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Tetramethyltetraselenafulvalene

Chemical compound From Wikipedia, the free encyclopedia

Tetramethyltetraselenafulvalene is the organoselenium compound with the chemical formula ((CH3)2C2Se2C)2.[1] It is one of the heterofulvalenes.[2][3]

Quick facts Names, Identifiers ...
Tetramethyltetraselenafulvalene
Names
IUPAC name
2-(4,5-dimethyl-1,3-diselenol-2-ylidene)-4,5-dimethyl-1,3-diselenole
Other names
  • TMTSF
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.152.166 Edit this at Wikidata
EC Number
  • 623-491-9
  • InChI=1S/C10H12Se4/c1-5-6(2)12-9(11-5)10-13-7(3)8(4)14-10/h1-4H3
    Key: YMWLPMGFZYFLRP-UHFFFAOYSA-N
  • CC1=C([Se]C(=C2[Se]C(=C([Se]2)C)C)[Se]1)C
Properties
C10H12Se4
Molar mass 448.090 g·mol−1
Appearance purple powder
Density g/cm3
Melting point 275 °C (527 °F; 548 K)
Boiling point 338.8 °C (641.8 °F; 612.0 K)
Hazards
GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H331, H373, H410
P260, P264, P273, P301, P304, P310, P311, P314, P340
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Structure

TMTSF is a planar molecule with C2v symmetry. It is structually analogous to tetramethyltetrathiafulvalene (TMTTF).[4] This structure is suitable for the role of TMTSF as an electron donor and the formation of some charge-transfer salts. A notable family of derivatives are the Bechgaard salts, e.g., (TMTSF)2PF6, the first organic superconductor.[5][6]

Synthesis

TMTSF is prepared from 3-chloro-2-butanone via a triselenocarbonate. Diethylselenocarbamate is a source of Se.[7]

CH3C(O)CHClCH3 + (CH3CH2)2NCSe−2 → (CH3CH2)2NC(Se)SeCHC(O)(CH3)2 + Cl−
(CH3CH2)2NC(Se)SeCHC(O)(CH3)2 + 2H+ → (CH3CH2)2N=CSe2C2(CH3)+2 + H2O
(CH3CH2)2N=CSe2C2(CH3)+2 + SeH− → Se=CSe2C2(CH3)2 + (CH3CH2)2NH
2 Se=CSe2C2(CH3)2 + 2 P(OCH3)3 → (CH3)2C2Se2C=CSe2C2(CH3)2 + 2 SeP(OCH3)3

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