33863-75-1

Basic information

• Product Name: Oxiranecarbonitrile, 3-phenyl-
• CAS NO: 33863-75-1
• Molecular Formula: C9H7NO
• Molecular Weight: 145.161
• Mol File: 33863-75-1.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: Oxiranecarbonitrile, 3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranecarbonitrile, 3-phenyl-(33863-75-1)
• EPA Substance Registry System: Oxiranecarbonitrile, 3-phenyl-(33863-75-1)

Safety Data

• Hazardous Substances Data: 33863-75-1(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 107-14-2 chloroacetonitrile 
• 1885-38-7 cinnamic nitrile 
• 24840-05-9 (Z)-cinnamonitrile 
• 33863-75-1 (±)-cis-phenyloxirane-2-carbonitrile 
• 28000-59-1 α,α-diiodotoluene 
• 3252-43-5 dibromoacetonitrile 

Downstream Products

• 19190-80-8 cis-methyl 2,3-epoxy-3-phenylpropanoate 
• 19190-80-8 methyl trans-3-phenylglycidate 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 79963-86-3 1-cyano 2-fluoro-2-phenylethanol 
• 343953-79-7 2,2-Dimethyl-5-phenyl-[1,3]dioxolane-4-carbonitrile 
• 133520-54-4 (-)-2,3-dihydroxy-3-phenylpropanenitrile 
• 133520-55-5 2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonitril 
• 124649-67-8 methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate 
• 33863-75-1 cis-3-phenyloxirane-2-carbonitrile 
• 133520-53-3 2,3-Dihydroxy-3-phenylpropannitril 
• 133520-56-6 2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonitril 
• 214194-15-7 (4S,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester 

Relevant articles and documents

Concerning the reactivity of dioxiranes. Observations from experiments and theory

The challenging hypothesis of a biphilic (i.e., electrophilic vs nucleophilic) character for dioxirane reactivity, which envisages that electron-poor alkenes are attacked by dioxiranes in a nucleophilic fashion, could not be sustained experimentally. Rate data, which estimate Hammett rho values for the epoxidation of 3- or 4-substituted cinnamonitriles X·Ph-CH=CH-CN, unequivocally allow one to establish that dioxiranes epoxidize electrophilically even alkenes carrying electron-withdrawing-groups. The greater propensity of methyl(trifluoromethyl) dioxirane TFDO (1b) to act as an electrophilic oxidant with respect to dimethyldioxirane DDO (1a) parallels the cathode reduction potentials for the two dioxiranes, as measured by cyclic voltammetry. A simple FMO approach for alkene epoxidation is helpful to conceive a likely rationale for the greater oxidizing power of TFDO as compared to DDO.

BF3·OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles

Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ generated toxic cyanide with boron trifluoride, making the reaction efficient, safe, and environmentally benign. The reaction occurs through an acid-promoted Meinwald rearrangement, producing arylacetyl cyanides, followed by an addition-elimination process with nitrogen or oxygen-containing nucleophilic amines, alcohols or water. The current method provides a new application of the tandem Meinwald rearrangement.

Metal-free and regiospecific synthesis of 3-arylindoles

A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ri

ALPHA-HYDROXY-BETA-AZIDO-TETRAZOLES

Alpha-hydroxy-beta-azido tetrazole compounds of formula (I): a process for manufacturing alpha-hydroxy-beta-azido tetrazoles of formula (I), and their use for synthesizing new compounds, e.g. in “click” chemistry.