Succinonitrile

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Succinonitrile
Succinonitrile structure image.png
Structure of succinonitrile
Names
IUPAC name
Butanedinitrile
Other names
1,2-Dicyanoethane
Ethylene cyanide
Ethylene Dicyanide
Succinodinitrile
Properties
C4H4N2
Molar mass 80.09 g/mol
Appearance Colorless, waxy crystals
Odor Odorless
Density 0.985 g/cm3 (25 °C)
Melting point 54.5 °C (130.1 °F; 327.6 K)
Boiling point 266.1 °C (511.0 °F; 539.2 K)
12.69 g/100 ml (20 °C)[1]
Solubility Soluble in acetone, chloroform, dioxane, methanol
Slightly soluble in benzene, carbon disulfide, diethyl ether, ethanol, hexane
Solubility in methanol 10 g/100 ml
Vapor pressure 0.00778 mmHg at 25 °C
Thermochemistry
191.59 J·K−1·mol−1
139.3–140.4 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Flash point 132 °C (270 °F; 405 K)
Lethal dose or concentration (LD, LC):
450 mg/kg (rat, oral)
Related compounds
Related compounds
Malononitrile
Dicyanoacetylene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Succinonitrile or butanedinitrile, is an organic chemical compound, a nitrile. It has the formula NCCH2CH2CN or C4H4N2.

Properties

Chemical

Hydrogenation of succinonitrile yields putrescine.

Physical

Succinonitrile is a waxy colorless solid, that slowly turns brownish in air. It is soluble in water and alcohols.

Availability

Butanedinitrile is sold by chemical suppliers.

Preparation

Succinonitrile is mainly produced by the addition of hydrogen cyanide to acrylonitrile:[2]

CH2=CHCN + HCN → NCCH2CH2CN

Alternatively, it can also be produced by reacting 1,2-dibromoethane or 1,2-diiodoethane with potassium or sodium cyanide.[3][4]

Projects

Handling

Safety

Succinonitrile is expected to be toxic, as it's metabolized to free cyanide which is very toxic. It can be absorbed via ingestion, inhalation and skin/eye contact.[5]

Storage

In closed bottles, away from corrosive reagents.

Disposal

Should be carefully mixed with bleach. Alternatively it can be dissolved in a flammable solvent and burned in an incinerator.

References

  1. Yalkowsky, S.H., He, Yan., Handbook of Aqueous Solubility Data: An Extensive Compilation of Aqueous Solubility Data for Organic Compounds Extracted from the AQUASOL dATAbASE. CRC Press LLC, Boca Raton, FL. 2003., p. 82
  2. http://www.mrw.interscience.wiley.com/emrw/9783527306732/ueic/article/a17_363/current/html?hd=All%2Csuccinonitrile
  3. https://i.imgur.com/6uBH0bE.png
  4. https://pubs.acs.org/doi/10.1021/jo01072a600
  5. https://www.cdc.gov/niosh/npg/npgd0573.html

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