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

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

Downstream Products

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

Relevant articles and documents

Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols

We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.

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.