1,5-Dicyanopentane
[CAS# 646-20-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Alkane
• Name: 1,5-Dicyanopentane
• Synonyms: Pimelonitrile
• Molecular Formula: C₇H₁₀N₂
• Molecular Weight: 122.17
• CAS Registry Number: 646-20-8
• EC Number: 211-469-8
• SMILES: C(CCC#N)CCC#N

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*, 0.948 g/mL (Expl.)
• Index of Refraction: 1.437, Calc.^*, 1.441 (Expl.)
• Boiling Point: 310.8 °C (760 mmHg), Calc.^*, 340.4-341.8 °C (Expl.)
• Flash Point: 143.4±16.5 °C, Calc.^*, 112 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H312-H332
• Safety Statements: P261-P264-P270-P271-P280-P301+P316-P302+P352-P304+P340-P317-P321-P330-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 3276

Discovery and Applications

1,5-Dicyanopentane, with the chemical formula C7H10N2, is a simple organic compound containing two nitrile (-CN) groups attached to a five-carbon alkane chain. It is commonly used as a chemical intermediate in organic synthesis and has applications in materials science.

The compound was first synthesized and characterized in the mid-20th century as part of research into nitrile compounds and their reactivity. Its structure consists of a linear alkane chain with the nitrile groups positioned at the 1 and 5 positions, hence its name. The synthesis of 1,5-dicyanopentane is typically carried out via methods involving the substitution of halogenated hydrocarbons with cyanide salts under suitable conditions, such as using sodium cyanide in a polar solvent.

One of the primary applications of 1,5-dicyanopentane is in the synthesis of other organic compounds. Its nitrile groups make it an important building block in the construction of more complex molecules. For instance, the nitrile groups can undergo hydrolysis to form carboxylic acids or can be converted into amides, imides, or other functional groups through various chemical reactions. This versatility in chemical reactivity makes 1,5-dicyanopentane valuable for the preparation of polymers, pharmaceuticals, and other specialty chemicals.

In materials science, 1,5-dicyanopentane can be used in the production of cross-linked polymers. The nitrile groups can react with other functional groups to form networks, which are useful in producing plastics with desirable mechanical properties. These polymers have applications in industries such as electronics, automotive, and construction, where materials with high strength, thermal stability, and chemical resistance are required.

Additionally, 1,5-dicyanopentane serves as a precursor in the synthesis of various heterocyclic compounds. By undergoing chemical transformations such as cyclization reactions, it can lead to the formation of cyclic structures with significant biological and chemical activity. These heterocycles are of interest in the pharmaceutical industry, as many biologically active compounds contain such rings.

In conclusion, 1,5-dicyanopentane is an important compound in organic chemistry due to its reactivity and versatility. It plays a role in the synthesis of polymers, specialty chemicals, and heterocyclic compounds. Its applications are particularly prominent in materials science, organic synthesis, and the development of new chemical intermediates.

References

1985. Structure-acute toxicity relationship of dinitriles in mice. Archives of Toxicology, 57(2).
DOI: 10.1007/bf00343116

2010. A nitrilase from a metagenomic library acts regioselectively on aliphatic dinitriles. Applied Microbiology and Biotechnology, 88(2).
DOI: 10.1007/s00253-010-2831-9

2019. Recent research advancements on regioselective nitrilase: fundamental and applicative aspects. Applied Microbiology and Biotechnology, 103(14).
DOI: 10.1007/s00253-019-09915-8