36739-86-3

Basic information

• Product Name: 3-Benzofuranmethanol, -alpha--methyl-
• Synonyms: 3-Benzofuranmethanol, -alpha--methyl-;1-(benzofuran-3-yl)ethanol
• CAS NO: 36739-86-3
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Mol File: 36739-86-3.mol

Chemical Properties

• Boiling Point: 182.2±7.0 °C(Predicted)
• Appearance: /
• Density: 1.180±0.06 g/cm3(Predicted)
• PKA: 14.22±0.20(Predicted)
• CAS DataBase Reference: 3-Benzofuranmethanol, -alpha--methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Benzofuranmethanol, -alpha--methyl-(36739-86-3)
• EPA Substance Registry System: 3-Benzofuranmethanol, -alpha--methyl-(36739-86-3)

Safety Data

• Hazardous Substances Data: 36739-86-3(Hazardous Substances Data)

Upstream product

• 917-64-6 methyl magnesium iodide 
• 4687-25-6 1-benzofuran-3-carbaldehyde 
• 21535-97-7 3-methyl-benzofuran 
• 38281-60-6 ethyl 3-formylbenzofuran-2-carboxylate 
• 136229-42-0 3-formylbenzofuran-2-carboxylic acid 
• 74-88-4 methyl iodide 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 66611-15-2 3-acetylbenzo[b]furan 
• 136229-46-4 2-(2-hydroxyphenyl)anthraquinone 
• 343614-12-0 (S)-(+)-(benzofuran-3-yl)oxirane 

Relevant articles and documents

Tailored sol-gel immobilized lipase preparates for the enzymatic kinetic resolution of heteroaromatic alcohols in batch and continuous flow systems

Tailored immobilized lipases from Candida antarctica B and Pseudomonas fluorescens, with improved thermal and operational stability, were prepared through fine tuning of the structure of the sol-gel matrix, using various binary or ternary precursor mixtures for the EKR of various chiral heteroaromatic secondary alcohols with benzofuran, benzo[b]thiophen, phenothiazine and 2-phenylthiazol moieties. The operational stability in batch process was studied for five selected systems by performing reuse experiments, using the conversion, enantiomeric excesses and enantiomeric ratio as parameters, demonstrating the dependence of the sol-gel lipase preparate performance on the structure of both biocatalyst and substrate. The resolution of the benzofuranic substrates with the best performing biocatalysts was studied in continuous-flow mode, using the productivity as a criterion. The specific reaction rates under continuous-flow operation (rflow) were higher than those obtained in batch mode (rbatch) in both cases, sustaining its usefulness for further process development.

Lipase-catalyzed kinetic resolution of racemic 1-heteroarylethanols-experimental and QM/MM study

The kinetic resolution of racemic 1-(benzothiazol-2-yl)ethanol rac-2a, 1-(benzo[b]thiophen-2-yl)ethanol rac-2b, 1-(benzo[b]furan-3-yl)ethanol rac-2c and 1-(benzo[b]thiophen-3-yl)ethanol rac-2d was studied by enantiomer selective acylation catalyzed by a selection of commercially available and in house produced lipases. Alcoholysis of the corresponding racemic acetates rac-3a-d catalyzed by Candida antarctica lipase B (CaLB) was also investigated. Two racemic 1-heteroarylethanols rac-2a,b were prepared by addition of the corresponding lithiated heteroarylic compounds 1a,b to acetaldehyde, whereas two others, rac-2c,d were synthesized by the addition of MeMgI onto the corresponding heteroaryl-carbaldehydes 1c,d. The high enantiomer selectivities of CaLB in the acylation of racemic 1-heteroarylethanols rac-2a-d allowed the determination of the enantiomeric preference of these enzymatic acetylation reactions by QM/MM [pm3/uff or hf(3-21+g**)/uff] calculations. For acetylation of each of the racemic alcohols rac-2a-d, four possible tetrahedral intermediate states were compared and analyzed.

Chemoenzymatic synthesis of (R)- and (S)-1-heteroarylethanols

A chemoenzymatic methodology for the synthesis of highly enantiomerically enriched (S)- and (R)-1-heteroarylethanols by enantioselective bioreduction with baker's yeast of the corresponding 1-heteroarylethanones followed by three racemization free chemical steps including a Mitsunobu reaction was developed.

Enantioselective synthesis of 2- and 3-benzofuryl β-amino alcohols

Enantioselective reduction of 2- and 3-bromoacetylbenzofurans with (-)-B-chlorodiisopinocampheylborane produced the corresponding bromohydrins which were transformed into (S)-(benzofuran-2-yl)oxirane of 70% ee and (S)-(benzofuran-3-yl)oxirane of 71% ee, respectively. The epoxides treated with primary alkylamines gave the corresponding (S)-1-(benzofuran-2- and -3-yl)-2-(alkylamino) ethanols.

Vinylindenes and Some Heteroanalogues in the Diels-Alder Reaction. IX. 3-Vinylbenzofuran and 1,4-Naphthoquinone

3-Vinylbenzofuran and 1,4-naphthoquinone react to give r-5a,6,c-12a,c,12b-tetrahydroanthrabenzofuran-5,13-quinone.This adduct undergoes ring opening to 2-(2-hydroxyphenyl)anthraquinone with base and oxygen, but shows no rearrangement to anthrabenzofuran-5,13-quinone.