25501-32-0

Basic information

• Product Name: (S)-(+)-1-Indanol
• Synonyms: (S)-(+)-1-HYDROXYINDAN;(S)-(+)-1-INDANOL;(1S)-2,3-Dihydro-1H-indene-1β-ol;(1S)-Indan-1β-ol;(3S)-Indan-3-ol;(S)-2,3-Dihydro-1H-indene-1β-ol;[1S,(+)]-1-Indanol;(S)-(+)-1-Indanol
• CAS NO: 25501-32-0
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.18
• Product Categories: Chiral
• Mol File: 25501-32-0.mol
• Article Data: 228

Chemical Properties

• Melting Point: 69-73 °C(lit.)
• Boiling Point: 255.1ºC at 760 mmHg
• Flash Point: 89.2ºC
• Appearance: /
• Density: 1.161g/cm3
• Vapor Pressure: 0.00859mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: 2-8°C
• PKA: 14.23±0.20(Predicted)
• BRN: 2206709
• CAS DataBase Reference: (S)-(+)-1-Indanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-1-Indanol(25501-32-0)
• EPA Substance Registry System: (S)-(+)-1-Indanol(25501-32-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 25501-32-0(Hazardous Substances Data)

Usage

Description

(S)-(+)-1-Indanol, also known as (S)-1-hydroxyindan, is an organic compound with the molecular formula C8H10O. It is a chiral molecule, which means it has a non-superimposable mirror image, and in this case, it is the (S)-enantiomer. (S)-(+)-1-Indanol is characterized by its unique structure, which includes a hydroxyl group attached to an indan ring system. It is a versatile intermediate in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Synthesis:
(S)-(+)-1-Indanol is used as a building block for the synthesis of pharmaceutical compounds, particularly for the development of orally bioavailable GPR40 agonists. One such example is DS-1558, which is used to stimulate insulin secretion. The compound's unique structure and chirality make it a valuable component in the design and synthesis of novel drugs targeting specific receptors.

InChI:InChI=1/C9H10O/c10-9-6-5-7-3-1-2-4-8(7)9/h1-4,9-10H,5-6H2/t9-/m0/s1

Upstream product

• 83-33-0 inden-1-one 
• 108-22-5 Isopropenyl acetate 
• 6351-10-6 1-Indanol 
• 100465-50-7 <1,1'-Binaphthalene>-2,2'-diol dibutanoate 
• 26452-98-2 2,3-dihydro-1H-inden-1-yl-acetate 
• 95-13-6 1-indene 
• 68567-23-7 (S)-(-)-2,3-dihydro-1H-inden-yl acetate 
• 85354-34-3 (1R,2R)-(-)-2-bromo-1-acetoxyindan 
• 109129-77-3 succinic acid mono-((S)-indan-1-yl ester) 
• 124040-95-5 <1,1'-Binaphthalene>-2,2'-diol butanoate 
• 5177-66-2 1-ethoxyvinyl acetate 
• 92799-73-0 1-indanyl hydroperoxide 
• 123-20-6 vinyl n-butyrate 
• 57-10-3 1-hexadecylcarboxylic acid 

Downstream Products

• 175288-46-7 [2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-isopropyl-carbamic acid (S)-indan-1-yl ester 
• 83-33-0 inden-1-one 
• 256237-45-3 (S)-N,N-diisopropyl O-(indan-1-yl)carbamate 
• 415975-55-2 (2S,2R')-(3,4-dichlorophenyl)(tetrahydropyran-2-yl)acetic acid indanyl ester 
• 415975-56-3 (2R,2S')-(3,4-dichlorophenyl)(tetrahydropyran-2-yl)acetic acid indanyl ester 
• 666824-82-4 triethyl (1R)-2,3-dihydro-1H-inden-1-ylmethanetricarboxylate 
• 907562-44-1 (S)-2-((S)-Indan-1-yloxycarbonylamino)-hexanoic acid methyl ester 
• 6351-10-6 1-Indanol 
• 854001-42-6 (S)-2-((S)-Indan-1-yloxycarbonylamino)-hexanoic acid 
• 854001-46-0 {(S)-1-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-pentyl}-carbamic acid (S)-indan-1-yl ester 

Relevant articles and documents

Asymmetric transfer hydrogenation of ketonic substrates catalyzed by (η5-C5Me5)MCl complexes (M = Rh and Ir) of (1S, 2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine

The rhodium and iridium (η5-C5Me5)MCl complexes (3a: M = Rh; 3b: M = Ir) of (1S,25)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine were found to be catalyst precursors for asymmetric transfer hydrogenation of acetophenone, 2-acetonaphthone, 1-tetralone, and 1-indanone to give (S)-1-phenylethanol (90% ee), (S)-1-(2-naphthyl)ethanol (85% ee), (S)-1-tetralol (97% ee), and (S)-indanol (99% ee), respectively.

Designer Outer Membrane Protein Facilitates Uptake of Decoy Molecules into a Cytochrome P450BM3-Based Whole-Cell Biocatalyst

We report an OmpF loop deletion mutant, which improves the cellular uptake of external additives into an Escherichia coli whole-cell biocatalyst. Through co-expression of the OmpF mutant with wild-type P450BM3 in the presence of decoy molecules, the yield

Biocatalytic asymmetric synthesis of (S)-1-indanol using Lactobacillus paracasei BD71

Enantiopure benzo-fused cyclic alcohols have been used as a building block of a drug for Parkinson’s disease. Biocatalytic reduction of ketones is one of the most promising and significant routes to prepare optically active alcohols. In this study, the reductive capacity of seven lactic acid bacteria (LAB) strains were investigated as whole-cell biocatalyst in the enantioselective reduction of 1-indanone (1). Lactobacillus paracasei BD71 was found to have the best reductive capacity. Effects of different parameters such as pH, incubation time, agitation speed and temperature, on enantiomeric excess (ee) and conversion were investigated in a bioconversion. (S)-1-indanol ((S)-2) could be used as precursor for the synthesis of rasagiline mesylate TVP1012 for the therapy of Parkinson’s illness. It was produced in gram-scale (5.24 g), high yield (93%) and enantiomerically pure form using L. paracasei BD71 whole-cell biocatalysts. Also, to our knowledge, this is the first report on production of (S)-2 using whole-cell catalyst in enantiopure form, excellent yield, conversion and gram scale. This is a cheap, clean and eco-friendly process for production of (S)-2 compared to chemical processes.

Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts

A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.