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190357

Sigma-Aldrich

(R)-(−)-2-Phenylglycinol

98%, for peptide synthesis

Synonym(s):

(R)-2-Amino-2-phenylethanol, D-(−)-α-Phenylglycinol

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About This Item

Linear Formula:
C6H5CH(NH2)CH2OH
CAS Number:
56613-80-0
Molecular Weight:
137.18
Beilstein:
2935848
EC Number:
260-287-5
MDL number:
MFCD00008062
UNSPSC Code:
12352209
PubChem Substance ID:
24851431
NACRES:
NA.22

product name

(R)-(−)-2-Phenylglycinol, 98%

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

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

11 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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298417

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Tetrahedron Letters, 45, 5287-5287 (2004)
Amedjkouh, M.; Westerlund, K.
Tetrahedron Letters, 45, 5175-5175 (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

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