tert-butyl N-[(1R)-2-hydroxy-1-phenylethyl]carbamate

• ChemBase ID: 68506
• Molecular Formular: C13H19NO3
• Molecular Mass: 237.29486
• Monoisotopic Mass: 237.13649347
• SMILES: C([C@H](NC(=O)OC(C)(C)C)c1ccccc1)O
• Canonical SMILES: OC[C@@H](c1ccccc1)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C13H19NO3/c1-13(2,3)17-12(16)14-11(9-15)10-7-5-4-6-8-10/h4-8,11,15H,9H2,1-3H3,(H,14,16)/t11-/m0/s1
• InChIKey: IBDIOGYTZBKRGI-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(1R)-2-hydroxy-1-phenylethyl]carbamate
• IUPAC Traditional name: tert-butyl N-[(1R)-2-hydroxy-1-phenylethyl]carbamate
• Synonyms: (R)-N-(tert-Butoxycarbonyl)-2-phenylglycinol; Boc-D-Phg-ol; N-Boc-D-alpha-phenylglycinol; (R)-(-)-2-(Boc-amino)-2-phenylethanol; (-)-N-Boc-D-α-phenylglycinol; N-Boc-D-α-苯基甘氨酸; (R)-(-)-2-(Boc-氨基)-2-苯乙醇; (R)-N-叔丁氧羰基-2-苯甘氨醇

Database IDs

• CAS Number: 102089-74-7
• MDL Number: MFCD00274205
• Beilstein Number: 4688248
• PubChem SID: 24866892; 162034237
• PubChem CID: 7016461

CALCULATED PROPERTIES

• Acid pKa: 13.968376
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.9607767
• LogD (pH = 7.4): 1.9607766
• Log P: 1.9607767
• Molar Refractivity: 65.3669 cm^3
• Polarizability: 25.738205 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 137-139 °C(lit.); 137-141°C
• Optical Rotation: [α]19/D -38°, c = 1 in chloroform; -40 (c=1 in chloroform)

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: 95+%; 98%; 99%
• Optical Purity: ee: 99% (GLC)
• Linear Formula: (CH3)3CO2CNHCH(C6H5)CH2OH

DETAILS

Sigma Aldrich - 429813

Application
Used for the synthesis of homochiral N-protected β-amino sulfoxides1 and α-amino acids.2 Chiral synthon, which undergoes heterocyclizations.3 Precursor to chiral oxazolidinones.4
Packaging
1 g in glass bottle