D-Phenylalaninol - CAS 5267-64-1

Name: D-Phenylalaninol
Brand: BOC Sciences
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D-Phenylalaninol is a chiral amino alcohol derived from the reduction of D-phenylalanine, appearing as a crystalline powder. With its structural motif combining an alcohol and an aromatic side chain, it functions as a versatile intermediate in asymmetric synthesis and chiral auxiliaries production. Its stereochemistry is crucial for the generation of optically active pharmaceuticals and fine chemicals. D-Phenylalaninol is frequently utilized in peptide modification, ligand design, and enantioselective catalysis research.

Catalog Number

BCC-01282

CAS

5267-64-1

IUPAC Name

(2R)-2-amino-3-phenylpropan-1-ol

Synonyms

(R)-2-Amino-3-phenyl-1-propanol; D-Phe-ol; (R)-2-Amino-3-phenylpropan-1-ol; D(+)-Phenylalaninol; (+)-D-Phenylalaninol; (2R)-2-amino-3-phenylpropan-1-ol

Molecular Weight

151.21

Molecular Formula

C9H13NO

Product Information

Canonical SMILES

C1=CC=C(C=C1)CC(CO)N

InChI

InChI=1S/C9H13NO/c10-9(7-11)6-8-4-2-1-3-5-8/h1-5,9,11H,6-7,10H2/t9-/m1/s1

InChI Key

STVVMTBJNDTZBF-SECBINFHSA-N

Purity

> 95 % by HPLC

MDL

MFCD00064298

Physical State

Solid

Appearance

White to light yellow crystalline powder

Storage

Store at -20 °C

Boiling Point

122 °C / 4 mmHg

Melting Point

93-95 °C(lit.)

Density

1.077 g/cm³

Optical Activity

+22.8°( c = 1.2 in 1 M HCl)

Solubility

Soluble in Dichloromethane, Ethyl Acetate, Methanol

Hazard Class

TSCA

WGK Germany

Packing Groups

III

Safety Information

Signal Word

Danger

Precautionary Statement

P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501

Hazard Statements

H314

Physicochemical Properties

LogP

1.24900

Reference Reading

1. A new chiral binaphthalene-based fluorescence polymer sensor for the highly enantioselective recognition of phenylalaninol.

Guo Wei, Yiwu Quan, Yixiang Cheng, Chunhui Dai, Shuwei Zhang, Chengjian Zhu. Chemistry. 2013 Nov 18; 19(47): 16066-71. DOI: 10.1002/chem.201302726. PMID: 24123510.

A new (S)-binaphthalene-based polymer (P-1) was synthesized by the polymerization of 5,5'-((2,5-dibutoxy-1,4-phenylene)bis(ethyne-2,1-diyl))bis(2-hydroxy-3-(piperidin-1-ylmethyl) benzaldehyde (M-1) with (S)-2,2'-dimethoxy-(1,1'-binaphthalene)-3,3'-diamine (M-2) through the formation of a Schiff base; the corresponding chiral polymer (P-2) could be obtained by the reduction of polymer P-1 with NaBH4 . Chiral polymer P-1 exhibited a remarkable "turn-on" fluorescence-enhancement response towards (D)-phenylalaninol and excellent enantioselective recognition behavior with enantiomeric fluorescence difference ratios (ef) as high as 8.99. More importantly, chiral polymer P-1 displays a bright blue fluorescence color change upon the addition of (D)-phenylalaninol under a commercially available UV lamp, which can be clearly observed by the naked eye. On the contrary, chiral polymer P-2 showed weaker enantioselective fluorescence ability towards the enantiomers of phenylalaninol.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass