(R)-(-)-1-Phenyl-1,2-ethanediol

• CAS: 16355-00-3
• Catalog Number: ACM16355003
• Category: Main Products
• Molecular Weight: 138.20
• Molecular Formula: C₈H₁₀O₂
• Synonyms: (R)-(-)-1-Phenylethane-1,2-diol; (R)-(-)-Phenylethylene Glycol; (R)-(-)-Styrene Glycol; (R)-(-)-1-Phenyl-1,2-Ethanediol; (R)-(+)-1-Phenylethane-1,2-diol; (R)-(+)-Styreneglycol; (1R)-1-phenylethane-1,2-diol; (R)-1-Phenylethane-1,2-diol
• IUPAC Name: (1R)-1-phenylethane-1,2-diol
• SMILES: C1=CC=C(C=C1)C(CO)O
• InChI Key: PWMWNFMRSKOCEY-QMMMGPOBSA-N
• Boiling Point: 272-274ºC
• Melting Point: 65-68ºC
• Flash Point: 272-274ºC
• Density: 1.17 g/cm³
• Appearance: white to light yellow crystal powder
• Exact Mass: 138.06800
• Hazard Statements: Xi:Irritant
• Safety Description: S24/25
• WGK Germany: 3

Case Study

Efficient Biosynthetic Strategy for Optically Pure 1-Phenyl-1,2-Ethanediol

Cui, Zhi-Mei, et al. Journal of biotechnology, 2017, 243, 1-9.

Optically pure 1-phenyl-1,2-ethanediol is a vital chiral building block and intermediate in the fine chemical and pharmaceutical sectors. Two enantiocomplementary carbonyl reductases, BDHA (2,3-butanediol dehydrogenase from Bacillus subtilis) and GoSCR (polyol dehydrogenase from Gluconobacter oxydans), were identified for the first time as effective catalysts for converting 2-hydroxyacetophenone (2-HAP) into (R)-1-phenyl-1,2-ethanediol ((R)-PED) and (S)-1-phenyl-1,2-ethanediol ((S)-PED) with remarkable stereochemical selectivity.
Efficiency of biosynthesis for (S)- and (R)-1-phenyl-1,2-ethanediol
· The efficiency of biosynthesis for (S)- and (R)-1-phenyl-1,2-ethanediol was demonstrated through the in vitro bioreduction of 2-HAP catalyzed by BDHA and GoSCR, in conjunction with glucose dehydrogenase (GDH) from Bacillus subtilis for cofactor regeneration, resulting in both (R)-PED and (S)-PED with over 99% enantiomeric excess (ee) and 99% conversion.
· Recombinant Escherichia coli whole cells co-expressing GDH and either BDHA or GoSCR were employed for the asymmetric reduction of 2-HAP to yield (R)-PED or (S)-PED. Under optimized conditions, the bioreduction proceeded smoothly with 400 mM (54 g/L) of substrate without the need for external cofactor addition, resulting in products with a yield of 99%, an ee of over 99%, and a volumetric productivity of 18.0 g/L/h.

Hydrogenolysis of 1-Phenyl-1,2-Ethanediol to Produce Toluene

Stanowski, Sylvain, et al. Organometallics, 2012, 31(2), 515-518.

The transformation of ethylene glycol into hydrocarbons through hydrogenolysis offers a significant opportunity for generating chemicals and fuels from biomass-derived polyols. [Cp*Ru(CO)2]2 (Cp* = 1,2,3,4,5-pentamethylcyclopentadienyl) was found to catalyze the hydrogenolysis of ethylene glycol to alkanes by molecular hydrogen at 170-200 °C and 4-27 atm. This work established a new process for the production of alkanes with a smaller carbon number from ethylene glycol: for example, toluene from 1-phenyl-1,2-ethanediol.
Synthesis procedure
The research began with 1-phenyl-1,2-ethanediol serving as the model glycol substrate (R = Ph) and utilized the accessible precursor catalyst [Cp*Ru(CO)2]2 (1; Cp* = η5 -C5Me5). The hydrogenation reaction of the glycol occurred initially in benzene with 10 mol % of [Cp*Ru(CO)2]2 inside a steel autoclave at 170 °C under 4 atm pressure. Gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) analyses of the reaction mixture over 30 hours revealed a gradual and nearly simultaneous production of ethylbenzene and notably toluene (approximately 2:1 ratio). The products had one carbon less than the original glycol (entry 1, Table 1) and showed no evidence of styrene or monoalcohols in their composition.