3-Hexenedinitrile
[CAS# 1119-85-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Cyanide/nitrile
• Name: 3-Hexenedinitrile
• Synonyms: 1,4-Dicyano-2-butene; NSC 11685; beta-Hydromucononitrile
• Molecular Formula: C₆H₆N₂
• Molecular Weight: 106.13
• CAS Registry Number: 1119-85-3
• EC Number: 214-287-7
• SMILES: C(/C=C/CC#N)C#N

Properties

• Solubility: Slightly soluble (9.8 g/L) (25 °C), Calc.^*
• Density: 0.983±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 76 °C^**
• Index of Refraction: 1.463, Calc.^*
• Boiling Point: 289.6±20.0 °C (760 mmHg), Calc.^*
• Flash Point: 146.2±15.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2019 ACD/Labs)

^** Cornforth, David A.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H301

Discovery and Applications

3-Hexenedinitrile, also known as 3-butene-1,2-dinitrile, is an organic compound with the molecular formula C₆H₈N₂. This compound consists of a six-carbon chain with two nitrile (−C≡N) groups attached to the first and second carbon atoms of the chain. It is a colorless to pale yellow liquid under standard laboratory conditions and has a distinct, sharp odor.

The synthesis of 3-hexenedinitrile typically involves the reaction of an appropriate hexene derivative with a nitrile source, such as cyanogen bromide, or through the use of diene intermediates in a process known as conjugate addition. In one method, hex-2-yne is reacted with cyanogen bromide under suitable conditions to yield 3-hexenedinitrile. The nitrile groups present in the compound make it highly reactive in nucleophilic substitution reactions, which is a key feature in its synthetic utility.

3-Hexenedinitrile is primarily used as a versatile intermediate in organic synthesis. Its functional nitrile groups allow for the introduction of a variety of other functional groups, facilitating the creation of more complex molecules. It is often utilized in the preparation of chemicals for pharmaceuticals, agrochemicals, and other specialty chemicals.

One of the primary applications of 3-hexenedinitrile is in the synthesis of polycyclic compounds, where the nitrile groups can undergo hydrolysis or reduction to produce amides or amines. These derivatives are important building blocks for a range of compounds, particularly in the development of complex organic molecules for the pharmaceutical industry.

In addition to its use as an intermediate for organic synthesis, 3-hexenedinitrile is employed in the preparation of various heterocyclic compounds. The nitrile groups can undergo hydrolysis, leading to carboxylic acids or amides, which can then be further functionalized to form a wide range of compounds with applications in medicinal chemistry and other fields.

The compound’s conjugated diene structure also enables it to participate in polymerization reactions, where it can be incorporated into polymers or copolymers. The nitrile groups in 3-hexenedinitrile are useful for introducing polar functionality into polymer chains, which can enhance the physical properties of the resulting materials, such as increased solubility, strength, or resistance to chemical degradation.

From a safety and handling perspective, 3-hexenedinitrile is a hazardous chemical. It is toxic if inhaled or ingested and may cause skin and eye irritation. Proper safety precautions, including the use of gloves, goggles, and adequate ventilation, should be taken when handling this substance. It should be stored in a cool, dry, and well-ventilated area, away from heat sources and incompatible materials such as strong acids and bases.

In conclusion, 3-hexenedinitrile is a well-established chemical intermediate with applications in organic synthesis, particularly in the preparation of polycyclic compounds, heterocyclic derivatives, and polymers. Its nitrile groups provide significant reactivity, making it a versatile building block in the synthesis of complex molecules for various industrial applications, including pharmaceuticals and specialty chemicals. The chemical’s properties and handling guidelines are well-documented, ensuring its safe and effective use in laboratory and industrial settings.

References

2018. Conversion of aliphatic nitriles by the arylacetonitrilase from Pseudomonas fluorescens EBC191. World Journal of Microbiology and Biotechnology, 34(7), 91.
DOI: 10.1007/s11274-018-2477-9

2015. Bringing nitrilase sequences from databases to life: the search for novel substrate specificities with a focus on dinitriles. Applied Microbiology and Biotechnology, 99(24), 10541-10553.
DOI: 10.1007/s00253-015-7023-1

2010. Reaction of unsaturated nitriles with hydrosilanes. Russian Journal of General Chemistry, 80(5), 926-930.
DOI: 10.1134/s1070363210050105