168280-46-4

Basic information

• Product Name: 1,3,5-CYCLOHEXANETRICARBONITRILE
• Synonyms: 1,3,5-CYCLOHEXANETRICARBONITRILE;1,3,5-TRICYANOCYCLOHEXANE;(1alpha,3alpha,5alpha)-1,3,5-Cyclohexanetricarbonitrile;(1alpha,3alpha,5alpha)-1,3,5-Tricyanocyclohexane;(1α,3α,5α)-1,3,5-Cyclohexanetricarbonitrile
• CAS NO: 168280-46-4
• Molecular Formula: C₉H₉N₃
• Molecular Weight: 159.19
• Product Categories: Dinitriles & Trinitriles;Trinitriles
• Mol File: 168280-46-4.mol

Chemical Properties

• Melting Point: 170 °C
• Boiling Point: 421.7 °C at 760 mmHg
• Flash Point: 220.8 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 2.56E-07mmHg at 25°C
• Refractive Index: 1.494
• CAS DataBase Reference: 1,3,5-CYCLOHEXANETRICARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-CYCLOHEXANETRICARBONITRILE(168280-46-4)
• EPA Substance Registry System: 1,3,5-CYCLOHEXANETRICARBONITRILE(168280-46-4)

Safety Data

• RIDADR: 3439
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 168280-46-4(Hazardous Substances Data)

Usage

Uses

1. Chemical Intermediates:
1,3,5-Cyclohexanetricarbonitrile is used as a chemical intermediate for the synthesis of various organic compounds. The presence of three nitrile groups allows for multiple reactions, such as hydrolysis, reduction, or polymerization, which can lead to the formation of a wide range of products.
2. Pharmaceutical Industry:
1,3,5-Cyclohexanetricarbonitrile is used as a building block in the development of new pharmaceutical compounds. The nitrile groups can be converted into other functional groups, such as amines or amides, which are common in many drug molecules. This versatility makes it a valuable starting material for the synthesis of potential therapeutic agents.
3. Material Science:
1,3,5-Cyclohexanetricarbonitrile is used as a precursor in the production of advanced materials, such as polymers and composites. The nitrile groups can be polymerized to form high-performance materials with unique properties, such as increased strength, flexibility, or chemical resistance.
4. Agrochemicals:
1,3,5-Cyclohexanetricarbonitrile is used as a starting material in the synthesis of agrochemicals, such as pesticides and herbicides. The nitrile groups can be modified to create compounds with specific biological activities, making them effective in controlling pests and weeds in agricultural settings.
5. Research and Development:
1,3,5-Cyclohexanetricarbonitrile is used as a research compound in academic and industrial laboratories. Its unique structure and reactivity make it an interesting subject for studies in organic chemistry, materials science, and related fields. Researchers can explore its properties and potential applications, contributing to the advancement of scientific knowledge and the development of new technologies.

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

Upstream product

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

Downstream Products

• 168280-47-5 cis,cis-1,3,5-Tris(cyano)-1,3,5-tris(diphenylphosphanyl)cyclohexane 
• 183582-92-5 cis,trans-cyclohexane-1,3,5-tricarbonitrile 

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.

A flexible solution to anion transport: Powerful anionophores based on a cyclohexane scaffold

Transmembrane anion carriers (anionophores) have potential for biological activity, including the treatment of channelopathies such as cystic fibrosis. A new family of anionophores has been synthesized, in which three thiourea groups are mounted on a cyclohexane-based scaffold. Though conceptually related to earlier polycyclic systems, these molecules are simpler and far more accessible. Preorganization is somewhat reduced compared to earlier systems, and anion affinities are correspondingly lower. However, transport activities set new records. This surprising performance suggests a role for controlled flexibility in the design of transmembrane anion carriers. Speedy shuttling: New anionophores were developed which are simpler and far more accessible than conceptually related earlier systems. They are also less preorganized and anion affinities are lower (as expected), but transport activities set new records. This surprising performance suggests a role for controlled flexibility in the design of transmembrane anion carriers.

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.

Anionic polymerization of an acrylonitrile trimer studied by photoelectron spectroscopy

Anionic polymerization of an acrylonitrile trimer was discussed. Photoelectron spectrum was studied which is produced by electron impact on an acrylonitrile cluster. Results showed that the formation of stereoisomer is determined by the energetics and the entropy requirement of the reaction system.

Synthesis and Complexation Behavior of the Functionalized Tripodal Phosphane cis,cis-1,3,5-Tris(cyano)-1,3,5-tris(diphenylphosphanyl)cyclohexane (tdppcycn)

The synthesis of the novel potentially bistripodal ligand cis,cis-1,3,5-tris(cyano)-1,3,5-tris(diphenylphosphanyl)cyclohexane (tdppcycn) (6) is described.Starting from the tricarboxylic acid cis,cis-1,3,5-C6H9(COOH)3 (1), which is converted stepwise into triacid chloride cis,cis-1,3,5-C6H9(COCl)3 (2), the triphenyl ester cis,cis-1,3,5-C6H9(COOPh)3 (3), the tricarboxamide cis,cis-1,3,5-C6H9(CONH2)3 (4), and the tricarbonitrile cis,cis-1,3,5-C6H9(CN)3 (5), we obtained tdppcycn (6) by α-deprotonation of 5 followed by treatment with ClPPh2 in good yield.Treatment of 6 with Mo(CO)3(η6-C7H8) and Ir(PPh3)2(CO)Cl gave octahedral Mo(tdppcycn)(CO)3 (7) and pentacoordinate Ir(tdppcycn)(CO)Cl (8), respectively, with a facially P-coordinated tdppcycn ligand.The stereochemistry of compounds 2-8 was established by 1H-, 13C-, 31P-NMR, and IR spectroscopy.An X-ray crystal structure analysis of complex 8 confirms the trigonal-bipyramidal ground-state structure in the solid state. - Keywords: Phosphane ligands, tripodal; Molybdenum complexes; Iridium complexes