21966-60-9

Basic information

• Product Name: (R)-2-AMINOTETRALIN
• Synonyms: (R)-(+)-2-AMINOTETRALIN;(R)-2-AMINOTETRALIN;(2R)-Tetralin-2α-amine;(R)-1,2,3,4-Tetrahydronaphthalene-2-amine;[2R,(+)]-1,2,3,4-Tetrahydro-2-naphthalenamine;(R)-1,2,3,4-Tetrahydro-2-naphthylamine;(R)-1,2,3,4-Tetrahydro-naphthalen-2-ylaMine;(R)-1,2,3,4-Tetrahydronaphthalen-2-amine
• CAS NO: 21966-60-9
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.22
• Mol File: 21966-60-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 246-247°C
• Flash Point: >110°C
• Appearance: /
• Density: 1.023g/cm³
• Vapor Pressure: 0.0214mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: (R)-2-AMINOTETRALIN(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-AMINOTETRALIN(21966-60-9)
• EPA Substance Registry System: (R)-2-AMINOTETRALIN(21966-60-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 21966-60-9(Hazardous Substances Data)

Usage

General Description

(R)-2-aminotetralin is a chemical compound that belongs to the class of amines. It is a chiral molecule, meaning that it has a non-superimposable mirror image. (R)-2-AMINOTETRALIN has a tetralin backbone with an amino group attached to the second carbon atom. It has potential pharmacological properties and has been studied for its potential use in the treatment of various neurological and psychiatric disorders, such as Parkinson's disease and depression. (R)-2-aminotetralin is also used as a precursor in the synthesis of other organic compounds, particularly those with biological activity. Overall, (R)-2-aminotetralin is a versatile chemical with potential applications in both therapeutic and synthetic fields.

InChI:InChI=1/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2/t10-/m1/s1

Upstream product

• 2954-50-9 2-aminotetralin 
• 1384127-07-4 N-octanoyl dimethyl glycine trifluoroethyl ester 
• 1246472-55-8 benzyl(1,2,3,4-tetrahydronaphthalen-2-yl)amine 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 3852-09-3 methyl 3-methoxypropionate 
• 460740-17-4 (2S)-2-p-toluenesulphonyloxy-1,2,3,4-tetrahydronaphthalene 
• 530-91-6 (S)-2-tetralol 
• 57495-92-8 (1R,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol 
• 51268-88-3 (1R,2S)-1,2-dihydronaphthalene-1,2-diol 
• 460740-21-0 (2R)-2-azido-1,2,3,4-tetrahydronaphthalene 
• 61523-37-3 (R)-2-(1,2,3,4-Tetrahydro-naphthalen-2-yl)-isoindole-1,3-dione 
• 1262722-75-7 (S)-2-trifluoroacetylamino-1,2,3,4-tetrahydro-naphthalene 
• 591-50-4 iodobenzene 

Downstream Products

• 131813-62-2 N-[-(R)-1,2,3,4-tetrahydronaphth-2-yl]-(S)-2-hydroxy-3-(2-allylphenoxy)propanamine 

Relevant articles and documents

Amine Transaminase from Exophiala Xenobiotica - Crystal Structure and Engineering of a Fold IV Transaminase that Naturally Converts Biaryl Ketones

Amine transaminases are frequently used for the production of chiral amines starting from prochiral ketones. These amines can be applied as active pharmaceutical ingredients or drug precursors. However, there are still limitations to the use of amine transaminases when it comes to bulky ketone substrates, such as biaryl ketones. Using data mining, an (R)-selective amine transaminase from Exophiala xenobiotica was identified which naturally converts biaryl ketone substrates to the corresponding amines with up to 85% conversion and excellent enantioselectivity (>99% ee). Its protein crystal structure was obtained with a resolution of 1.52 ?, which enabled us to explain this interesting substrate acceptance. Structure-guided protein engineering resulted in a quintuple variant with increased stability. Moreover, the amino acid exchange T273S increased the activity and broadened the substrate scope, enabling conversions of various biaryl ketones with up to >99%. A preparative biotransformation of 1-(4-(pyridin-3-yl)phenyl)ethenone at 75 mM (15 g/L) resulted in 96% of isolated yield of the respective amine.

Asymmetric amination of tetralone and chromanone derivatives employing ω-transaminases

Various (S)-selective and (R)-selective ω-transaminases were investigated for the amination of 1- and 2-tetralone and derivatives as well as of 3- and 4-chromanone. All ketones tested were aminated to give the corresponding enantiopure amines (ee > 99%) employing at least one of the enzymes investigated. In most of the cases the (S)- as well as the (R)-enantiomer was obtained in optically pure form. The amination of 3-chromanone was performed on a 100 mg scale leading to optically pure (R)-3-aminochromane (ee > 99%) with complete conversion and 78% isolated yield.

N-octanoyldimethylglycine trifluoroethyl ester, an acyl donor leading to highly enantioselective protease-catalysed kinetic resolution of amines

The use of N-octanoyldimethylglycine trifluoroethyl ester as acyl donor in the kinetic resolution of aliphatic amines catalysed by proteases led to enantiomeric ratios >200 in most cases. The resolutions mediated by Protex 6L were shown to be much faster