(1R)-3-Chloro-1-phenyl-propan-1-ol Chemical Properties

Melting point:

58-60 °C (lit.)

Boiling point:

296.4±20.0 °C(Predicted)

alpha 

26 º (c=1, chloroform)

Density 

1.149±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

13.92±0.20(Predicted)

form 

Powder

color 

White to yellow

optical activity

[α]24/D +26°, c = 1 in chloroform

BRN 

5250766

InChI

InChI=1/C9H11ClO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5,9,11H,6-7H2/t9-/s3

InChIKey

JZFUHAGLMZWKTF-SECBINFHSA-N

SMILES

[C@@H](C1C=CC=CC=1)(O)CCCl |&1:0,r|

CAS DataBase Reference

100306-33-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29062990

MSDS

• Language:English Provider:SigmaAldrich

(1R)-3-Chloro-1-phenyl-propan-1-ol Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

Intermediate in the preparation of (S)-Norfluoxetine

Uses

(R)-(+)-3-Chloro-1-phenyl-1-propanol may be used as a building block in the synthesis of antidepressants such as (R)- and (S)-tomoxetine, fluoxetine and nisoxetine. It may also be used in the synthesis of biologically active 2-substituted chromans such as tephrowatsin E.

Synthesis

Step 1: To a dry flask was added (S)-(-)-α,α-diphenylprolinol (0.30 g, 1.19 mmol) and anhydrous toluene (7 mL). The reaction system was placed under a nitrogen atmosphere by evacuating and displacing three times with nitrogen. A solution of borane tetrahydrofuran complex [BH3?THF; 1 M solution of THF] stabilized with 5 mM NaBH4 (0.35 mL, 3.56 mmol) was added slowly and dropwise at 30 °C, followed by stirring the clarified solution for 30 min. Step 2: To the above stirred solution was added a solution of anhydrous toluene (1 mL) of 3-chloro-1-phenylpropan-1-one (1 g, 5.93 mmol). The reaction mixture was stirred at room temperature for 15 min before BH3?THF (6 mL, 61.44 mmol) was added within 3 min. After continued stirring for 9 min, the reaction flask was cooled in an ice bath, the reaction was quenched sequentially with methanol (10 mL), isopropanol (10 mL), and hydrochloric acid (3 mL), and filtered through a pad of diatomaceous earth. The filtrate was concentrated to dryness and the product was crystallized from hexane to give (R)-(+)-3-chloro-1-phenyl-1-propanol as a white fluffy solid (4.91 g). Yield: 97%; Melting point: 57-59°C; [α]D25 = +25.7° (c 1, CHCl3); 1H NMR (400 MHz, CDCl3): δ 2.07-2.16 (m, 2H), 2.20-2.32 (m, 1H), 3.51-3.62 (m, 1H), 3.71-3.80 (m, 1H), 4.91 -4.98 (m, 1H), 7.37-7.43 (m, 5H); 13C NMR (400 MHz, CDCl3): δ 41.45, 41.73, 71.34, 125.80, 127.94, 128.69, 143.71; MS (EI+) m/z: 170 [M+], 172 [M+2], relative intensity ratio ca. is 3:1.

References

[1] Tetrahedron Letters, 1989, vol. 30, # 39, p. 5207 - 5210
[2] Synthetic Communications, 2009, vol. 39, # 15, p. 2737 - 2746
[3] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 3, p. 431 - 435
[4] Chemical Communications, 2015, vol. 51, # 26, p. 5725 - 5727
[5] European Journal of Medicinal Chemistry, 2016, vol. 109, p. 157 - 172

(1R)-3-Chloro-1-phenyl-propan-1-ol(100306-33-0)Related Product Information

• 3-Phenyl-1-propanol
• PHENYL VALERATE
• Diphenyl ether
• Phenyl salicylate
• Chlorphenamine maleate
• Dextran
• Isopropyl alcohol
• PROPYL-D7 ALCOHOL
• Triphenylmethyl Chloride
• tert-Butylchlorodiphenylsilane
• 1-Chloro-2-propanol
• 3-Chloro-1-propanol
• 4-Chlorophenyl isocyanate
• Iron-dextran
• Propane
• 3'-Chloropropiophenone
• Chlorodimethylphenylsilane
• CHLOROPHENYLSILANE