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7,7,8,8-Tetracyanoquinodimethane is an electron-acceptor molecule used to form charge-transfer superconductors. It is an effective catalyst used for the ?-chlorination of carboxylic acids using chlorosulfonic acid; the presence of TCNQ suppresses competing free-radical chlorination.
K. Sutter.; J. Hulliger.; P. Günter. Photorefractive effects observed in the organic crystal 2-cyclooctylamino-5-nitropyridine doped with 7,7,8,8-tetracyanoquinodimethane. Solid State Communications. 1990, 74, (8), 867-870.
Long, R. E.; Sparks, R. A.; Trueblood, K. N. The crystal and molecular structure of 7, 7, 8, 8-tetracyanoquinodimethane. Acta Crystallographica. 1965, 18 (5), 932-939.
Electron-acceptor, forming stable radical anions: J. Am. Chem. Soc., 82, 6408 (1960); 84, 3370, 3374 (1962).
Forms charge-transfer complexes with electron-rich donors: J. Am. Chem. Soc., 95, 948 (1973).
For a review of the differences between "metallic" and "non-metallic" salts of TCNQ, see: Acc. Chem. Res., 12, 79 (1979).
Effective catalyst for the ɑ-chlorination of carboxylic acids using chlorosulfonic acid; the presence of TCNQ suppresses competing free-radical chlorination: J. Org. Chem., 48, 1364 (1983).
Hazard Statements: H302-H312-H331
Harmful if swallowed. Harmful in contact with skin. Toxic if inhaled.
Precautionary Statements: P261-P280h-P304+P340-P311a-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/clothing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER/doctor. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.