82769-76-4

Basic information

• Product Name: (S)-3-Amino-3-phenylpropan-1-ol
• Synonyms: (S)-3-AMINO-3-PHENYLPROPAN-1-OL;(S)-1-PHENYL-3-PROPANOLAMINE;(S)-BETA-PHENYLALANINOL;(S)-3-Amino-3-phenylpropan-1-ol(e.e.);(S)-3-Amino-3-phenylpropan-1-ol, 98% ee, 95%;(S)-3-PHENYL-BETA-ALANINOL ;(S)-3-Amino-3-phenylpropanol;(S)-3-Amino-3-phenylpropan-1-ol, 95%, ee:98%
• CAS NO: 82769-76-4
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• EINECS: 1312995-182-4
• Product Categories: Alcohol Aldehyde & acid series
• Mol File: 82769-76-4.mol
• Article Data: 45

Chemical Properties

• Melting Point: 68-69 °C
• Boiling Point: 273.23°C (rough estimate)
• Flash Point: 131 °C
• Appearance: Colorless or white/Viscous Liquid or Low Melting Solid
• Density: 1.0406 (rough estimate)
• Vapor Pressure: 9.47E-05mmHg at 25°C
• Refractive Index: 1.4755 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 14.90±0.10(Predicted)
• CAS DataBase Reference: (S)-3-Amino-3-phenylpropan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Amino-3-phenylpropan-1-ol(82769-76-4)
• EPA Substance Registry System: (S)-3-Amino-3-phenylpropan-1-ol(82769-76-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-26
• RIDADR: 3259
• HazardClass: 8
• PackingGroup: Ⅲ
• Hazardous Substances Data: 82769-76-4(Hazardous Substances Data)

Usage

Chemical Properties

colorless viscous liquid or

Uses

(S)-3-Amino-3-phenylpropan-1-ol is a useful intermediate for the synthesis of dapoxetine.

InChI:InChI=1/C9H13NO.ClH/c10-9(6-7-11)8-4-2-1-3-5-8;/h1-5,9,11H,6-7,10H2;1H/t9-;/m0./s1

Upstream product

• 6335-76-8 3-amino-3-phenylpropionic acid ethyl ester 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 281681-23-0 1-acetoxy-3-acetylamino-3-phenylpropane 
• 86260-84-6 5-ethoxy-3-phenyl-4,5-dihydroisoxazole 
• 14397-33-2 3-phenyl-2-isoxazoline 
• 98748-93-7 3-trimethylsiloxy-1-phenylpropyl isocyanide 
• 81548-17-6 N-(3-hydroxy-1-phenylpropyl)acetamide 
• 81548-21-2 2-vinyl-4-phenyl-4H-5,6-dihydro-1,3-oxazine 
• 772-00-9 4-phenyl-1,3-dioxane 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 14898-52-3 methyl 3-amino-3-phenylpropanoate 
• 5650-41-9 3-hydroxy-1-phenylpropan-1-one 
• 4436-23-1 2-phenyloxetane 
• 81548-15-4 2-Methyl-4-phenyl-5,6-dihydro-4H-[1,3]oxazine 

Downstream Products

• 102877-48-5 3-amino-3-phenyl-propionaldehyde 
• 903635-44-9 trans-4-phenylcyclophosphamide 
• 68208-27-5 (2RS,4SR)-2--4-phenyl-2H-1,3,2-oxazaphosphorinane 2-oxide 
• 292140-03-5 (+/-)-2-[2-(diphenylphosphino)phenyl]-5,6-dihydro-4-phenyl-4H-1,3-oxazine 
• 281681-23-0 1-acetoxy-3-acetylamino-3-phenylpropane 
• 499193-75-8 3-[N-(2-bromo-3-methyl-2-butenyl)amino]-3-phenylpropan-1-ol 
• 499193-70-3 3-[N-(2-bromo-2-propenyl)amino]-3-phenylpropan-1-ol 
• 218449-48-0 (3-hydroxy-1-phenylpropyl)carbamate tert-butyl ester 
• 82769-75-3 (S)-(+)-3-(dimethylamino)-3-phenyl-1-propanol 
• 81548-17-6 N-(3-hydroxy-1-phenylpropyl)acetamide 
• 888298-12-2 3-amino-O-tert-butyldimethylsilyl-3-phenylpropan-1-ol 

Relevant articles and documents

Synthesis method of dapoxetine

The present invention provides a synthesis method of dapoxetine, comprising the following steps: S1, the (s)-3-amino-3-phenylpropionic acid or ester compounds dispersed in a solvent, reflux reaction under the action of a reducing agent, to give (s) - amino-3-phenylpropanol; S2, the (s) - amino-3-phenylpropanol dissolved in aqueous solution of carboxylic acid, added paraformaldehyde to warm up the reaction, to give (s) -3-dimethylamino-3-phenylpropanol; S3, (s)-3-Dimethylamino-3-phenylpropanol was dissolved in a solvent, protected by nitrogen, and reacted in a solution of alkali added dropwise at a higher temperature, and then 1-fluoronaphthalene was added to produce Williamson etherization reaction, to give (s)-N, N-dimethyl-3-(1-naphthooxy) amphetamine, i.e., dapoxetine. The synthesis method of dapoxetine of the present invention is inexpensive and easy to obtain raw materials, does not use toxic and dangerous reagents, will not react to the phenomenon of aggregation spray, the process is simple, suitable for industrial production.

Synthetic method of dapoxetine and intermediate thereof

The invention discloses a synthetic method of dapoxetine and its intermediate, i.e., (S)-3-(tert-butyloxycarbonyl)amino-3-phenylpropanol as shown in a formula 5 which is described in the specification. The synthetic method of (S)-3-(tert-butyloxycarbonyl)amino-3-phenylpropanol is as shown in a synthesis route which is described in the specification, wherein a compound 3 and acetaldehyde are subjected to a Mannich reaction in an organic solvent under the action of a supramolecular catalyst constructed by a chiral catalyst and a polymer so as to obtain a compound 4, and the polymer is at least one selected from of the group consisting of PEG 200, PEG 400, PEG 600, MeOPEG 750, PEG 800, PEG 1000, PPG 800 and PPG 1000. The dapoxetine is synthesized from the (S)-3-(tert-butyloxycarbonyl)amino-3-phenylpropanol prepared by using the above method according to steps as shown in the synthesis route. The synthetic method of dapoxetine and the intermediate thereof has the characteristics of usage of cheap and easily available raw materials, high yield and low cost, and is more beneficial to industrial production.

Method for preparing amino alcohol compound by using halogenated intermediate

The invention discloses a method for preparing an amino alcohol compound by utilizing a halogenated intermediate. According to the method, an oxygen-halogen bond can be prepared by utilizing cyclic diacyl peroxide and halogenated salt under an illumination condition, and the oxygen-halogen bond is prone to homolysis under an illumination condition to form an active free radical, so the amino alcohol is finally prepared. The novel method for synthesizing the amino alcohol is high in atom utilization rate, simple in synthesis method and high in yield, so the consumption of halide for reactions with synthesis values is reduced, and the purposes of environmental protection and green chemistry are better achieved.