(2R)-2-amino-2-phenylethan-1-ol

• ChemBase ID: 69363
• Molecular Formular: C8H11NO
• Molecular Mass: 137.17904
• Monoisotopic Mass: 137.08406398
• SMILES: C([C@H](N)c1ccccc1)O
• Canonical SMILES: OC[C@@H](c1ccccc1)N
• InChI: InChI=1S/C8H11NO/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2/t8-/m0/s1
• InChIKey: IJXJGQCXFSSHNL-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-2-phenylethan-1-ol
• IUPAC Traditional name: (2R)-2-amino-2-phenylethanol
• Synonyms: (R)-2-Amino-2-phenylethanol; H-D-Phg-ol; (-)-(R)-β-Aminobenzeneethanol; (2R)-2-Amino-2-phenylethanol; (R)-(-)-2-Amino-2-phenylethanol; (R)-(-)-2-Phenyl-2-aminoethanol; (R)-(-)-2-Phenylglycinol; (R)-α-Phenylglycinol; (βR)-β-Aminobenzeneethanol; D-(-)-2-Amino-2-phenylethanol; [(R)-2-Hydroxy-1-phenylethyl]amine; D-Phenylglycinol; (R)-(-)-2-Phenylglycinol; D-Phenylglycinol; (2R)-2-Amino-2-phenylethan-1-ol; L-Phenylglycinol; (2S)-2-Amino-2-phenylethan-1-ol; 2-Amino-2-phenylethanol; D-(-)-α-PHENYLGLYCINOL; D-(-)-α-Phenylglycinol; D-(-)-α-Phenylglycinol; (R)-(-)-2-Phenylglycinol; (R)-2-Amino-2-phenylethanol; (R)-(-)-2-苯基甘氨醇; D-(-)-α-苯甘氨醇; (R)-2-氨基-2-苯乙醇; D-(-)-α-苯甘氨醇; (R)-(-)-2-苯甘氨醇

Database IDs

• CAS Number: 56613-80-0; 20989-17-7
• EC Number: 260-287-5
• MDL Number: MFCD00064404; MFCD00008062
• Beilstein Number: 2935848
• PubChem SID: 162035089; 24887331; 24851431
• PubChem CID: 2724025

CALCULATED PROPERTIES

• Acid pKa: 15.034467
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -2.4697678
• LogD (pH = 7.4): -1.2631787
• Log P: 0.4686793
• Molar Refractivity: 40.4939 cm^3
• Polarizability: 16.162655 Å^3
• Polar Surface Area: 46.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous HCl; Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 75-77 °C(lit.); 75-78°C; 76°C; 76-78°C; 76-79 °C; 77-79°C
• Optical Rotation: [α]20/D -25.5±1°, c = 6% in methanol; [α]24/D -31.7°, c = 0.76 in 1 M HCl; -30 (c=0.75 in 1N HCl)
• Hydrophobicity(logP): 0.193

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Air Sensitive; IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (sum of enantiomers, HPLC); 95%; 95+%; 98%
• Grade: purum
• Optical Purity: ee: 99% (GLC); enantiomeric ratio: ≥99:1 (HPLC)
• Linear Formula: C6H5CH(NH2)CH2OH
• Empirical Formula (Hill Notation): C8H11NO

DETAILS

MP Biomedicals - 02151836

Crystalline

MP Biomedicals - 05205021

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 190357

Application
Amino alcohol used to prepare a chiral imine or oxazolidine from ethyl trifluoropyruvate. These intermediates were then employed in a synthesis of both enantiomers of α-trifluoromethylproline.1
Chiral β-amino alcohol used as a synthetic building block.
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 78590

Other Notes
Chiral hydroxy amine used for the resolution of acids via their amides which are mildly hydrolyzed by neighbouring-group participation 1; chiral auxiliary2,3

Toronto Research Chemicals - P327295

A chiral arylalkylamine used as organocatalysts. Used in the synthesis and chiral recognition properties of novel fluorescent chemosensors for amino acid.

REFERENCES

• Kristensen, T. E. et al.: Eur. J. Org. Chem., 30, 5185 (2009)
• Liu, W. et al.: You. Xua., 26, 518 (2009)
• Condensation with glutaraldehyde gives a useful intermediate in asymmetric synthesis of alkaloids: Org. Synth. Coll., 9, 176 (1998):
  
• Starting material for the enantioselective synthesis of 2,6-disubstituted piperazines: Synthesis, 833 (1996), and for chiral ɑ-amino phosphonates: Org. Synth., 75, 19 (1997).