(1R,2S)-2-amino-1,2-diphenylethan-1-ol

• ChemBase ID: 67999
• Molecular Formular: C14H15NO
• Molecular Mass: 213.275
• Monoisotopic Mass: 213.11536411
• SMILES: [C@H]([C@H](c1ccccc1)N)(c1ccccc1)O
• Canonical SMILES: N[C@H]([C@@H](c1ccccc1)O)c1ccccc1
• InChI: InChI=1S/C14H15NO/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14,16H,15H2/t13-,14+/m0/s1
• InChIKey: GEJJWYZZKKKSEV-UONOGXRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S)-2-amino-1,2-diphenylethan-1-ol
• IUPAC Traditional name: (1R,2S)-2-amino-1,2-diphenylethanol
• Synonyms: (1R,2S)-erythro-(-)-2-Amino-1,2-diphenylethanol; (1R,2S)-Diphenyl-2-aminoethanol; (1R,2S)-1,2-Diphenyl-2-aminoethanol; (1R,2S)-2-Amino-1,2-diphenylethanol; (αR,βS)-β-Amino-α-phenylbenzeneethanol; (1R,2S)-(-)-2-Amino-1,2-diphenylethanol; (1R,2S)-2-Amino-1,2-diphenylethanol; (1R,2S)-(-)-2-Amino-1,2-diphenylethanol; (1R,2S)-(-)-2-氨基-1,2-二苯乙醇; (1R,2S)-(-)-2-氨基-1,2-二苯基乙醇

Database IDs

• CAS Number: 23190-16-1
• MDL Number: MFCD00074960
• Beilstein Number: 2806218
• PubChem SID: 162033731; 24860006
• PubChem CID: 719819

CALCULATED PROPERTIES

• Acid pKa: 13.783489
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.67245746
• LogD (pH = 7.4): 0.57994777
• Log P: 2.2529194
• Molar Refractivity: 64.7767 cm^3
• Polarizability: 25.791145 Å^3
• Polar Surface Area: 46.25 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 141-143°C; 142-144 °C(lit.); 142-144°C; 142-145 °C
• Optical Rotation: [α]20/D -7±1°, c = 0.6% in ethanol; [α]25/D -7.0°, c = 0.6 in ethanol

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (NT); 95+%; 98%; 99%
• Grade: puriss.
• Linear Formula: C6H5CH(NH2)CH(C6H5)OH

DETAILS

Sigma Aldrich - 331899

Packaging
1, 5 g in glass bottle
Application
Chiral auxiliary used for Pd(II)-assisted chiral tandem alkylation and carbonylative coupling reactions.1,2

Sigma Aldrich - 07930

Other Notes
Chiral auxiliary used for Pd(II)-assisted chiral tandem alkylation/carbonylative coupling reactions1,2

Toronto Research Chemicals - A607880

(1R,2S)-(-)-2-Amino-1,2-diphenylethanol is a hydroxylated 1,2-diphenethylamine derivative with affinity for the NMDA receptor.

REFERENCES

• Berger, M.L. et al.: Bioorg. Med. Chem., 17, 3456 (2009)