147600-17-7

Basic information

• Product Name: (R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE
• Synonyms: (R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE
• CAS NO: 147600-17-7
• Molecular Formula: C5H7NO
• Molecular Weight: 97.12
• Mol File: 147600-17-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE(147600-17-7)
• EPA Substance Registry System: (R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE(147600-17-7)

Safety Data

• Hazardous Substances Data: 147600-17-7(Hazardous Substances Data)

Usage

Description

(R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE is a chemical compound with the molecular formula C5H7NO and a molecular weight of 97.11 g/mol. It is a nitrile compound characterized by the presence of a hydroxyl group and a double bond in its carbon chain.

Uses

Used in Organic Synthesis:
(R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE is used as an intermediate in the production of various pharmaceuticals and agrochemicals, playing a crucial role in the synthesis of these compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE is used as a building block in the synthesis of complex organic molecules, contributing to the development of new drugs and therapeutic agents.
Used in Chiral Ligand Preparation:
(R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE is also employed in the preparation of chiral ligands, which are essential in asymmetric catalysis and the synthesis of enantiomerically pure compounds.
Used in Biological Activity and Pharmacological Property Studies:
Furthermore, (R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE has been studied for its potential biological activities and pharmacological properties, indicating its importance in the field of chemistry and pharmaceutical research.

Upstream product

• 78-85-3 2-methylpropenal 
• 74-90-8 hydrogen cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 143-33-9 sodium cyanide 

Downstream Products

• 4450-34-4 4-chloro-3-methyl-2-butenenitrile 
• 123810-33-3 2-chloro-3-methyl-3-butenenitrile 

Relevant articles and documents

α-Pinene-type chiral Schiff bases as tridentate ligands in asymmetric addition reactions

A group of tridentate Schiff bases derived from (+)-α-pinene were synthesized. The steric effects in the transition state, the importance of π-π stacking interactions as well as the electronic effects of aryl aldehydes according to Hammett constant values in the enantioselective addition of Et2Zn to aldehydes with the use of Schiff bases as chiral ligands are described. Also, a variety of aldehydes were cyanated using a catalyst prepared in situ from titanium tetraisopropoxide and chiral Schiff bases. The influence of a conjugated double-bond in the cyanation substrates on enantioselectivity was observed. The chemical structures of the chiral Schiff base-titanium alkoxide complexes are discussed based on their 1H and 13C NMR spectra. 3D models of the Zn2-complex catalyst and Ti-complex catalyst containing α-pinane-type Schiff bases based on X-ray diffraction experiments are postulated. The models presented were consistent with the reported chirality of the addition product and observed ee.

Salicylaldehyde Schiff bases derived from 2-ferrocenyl-2-amino alcohols. Part 1: New chiral ligands for the titanium-catalyzed enantioselective cyanation of aldehydes

The condensation of a set of diversely substituted (S)-2-amino-2-ferrocenyl ethanol derivatives 1a-e with the salicylaldehydes 5A-C resulted in the generation of a small library of new chiral Schiff base-ligands, whose titanium isopropoxide complexes have

Asymmetric Carbon-Carbon Bond Forming Reactions Catalyzed by Chiral Schiff Base-Titanium Alkoxide Complexes

The enantioselective addition of trimethylsilyl cyanide to a variety of aldehydes proceeded by the aid of a catalyst prepared in situ from titanium tetraisopropoxide and chiral Schiff bases and gave the corresponding cyanohydrins in high optical yield (up to 96percent e.e.).A remarkable rate enhancement was brought about by the addition of the Schiff base to the titanium alkoxide mediated silylcyanation of aldehydes.This catalyst system also promoted the highly enantioselective reaction of diketene with aldehydes, which led to the formation of optically active 5-hydroxy-3-oxoesters.