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

Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity

A chiral cobalt pincer complex, when combined with an achiral electron-rich mono-phosphine ligand, catalyzes efficient asymmetric hydrogenation of a wide range of aryl ketones, affording chiral alcohols with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand shows a remarkable effect on the enantioselectivity of the reaction.

Supramolecular chiral electrochemical reduction of acetophenone with hybridization of a chiral multifarene and Au nanoparticles

A supramolecular chiral electrode was constructed by layer-by-layer assembly of gold nanoparticles (AuNPs) and an S-chiral multifarene [3,2,1] (S-CMF) on the surface of a glassy carbon electrode, which was applied for the electroreduction of acetophenone. The host-guest encapsulation of the substrate within the chiral cavity was confirmed by 1H NMR, fluorescence titration, and molecular simulation. The composite on the electrode surface was characterized by electrochemical impedance spectroscopy (EIS) and transmission electron microscopy (TEM). Optimization of the electrolysis process was performed to give a high yield of 70.9% and high enantioselectivity of 63.9% ee, which exhibited superior reactivity to the previously reported materials. The repeatability of the experiment was tested via five separate experiments and indicated consistent stability, recyclability, and reusability of the novel chiral electrode. The proposed mechanism involved supramolecular encapsulation, two single-electron transfer steps, and proton addition. The chiral electroorganic reduction was extended to more substrates to provide successful yields and enantioselectivity.