73404-00-9

Basic information

• Product Name: alpha-[4-[2-(diethylamino)ethoxy]phenyl]-alpha-phenylphenethyl alcohol
• Synonyms: alpha-[4-[2-(diethylamino)ethoxy]phenyl]-alpha-phenylphenethyl alcohol;1-(4-(2-(Diethylamino)ethoxy)phenyl)-1,2-diphenylethanol;α-(4-(2-(Diethylamino)ethoxy)phenyl)-phenylbenzeneethanol;1-[p-[2-(N,N-Diethylamino)ethoxy]phenyl]-1,2-diphenylethanol;α-[4-[2-(diethylamino)ethoxy]phenyl]-α-phenylphenethyl alcohol;1-(4-(2-(diethylamino)ethoxy)phenyl)-1,2-diphenylethan-1-ol;alpha-[4-[2-(Diethylamino)ethoxy]phenyl]-alpha-phenylbenzeneethanol
• CAS NO: 73404-00-9
• Molecular Formula: C₂₆H₃₁NO₂
• Molecular Weight: 389.52984
• EINECS: 277-461-1
• Product Categories: API
• Mol File: 73404-00-9.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 512.6°C at 760 mmHg
• Flash Point: 263.8°C
• Appearance: /
• Density: 1.087g/cm³
• Vapor Pressure: 2.49E-11mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: 2-8°C
• CAS DataBase Reference: alpha-[4-[2-(diethylamino)ethoxy]phenyl]-alpha-phenylphenethyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-[4-[2-(diethylamino)ethoxy]phenyl]-alpha-phenylphenethyl alcohol(73404-00-9)
• EPA Substance Registry System: alpha-[4-[2-(diethylamino)ethoxy]phenyl]-alpha-phenylphenethyl alcohol(73404-00-9)

Safety Data

• Hazardous Substances Data: 73404-00-9(Hazardous Substances Data)

Usage

General Description

Alpha-[4-[2-(diethylamino)ethoxy]phenyl]-alpha-phenylphenethyl alcohol, also known as phenoxybenzamine, is a chemical compound that is used as an alpha blocker medication. It works by blocking the action of adrenaline on certain receptors in the body, leading to relaxation of smooth muscle and dilation of blood vessels. This can be beneficial in conditions such as high blood pressure, certain types of heart disease, and certain endocrine tumors. Phenoxybenzamine is also used off-label for the treatment of conditions such as Raynaud's syndrome and complex regional pain syndrome. It is often administered orally or intravenously under medical supervision and can have side effects such as low blood pressure, dizziness, and drowsiness. Overall, phenoxybenzamine is an important medication in the management of various medical conditions.

InChI:InChI=1/C26H31NO2/c1-3-27(4-2)19-20-29-25-17-15-24(16-18-25)26(28,23-13-9-6-10-14-23)21-22-11-7-5-8-12-22/h5-18,28H,3-4,19-21H2,1-2H3

Synthetic route

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → 2-{4-[(Z)-1,2-diphenylvinyl]phenoxy}-N,N-diethylethanaminium hydrogen sulfate

Conditions	Yield
With sulfuric acid In dichloromethane at 0 - 20℃; for 1h;	100%

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → clomiphene citrate (7599-79-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sulfuric acid / dichloromethane / 1 h / 0 - 20 °C 2.1: N-chloro-succinimide / dichloromethane / 32 h / 20 °C 2.2: 0.5 h / 20 °C / pH 8 - 9 3.1: methanol / 2 h / 20 °C 4.1: ammonia / ethyl acetate 4.2: 1 h / 20 °C View Scheme

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → clomiphene (911-45-5, 15690-55-8, 15690-57-0) + Zuclomiphene (911-45-5, 15690-55-8, 15690-57-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethanol / 3 h / 50 °C / Reflux 2.1: N-chloro-succinimide / dichloromethane / 20 h / 20 °C 2.2: 0.5 h / 20 °C View Scheme

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → 2-{4-[(Z)-1,2-diphenylvinyl]phenoxy}-N,N-diethylethanaminium hydrochloride

Conditions	Yield
With hydrogenchloride In ethanol at 50℃; for 3h; Reflux;

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → clomiphene (911-45-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / dichloromethane / 1 h / 0 - 20 °C 2.1: N-chloro-succinimide / dichloromethane / 32 h / 20 °C 2.2: 0.5 h / 20 °C / pH 8 - 9 View Scheme

1-{4-[2-(diethylamino)ethoxy]phenyl}-1,2-diphenylethanol (73404-00-9) → ethanamine, 2-[4-[(1E)-2-chloro-1,2-diphenyl ethenyl]phenoxy]-N,N-diethyl-, (±)-1,1‘-binaphthyl-2,2’-diylhydrogenphosphate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / dichloromethane / 1 h / 0 - 20 °C 2.1: N-chloro-succinimide / dichloromethane / 32 h / 20 °C 2.2: 0.5 h / 20 °C / pH 8 - 9 3.1: methanol / 2 h / 20 °C View Scheme

Downstream Products

• 911-45-5 clomiphene 
• 74056-26-1 2-{4-[(Z)-1,2-diphenylvinyl]phenoxy}-N,N-diethylethanaminium hydrochloride 
• 911-45-5 clomiphene 
• 911-45-5 Zuclomiphene 
• 7599-79-3 clomiphene citrate