86939-10-8

Basic information

• Product Name: (1R,3S)-REL-3-(3,4-DICHLOROPHENYL)-2,3-DIHYDRO-N-METHYL-1H-INDEN-1-AMINE HYDROCHLORIDE
• Synonyms: Indatraline;IndatralineHCl;(1R)-1α-Methylamino-2,3-dihydro-3β-(3,4-dichlorophenyl)-1H-indene;( -)-trans-3-(3,4-Dichlorophenyl)-N-methyl-1-indanamine;Indatralinum
• CAS NO: 86939-10-8
• Molecular Formula: C16H16Cl3N
• Molecular Weight: 328.66
• Mol File: 86939-10-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 398.3°Cat760mmHg
• Flash Point: 194.7°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 1.49E-06mmHg at 25°C
• Storage Temp.: Desiccate at RT
• CAS DataBase Reference: (1R,3S)-REL-3-(3,4-DICHLOROPHENYL)-2,3-DIHYDRO-N-METHYL-1H-INDEN-1-AMINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3S)-REL-3-(3,4-DICHLOROPHENYL)-2,3-DIHYDRO-N-METHYL-1H-INDEN-1-AMINE HYDROCHLORIDE(86939-10-8)
• EPA Substance Registry System: (1R,3S)-REL-3-(3,4-DICHLOROPHENYL)-2,3-DIHYDRO-N-METHYL-1H-INDEN-1-AMINE HYDROCHLORIDE(86939-10-8)

Safety Data

• Hazardous Substances Data: 86939-10-8(Hazardous Substances Data)

Usage

Biological Activity

Potent monoamine uptake inhibitor. Inhibits transporters for 5-HT (SERT), dopamine (DAT) and noradrenalin (NET) (K i values are 0.42, 1.7 and 5.8 nM respectively). Centrally active following systemic administration in vivo .

InChI:InChI=1/C16H15Cl2N.ClH/c1-19-16-9-13(11-4-2-3-5-12(11)16)10-6-7-14(17)15(18)8-10;/h2-8,13,16,19H,9H2,1H3;1H/t13-,16+;/m0./s1

Upstream product

• 593-51-1 methylamine hydrochloride 
• 85662-98-2 3-(3',4'-dichlorophenyl)-indan-1-one 
• 95-50-1 1,2-dichloro-benzene 
• 113093-58-6 C₁₇H₁₆Cl₂O₂ 
• 203317-12-8 2-Cyano-3-(3,4-dichloro-phenyl)-3-phenyl-propionic acid ethyl ester 
• 2025-40-3 ethyl benzylidenecyanoacetate 
• 7312-27-8 3,4-Dichlorocinnamic acid 
• 80272-06-6 3-(3',4'-dichlorophenyl)-3-phenylpropanoic acid 
• 71-43-2 benzene 
• 100-52-7 benzaldehyde 
• 74-89-5 methylamine 
• 2142-69-0 2-bromophenyl methyl ketone 
• 6287-38-3 3,4-dichlorobenzaldehyde 
• 1338922-82-9 (1R,3S)-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-ol 

Relevant articles and documents

Asymmetric synthesis of (+)-indatraline using rhodium-catalyzed C-H activation

The potent monoamine reuptake inhibitor (+)-indatraline, 1, was prepared in greater than 98% ee employing a highly enantioselective carbenoid C-H insertion reaction into 1,4-cyclohexadiene catalyzed by the chiral rhodium complex, Rh2(S-DOSP)4.

Efficient kinetic resolution in the asymmetric transfer hydrogenation of 3-aryl-indanones: Applications to a short synthesis of (+)-indatraline and a formal synthesis of (R)-tolterodine

Efficient kinetic resolution (KR) occurs in asymmetric transfer hydrogenation (ATH) reactions of racemic 3-aryl-1-indanones using commercial (R,R)- or (S,S)-Ts-DENEB as a catalyst, a 1?:?5 mixture of HCO2H and Et3N as a hydrogen source and MeOH as solvent

Asymmetric Hydroarylation of Enones via Nickel-Catalyzed 5- Endo-Trig Cyclization

A nickel-catalyzed reductive cyclization of enones affords a wide array of indanones in high enantiomeric induction. The reaction is featured with an unprecedented broad scope of substrates. The versatility of the new method is demonstrated in several short stereoselective syntheses of medically valuable (R)-tolterodine, parent and deuterated (+)-indatraline, and an antitumor natural product, (+)-multisianthol. In comparison, these compounds cannot be prepared satisfactorily via analogous processes catalyzed by palladium.