(1S)-1-(2-CHLOROPHENYL)ETHANE-1,2-DIOL Chemical Properties

Melting point:

68-75 °C(lit.)

Boiling point:

293 °C(lit.)

Density 

1.1910 (rough estimate)

refractive index 

1.5530 (estimate)

Flash point:

108 °C

storage temp. 

Sealed in dry,Room Temperature

pka

13.24±0.20(Predicted)

optical activity

[α]20/D +70°, c = 0.2 in chloroform

InChI

1S/C8H9ClO2/c9-7-4-2-1-3-6(7)8(11)5-10/h1-4,8,10-11H,5H2/t8-/m1/s1

InChIKey

YGOPULMDEZVJGI-MRVPVSSYSA-N

SMILES

OC[C@@H](O)c1ccccc1Cl

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HS Code 

2906290090

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:ACROS

(1S)-1-(2-CHLOROPHENYL)ETHANE-1,2-DIOL Usage And Synthesis

Uses

o-Chlorophenyl glycol is an organic intermediate that can be obtained by oxidizing 2-chlorostyrene with hydrogen peroxide in the presence of a Cr-Anderson type polyacid modified by the catalyst (S)-1-(2-hydroxy-1-phenylethyl)thiourea.

Chemical Properties

white to beige crystals and / or chunks

Synthesis

General procedure for the synthesis of (R)-1-(2-chlorophenyl)-1,2-ethanediol from methyl 2-(2-chlorophenyl)-2-oxoacetate: In an inert atmosphere glove box, the substrate methyl 2-(2-chlorophenyl)-2-oxoacetate (0.5 mmol), base (0.05 mmol), Ru-MACHO catalyst (5 μmol) and methanol (0.5 mL). The glass reactor was sealed and transferred to an autoclave, followed by replacing the air in the kettle with hydrogen three times. The reaction was carried out at 25°C or 80°C with constant stirring for 12-24 h under 10-50 bar hydrogen pressure. Upon completion of the reaction, the autoclave was cooled to room temperature. The residual hydrogen was slowly released in a fume hood and the reaction mixture was transferred to a conical flask containing deionized water (2 mL) and extracted with ethyl acetate (3 x 5 mL). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford the pure target product (R)-1-(2-chlorophenyl)-1,2-ethanediol.

References

[1] Synlett, 2016, vol. 27, # 11, p. 1748 - 1752
[2] Green Chemistry, 2012, vol. 14, # 5, p. 1372 - 1375

(1S)-1-(2-CHLOROPHENYL)ETHANE-1,2-DIOL(133082-13-0)Related Product Information

• 1-(4-chlorophenyl)ethane-1,2-diol
• 1,2-Diphenyl-1,2-bis(4-chlorophenyl)ethane-1,2-diol
• 1,1,2,2-Tetra(4-chlorophenyl)ethane-1,2-diol,1,1,2,2-Tetrakis(4-chlorophenyl)ethane-1,2-diol
• 4-CHLORO-2-[2-(2,4-DICHLORO-PHENYL)-[1,3]DIOXOLAN-2-YLMETHOXY]-BENZOTHIAZOLE
• 2,2'-DICHLOROBENZILIC ACID
• [2-(2,4-DICHLOROPHENYL)-[1,3]DIOXOLAN-2-YL]METHANOL
• Losigamone
• cis-[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl-4-methylbenzenesulphonate
• (1S)-1-(2-CHLOROPHENYL)ETHANE-1,2-DIOL
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