(1S,2R)-(-)-cis-1-Amino-2-indanol

Base Information

• Chemical Name: (1S,2R)-(-)-cis-1-Amino-2-indanol
• CAS No.: 126456-43-7
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.192
• Hs Code.: 29052900
• UNII: LU3GK925A8
• DSSTox Substance ID: DTXSID10155191,DTXSID601335000
• Nikkaji Number: J655.021E
• Wikidata: Q27283183
• Mol file: 126456-43-7.mol

Synonyms:1H-Inden-2-ol,1-amino-2,3-dihydro-, (1S-cis)-;(-)-cis-1-Aminoindan-2-ol;(1S)-Amino-(2R)-indanol;(1S,2R)-(-)-1-Amino-2-indanol;(1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol;(1S,2R)-1-Aminoindan-2-ol;(1S-cis)-1-Amino-2-indanol;(2R-cis)-1-Amino-2,3-dihydro-1H-inden-2-ol;2(R)-Hydroxy-1(S)-aminoindane;[(1S,2R)-2-Hydroxy-2,3-dihydro-1H-inden-1-yl]amine;(1S,2R)-(+)-cis-1-Aminoindan-2-ol;

Chemical Property of (1S,2R)-(-)-cis-1-Amino-2-indanol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 118-121 °C(lit.)
• Refractive Index: 1.5760 (estimate)
• Boiling Point: 290.031 °C at 760 mmHg
• PKA: 14.79±0.40(Predicted)
• Flash Point: 129.207 °C
• PSA: 46.25000
• Density: 1.212 g/cm³
• LogP: 1.30370
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Air Sensitive
• Solubility.: soluble in Methanol
• Water Solubility.: slightly soluble
• XLogP3: 0.2
• 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

[1S- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C2=CC=CC=C21)N)O
• Isomeric SMILES: C1[C@H]([C@H](C2=CC=CC=C21)N)O
• General Description: (1S,2R)-(-)-cis-1-Amino-2-indanol is an optically pure cis-amino alcohol of significant medicinal and chemical importance, synthesized through a lipase-mediated resolution of racemic trans-1-azidoindan-2-ol followed by chemical transformations. This enantiomerically pure compound is obtained via a series of steps, including kinetic transesterification, methanesulfonation, acetylation, and hydrogenation, ensuring high optical purity as confirmed by chiral HPLC analysis. Its structural and stereochemical properties make it a valuable intermediate in pharmaceutical and synthetic applications.

Technology Process of (1S,2R)-(-)-cis-1-Amino-2-indanol

There total 105 articles about (1S,2R)-(-)-cis-1-Amino-2-indanol 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: 98.3%

(1S,2R)-1-azido-2,3-dihydro-1H-inden-2-ol (172881-85-5) → (1S,2R)-1-amino-2-indanol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2h; under 750.06 Torr;

DOI:10.1055/s-1996-4328

Reference yield: 93.0%

(L)-phenylalanine <2(R)-hydroxy-1(S)-indanyl>amide (140468-56-0) → (1S,2R)-1-amino-2-indanol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8)

Guidance literature:

With sodium hydroxide; In ethanol; for 16h; Heating;

DOI:10.1021/jm00088a003

Reference yield: 92.0%

(3aS,8aR)-2-Phenyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazole (176587-85-2) → (1S,2R)-1-amino-2-indanol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8)

Guidance literature:

With sulfuric acid; In dichloromethane; for 10h; Heating;

DOI:10.1021/jm9508696

upstream raw materials:

3,3α,8,8α-tetrahydro-2H-indeno[1,2-d]oxazol-2-one

2-phenyl-3a,8a-dihydro-8(H)-indeno<1,2-d>oxazole

2,3-dihydro-1H-indene 2,3-oxide

cis-indane-1,2-diol

Downstream raw materials:

[(R)-1-((1S,2R)-2-Hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

[(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-carbamic acid tert-butyl ester

[(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-((1R,2S)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-carbamic acid tert-butyl ester

(1R,2S)-1-Amino-2-indanol

Refernces

Lipase-mediated resolution of trans-1-azidoindan-2-ol: A new route to optically pure cis-1-aminoindan-2-ol

10.1055/s-1996-4328

The research focuses on the development of a method to obtain optically pure cis-1-aminoindan-2-ol, a compound of significant medicinal and chemical importance. The researchers utilized lipase-mediated kinetic transesterification to resolve racemic trans-1-azidoindan-2-ol into its enantiomers. Key chemicals involved in this process include indene as a starting material, N-bromosuccinimide for the formation of bromohydrin, and vinyl acetate as the esterifying agent in the presence of lipase PS (Pseudomonas sp., Amano) for the transesterification step. The resolved trans-azides were then converted into the corresponding enantiomers of optically pure cis-amino alcohol through various chemical transformations, including methanesulfonation, acetylation, and hydrogenation. The use of chiral columns for HPLC analysis was crucial for determining the optical purity of the synthesized compounds.

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