MilliporeSigma
All Photos(2)

190357

Sigma-Aldrich

(R)-(−)-2-Phenylglycinol

98%

Synonym(s):
D-(−)-α-Phenylglycinol, (R)-2-Amino-2-phenylethanol
Linear Formula:
C6H5CH(NH2)CH2OH
CAS Number:
Molecular Weight:
137.18
Beilstein:
2935848
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

optical activity

[α]24/D −31.7°, c = 0.76 in 1 M HCl

optical purity

ee: 99% (GLC)

reaction suitability

reaction type: solution phase peptide synthesis

mp

75-77 °C (lit.)

application(s)

peptide synthesis

SMILES string

N[C@@H](CO)c1ccccc1

InChI

1S/C8H11NO/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2/t8-/m0/s1

InChI key

IJXJGQCXFSSHNL-QMMMGPOBSA-N

Packaging

5, 25 g in glass bottle

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.
Chiral β−amino alcohol used as a synthetic building block.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Tetrahedron Letters, 45, 5287-5287 (2004)
Grégory Chaume et al.
Organic letters, 8(26), 6123-6126 (2006-12-15)
[Structure: see text] A concise synthesis of both enantiomers of alpha-Tfm-proline and (S)-alpha-Tfm-prolinol from ethyl trifluoropyruvate is reported. The key step is a diastereoselective allylation reaction of ethyl trifluoropyruvate and (R)-phenylglycinol-based oxazolidines or imine. The lactone obtained by cyclization of
Amedjkouh, M.; Westerlund, K.
Tetrahedron Letters, 45, 5175-5175 (2004)

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