p-(phenylthio)benzyl alcohol

p-(phenylthio)benzyl alcohol Property

Melting point:

46-48°C

Boiling point:

390.2±25.0 °C(Predicted)

Density 

1.21±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

14.26±0.10(Predicted)

color 

Pale Beige to Light Beige

InChI

InChI=1S/C13H12OS/c14-10-11-6-8-13(9-7-11)15-12-4-2-1-3-5-12/h1-9,14H,10H2

InChIKey

PGOAWMRWDZJQTB-UHFFFAOYSA-N

SMILES

C1(CO)=CC=C(SC2=CC=CC=C2)C=C1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

p-(phenylthio)benzyl alcohol Chemical Properties,Usage,Production

Chemical Properties

Pale Beige Solid

Uses

An impurity of Fenticonazole nitrate (F279250), a new potent antimycotic compound.

Synthesis

The general procedure for the synthesis of p-phenylthiobenzyl alcohol from 4-phenylthiobenzaldehyde: 4-phenylthiobenzaldehyde and methanol were added to a reaction flask, and sodium borohydride was added in batches under stirring conditions, and the reaction mixture was naturally warmed up to 55 °C due to exotherm. The reaction was monitored by thin-layer chromatography (Expanding Agent: hexane/ethyl acetate=10:1) and took about 1 hour to complete. At the end of the reaction, the pH was adjusted to 6 by dropwise addition of hydrochloric acid and the reaction mixture was filtered. The filtrate was concentrated to dryness under reduced pressure (pressure 1330 Pa, temperature 45 °C) and methanol was recovered to give a viscous residue. To the residue was added an appropriate amount of dichloromethane, and the resulting mixture was washed with water until neutral and then dried with anhydrous sodium sulfate. The dried mixture was filtered and the filtrate was concentrated under reduced pressure (pressure 1720 Pa, temperature 25°C) to recover methylene chloride. After the concentrate was cooled to room temperature, a light yellow solid product was precipitated.

References

[1] Journal of Medicinal Chemistry, 2006, vol. 49, # 17, p. 5217 - 5225
[2] Patent: CN107652238, 2018, A. Location in patent: Paragraph 0022; 0023
[3] Patent: CN107573288, 2018, A. Location in patent: Paragraph 0015; 0023
[4] Chemical Communications, 2009, # 7, p. 827 - 829
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3708 - 3712