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

Uses

Different sources of media describe the Uses of 136030-00-7 differently. You can refer to the following data:
1. (1R,2S)-1-Amino-2-indanol??Class of catalytic ligands which when used with a reducing agent, exhibit enantioselectivity in the reduction of a wide range of substrates.
2. This cis-aminoindanol and its antipode have been used in the preparation of a series of potent HIV-1 protease inhibitory peptides. Also, they have served as chiral ligands in the catalytic asymmetric reduction of prochiral ketones with boranes.

Chemical Properties

(1R,2S)-1-Amino-2-indanol is white to light yellow crystal powder

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

• 768-22-9 (1aR,6aS)-6,6a-dihydro-1aH-indeno[1,2-b]oxirene 
• 7480-35-5 (+/-)-cis-1-amino-indan-2-ol 
• 615-13-4 2-indanone 
• 7480-28-6 3,3α,8,8α-tetrahydro-2H-indeno[1,2-d]oxazol-2-one 
• 768-22-9 2,3-dihydro-1H-indene 2,3-oxide 
• 4254-29-9 indan-2-ol 
• 5400-80-6 2-bromo-1-indanol 
• 83-33-0 inden-1-one 
• 185436-24-2 (1S,2R)N-(2-hydroxy-2,3-dihydro-1H-inden-1-yl)acetamide 
• 98995-78-9 hydrochloride of cis-(1S,2R)-1-aminoindan-2-ol 
• 135969-64-1 (3aS,8aR)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-2-one 
• 172881-85-5 (1S,2R)-1-azido-2,3-dihydro-1H-inden-2-ol 
• 197566-42-0 4-Nitro-benzoic acid (1S,2R)-1-azido-indan-2-yl ester 
• 232257-83-9 (Z)-(R)-2-hydroxy-1-indanone oxime 

Downstream Products

• 7480-35-5 (+)-trans-1-Amino-indan-2-ol 
• 7480-35-5 (-)-trans-1-Amino-indan-2-ol 
• 147912-04-7 [(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 
• 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 
• 165883-48-7 (R)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-pent-4-en-1-one 
• 135969-64-1 (3aS,8aR)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-2-one 
• 180186-94-1 bis[(3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl]methane 
• 173240-58-9 (2S,6S)-2,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-heptanedioic acid bis-[((1S,2R)-2-hydroxy-indan-1-yl)-amide] 
• 173084-01-0 (2R,6R)-2,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-heptanedioic acid bis-[((1S,2R)-2-hydroxy-indan-1-yl)-amide] 
• 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 
• 213895-65-9 BEA369 
• 221127-98-6 N-((1S,2R)-2-Hydroxy-indan-1-yl)-2-oxo-2-phenyl-acetamide 

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.].

Enantioselective Cascade Biocatalysis for Deracemization of Racemic β-Amino Alcohols to Enantiopure (S)-β-Amino Alcohols by Employing Cyclohexylamine Oxidase and ω-Transaminase

Optically active β-amino alcohols are very useful chiral intermediates frequently used in the preparation of pharmaceutically active substances. Here, a novel cyclohexylamine oxidase (ArCHAO) was identified from the genome sequence of Arthrobacter sp. TYUT010-15 with the R-stereoselective deamination activity of β-amino alcohol. ArCHAO was cloned and successfully expressed in E. coli BL21, purified and characterized. Substrate-specific analysis revealed that ArCHAO has high activity (4.15 to 6.34 U mg?1 protein) and excellent enantioselectivity toward the tested β-amino alcohols. By using purified ArCHAO, a wide range of racemic β-amino alcohols were resolved, (S)-β-amino alcohols were obtained in >99 % ee. Deracemization of racemic β-amino alcohols was conducted by ArCHAO-catalyzed enantioselective deamination and transaminase-catalyzed enantioselective amination to afford (S)-β-amino alcohols in excellent conversion (78–94 %) and enantiomeric excess (>99 %). Preparative-scale deracemization was carried out with 50 mM (6.859 g L?1) racemic 2-amino-2-phenylethanol, (S)-2-amino-2-phenylethanol was obtained in 75 % isolated yield and >99 % ee.

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.