ChemicalBook CAS DataBase List 1,8-Dicyanonaphthalene

1,8-Dicyanonaphthalene synthesis

5synthesis methods

Product Name:1,8-Dicyanonaphthalene
CAS Number:5690-48-2
Molecular formula:C12H6N2
Molecular Weight:178.19

8-Thia-7,9-diaza-cyclopenta[a]acenaphthylene 8,8-dioxide

51485-73-5
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5690-48-2
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Yield:5690-48-2 90.6%

Reaction Conditions:

at 180; under 0.15 Torr;Pyrolysis;

Steps:

7 Synthesis of 1,8-dicyanonaphthalene, 2

Acenaphtho[1,2-c][1,2,5]thiadiazole 8,8-dioxide (1) (2.04 g, 8.41 mmol) was pyrolyzed under vacuum (150 mTorr) at 180°C in a water-cooled sublimation apparatus overnight. The resulting solids were collected and resublimed under vacuum (150 mTorr) at 180 °C overnight to give the product as a pure yellow solid (1.36 g, 90.6% yield). ¹H NMR (CDCl₃, 499.74 MHz): δ 8.18 (d, J = 8.4 Hz, 2H), 8.13 (d, J = 8.4 Hz, 2H), 7.68 (t, J = 7.6 Hz, 2H). ¹³C NMR (CDCl₃, 125.67 MHz): δ 138.00, 134.68, 133.55, 128.99, 126.84, 116.81, 109.05. IR (neat): 3061, 2227, 2215, 1586, 1571, 1512, 1372, 1360, 1230, 1218, 1174, 1111, 1092, 990, 970, 943, 828, 779, 761, 694, 666 cm^-1. HR-DART/MS (m/z): [M+H]⁺ 179.0605 (found); C₁₂H₇N₂ 179.0609 (calcd).

References:

Bernstein, Karl J.;Do-Thanh, Chi-Linh;Penchoff, Deborah A.;Alan Cramer;Murdock, Christopher R.;Lu, Zheng;Harrison, Robert J.;Camden, Jon P.;Jenkins, David M. [Inorganica Chimica Acta,2014,vol. 421,p. 374 - 379]

1,2-Acenaphthylenedione, 1,2-dihydrazone

1932-07-6
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5690-48-2
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2008-77-7
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Benzenesulfonic acid, 4-bromo-, 1,2-acenaphthylenediylidenedihydrazide (9CI)

84300-93-6
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5690-48-2
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References

Benzenesulfonic acid, 2,4,6-trimethyl-, 1,2-acenaphthylenediylidenedihydrazide (9CI)

84331-69-1
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5690-48-2
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Benzenesulfonic acid, 4-methyl-,1,2-acenaphthylenediylidenedihydrazide (9CI)

74340-05-9
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5690-48-2
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References