(S)-(+)-1-Phenyl-1,2-ethanediol
(S)-(+)-1-Phenyl-1,2-ethanediol Basic information
- Product Name:
- (S)-(+)-1-Phenyl-1,2-ethanediol
- Synonyms:
-
- (S)-1-Phenyl-1,2-ethanediol,99%e.e.
- (S)-(+)-1-PHENYLETHANEDIOL
- (S)-(-)-1-PHENYL-1,2-ETHANEDIOL
- (S)-ALPHA,BETA-DIHYDROXYETHYLBENZENE
- S(+)-PHENYLETHYLENE GLYCOL
- (S)-(+)-PHENYL-1,2-ETHANEDIOL
- (S)-(+)-STYRENEGLYCOL
- (S)-STYRENE GLYCOL
- CAS:
- 25779-13-9
- MF:
- C8H10O2
- MW:
- 138.16
- Product Categories:
-
- Aromatics
- Chiral Reagents
- Intermediates
- Chiral Compounds
- Diols
- chiral
- Chiral Building Blocks
- Simple Alcohols (Chiral)
- Synthetic Organic Chemistry
- Mol File:
- 25779-13-9.mol
(S)-(+)-1-Phenyl-1,2-ethanediol Chemical Properties
- Melting point:
- 64-67 °C(lit.)
- alpha
- 66 º (c=1, chloroform)
- Boiling point:
- 272-274 °C (755 mmHg)
- Density
- 1.0742 (rough estimate)
- refractive index
- 40 ° (C=3, H2O)
- Flash point:
- 320 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 13.61±0.20(Predicted)
- color
- Off-White
- optical activity
- [α]18/D +66°, c = 1 in chloroform
- Water Solubility
- soluble
- BRN
- 3196197
- InChI
- 1S/C8H10O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8-10H,6H2/t8-/m1/s1
- InChIKey
- PWMWNFMRSKOCEY-MRVPVSSYSA-N
- SMILES
- OC[C@@H](O)c1ccccc1
- CAS DataBase Reference
- 25779-13-9(CAS DataBase Reference)
Safety Information
- Hazard Codes
- Xi,T
- Risk Statements
- 23/24/25-36/37/38
- Safety Statements
- 24/25-45-36/37/39-26
- WGK Germany
- 3
- Hazard Note
- Irritant
- HS Code
- 29062900
- Storage Class
- 11 - Combustible Solids
MSDS
- Language:English Provider:ACROS
- Language:English Provider:SigmaAldrich
- Language:English Provider:ALFA
(S)-(+)-1-Phenyl-1,2-ethanediol Usage And Synthesis
Chemical Properties
(S)-(+)-1-Phenyl-1,2-ethanediol is white to light yellow crystal powde
Uses
(S)-(+)-1-Phenyl-1,2-ethanediol used as a chiral building block in organic synthesis, used in the preparation of chiral 2-amino-1-phenylethanols as pharmaceutical intermediates.
Uses
Extremely valuable and versatile alcohol used as a chiral building block in organic synthesis, used in the preparation of chiral 2-amino-1-phenylethanols as pharmaceutical intermediates.
Biosynthesis
Terminal vicinal diols are important chiral building blocks and intermediates in organic synthesis. Reduction of α-hydroxy ketones provides a straightforward approach to access these important compounds. It has been found that asymmetric reduction of a series of α-hydroxy aromatic ketones and 1-hydroxy-2-pentanone, catalyzed by Candida magnolia carbonyl reductase (CMCR) with glucose dehydrogenase (GDH) from Bacillus subtilis for cofactor regeneration, afforded 1-aryl-1,2-ethanediols ((S)-(+)-1-Phenyl-1,2-ethanediol) and pentane-1,2-diol, respectively, in up to 99 % ee.[1]
Purification Methods
Purify the diol by recrystallisation from *C6H6/ligroin and sublime it at 1-2mm. [Arpesella et al. Gazetta 85 1354 1955, Prelog et al. Helv Chim Acta 37 221 1954, Beilstein 6 IV 5939.]
References
[1] Highly Efficient Synthesis of Optically Pure (S)-1-phenyl-1,2-ethanediol by a Self-Sufficient Whole Cell Biocatalyst. DOI:10.1002/open.201500045
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