(R)-(-)-6-hydroxy-1-aminoindan

Base Information

• Chemical Name: (R)-(-)-6-hydroxy-1-aminoindan
• CAS No.: 169105-01-5
• Molecular Formula: C9H11NO
• Molecular Weight: 149.192
• Hs Code.: 2922199090
• European Community (EC) Number: 693-907-1
• DSSTox Substance ID: DTXSID50564884
• Nikkaji Number: J2.522.038B
• Wikidata: Q72483129
• Mol file: 169105-01-5.mol

Synonyms:169105-01-5;(R)-(-)-6-hydroxy-1-aminoindan;(R)-(-)-1-Amino-6-hydroxyindan;(3R)-3-AMINO-2,3-DIHYDRO-1H-INDEN-5-OL;(R)-3-AMINO-2,3-DIHYDRO-1H-INDEN-5-OL;(R)-3-aminoindan-5-ol;(1R)-6-Hydroxy-2,3-dihydro-1H-inden-1-amine;(R)-3-Amino-5-hydroxyindane;(R)-1-Amino-6-hydroxyindan;1H-Inden-5-ol, 3-amino-2,3-dihydro-, (3R)-;SCHEMBL1370800;DTXSID50564884;MOUPGBDOLGDVNW-SECBINFHSA-N;(R)-3-AMINO-INDAN-5-OL;(R)-(?)-1-Amino-6-hydroxyindan;AM9194;MFCD04972514;(R)-(-)-1-Amino-6-hydroxyindan, 97%;J-010508

Chemical Property of (R)-(-)-6-hydroxy-1-aminoindan

Chemical Property:

• Refractive Index: 1.622
• Boiling Point: 292.3 °C at 760 mmHg
• Flash Point: 130.6 °C
• PSA: 46.25000
• Density: 1.198 g/cm³
• LogP: 2.03850
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.084063974
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

99%, ^*data from raw suppliers

(R)-3-Aminoindan-5-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C1N)C=C(C=C2)O
• Isomeric SMILES: C1CC2=C([C@@H]1N)C=C(C=C2)O
• Uses: R-(-)-6-hydroxy-1-aminoindan is the hydroxy derivative of Aminoindane (A611715), an metabolite of Rasagiline (R126000), a selective irreversible MAO-B inhibitor used as an Antiparkinsonian agent.

Technology Process of (R)-(-)-6-hydroxy-1-aminoindan

There total 5 articles about (R)-(-)-6-hydroxy-1-aminoindan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 43.0%

6-chloroacetoxy-N-trifluoroacetyl-(R)-1-aminoindan (209394-88-7) → (R)-3-amino-2,3-dihydro-1H-inden-5-ol (169105-01-5,1213899-46-7)

Guidance literature:

With potassium carbonate; In methanol; at 70 ℃; for 1.5h;

DOI:10.1021/jm020120c

Reference yield:

(R)-1-Aminoindane (10277-74-4) → (R)-3-amino-2,3-dihydro-1H-inden-5-ol (169105-01-5,1213899-46-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / aq. KOH / toluene / 2 h / 20 °C

2: 68 percent / AlCl₃ / 1,2-dichloro-ethane / 0.5 h

3: 48 percent / mCPBA; TFA / CH₂Cl₂ / 20 °C

4: 43 percent / aq. K₂CO₃ / methanol / 1.5 h / 70 °C

With potassium hydroxide; aluminium trichloride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In methanol; dichloromethane; 1,2-dichloro-ethane; toluene; 2: Friedel-Crafts reaction / 3: Baeyer-Villiger oxidation;

DOI:10.1021/jm020120c

Reference yield:

N-trifluoroacetyl-(R)-1-aminoindan (155666-94-7) → (R)-3-amino-2,3-dihydro-1H-inden-5-ol (169105-01-5,1213899-46-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / AlCl₃ / 1,2-dichloro-ethane / 0.5 h

2: 48 percent / mCPBA; TFA / CH₂Cl₂ / 20 °C

3: 43 percent / aq. K₂CO₃ / methanol / 1.5 h / 70 °C

With aluminium trichloride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In methanol; dichloromethane; 1,2-dichloro-ethane; 1: Friedel-Crafts reaction / 2: Baeyer-Villiger oxidation;

DOI:10.1021/jm020120c

upstream raw materials:

6-chloroacetoxy-N-trifluoroacetyl-(R)-1-aminoindan

(R)-1-Aminoindane

N-trifluoroacetyl-(R)-1-aminoindan

6-chloroacetyl-N-trifluoroacetyl-(R)-1-aminoindan

Downstream raw materials:

ladostigil

N-[(R)-6-hydroxyindan-1-yl]carbamic acid tert-butyl ester

Refernces

• 1、 Sterling, Jeffrey,Herzig, Yaacov,Goren, Tamar,Finkelstein, Nina,Lerner, David,Goldenberg, Willy,Miskolczi, Istvan,Molnar, Sandor,Rantal, Ferenc,Tamas, Tivadar,Toth, Gyorgy,Zagyva, Adela,Zekany, Andras,Lavian, Gila,Gross, Aviva,Friedman, Rachel,Razin, Michal,Huang, Wei,Krais, Boris,Chorev, Michael,Youdim, Moussa B.,Weinstock, Marta. "Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease". . p. 5260 - 5279. Retrieved 2007/10/03.
• 2、 -. "Method for preparing optically active 1-aminoindan derivatives". . . Retrieved 2008/06/13.