183582-92-5

Basic information

• Product Name: 1,3,5-Cyclohexanetricarbonitrile (cis- and trans- mixture)
• Synonyms: 1,3,5-Cyclohexanetricarbonitrile (cis- and trans- mixture);1,3,5-Cyclohexanetricarbonitrile (cis- and trans- mixture)
• CAS NO: 183582-92-5
• Molecular Formula: C9H9N3
• Molecular Weight: 159.18786
• Mol File: 183582-92-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 170℃
• Boiling Point: 200°C/0.2mmHg(lit.)
• Flash Point: 220.8°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 2.56E-07mmHg at 25°C
• Refractive Index: 1.494
• CAS DataBase Reference: 1,3,5-Cyclohexanetricarbonitrile (cis- and trans- mixture)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Cyclohexanetricarbonitrile (cis- and trans- mixture)(183582-92-5)
• EPA Substance Registry System: 1,3,5-Cyclohexanetricarbonitrile (cis- and trans- mixture)(183582-92-5)

Safety Data

• RIDADR: 3439
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 183582-92-5(Hazardous Substances Data)

Usage

Description

1,3,5-Cyclohexanetricarbonitrile (cisand transmixture) is a colorless solid with the chemical formula C9H9N3, consisting of a mixture of cis and trans isomers. It is insoluble in water and most organic solvents and is primarily used as an intermediate in the production of pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
1,3,5-Cyclohexanetricarbonitrile (cisand transmixture) is used as a building block for the synthesis of various compounds in the pharmaceutical industry. Its unique structure allows for the creation of a wide range of pharmaceutical products.
Used in Agrochemical Industry:
1,3,5-Cyclohexanetricarbonitrile (cisand transmixture) is also used as an intermediate in the production of agrochemicals, contributing to the development of various agricultural products.
Used in Organic Synthesis:
1,3,5-Cyclohexanetricarbonitrile (cisand transmixture) is utilized in organic synthesis, serving as a reagent in chemical reactions to produce a variety of organic compounds.
Used as a Chemical Reagent:
In addition to its applications in the pharmaceutical and agrochemical industries, 1,3,5-Cyclohexanetricarbonitrile (cisand transmixture) is used as a reagent in various chemical reactions, aiding in the synthesis of different types of compounds.
It is important to handle 1,3,5-Cyclohexanetricarbonitrile (cisand transmixture) with care, as it may be harmful if swallowed, inhaled, or in contact with skin. It should be stored and handled in a well-ventilated area with appropriate protective equipment.

InChI:InChI=1/C9H9N3/c10-4-7-1-8(5-11)3-9(2-7)6-12/h7-9H,1-3H2

Upstream product

• 168280-44-2 triphenyl cis,cis-cyclohexane-1,3,5-tricarboxylate 
• 147365-19-3 (1S,3S,5S)-cyclohexane-1,3,5-tricarbonyl trichloride 
• 99063-92-0 cis,cis-cyclohexane-1,3,5-tricarboxamide 
• 16526-68-4 cis-1,3,5-cyclohexane tricarboxylic acid 
• 168280-46-4 (1α,3α,5α)-1,3,5-tricyanocyclohexane 

Relevant articles and documents

A multi-step continuous (1 α, 3 α, 5 α) - 1, 3, 5 - [...] preparation method

The present invention discloses a multi-step continuous (1 α, 3 α, 5 α) - 1, 3, 5 - [...] preparation method. The invention provides a multi-step continuous (1 α, 3 α, 5 α) - 1, 3, 5 - [...] preparation method, comprising the following steps: (1) in a solvent, in the presence of an organic base, the compound 2 with phenol to carry out the esterification reaction, to obtain compound 3 of the reaction solution can be; (2) the step (1) the obtained containing compound 3 of reaction liquid and ammonia gas to ammonolysis reaction, to obtain compound 4 can be. The method raw materials are cheap, simple and convenient operation, high yield, the product quality is good, few by-products at the same time, omit the after-processing, the generated three waste a significant reduction of the and the like, and is suitable for industrial production.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.

A conformational study of cyclohexane-1,3,5-tricarbonitrile derivatives

Cyclohexane-1,3,5-tricarbonitrile reached equilibrium having 1,3-cis-1,5-cis and 1,3-cis-1,5-trans isomers in a ratio of 3:7. The cis,cis-isomer preferred the conformation with three equatorial cyano groups, whereas the cis,trans-isomer displayed two cyano groups on equatorial positions and another cyano group on axial position. Condensation of cis,cis-cyclohexane-1,3,5-tricarbonitrile with L-(S)-valinol by the catalysis of ZnCl2 in refluxing 1,2-dichlorobenzene afforded two isomeric cyclohexane-1,3,5-trioxazolines in favor of the 1,3-cis-1,5-trans isomer. Metalation of cis,cis-cyclohexane-1,3,5-tricarbonitrile, followed by alkylations with dimethyl sulfate, benzyl bromide or allyl bromide, gave the corresponding trialkylation products with predominance of 1,3-cis-1,5-trans isomers. The cis,trans-isomer showed two cyano groups on axial positions and another cyano group on equatorial position, whereas the cis,cis-isomer exhibited three axial cyano groups. Treatment of trimethyl cis,cis-cyclohexane-1,3,5-tricarboxylate with lithium diisopropylamide and dimethyl sulfate afforded mainly the trimethyl ester of Kemp's triacid, which showed three axial carboxylate groups. Two competitive factors, i.e. the steric effect of incoming electrophiles and the dipole-dipole interactions of the cyano or carboxylate groups, might interplay to give different stereoselectivities in these reaction systems.