Carbon diselenide

Carbon diselenide
Carbon diselenide
CAS number 506-80-9
Molecular formula CSe2
Molar mass 169.93 g/mol
Appearance yellow liquid
Density 2.69 g/cm3
Melting point

−43.7 °C

Boiling point

125.5 °C

Solubility in water insoluble in water
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Carbon diselenide is an inorganic compound with the chemical formula CSe2. It is a yellow-orange oily liquid with pungent odor. It is an analogue of carbon disulfide (CS2). This light-sensitive compound is insoluble in water and soluble in organic solvents.

Synthesis, structure and reactions

Carbon diselenide is a linear molecule with D∞h symmetry. It is produced by reacting selenium powder with dichloromethane vapor near 550 °C.[1]

2 Se + CH2Cl2 → CSe2 + 2 HCl

It was first reported by Grimm and Metzger, who prepared it by treating hydrogen selenide with carbon tetrachloride in a hot tube.[2]

Like carbon disulfides, carbon diselenide polymerizes under high pressure. The structure of the polymer is thought to be a head-to-head structure with a backbone in the form of –[Se–C(=Se)–C(=Se)–Se]–.[3] The polymer is a semiconductor with a room-temperature conductivity of 50 S/cm.

In addition, carbon diselenide is a precursor to tetraselenafulvalenes,[4] the selenium analogue of tetrathiafulvalene, which can be further used to synthesize organic conductors and organic superconductors.

Carbon diselenide reacts with secondary amines to give dialkydiselenocarbamates:[1]

2 Et2NH + CSe2 → (Et2NH2+)(Et2NCSe2)


Carbon diselenide has high vapor pressure. It is toxic and presents an inhalation hazard. It may be dangerous due to its easy membrane transport. It decomposes slowly in storage (about 1% per month at –30 °C). When obtained commercially, its cost is high.[5]

Mixed with air, CSe2 releases an extremely offensive odor.[6] Its smell forced an evacuation of a nearby village when it was first synthetized in 1936. The stench can be neutralized by oxidizing with bleach.[7] Because of the odor, synthetic pathways have been developed to avoid its use.[8]


  1. ^ a b W. Pan and J. P. Fackler, Jr. (1982). "Diselenocarbamates from carbon diselenide". Inorganic Syntheses. Inorganic Syntheses 21: 6. doi:10.1002/9780470132524.ch2. ISBN 9780470132524. 
  2. ^ H. G. Grimm, H. Metzger (1936). "Über Darstellung und Eigenschaften des Selenkohlenstoffs". Berichte der deutschen chemischen Gesellschaft (A and B Series) 69 (6): 1356–1364. doi:10.1002/cber.19360690626. 
  3. ^ C. E. Carraher, Jr. and C.U. Pittman, Jr. (2005). "Poly(Carbon Disulfide), Poly(Carbon Diselenide), and Polythiocyanogen". Inorganic Polymers 21. doi:10.1002/14356007.a14_241. ISBN 3527306730. 
  4. ^ Edward M. Engler, Vishnu V. Patel (1974). "Structure control in organic metals. Synthesis of tetraselenofulvalene and its charge transfer salt with tetracyano-p-quinodimethane". Journal of American Chemical Society 96 (23): 7376–7378. doi:10.1021/ja00810a042. 
  5. ^ "Carbon Diselenide CSe2". Retrieved 2010-02-27. 
  6. ^ ""carbon diselenide has by far the worst odor this author has experienced in his lifetime of working with selenium compounds"" Wolfgang H.H. Gunther: Organic Selenium Compounds: Their Chemistry and Biology
  7. ^ Derek. "Things I Won't Work With: Carbon Diselenide. In the Pipeline:". Retrieved 2010-02-27. 
  8. ^ "Process for producing chalcogen containing compounds - Patent 4462938". Retrieved 2010-02-27. 

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