.17292
• Monoisotopic Mass: 131.09462866
• SMILES: C(=O)([C@H](N)C(C)(C)C)O
• Canonical SMILES: N[C@H](C(C)(C)C)C(=O)O
• InChI: InChI=1S/C6H13NO2/c1-6(2,3)4(7)5(8)9/h4H,7H2,1-3H3,(H,8,9)/t4-/m0/s1
• InChIKey: NPDBDJFLKKQMCM-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3,3-dimethylbutanoic acid
• IUPAC Traditional name: (2R)-2-amino-3,3-dimethylbutanoic acid
• Synonyms: (R)-2-Amino-3,3-dimethylbutyric acid; D-α-tert-Butylglycine; D-2-tert-Butylglycine; (2R)-2-amino-3,3-dimethylbutanoic acid; D-tert-Leucine; L-tert-Leucine; D-tert-Leucine; (R)-2-氨基-3,3-二甲基丁酸; D-α-叔丁基甘氨酸; D-叔亮氨酸

Database IDs

• CAS Number: 20859-02-3; 26782-71-8
• MDL Number: MFCD00004265; MFCD00064218
• Beilstein Number: 1721825
• PubChem SID: 162035624; 24856312; 24874860
• PubChem CID: 6950340

CALCULATED PROPERTIES

• Acid pKa: 2.7936387
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.5744301
• LogD (pH = 7.4): -1.5785921
• Log P: -1.5740803
• Molar Refractivity: 33.891 cm^3
• Polarizability: 13.835553 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300°C; ≥300 °C(lit.); 285-290°C
• Optical Rotation: [α]20/D -7±1°, c = 5% in 5 M HCl; [α]25/D +9.5°, c = 3% in H2O; -7 (c=5 in 5N HCl)
• Hydrophobicity(logP): -1.887

Safety Information

• Storage Warning: IRRITANT; Irritant
• German water hazard class: 3
• Safety Statements: 22-24/25
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (NT); 95%; 95+%; 98%; 99%
• Grade: puriss.
• Impurities: ~0.5% water
• Linear Formula: (CH3)3CCH(NH2)CO2H

DETAILS

Sigma Aldrich - 269115

Packaging
500 mg in glass bottle

Sigma Aldrich - 61835

Other Notes
Unnatural, "fat" amino acid 1; chiral auxiliary, e.g. in the synthesis of aldehydes by double alkylation of unsaturated aldimines of tert-Leu esters 2,3; Synthesis of amino acids4