93744-17-3

Basic information

• Product Name: (R)-2-(OXIRAN-2-YLMETHOXY)BENZONITRILE
• Synonyms: (R)-2-(OXIRAN-2-YLMETHOXY)BENZONITRILE
• CAS NO: 93744-17-3
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18396
• Mol File: 93744-17-3.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2-(OXIRAN-2-YLMETHOXY)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(OXIRAN-2-YLMETHOXY)BENZONITRILE(93744-17-3)
• EPA Substance Registry System: (R)-2-(OXIRAN-2-YLMETHOXY)BENZONITRILE(93744-17-3)

Safety Data

• Hazardous Substances Data: 93744-17-3(Hazardous Substances Data)

Usage

General Description

The chemical (R)-2-(oxiran-2-ylmethoxy)benzonitrile, also known as (R)-2-(2,3-Epoxypropoxy)benzonitrile, is a white solid compound with a molecular formula C10H9NO2. It is a chiral molecule, with the (R)-enantiomer having a specific rotation of -49.5°. (R)-2-(OXIRAN-2-YLMETHOXY)BENZONITRILE is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. It is also used as a building block in organic synthesis, particularly in the preparation of biologically active compounds. This chemical can be toxic if ingested, inhaled, or absorbed through the skin, and precautions should be taken when handling it in a laboratory setting.

Upstream product

• 93744-26-4 (S)-(+)-2-acetyloxy-1-bromo-3-(2-cyanophenoxy)propane 
• 611-20-1 salicylonitrile 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 38465-16-6 1,2-epoxy-3-(2-cyanophenyl)propane 
• 123750-60-7 (2R)-glycidyl 4-nitrobenzenesulfonate 
• 93744-25-3 (S)-(+)-4-(2-cyanophenoxy)methyl-2,2-dimethyl-1,3-dioxolane 
• 115314-14-2 (R)-glycidyl nosylate 

Downstream Products

• 46905-83-3 (S)-1-(2-cyanophenoxy)-2-hydroxy-3-tert-butylamino-propane 
• 46905-83-3 (R)-1-(2-cyanophenoxy)-2-hydroxy-3-tert-butylamino-propane 
• 131769-23-8 (R)-(+)-1-<2-<3-(2-cyanophenoxy)-2-hydroxypropyl>aminoethyl>-2,4-dioxo-3-phenyl-1H,3H-imidazolidine 

Relevant articles and documents

Efficient chemoenzymatic synthesis of (RS)-, (R)-, and (S)-bunitrolol

A new chemical and the first chemoenzymatic synthesis of β-adrenergic receptor blocking agent bunitrolol is reported in racemic (RS) and enantioenriched forms (R and S). The intermediates (R)- and (S)-1-chloro-3-(2- cyanophenoxy)propan-2-ol intermediates were synthesized from the corresponding racemic alcohol through enzymatic kinetic resolution. The commercial available lipases PS-C and CCL exhibited complementary enantioselectivity during transesterification of the racemic alcohol with vinyl acetate affording the (R)-alcohol along with (S)-acetate and the (S)-alcohol along with (R)-acetate, respectively, and represent an example of enzymatic switch for reversal of enantioselectivity. The effects of various reaction parameters, such as temperature, time, substrate and enzyme concentration, and reaction medium, on the activity and enantioselectivity were optimized. The (R)- and (S)-alcohols were converted into (S)-and and (R)-bunitrolol, respectively, by treatment with tert-butylamine. The (R)- and (S)-acetates, obtained enzymatically were deacetylated to the corresponding alcohol by chemical hydrolysis and further converted into (S)-and and (R)-bunitrolol by chemical means. This is the first chemoenzymatic synthesis of both of the enantiomers of the drug. (RS)-, (R)-, and (S)-Bunitrolol were also synthesized following the 'all chemical' routes from (RS)-, (R)-, and (S)-epichlorohydrin via the corresponding (RS)-, (S)-, and (R)-2-cyanoglycidyl ether and the (RS)-, (R)-, and (S)-1-chloro-3-(2- cyanophenoxy)propan-2-ol intermediates with improved overall yields and better enantiomeric excesses compared to the reported processes.

METHODS AND COMPOSITIONS INVOLVING (S)-BUCINDOLOL

Disclosed is bucindolol substantially free of its R-stereoisomer. Also disclosed are pharmaceutical compositions that include bucindolol substantially free of its R-stereoisomer or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. Also disclosed are methods of treating a patient that involve administering to the patient a therapeutically effective amount of a composition of the present invention. Formula (I).

Spontaneous resolution amongst chiral ortho-cyanophenyl glycerol derivatives: an effective preferential crystallization approach to a single enantiomer of the β-adrenoblocker bunitrolol

The β-adrenoblocker bunitrolol 1 as well as intermediate cyclic sulfate 6 and glycidyl ether 8 have been prepared in enantiopure form by starting from enantiopure o-cyanophenyl glycerol ether 2 by an entrainment resolution procedure. Thermal investigations reveal that 1·HCl forms a moderately stable racemic compound, whereas 2, 6 and 8 are conglomerate forming substances potentially capable of entrainment resolution. Some chemical and chiroptical characteristics for bunitrolol and possible intermediates in its synthesis were corrected, and configurations were verified with the configuration of 1·HCl.