(S)-3-Chloro-1-phenyl-1-propanol Chemical Properties

Melting point:

58-60 °C (lit.)

Boiling point:

296 °C

Density 

1.149

Flash point:

132 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Solid

pka

13.92±0.20(Predicted)

color 

White to Off-White

optical activity

[α]19/D 25°, c = 1 in chloroform

InChI

InChI=1S/C9H11ClO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5,9,11H,6-7H2/t9-/m0/s1

InChIKey

JZFUHAGLMZWKTF-VIFPVBQESA-N

SMILES

C1C=C([C@@H](O)CCCl)C=CC=1

CAS DataBase Reference

100306-34-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-38-37-36

Safety Statements 

26-37/39-39-37

WGK Germany 

3

HS Code 

29062990

MSDS

• Language:English Provider:SigmaAldrich

(S)-3-Chloro-1-phenyl-1-propanol Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(S)-(-)-3-Chloro-1-phenyl-1-propanol (cas# 100306-34-1) is a compound useful in organic synthesis.

Synthesis

The general procedure for the synthesis of (S)-(-)-3-chloro-1-phenyl-1-propanol from 3-chloropropiophenone was as follows: 3.36 g (40.0 mmol) of potassium formate (HCOOK) was used as a hydrogen source under argon protection, 2.609 mg (4.0 μmol) of Cp*IrCl[(S,S)-MsDPEN] was used as a catalyst, and 1.349 g (8.0 mmol) β-chloropropiophenone in a 20 mL Schlenk tube. 2 mL of water and 2 mL of toluene were added to the reaction system and the resulting mixture was stirred at 50 °C for 24 hours. Upon completion of the reaction, the organic phase was washed three times with 3 mL of water, followed by distillation under reduced pressure to remove toluene to give optically active (S)-(-)-3-chloro-1-phenyl-1-propanol. The optical purity of the product was confirmed by GC analysis to be 85% ee in 94% yield.

References

[1] Patent: US2009/62573, 2009, A1. Location in patent: Page/Page column 7; 14
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 6, p. 1009 - 1017
[3] Patent: KR2015/116956, 2015, A. Location in patent: Paragraph 0176-0179
[4] Patent: KR2016/44117, 2016, A. Location in patent: Paragraph 0063-0066
[5] Organic and Biomolecular Chemistry, 2011, vol. 9, # 10, p. 3854 - 3862

(S)-3-Chloro-1-phenyl-1-propanol(100306-34-1)Related Product Information

• Phenyl salicylate
• Chlorphenamine maleate
• L-carnitine
• 3-Phenyl-1-propanol
• 4-Chlorophenyl isocyanate
• 3-Chloro-1-propanol
• 1-Propanol
• Isopropyl alcohol
• Triphenylmethyl Chloride
• Levamisole
• tert-Butylchlorodiphenylsilane
• 1-Chloro-2-propanol
• PHENYL VALERATE
• Diphenyl ether
• Chlorodimethylphenylsilane
• 3'-Chloropropiophenone
• CHLOROPHENYLSILANE
• PHENYL RESIN