synonymCyanoacetylene(Cyanoacetylene) generally refers to propargyronitrile
Cyanoacetylene is a kind ofOrganic compoundIts molecule is C3HN or H-C ∨ C-C ∨ N.Cyanoacetylene in astronomytelemeteringMedium observableInterstellar cloud。So is cyanoacetyleneMiller discharge experimentOne of the compounds produced in.
Chinese name
Propargyronitrile
Foreign name
cyanaethylene
Alias
Cyanoacetylene
chemical formula
C3HN
molecular weight
fifty-one point zero four six seven
CAS login number
1070-71-9
Melting point
5 ℃
Boiling point
42.50 ℃
Water solubility
Easily soluble in ethanol, hardly soluble in water.
Density
0.925g/cm³
Flash point
-30.50 ℃
Application
Medical intermediate materials, interstellar cloud observation
Propynenitrile can produce (Z) - alkenes by nucleophilic addition, and can also undergo Diels Alder reaction with nitro orDiazo compoundhappenCycloaddition reaction。
Propynenitrile and acetyleneNucleophile(Z) - alkynide can also be obtained by addition of, and (Z) - 3-bromopropylonitrile can be obtained by bromine substitution, and then acetylene can be obtained in the presence of palladium
Ritter reaction Propynenitrile can be used in Ritter reaction, but the yield is not high, and different reaction temperatures will produce different products
Diels Alder cycloaddition to propargyronitrile can occur Diels Alder cycloaddition with diene.Affected by the structure of diene, the corresponding cyclohexadiene can be generated
Multi ring additionCycloaddition reactionIt is often related to nitrates and diazo compounds
Other cycloaddition can also form novel bicyclic compounds andCyclooctetraeneStructure, but the mechanism of these two reactions is not completely clear
Preparation method
Announce
edit
1. It is oxidized by propargyl alcohol and chromic anhydrideHydroxylamine hydrochloride, oximation of potassium carbonate, dehydration of acetic anhydride.
2. In the laboratory, propargyl aldehyde amine andPhosphorus pentoxideDehydrate to prepare.After reaction under nitrogen, the solid mixture is treated at high temperature and the distillate at 5oC is collected.
3. Preparation method:
Propargyronitrile[2]
a. β - Dibromopropane (3): add 100g (1.89mol) of acrylonitrile (2) in the reaction with agitator, thermometer and dropping funnel, cool to 15 ℃ under stirring, irradiate the reaction bottle with 200W bulb, and slowly drop 302g of bromine.Control the dropping acceleration so that the internal temperature does not exceed 30 ℃.After addition, continue to stir until the color of bromine fades.Distill under reduced pressure and collect the fraction of 105~112 ℃/2.66kPa to obtain a, β - dibromopropane (3) in 85% yield.Propynenitrile (1): heat and adjust the silicon carbon tube to 570 ℃, the system pressure is 2.67kPa, cool the receiver with dry ice to - 50 ℃, and slowly drip compound (3).After pyrolysis, hydrogen bromide gas and propargyronitrile are generated.The generated propiononitrile is solidified in the acceptor.Melt the solidified product in a cold water bath, distill it under reduced pressure, and collect 42~45 ℃/2.67kPa fraction to obtain propiononitrile ① with a yield of 50%.Note: ① It can also be prepared by oxidation, oximation and dehydration of propargyl alcohol
