Carbon diselenide

Source: Wikipedia, the free encyclopedia.
Carbon diselenide
Names
IUPAC name
Carbon diselenide
Systematic IUPAC name
Methanediselenone
Other names
Carbon selenide
Diselenoxomethane
Methanediselone
Carbon(IV) selenide
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.007.323 Edit this at Wikidata
EC Number
  • 208-054-9
UNII
  • InChI=1S/CSe2/c2-1-3 checkY
    Key: JNZSJDBNBJWXMZ-UHFFFAOYSA-N checkY
  • InChI=1/CSe2/c2-1-3
    Key: JNZSJDBNBJWXMZ-UHFFFAOYAM
  • [Se]=C=[Se]
Properties
CSe2
Molar mass 169.953 g·mol−1
Appearance Yellow liquid
Density 2.6824 g/cm3
Melting point −43.7 °C (−46.7 °F; 229.5 K)
Boiling point 125.5 °C (257.9 °F; 398.6 K)
0.054 g/(100 mL)
Solubility Soluble in CS2, toluene
0 D
Thermochemistry
50.32 J/(mol·K) (gas)
263.2 J/(mol·K) (gas)
Std enthalpy of
formation
(ΔfH⦵298)
 219.2 kJ/mol (liquid)
Hazards
Flash point 30 °C (86 °F; 303 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Carbon diselenide is an

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

backbone in the form of [−C(=Se)−Se−]n.[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 (CH3CH2)2NH + CSe2 → [(CH3CH2)2NH+2]((CH3CH2)2N−CSe−2)

Safety

Carbon diselenide has high vapor pressure. It has a moderate toxicity 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]

Pure distilled carbon diselenide has an odor very similar to that of carbon disulfide, but mixed with air, it creates extremely offensive odors (corresponding to new, highly toxic reaction products).[6][7] Its smell forced an evacuation of a nearby village when it was first synthesized in 1936.[7] Because of the odor, synthetic pathways have been developed to avoid its use.[8]

References

  1. ^
    ISBN 978-0-470-13252-4
    .
  2. doi:10.1002/cber.19360690626
    .
  3. ISBN 3-527-30673-0
    .
  4. PMID 4814748
    .
  5. ^ "Carbon Diselenide CSe2". Cse2.com. Retrieved 2012-04-04.
  6. ^ Wolfgang H. H. Gunther. Organic Selenium Compounds: Their Chemistry and Biology. carbon diselenide has by far the worst odor this author has experienced in his lifetime of working with selenium compounds
  7. ^ a b Lowe, Derek (2005-03-03). "Things I Won't Work With: Carbon Diselenide". In the Pipeline. Science. Archived from the original on 23 September 2015. Retrieved 20 November 2015.
  8. ^ US patent 4462938, Wudl, F., "Process for producing chalcogen containing compounds", issued 1984-07-31, assigned to AT&T Bell Laboratories .
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