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3'-Chloropropiophenone Basic information

Product Name:3'-Chloropropiophenone

Synonyms:3-CHLOROPHENYL ETHYL KETONE;(3-CHLOROPHENYL)PROPAN-1-ONE;M-CHLOROPROPIOPHENONE;MCPP;1-(3-CHLOROPHENYL)-1-PROPANONE;3-CHLORO-1-PHENYL-PROPANONE;3-CHLOROPROPIOPHENONE M-CHLORO PROPIOPHENONE;3-Chloro-Propiophenone(M-ChloroProiophenone)

CAS:34841-35-5

MF:C9H9ClO

MW:168.62

EINECS:252-242-3

Product Categories:C9;Carbonyl Compounds;Aromatic Propiophenones (substituted);Aromatic Ketones (substituted);Aromatic Halides (substituted);Ketones

Mol File:34841-35-5.mol

3'-Chloropropiophenone Structure

3'-Chloropropiophenone Chemical Properties

Melting point45-47 °C(lit.)

Boiling point124 °C14 mm Hg(lit.)

density1.1115 (rough estimate)

refractive index1.5350 (estimate)

Fp>230 °F

storage temp.Sealed in dry,Room Temperature

solubilitySoluble in methanol.

formCrystalline Solid

colorWhite to light yellow

InChIKeyPQWGFUFROKIJBO-UHFFFAOYSA-N

CAS DataBase Reference34841-35-5(CAS DataBase Reference)

Safety Information

Hazard CodesXi

Risk Statements36/37/38

Safety Statements37/39-26-24/25

WGK Germany3

HS Code29147000

MSDS Information

ProviderLanguage

1-(3-Chlorophenyl)-1-propanoneEnglish

SigmaAldrichEnglish

ACROSEnglish

ALFAEnglish

3'-Chloropropiophenone Usage And Synthesis

DescriptionInfluence of solvents and temperature on the yield and enantioselectivity of the phenylation of 3′-chloropropiophenone has been investigated.

Chemical PropertiesWHITE TO LIGHT YELLOW CRYSTALLINE SOLID

Uses3'-Chloropropiophenone is a reagent used in the vinylation, alkylation and dienylation of ketones. It is also used in the preparation of thizaine derivatives that show antibacterial activity.

Uses3'-Chloropropiophenone has been used in the preparation of 1-(3-chlorophenyl)-1-phenyl-1-propanol.

Application3′-Chloropropiophenone can be used as a reactant to synthesize:

(S)-3-chloro-1-phenylpropanol via bio-catalyzed asymmetric reduction method.

1-(3-Chlorophenyl)-1-phenyl-1-propanol by phenylation with diphenylzinc in the presence of dihydroxy bis(sulfonamide) ligand.

(S)-Dapoxetine, a selective serotonin reuptake inhibitor.

Preparation4.86 g (0.2 mol) of magnesium turnings, 30 ml of dry diethyl ether and a grain of iodine are placed in a one liter three-necked round-bottomed flask equipped with a condenser, a calcium chloride drying tube, a pressure equalizing funnel and a magnetic stirrer; the flask is purged with nitrogen, and 21.8 g (0.2 mol) of ethyl bromide in 30 ml of dry diethyl ether are then added. The mixture is then heated under reflux for one hour and left to cool. At ambient temperature, 16.51 g (0.12 mol) of 3-chlorobenzonitrile in 70 ml of dry diethyl ether are then added. A copious precipitate forms. The mixture is stirred overnight at ambient temperture and then cooled in an ice bath and hydrolysed by slowly adding 50 ml of water and then about 100 ml of 6N hydrochloric acid until the pH is acid. The mixture is stirred for one and a half hours and then extracted with ethyl acetate. The organic extract is then washed twice with water, dried and concentrated on a rotary evaporator. This gives 26 g of an orange oil, which is concentrated in vacuo to give about 18.2 g of ochre crystals of 3'-chloropropiophenone melting at about 40° C.

Literature source US04690931

General Description

Influence of solvents and temperature on the yield and enantioselectivity of the phenylation of 3′-chloropropiophenone has been investigated.

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Davy Lee

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