1,3,6-Hexanetricarbonitrile
[CAS# 1772-25-4]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: 1,3,6-Hexanetricarbonitrile
• Synonyms: Hexane-1,3,6-tricarbonitrile
• Molecular Formula: C₉H₁₁N₃
• Molecular Weight: 161.2
• CAS Registry Number: 1772-25-4
• EC Number: 217-199-7
• SMILES: C(CC#N)CC(CCC#N)C#N

Properties

• Solubility: 2.115e+004 mg/L (25 ºC water)
• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.463, Calc.^*
• Melting point: 91.23 ºC
• Boiling Point: 339.29 ºC, 441.0±30.0 ºC (760 mmHg), Calc.^*
• Flash Point: 229.5±18.5 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06 Danger
• Hazard Statements: H227-H301+H311+H331-H315-H319
• Precautionary Statements: P210-P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P370+P378-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H331

Discovory and Applicatios

1,3,6-Hexanetricarbonitrile, also known by its chemical formula C6H3N3, is an organic compound that contains three nitrile groups (-C≡N) attached to a hexane backbone. This compound is synthesized through various chemical processes, typically involving the reaction of an appropriate hexane derivative with cyanogen or other nitrile-forming reagents. The presence of three nitrile groups in the molecule makes it a valuable compound in the field of organic chemistry due to its ability to participate in a range of reactions, such as nucleophilic substitution and cyclization.

The discovery of 1,3,6-hexanetricarbonitrile is attributed to early studies in the area of nitrile chemistry, where researchers were exploring methods to synthesize complex molecules with multiple nitrile groups. Its synthesis and properties were explored in the context of expanding the versatility of nitrile chemistry, particularly for applications in polymer chemistry, material science, and the creation of various chemical intermediates.

One of the primary applications of 1,3,6-hexanetricarbonitrile is in the field of polymer chemistry. It can be used as a monomer or building block in the synthesis of polyurethanes, polyamides, and other polymeric materials. The nitrile groups in the molecule provide reactivity that can be utilized in polymerization reactions or in the modification of existing polymers. This makes the compound a useful intermediate in the production of specialty materials with enhanced chemical resistance, thermal stability, and mechanical properties.

In addition to its role in polymer chemistry, 1,3,6-hexanetricarbonitrile is also utilized in the synthesis of various organic compounds that are of interest in both industrial and pharmaceutical applications. The nitrile groups in this molecule can undergo nucleophilic substitution reactions with various nucleophiles, such as alcohols, amines, or thiols, leading to the formation of a variety of functionalized compounds. These functionalized derivatives can then be used in the synthesis of drugs, agrochemicals, and other biologically active molecules.

The compound is also used as a precursor in the synthesis of complex ligands for coordination chemistry. The nitrile groups are highly polar and can coordinate with metal ions, leading to the formation of metal complexes that have potential applications in catalysis, sensor technology, and material science. These complexes can exhibit unique properties based on the coordination environment around the metal center, which is influenced by the presence of the nitrile groups.

Furthermore, 1,3,6-hexanetricarbonitrile has found applications in the field of organocatalysis, where it can be employed as a catalyst or co-catalyst in various chemical reactions. The presence of the nitrile groups can enhance the reactivity of certain molecules, making them suitable for catalyzing reactions such as the synthesis of heterocyclic compounds, polymerization reactions, and other processes in fine chemical production.

In summary, 1,3,6-hexanetricarbonitrile is an important compound in synthetic chemistry with a wide range of applications. Its primary uses are in polymer chemistry, organic synthesis, coordination chemistry, and catalysis. The compound’s properties, particularly its nitrile functionality, make it a versatile building block in the creation of materials and molecules with diverse industrial and pharmaceutical applications. The well-documented history of its discovery and application confirms its value in these areas of research and industry.