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Chemical Structure| 91-15-6 Chemical Structure| 91-15-6

Structure of 91-15-6

Chemical Structure| 91-15-6

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Product Details of [ 91-15-6 ]

CAS No. :91-15-6
Formula : C8H4N2
M.W : 128.13
SMILES Code : C1=CC=CC(=C1C#N)C#N
MDL No. :MFCD00001771
InChI Key :XQZYPMVTSDWCCE-UHFFFAOYSA-N
Pubchem ID :7042

Safety of [ 91-15-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H370-H372-H373-H412
Precautionary Statements:P273-P260-P270-P264-P308+P311-P301+P310+P330-P405-P501
Class:6.1
UN#:3439
Packing Group:

Application In Synthesis of [ 91-15-6 ]

* 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 [ 91-15-6 ]

[ 91-15-6 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 24629-25-2 ]
  • [ 91-15-6 ]
  • [ 131380-81-9 ]
  • 2
  • [ 2346-00-1 ]
  • [ 91-15-6 ]
  • 3-[(Z)-1-(4,5-dihydro-1,3-thiazol-2-yl)methylidene]-2,3-dihydro-1H-isoindol-1-imine [ No CAS ]
  • 3
  • [ 7446-70-0 ]
  • [ 91-15-6 ]
  • [ 14154-42-8 ]
YieldReaction ConditionsOperation in experiment
92.5% With 1-Chloronaphthalene; In water; acetone; toluene; at 70 - 240℃; for 10h; Synthesis Example 5 Synthesis of chloroaluminum phthalocyanine (A method described in Synthesis Example 1 of Japanese Patent Kokai Publication No. H9(1997) 217020) Phthalonitrile (180.0 g, (1.41 mol)), 900 ml of 1-chloronaphthalene and 47.0 g (0.353 mol) of aluminum (III) chloride were charged into a four-necked flask, and heated and stirred under reflux at 240C for 6 hours. Thereafter, the reflux was stopped and the mixture was allowed to cool to a temperature of approximately 130C, and thereafter was filtered under heating, sprinkled and washed with 1800 ml of hot toluene (100C), 80 ml of toluene and 900 ml of acetone, and substituted with 100 ml of toluene. The obtained cake was stirred and refluxed in 750 ml of toluene for 3 hours, thereafter filtered under heating at 100C, and thereafter was washed with 1800 ml of hot toluene (100C), 180 ml of toluene and 900 ml of acetone, and the solvent was substituted with 400 ml of water. The obtained cake was added to 4500 ml of water and heat-dispersed at 70C for 1 hour. After being filtered under heating, the obtained cake was washed with 900 ml of acetone and 1000 ml of water, and dried at 70C to obtain 187.6 g of chloroaluminum phthalocyanine ClAlPc (yield: 92.5%).
92.5% Synthesis Example 7 Synthesis of chloroaluminum phthalocyanine ClAlPc (A method described in Synthesis Example 1 of Japanese Patent Laid-Open Publication No. H9(1997) 217020) 180.0 g (1.41 mol) of phthalonitrile, 900 ml of 1-chloronaphthalene and 47.0 g (0.353 mol) of aluminum (III) chloride were charged into a four-necked flask, and heated and stirred under reflux at a temperature of 240C for 6 hours. Thereafter, the reflux was stopped and the mixture stood to cool to a temperature of approximately 130C, and thereafter was filtered under heating, sprinkled and washed with 1800 ml of hot toluene (100C), 80 ml of toluene and 900 ml of acetone, and substituted with 100 ml of toluene. The obtained cake was stirred and refluxed in 750 ml of toluene for 3 hours, thereafter filtered under heating at a temperature of 100C, and thereafter was washed with 1800 ml of hot toluene (100C), 180 ml of toluene and 900 ml of acetone, and the solvent was substituted with 400 ml of water. The obtained cake was added to 4500 ml of water and heat-dispersed at a temperature of 70C for 1 hour. After being filtered under heating, the obtained cake was washed with 900 ml of acetone and 1000 ml of water, and dried at a temperature of 70C to obtain 187.6 g of chloroaluminum phthalocyanine ClAlPc (yields 92.5%).
84.5% at 200℃; for 15h; Example 1 Comparative Method-No Ammonium Salt A chloroaluminum phthalocyanine pigment (Pigment 1) was prepared by adding 614.4 g phthalonitrile, 160.0 g anhydrous aluminum(III) chloride and 3248 g dichlorotoluenes (isomer mixture) to a 4 L glass kettle. The reaction mixture was stirred as the temperature was raised to 200 C. over a period of two hours and maintained for an additional 13 hours at 200 C. before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 2.5 L of 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain 582.35 g (84.5%) of a purified reaction product.
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In pentan-1-ol; at 136℃; for 5h; 225 parts of phthalodinitrile and 78 parts of aluminum chloride anhydride were added to 1250 parts of n-amyl alcohol in a reaction vessel and stirred. To this, 266 parts of DBU (1,8-Diazabicyclo [5.4.0] undec-7-ene) was added, the temperature was raised and refluxed at 136 C. for 5 hours. The reaction solution cooled to 30 C. with stirring was injected into a mixed solvent of 5000 parts of methanol and 10000 parts of water under stirring to obtain a blue slurry. The slurry was filtered, washed with a mixed solvent of 2000 parts of methanol and 4000 parts of water, and dried to obtain 135 parts of chloroaluminum phthalocyanine

  • 4
  • [ 7787-87-3 ]
  • [ 30757-50-7 ]
  • [ 91-15-6 ]
YieldReaction ConditionsOperation in experiment
77.0% With hydrogenchloride; potassium carbonate; In N,N-dimethyl-formamide; Preparation Example 4 Preparation of Phthalonitrile : In 200 ml of N,N-dimethylformamide were dissolved with heating 20 g of <strong>[30757-50-7]4-hydroxyphthalonitrile</strong> and 10.55 g of potassium carbonate, to which 20 g of chloroethyl- trimethylsilane were added dropwise at 40C in the atmosphere of argon. Immediately after the addition, the mixture was stirred for 18 hours while maintaining the reaction temperature at 85-105C. The reaction vessel was then cooled to room temperature and 250 ml of dilute hydrochloric acid was added. The mixture was extracted with 1.2 liters of toluene. The organic layer was washed well with water and water was removed with magnesium sulfate. Thereafter, toluene was removed by distillation and the residue was purified with a toluene/silica gel column to obtain 24.6 g (yield: 77.0 %) of a compound having the formula (XVII) below.
  • 7
  • [ 695-53-4 ]
  • [ 91-15-6 ]
  • [ 1310681-91-4 ]
YieldReaction ConditionsOperation in experiment
4.2% With ammonium molybdate; urea; nickel dichloride; In quinoline; at 250℃; for 0.5h;Inert atmosphere; (a) A mixture of 1 (0.10 g, 0.77 mmol), 2 (0.10 g, 0.77 mmol), anhydrous NiCl2 (0.1 g, 0.8 mmol), urea (0.09 g, 1.55 mmol), and a catalytic amount of MOA was stirred in quinoline (5 mL) at 250 C under argon for 30 min. After cooling to room temperature, the reaction mixture was diluted with 50% ethanol (50 mL). The resulting precipitate was filtered, and washed successively with hot water and hot 50% ethanol until the washings were colorless. The crude residue was transferred to a Soxhlet apparatus, and was extracted with toluene. The toluene solution was concentrated to approximately 5 mL under a reduced pressure, which was purified by silica gel column chromatography using toluene as eluent. The blue fraction was collected to give 6 mg of 3 (4.2%) after evaporation of the solvent. MASS (MALDI) (m/z): 553 (M++1). Anal Calcd for C29H18N8O1Ni: C, 62.96; H, 3.28; N, 20.26. Found: C, 62.69; H, 3.51; N, 19.95.
  • 8
  • [ 7446-70-0 ]
  • [ 631-61-8 ]
  • [ 91-15-6 ]
  • [ 14154-42-8 ]
YieldReaction ConditionsOperation in experiment
74.5% at 200℃; for 12h; Example 6 Synthesis of Chloroaluminum Phthalocyanine Pigments Using Ammonium Acetate Without the Use of a Heavy Metal Catalyst A chloroaluminum phthalocyanine pigment (Pigment 6) was synthesized using equal molar ratios of an ammonium salt, ammonium acetate (CH3COONH4), and aluminum(III) chloride (AlCl3), without using a heavy metal catalyst, according to the following procedure. 76.80 g phthalonitrile, 20.00 g anhydrous aluminum(III) chloride, 11.79 g ammonium acetate and 406.0 g dichlorotoluenes (isomer mixture) were added to a 1 L glass kettle. The reaction mixture was stirred as the temperature was raised to 200 C. over a period of one hour and maintained for a total of 11 hours at 200 C. before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 2.5 L of 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain 64.21 g (74.5%) of a purified reaction product.
  • 9
  • [ 7446-70-0 ]
  • [ 57-13-6 ]
  • [ 91-15-6 ]
  • [ 14154-42-8 ]
YieldReaction ConditionsOperation in experiment
99.26% With ammonium molybdate; at 200℃; for 12h; Example 2 Comparative Method-No Ammonium Salt A chloroaluminum phthalocyanine pigment (Pigment 2) was prepared by adding 153.6 g phthalonitrile, 40.00 g anhydrous aluminum(III) chloride, 32.00 g urea, 1.20 g ammonium dimolybdate and 812.0 g dichlorotoluenes (isomer mixture) to a 1 L glass kettle. The reaction mixture was stirred as the temperature was raised to 200 C. over a period of three hours and maintained for a total of nine hours at 200 C. before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain a 99.26% yield of a purified reaction product.
  • 10
  • [ 7446-70-0 ]
  • [ 7664-41-7 ]
  • [ 91-15-6 ]
  • [ 14154-42-8 ]
YieldReaction ConditionsOperation in experiment
85.37% at 200℃; for 10.75h; Example 3 Comparative Method-No Ammonium Salt A chloroaluminum phthalocyanine pigment (Pigment 3) was prepared by adding 76.8 g phthalonitrile, 20.00 g anhydrous aluminum(III) chloride and 406.0 g dichlorotoluenes (isomer mixture) to a 1 L glass kettle. The reaction mixture was stirred as ammonia gas was bubbled beneath the reaction surface as the temperature was raised to 200 C. over a period of 1.25 hours. Ammonia gas was continuously bubbled into the reaction mixture over the next two hours while the temperature was maintained at 200 C. After the bubbling of ammonia gas was discontinued, the reaction mixture was maintained at 200 C. for an additional 7.5 hours (10.75 hours at 200 C. total) before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 2.5 L of 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain 73.57 g (85.37%) of a purified reaction product.
  • 11
  • [ 7446-70-0 ]
  • [ 12125-02-9 ]
  • [ 91-15-6 ]
  • [ 14154-42-8 ]
YieldReaction ConditionsOperation in experiment
at 200℃; for 10.5h; Example 4 Synthesis of Chloroaluminum Phthalocyanine Pigments Using Ammonium Chloride Without the Use of a Heavy Metal Catalyst Several chloroaluminum phthalocyanine pigments were synthesized using varying molar ratios of ammonium chloride (NH4Cl) and aluminum(III) chloride (AlCl3) without using a heavy metal catalyst. Pigments 4A-4E were synthesized using 0.45:1, 0.9:1, 1:1, 1.8:1 and 3.6:1 molar equivalents of ammonium chloride to 53 aluminum(III) chloride, respectively, according to the following general procedure. Phthalonitrile, anhydrous aluminum(III) chloride, ammonium chloride and dichlorotoluenes (isomer mixture) were added to a 1 L glass kettle. The reaction mixture was stirred as the temperature was raised to 200 C. over a period of 1-1.5 hours and maintained for a total of 10.5 to 17 hours at 200 C. before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 2.5 L of 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain a purified reaction product.
  • 12
  • [ 7446-70-0 ]
  • ammonium sulfate [ No CAS ]
  • [ 91-15-6 ]
  • [ 14154-42-8 ]
YieldReaction ConditionsOperation in experiment
89.11 g at 200℃; for 12h; Example 5 Synthesis of Chloroaluminum Phthalocyanine Pigments Using Ammonium Sulfate Without the Use of a Heavy Metal Catalyst A chloroaluminum phthalocyanine pigment (Pigment 5) was synthesized using equal molar ratios of ammonium sulfate ((NH4)2SO4) and aluminum(III) chloride (AlCl3), without using a heavy metal catalyst, according to the following procedure. 76.80 g phthalonitrile, 20.00 g anhydrous aluminum(III) chloride, 19.80 g ammonium sulfate and 406.0 g dichlorotoluenes (isomer mixture) were added to a 1 L glass kettle. The reaction mixture was stirred as the temperature was raised to 200 C. over a period of two hours and maintained for a total of 10 hours at 200 C. before cooling to room temperature. After cooling, the solvent was removed by vacuum distillation to obtain a crude phthalocyanine reaction product. The crude phthalocyanine reaction product was purified by preparing a slurry in 2.5 L of 1% aqueous sulfuric acid and heating to 90 C. for two hours with stirring, followed by filtration at 90 C., washing with water until the filtrate was neutralized, and drying at 80 C. to obtain 89.11 g (103%) of a purified reaction product.
  • 13
  • [ 1095-03-0 ]
  • C20H22N2 [ No CAS ]
  • [ 91-15-6 ]
  • C42H32BN5O [ No CAS ]
  • 14
  • [ 1095-03-0 ]
  • C16H14N2O [ No CAS ]
  • [ 91-15-6 ]
  • C38H24BN5O2 [ No CAS ]
  • 15
  • [ 1095-03-0 ]
  • (Z)-1-(4-trifluoromethylphenylmethylene)-1H-isoindol-3-amine [ No CAS ]
  • [ 91-15-6 ]
  • C38H21BF3N5O [ No CAS ]
  • 16
  • [ 1095-03-0 ]
  • (Z)-1-(phenylmethylene)-1H-isoindol-3-amine [ No CAS ]
  • [ 91-15-6 ]
  • C37H22BN5O [ No CAS ]
 

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