911-45-5

Name	Clomifene
CAS	911-45-5
EINECS(EC#)	213-008-6
Molecular Formula	C26H28ClNO
MDL Number	MFCD00599444
Molecular Weight	405.96
MOL File	911-45-5.mol

Chemical Properties

Melting point	117.25°C
Boiling point	509.0±50.0 °C(Predicted)
density	1.0166 (rough estimate)
refractive index	1.5790 (estimate)
storage temp.	Amber Vial, -20°C Freezer
solubility	Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form	Solid
pka	9.54±0.25(Predicted)
color	White to Pale Yellow
NIST Chemistry Reference	Clomiphene(911-45-5)
EPA Substance Registry System	Ethanamine, 2-[4-(2-chloro-1,2-diphenylethenyl) phenoxy]-N,N-diethyl-(911-45-5)

Safety Data

Hazardous Substances Data

911-45-5(Hazardous Substances Data)

Hazard Information

Originator

Clomid,Lepetit,Italy,1966

Uses

Antiestrogen.

Definition

ChEBI: Zuclomifene is a stilbenoid.

Indications

Clomifene acts by enhancing follicular growth caused by ovulation. The primary indication for using clomifene is induction of ovulation in non-ovulating women who still have some estrogen production.

Manufacturing Process

A mixture of 20 g of 1-[p-(β-diethylaminoethoxy)phenyl]-1,2-diphenylethanol in 200 cc of ethanol containing an excess of hydrogen chloride was refluxed 3 hours. The solvent and excess hydrogen chloride were removed under vacuum, and the residue was dissolved in a mixture of ethyl acetate and methylene chloride. 1-[p-(β-diethylaminoethoxy)phenyl]-1,2-diphenylethylene hydrochloride was obtained, melting at 148° to 157°C. This hydrochloride salt was treated with N-chlorosuccinimide in dry chloroform under reflux. The product then obtained was converted to the free base and treated with citric acid. The dihydrogen citrate salt of 1-[p-(β-diethylaminoethoxy)phenyl]-1,2- diphenylchloroethylene was obtained, melting at 116.5° to 118°C.
The intermediate 1-[p-(β-diethylaminoethoxy)phenyl]-1,2-diphenylethanol was obtained by treating 4-(β-diethylaminoethoxy)benzophenone with benzylmagnesium chloride. It melted at 95° to 96°C.

Brand name

Clomid (Sanofi Aventis); Serophene (Serono).

Therapeutic Function

Antiestrogen

Synthesis

Clomifene, 2-[p-(2-chloro-1,2-diphenylvinyl)phenoxy]triethylamine (28.2.4), is synthesized from 4-hydroxybenzophenone by reacting it with 2-diethylaminoethylchloride in the presence of an alkali, which gives 4-(2-diethylaminoethoxy)benzophenone (28.2.1). This is reacted with benzylmagnesium chloride in a Grignard reaction, forming as a result the corresponding carbinol (28.2.2). Dehydrating this with hydrogen chloride gives 2-[p-(1,2-diphenylvinyl) phenoxy]triethylamine (28.2.4), the vinylic hydrogen atom of which is replaced with a chlorine atom using N-chlorosuccinimide, giving clomifene (28.2.4) .

Synthesis_911-45-5

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