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Chemical Structure| 3029-30-9 Chemical Structure| 3029-30-9
Chemical Structure| 3029-30-9

Naphthalene-1,4-dicarbonitrile

CAS No.: 3029-30-9

4.5 *For Research Use Only !

Cat. No.: A550769 Purity: 98%

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Product Details of [ 3029-30-9 ]

CAS No. :3029-30-9
Formula : C12H6N2
M.W : 178.19
SMILES Code : N#CC1=C2C=CC=CC2=C(C#N)C=C1
MDL No. :MFCD03093626
InChI Key :BENSWQOUPJQWMU-UHFFFAOYSA-N
Pubchem ID :76414

Safety of [ 3029-30-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301
Precautionary Statements:P301+P310
Class:6.1
UN#:3439
Packing Group:

Application In Synthesis of [ 3029-30-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3029-30-9 ]

[ 3029-30-9 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 28227-42-1 ]
  • [ 613-73-0 ]
  • [ 3029-30-9 ]
  • [ 75-64-9 ]
  • 2
  • [ 28227-41-0 ]
  • [ 613-73-0 ]
  • [ 3029-30-9 ]
  • [ 75-31-0 ]
  • 3
  • [ 3673-06-1 ]
  • [ 613-73-0 ]
  • [ 3029-30-9 ]
  • [ 108-91-8 ]
  • 4
  • [ 76509-14-3 ]
  • [ 613-73-0 ]
  • [ 3029-30-9 ]
  • [ 95-68-1 ]
  • 5
  • [ 49673-43-0 ]
  • [ 613-73-0 ]
  • [ 3029-30-9 ]
  • [ 87-62-7 ]
  • 6
  • [ 56222-36-7 ]
  • [ 613-73-0 ]
  • [ 3029-30-9 ]
  • [ 88-05-1 ]
  • 7
  • [ 51479-97-1 ]
  • [ 613-73-0 ]
  • [ 3029-30-9 ]
  • [ 95-53-4 ]
  • 8
  • [ 613-73-0 ]
  • [ 3029-30-9 ]
  • 9
  • glyoxal hydrate (trimer) (3C2 H2 O2.2H2 O) [ No CAS ]
  • [ 131543-46-9 ]
  • [ 613-73-0 ]
  • [ 3029-30-9 ]
YieldReaction ConditionsOperation in experiment
61.8% With potassium hydroxide; In methanol; water; EXAMPLE 1 15.6 parts of o-xylylene dicyanide and 8.5 parts of glyoxal hydrate (trimer) (3C2 H2 O2.2H2 O), containing 80% of glyoxal to be liberated, are stirred in 200 parts of methanol. The reaction mixture is treated at 15 C, with stirring and under nitrogen, with 11.2 parts of powdered potassium hydroxide added by small amounts. After addition of the potassium hydroxide, the reaction mixture is further stirred for 15 hours at room temperature and under nitrogen. The slightly brown coloured reaction mixture is then freed from methanol under vacuum and diluted with 500 parts by volume of water. The precipitated crude 1,4-dicyanonaphthalene is filtered off with suction and washed neutral with water. Yield: 11 parts of 1,4-dicyanonaphthalene (61.8% of theory) in the form of slightly brown coloured needles; m.p. 175-185 C. One recrystallisation from alcohol using 5 parts of activated carbon yields 5.5 parts of the compound STR41 as fine needles with a melting point of 204-205 C.
With potassium hydroxide; In methanol; EXAMPLE 2 78 parts of o-xylylene dicyanide and 42 parts of glyoxal hydrate (trimer) (3C2 H2 O2.2H2 O), containing 80% of glyoxal to be liberated, are stirred in 400 parts by volume of methanol. The reaction mixture is treated at 0 to 5 C, with stirring and under nitrogen, with 56 parts of powdered potassium hydroxide added by small amounts. After the addition of potassium hydroxide, stirring is continued for 12 hours at 0 to 5 C under nitrogen. The slightly brown coloured reaction mixture is subsequently neutralised with dilute hydrochloric acid, freed from methanol under vacuum, and filtered with suction. The filter cake is washed neutral with water and dried in vacuo. Yield: 88 parts (99% of theory) of 1,4-dicyanonaphthalene of formula STR42 in the form of a slightly brown coloured powder with a melting point of 158 to 168 C. The crude product is taken up in 700 parts by volume of 1,2-dichloroethane, treated with 50 parts by weight of sodium chloride and refluxed.
  • 10
  • [ 79-16-3 ]
  • N-(tertiary)-butylamine-glyoxalbisaldimine [ No CAS ]
  • [ 613-73-0 ]
  • [ 3029-30-9 ]
YieldReaction ConditionsOperation in experiment
68.5% EXAMPLE 2 15.6 Grams (0.1 mole) of o-phenylene-diacetonitrile, 20.1 g (0.1 mole) of N-(tertiary)-butylamine-glyoxalbisaldimine and 50 ml of dimethyl-formamide were heated at 130 C. for 1 hour, while stirring, and the stirring was continued for 3 to 4 hours at a temperature of from 130 to 135 C. In the course of this process 16 ml of tertiary butylamine (corresponding to 83.5% of reacted aldimine) were distilled off. After the reaction mixture had been cooled to 10 C. to 20 C., the crystal paste formed was suction-filtered, was washed with cold methanol and dried. Yield: 12 g of 1,4-naphthodinitrile (68.5% of the theory). Melting point: 209 C.
  • 11
  • N-o-toluidine-glyoxalbisaldimine [ No CAS ]
  • [ 613-73-0 ]
  • [ 3029-30-9 ]
YieldReaction ConditionsOperation in experiment
63% With potassium hydroxide; In dimethyl sulfoxide; EXAMPLE 3 15.6 Grams (0.1 mole) of o-phenylene-diacetonitrile, 26 g (0.11 mole) of N-o-toluidine-glyoxalbisaldimine and 50 ml of dimethylsulfoxide were dissolved by heating at 50 C., subsequently 1 g of pulverized potassium hydroxide solution was added, and the reaction mixture was heated further at a temperature of from 90 to 95 C. After the mixture had been stirred again for 3 to 4 hours at 95 C., it was cooled to 10 C., and the crystal paste was suction-filtered and washed with cold methanol. 11.2 Grams of 1,4-naphthodinitrile were obtained, which corresponded to a yield of 63% of the theory. The melting point was 208 C.
 

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