42973-56-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxy-3-methoxyphenylacetonitrile is used as a precursor in the synthesis of various organic compounds for the pharmaceutical industry. Its nitrile functional group makes it a valuable building block in the development of new drugs and pharmaceuticals, contributing to the creation of innovative therapeutic agents.
Used in Organic Chemistry:
In the field of organic chemistry, 2-Hydroxy-3-methoxyphenylacetonitrile is utilized as a versatile intermediate for the synthesis of a range of organic compounds. Its unique structure allows for various chemical reactions, facilitating the production of diverse chemical entities with potential applications in different industries.

InChI:InChI=1/C9H9NO2/c1-12-8-4-2-3-7(5-6-10)9(8)11/h2-4,11H,5H2,1H3

Upstream product

• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 773837-37-9 sodium cyanide 
• 4383-05-5 2-hydroxy-3-methoxybenzyl alcohol 
• 51771-52-9 (7Z)-(1R,3S,4R,5S)-2-(cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl β-D-glucopyranoside 
• 86855-27-8 2-(aminomethyl)-6-methoxyphenol 
• 151-50-8 potassium cyanide 

Downstream Products

• 1400574-32-4 5-methoxybenzo[b]thieno[2,3-f]oxepine-9-carbonitrile 
• 14385-51-4 7-methoxy-2-phenylbenzo[b]furan 
• 66495-84-9 2-(4-chlorophenyl)-7-methoxybenzo[b]furan 
• 1439923-33-7 2-(4-tert-butylphenyl)-7-methoxybenzo[b]furan 
• 838855-91-7 1,1-dimethylethyl 4-({[2-(cyanomethyl)-6-(methyloxy)phenyl]oxy}methyl)piperidine-1-carboxylate 
• 2074-95-5 2-(2-amino-ethyl)-6-methoxy-phenol 

Relevant academic research and scientific papers

Mechanism of simmondsin decomposition during sodium hydroxide treatment

Jojoba seed meal shows appetite-suppressing activity due to the presence of simmondsin. This pharmacological activity disappears with treatment of the meal with sodium hydroxide. To elucidate this mechanism of inactivation, the reaction of simmondsin in 1 N NaOH at 20 °C was monitored as a function of time. The end products of the reaction as well as intermediates were isolated and identified. The half-life of simmondsin was ～60 min with D-glucose and 2-hydroxy-3-methoxyphenylacetonitrile as reaction end products. The reaction mechanism could be elucidated by the isolation of isosimmondsin and a simmondsin lactone derivative. Those compounds were isolated and purified by a combination of column chromatography and HPLC and identified mainly by HRMS and NMR spectroscopy.

One-pot transition-metal-free synthesis of dibenzo[b,f]oxepins from 2-halobenzaldehydes

A one-pot transition-metal-free, base-mediated synthesis of dibenzo[b,f]oxepins was developed. The reaction of 2-halobenzaldehydes with (2-hydroxyphenyl)acetonitriles proceeds via a sequential aldol condensation and intramolecular ether formation reaction in the presence of Cs2CO 3 and molecular sieves in toluene.