5381-24-8

Basic information

• Product Name: 3-Hydroxymetnylbenzo[b]thiophene
• Synonyms: RARECHEM AL BD 0712;1-BENZOTHIOPHENE-3-YLMETHANOL;1-BENZOTHIOPHEN-3-YLMETHANOL;3-(HYDROXYMETHYL)BENZOTHIOPHENE;Benzo[b]thiophen-3-ylmethanol;3-Hydroxymetnyl benzo[b]thiophene;(1-Benzothiophen-3-yl)methanol, 3-(Hydroxymethyl)-1-benzothiophene;3-(Hydroxymethyl)benzo[b]thiophene
• CAS NO: 5381-24-8
• Molecular Formula: C₉H₈OS
• Molecular Weight: 164.22
• Product Categories: Heterocycles;Heterocyclic Compound
• Mol File: 5381-24-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 49 °C
• Boiling Point: 72 °C
• Flash Point: 149.8 °C
• Appearance: /
• Density: 1.294 g/cm³
• Vapor Pressure: 0.000103mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: 2-8°C
• PKA: 14.49±0.10(Predicted)
• CAS DataBase Reference: 3-Hydroxymetnylbenzo[b]thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxymetnylbenzo[b]thiophene(5381-24-8)
• EPA Substance Registry System: 3-Hydroxymetnylbenzo[b]thiophene(5381-24-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25
• Hazardous Substances Data: 5381-24-8(Hazardous Substances Data)

Usage

General Description

3-Hydroxymetnylbenzo[b]thiophene is a chemical compound with the molecular formula C9H8O2S. It is a derivative of benzo[b]thiophene, a heterocyclic compound containing a benzene ring fused to a thiophene ring. The presence of a hydroxymethyl group in 3-Hydroxymetnylbenzo[b]thiophene makes it a potential intermediate for the synthesis of various organic compounds. 3-Hydroxymetnylbenzo[b]thiophene has not been widely studied, but its structure suggests that it may have potential applications in the field of organic chemistry, particularly in the synthesis of biologically active compounds or as a building block for the development of new materials. Further research is needed to fully understand the potential uses and properties of 3-Hydroxymetnylbenzo[b]thiophene.

InChI:InChI=1/C9H8OS/c10-5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,10H,5H2

Upstream product

• 5381-25-9 benzo[b]thiophene-3-carboxylic acid 
• 22913-25-3 methyl benzothiophene-3-carboxylate 
• 5381-20-4 benzothiophene-3-carboxaldehyde 
• 95-15-8 Benzo[b]thiophene 

Downstream Products

• 3216-47-5 3-chloromethylbenzothiophene 
• 1318697-92-5 C₂₉H₂₆O₃S 
• 1318697-82-3 C₁₅H₁₁IOS 
• 5381-20-4 benzothiophene-3-carboxaldehyde 

Relevant articles and documents

Strategic vinyl sulfone nucleophile β-substitution significantly impacts selectivity in Vinylogous Darzens and aza-Darzens reactions

Vinylogous Darzens and aza-Darzens reactions employing a benzothiophene 1,1-dioxide nucleophile are reported. These new [2 + 1] annulation reactions, which proceed under mild reaction conditions, are γ-selective, affording trans-epoxides selectively and favoring trans-aziridines. The reactions are base-dependent, with KOtBu and Cs2CO3 being optimal for aldehyde and imine annulations, respectively. Comparison of the benzothiophene nucleophile to its acyclic counterpart reveals superior performance in the case of aldehydes, while the outcome varies depending on the sulfonamide imine used.

Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles

The first asymmetric cooperative Lewis base/palladium catalyzed benzylic alkylation of acyclic esters is reported. This reaction proceeds via stereodefined C1-ammonium enolate nucleophiles. Critical to its success was the identification of benzylic phosphate electrophiles, which were uniquely reactive. Alkylated products were obtained with very high levels of enantioselectivity, and this method has been applied toward the synthesis of the thrombin inhibitor DX-9065a.

Umpolung of protons from H2O: A metal-free chemoselective reduction of carbonyl compounds: Via B2pin2/H2O systems

H2O is routinely described as a proton donor, however, in the presence of diboron compounds, the umpolung reaction of H2O under metal-free conditions was successfully developed, which could afford hydride species, leading to a highly efficient and chemoselective reduction of CO bonds. This strategy exhibits excellent chemoselectivities toward carbonyl groups in the presence of ester, olefin, halogen, thioether, sulfonyl, cyano as well as heteroaromatic groups.