136030-00-7

Basic information

• Product Name: (1R,2S)-1-Amino-2-indanol
• Synonyms: (1R,2S)-(+)-cis-1-Amino-2-indanol,98%;1H-Inden-2-ol, 1-amino-2,3-dihydro-, (1R,2S)-;(1R,2S)-(+)-cis-1-Amino-2-indanol ,99%;2S)-1-AMino-2-indanol;(1R,2S)-1-Aminoindan-2-ol, (1R,2S)-1-Amino-2,3-dihydro-1H-inden-2-ol;(1R,2S)-(+)-cis-1-AMino-2-indanol, 98% 1GR;(1R,2S)-1-Aminoindan-2-ol, (1R,2S)-1-Amino-2,3-dihydro-1H-inden-2-ol, (1R,2S)-2-Hydroxyindan-1-amine;(1R,2S)-(+)-cis-1-AMino-2-indanol 99%
• CAS NO: 136030-00-7
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• EINECS: 1806241-263-5
• Product Categories: Amino Alcohols (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;CHIRAL CHEMICALS;organic alcohol;Chiral Nitrogen;chiral;API intermediates;CHIRAL COMPOUNDS
• Mol File: 136030-00-7.mol
• Article Data: 65

Chemical Properties

• Melting Point: 118-121 °C(lit.)
• Boiling Point: 270.27°C (rough estimate)
• Flash Point: 129.2 ºC
• Appearance: White to light beige/Powder
• Density: 1.0753 (rough estimate)
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 43 ° (C=1, MeOH)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 14.79±0.40(Predicted)
• Water Solubility: soluble
• BRN: 2803743
• CAS DataBase Reference: (1R,2S)-1-Amino-2-indanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-1-Amino-2-indanol(136030-00-7)
• EPA Substance Registry System: (1R,2S)-1-Amino-2-indanol(136030-00-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• RIDADR: 2811
• WGK Germany: 3
• F: 10-23
• TSCA: No
• Hazardous Substances Data: 136030-00-7(Hazardous Substances Data)

Usage

Description

(1R,2S)-1-Amino-2-indanol is a white to light yellow crystal powder that belongs to the class of catalytic ligands. It is known for its enantioselective properties when used with a reducing agent, making it a valuable compound in various chemical reactions and pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
(1R,2S)-1-Amino-2-indanol is used as a chiral ligand for the catalytic asymmetric reduction of prochiral ketones with boranes. This application is crucial in the synthesis of enantiomerically pure compounds, which are essential in the development of pharmaceuticals with improved efficacy and reduced side effects.
Used in HIV Treatment:
(1R,2S)-1-Amino-2-indanol is used as a key component in the preparation of potent HIV-1 protease inhibitory peptides. These peptides have shown significant promise in the development of antiretroviral drugs, offering new treatment options for patients suffering from HIV and AIDS.
Used in Chemical Synthesis:
(1R,2S)-1-Amino-2-indanol is used as a chiral ligand in the reduction of a wide range of substrates, exhibiting enantioselectivity when paired with a reducing agent. This property makes it an important tool in the synthesis of various organic compounds, particularly those with chiral centers that are crucial for biological activity.

InChI:InChI=1/C9H11NO/c10-9-7-4-2-1-3-6(7)5-8(9)11/h1-4,8-9,11H,5,10H2/p+1/t8-,9+/m0/s1

Upstream product

• 227079-00-7 (1R,2S)-2-acetoxy-1-indanol 
• 7480-35-5 (+/-)-cis-1-amino-indan-2-ol 
• 141-78-6 ethyl acetate 
• 768-22-9 2,3-dihydro-1H-indene 2,3-oxide 
• 5400-80-6 2-bromo-1-indanol 
• 768-22-9 2,3-epoxyindene 
• 135969-64-1 (3aS,8aR)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-2-one 
• 180681-90-7 (1S,2R)-2-bromo-2,3-dihydro-1H-inden-1-ol 
• 140468-55-9 2-phenyl-3a,8a-dihydro-8(H)-indeno<1,2-d>oxazole 
• 889949-58-0 (2R)-hydroxy-(1S)-amino-indane 
• 79465-06-8 trans-2-bromo-1-indanol 
• 20357-79-3 1,2-dibromoindane 
• 95-13-6 1-indene 
• 7480-35-5 trans-1-aminoindan-2-ol 

Downstream Products

• 7480-35-5 (+)-trans-1-Amino-indan-2-ol 
• 7480-35-5 (-)-trans-1-Amino-indan-2-ol 
• 135969-64-1 (3aS,8aR)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-2-one 
• 140468-58-2 [(R)-1-((1S,2R)-2-Hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 140468-58-2 (S)-2-(tert-butoxycarbonylamino)-N-((1S,2R)-2-hydroxy-1-indanyl)-3-phenylpropanamide 
• 140468-58-2 [(R)-1-((1S,2R)-2-Hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 141034-12-0 trans-N-(2-hydroxyindane-1-yl)-N'-benzoyl thiourea 
• 150323-20-9 (3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 
• 7480-35-5 (1S,2R)-1-amino-2-indanol 
• 175848-32-5 N-((1R,2S)-2-Hydroxy-indan-1-yl)-2,4,6-trimethyl-benzenesulfonamide 
• 180186-94-1 bis[(3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl]methane 
• 403860-45-7 tert-butyl N-[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamate 
• 218151-53-2 tert-butyl [(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-carbamate 

Relevant articles and documents

Continuous-Flow Kinetic Resolution of (±)- cis -1-Amino-2-indanol by Lipase-Catalyzed N-Acetylation

Selective N-acetylation of (1S,2R)-1-amino-2-indanol by immobilized lipase B from Candida antarctica showed high enantiomeric excess when ethyl acetate was used as the acyl donor in a THF solution. Combining this process with continuous-flow system, we could obtain enantiomerically pure N-acetyl-aminoindanol at a flow rate of 0.1 mL/min (residence time of 64 min). It has been demonstrated to be more efficient compared to the flask mode.

Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion

Chiral β-amino alcohols are important building blocks for the synthesis of drugs, natural products, chiral auxiliaries, chiral ligands and chiral organocatalysts. The catalytic asymmetric β-amination of alcohols offers a direct strategy to access this class of molecules. Herein, we report a general intramolecular C(sp3)-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors of chiral β-amino alcohols. Specifically, the ring-closing C(sp3)-H amination of N-benzoyloxycarbamates with 2 mol% of a chiral ruthenium catalyst provides cyclic carbamates in up to 99% yield and with up to 99% ee. The method is applicable to benzylic, allylic, and propargylic C-H bonds and can even be applied to completely non-activated C (sp3)-H bonds, although with somewhat reduced yields and stereoselectivities. The obtained cyclic carbamates can subsequently be hydrolyzed to obtain chiral β-amino alcohols. The method is very practical as the catalyst can be easily synthesized on a gram scale and can be recycled after the reaction for further use. The synthetic value of the new method is demonstrated with the asymmetric synthesis of a chiral oxazolidin-2-one as intermediate for the synthesis of the natural product aurantioclavine and chiral β-amino alcohols that are intermediates for the synthesis of chiral amino acids, indane-derived chiral Box-ligands, and the natural products dihydrohamacanthin A and dragmacidin A.[Figure not available: see fulltext.].

Efficient diastereoselective synthesis of cis-2-amino-1-indanol derivatives and cis- and trans-1-amino-2-indanol via Pd-catalyzed hydrogenation

(±)-cis-2-amino-1-indanol was diastereoselectively synthesized from 1,2-indanedion-2-oxime in ethanol at 25 °C under 10% Pd/C-catalyzed hydrogenation conditions. Under the same hydrogenation condition, 1,2-indanedion-2-oxime and their derivatives having one and/or two electron-donating groups in aliphatic or aromatic part of indanyl ring were diastereoselectively reduced to racemic cis-2-amino-1-indanol derivatives. From 1,2-indanedion-1-oxime, (±)-trans-1-amino-2-indanol was obtained in ethanol at 25 °C over a 10% Pd/BaSO4 catalyst. In contrast, the 10% Pd/BaSO4-catalyzed hydrogenation reaction in ethanol at 45 °C afforded cis-1-hydroxyamino-2-indanol from 1,2-indanedion-1-oxime, followed by reduction to form (±)-cis-1-amino-2-indanol. The diastereoselectivity of β-aminoindanols was dependent on the Pd catalyst, reaction temperature, and pH of the reaction medium.

Visible-Light-Driven N-Heterocyclic Carbene Catalyzed γ- and ?-Alkylation with Alkyl Radicals

The merging of photoredox catalysis and N-heterocyclic carbene (NHC) catalysis for γ- and ?-alkylation of enals with alkyl radicals was developed. The alkylation reaction of γ-oxidized enals with alkyl halides worked well for the synthesis γ-multisubstituted-α,β-unsaturated esters, including those with challenging vicinal all-carbon quaternary centers. The synthesis of ?-multisubstituted-α,β-γ,δ-diunsaturated esters by an unprecedented NHC-catalyzed ?-functionalization was also established.