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HomeProduct name list3'-Chloropropiophenone

3'-Chloropropiophenone

  • CAS NO.:34841-35-5
  • Empirical Formula: C9H9ClO
  • Molecular Weight: 168.62
  • MDL number: MFCD00009925
  • EINECS: 252-242-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-11 17:44:06
3'-Chloropropiophenone Structural

What is 3'-Chloropropiophenone?

Description

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

Chemical properties

WHITE TO LIGHT YELLOW CRYSTALLINE SOLID

The Uses of 3'-Chloropropiophenone

3'-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.

The Uses of 3'-Chloropropiophenone

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

What are the applications of Application

3′-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.

Preparation

4.86 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

Properties of 3'-Chloropropiophenone

Melting point: 45-47 °C(lit.)
Boiling point: 124 °C14 mm Hg(lit.)
Density  1.1115 (rough estimate)
refractive index  1.5350 (estimate)
Flash point: >230 °F
storage temp.  Sealed in dry,Room Temperature
solubility  Soluble in methanol.
form  Crystalline Solid
color  White to light yellow
InChI InChI=1S/C9H9ClO/c1-2-9(11)7-4-3-5-8(10)6-7/h3-6H,2H2,1H3
CAS DataBase Reference 34841-35-5(CAS DataBase Reference)

Safety information for 3'-Chloropropiophenone

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for 3'-Chloropropiophenone

InChIKey PQWGFUFROKIJBO-UHFFFAOYSA-N
SMILES C(C1=CC=CC(Cl)=C1)(=O)CC

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