796-77-0

Basic information

• Product Name: 4-[2-(diethylamino)ethoxy]benzophenone
• Synonyms: 4-[2-(diethylamino)ethoxy]benzophenone;N,N-Diethyl-2-(p-benzoylphenoxy)ethylamine;[4-[2-(DiethylaMino)ethoxy]phenyl]phenyl-Methanone;4-(β-DiethylaMinoethoxy)benzophenone
• CAS NO: 796-77-0
• Molecular Formula: C₁₉H₂₃NO₂
• Molecular Weight: 297.39142
• EINECS: 212-348-2
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 796-77-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 430.1°C at 760 mmHg
• Flash Point: 213.9°C
• Appearance: /
• Density: 1.057g/cm³
• Vapor Pressure: 1.33E-07mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Soluble), Dicloromethane (Slightly), Methanol (Sparingly)
• PKA: 9.50±0.25(Predicted)
• CAS DataBase Reference: 4-[2-(diethylamino)ethoxy]benzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[2-(diethylamino)ethoxy]benzophenone(796-77-0)
• EPA Substance Registry System: 4-[2-(diethylamino)ethoxy]benzophenone(796-77-0)

Safety Data

• Hazardous Substances Data: 796-77-0(Hazardous Substances Data)

Usage

Chemical Properties

Orange Oil

Uses

4-[2-(diethylamino)ethoxy]benzophenone is used in the preparation of antifertility agents.

InChI:InChI=1/C19H23NO2/c1-3-20(4-2)14-15-22-18-12-10-17(11-13-18)19(21)16-8-6-5-7-9-16/h5-13H,3-4,14-15H2,1-2H3

Synthetic route

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 4-Hydroxybenzophenone (1137-42-4) → 4-[2-(N,N-diethylamino)ethoxy]benzophenone (796-77-0)

Conditions	Yield
With potassium carbonate In acetone for 6h; Heating;	97%
With tetrabutylammomium bromide In acetone at 30 - 40℃; for 4.16667h;	8.32 g

2-(diethylamino)ethyl chloride (100-35-6) + 4-Hydroxybenzophenone (1137-42-4) → 4-[2-(N,N-diethylamino)ethoxy]benzophenone (796-77-0)

Conditions	Yield
(i) Na, (ii) /BRN= 605300/; Multistep reaction;

4-[2-(N,N-diethylamino)ethoxy]benzophenone (796-77-0) → C19H24(2)HNO2

Conditions	Yield
With water-d2; magnesium; ethylene dibromide In tetrahydrofuran at 70℃; for 2h; Inert atmosphere; Schlenk technique;	51%
With water-d2; magnesium; ethylene dibromide In tetrahydrofuran	51%

p-benzyloxybenzaldehyde (4397-53-9) + 4-[2-(N,N-diethylamino)ethoxy]benzophenone (796-77-0) → 1-<-4-<2-(diethylamino)ethoxy>phenyl>-1-phenyl-2-<(4-benzyloxy)phenyl>-2-hydroxyethene (117095-62-2)

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran 1) reflux, 2 h, 2) r.t.;	49%

benzyl ethyl ketone (1007-32-5) + 4-[2-(N,N-diethylamino)ethoxy]benzophenone (796-77-0) → 2-benzyl-1-phenyl-1-[4-(diethylaminoethoxy)phenyl]but-1-ene

Conditions	Yield
With titanium tetrachloride; zinc In 1,4-dioxane for 4h; Heating;	40%

3-methoxy-4-(phenylmethoxy)benzaldehyde (2426-87-1) + 4-[2-(N,N-diethylamino)ethoxy]benzophenone (796-77-0) → 1-<4-<2-(diethylamino)ethoxy>phenyl>-1-phenyl-2-hydroxy-2-<3-methoxy-4-(benzyloxy)phenyl>ethene (117095-63-3)

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran 1) reflux, 2 h, 2) r.t.;	36%

4-[2-(N,N-diethylamino)ethoxy]benzophenone (796-77-0) + vinylmagnesium chloride (3536-96-7) → 1-[4-(2-Diethylamino-ethoxy)-phenyl]-1-phenyl-prop-2-en-1-ol (56431-04-0)

Conditions	Yield
In tetrahydrofuran

4-[2-(N,N-diethylamino)ethoxy]benzophenone (796-77-0) + ethylmagnesium bromide (925-90-6) → 4-(β-diethylaminoethoxy)-α-ethyl-benzhydrol (56431-20-0)

Conditions	Yield
In diethyl ether

Dimethyl 1-Chloro-1-phenylmethanephosphonate (16965-75-6) + 4-[2-(N,N-diethylamino)ethoxy]benzophenone (796-77-0) → clomiphene (911-45-5)

Conditions	Yield
With tert.-butyl lithium 1.) THF/pentane, -78 deg C, 30 min; 2.) THF, reflux; Yield given. Multistep reaction;

ethyl bromide (74-96-4) + 4-[2-(N,N-diethylamino)ethoxy]benzophenone (796-77-0) → 4-(β-diethylaminoethoxy)-α-ethyl-benzhydrol (56431-20-0)

Conditions	Yield
With magnesium
With magnesium

Upstream product

• 869-24-9 2-chloro-N,N-diethylethylamine hydrochloride 
• 1137-42-4 4-Hydroxybenzophenone 
• 100-35-6 2-(diethylamino)ethyl chloride 

Downstream Products

• 56431-20-0 4-(β-diethylaminoethoxy)-α-ethyl-benzhydrol 
• 117095-62-2 1-<-4-<2-(diethylamino)ethoxy>phenyl>-1-phenyl-2-<(4-benzyloxy)phenyl>-2-hydroxyethene 
• 117095-63-3 1-<4-<2-(diethylamino)ethoxy>phenyl>-1-phenyl-2-hydroxy-2-<3-methoxy-4-(benzyloxy)phenyl>ethene 
• 911-45-5 clomiphene 
• 56431-04-0 1-[4-(2-Diethylamino-ethoxy)-phenyl]-1-phenyl-prop-2-en-1-ol 

Relevant articles and documents

Alkylating method of 4-hydroxybenzophenone

The invention discloses an alkylating method of 4-hydroxybenzophenone. The method is characterized in that an alkylating agent and 4-hydroxybenzophenone are alkylated in the presence of anion exchangeresin and phase transfer catalyst; then simple post-processing is carried out after reaction so as to obtain the high-yield and high-purity target product. According to the method, the reaction system is capable of improving the alkylating reaction performance through the anion exchange resin and the phase transfer catalyst, so that the byproducts are greatly decreased while the reaction is spedup, and as a result, the difficulty in post-processing and purifying can be reduced, and an alkylating product whose purity is 99% or more can be obtained through simple post-processing. With the adoption of the method, the problems of column chromatography and purifying, long reaction time and low yield in the prior art can be solved; the method is applicable to industrial production. The formulais shown in the description.

HYPOCHOLESTEREMIC AGENTS. 3. BASIC CARBINOLS AND RELATED COMPOUNDS.

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