Dayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities
Cas:91-15-6
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inquirySynonyms: 1,2-Benzenedicarbonitrile 1,2-Dicyanobenzene o-Phthalodinitrile Molecular Formula: C8H4N2 Molecular Weight: 128.13 CAS Registry Number: 91-15-6 EINECS: 202-044-8 Density: 1.24
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inquiryProduct Name: Phthalonitrile MF: C8H4N2 MW: 128.13 EINECS: 202-044-8 Mol File: 91-15-6.mol Phthalonitrile Structure Phthalonitrile Chemical Properties Melting point 137-139 °C (lit.) Boiling point 227.54°C (rough est
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inquiry1,we produce and sell good chemicals around the world. 2,our success rate is about 95%. this means, if customer order is accepted, the probability that the customer will obtain the ordered substances, is 95%. 3,our staff consists of highly qualifie
Cas:91-15-6
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inquiryHangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det
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inquiryPhthalonitrile Chemical Properties Melting point 137-139 °C(lit.) density 1.24 Fp 162°C storage temp. Store below +30°C. solubility benzene: 50 mg/
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Min.Order:1 Metric Ton
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Min.Order:1 Kilogram
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Min.Order:1 Kilogram
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Min.Order:1 Gram
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N,N'-o-phthaloylbis(P,P,P-triphenylphospha-λ5-azene)
phthalonitrile
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 140℃; intramolecular aza-Wittig reaction; | 100% |
Conditions | Yield |
---|---|
With potassium phenolate; palladium diacetate; potassium carbonate; dimethyl cis-but-2-ene-1,4-dioate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 24h; Schlenk technique; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With sodium carbonate; potassium ferrocyanide In N,N-dimethyl-formamide at 120℃; for 5h; | 93% |
1,2-benzenedimethanamine
phthalonitrile
Conditions | Yield |
---|---|
With aluminum oxide In N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere; | 92% |
With [Ru(p-cymene)(pzH-NP)(Cl)]Cl; potassium tert-butylate In toluene at 70℃; for 24h; Schlenk technique; Inert atmosphere; | 68% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; | 91% |
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h; Schlenk technique; Green chemistry; | 90% |
With 3% Pd/CeO2; sodium acetate In N,N-dimethyl-formamide; isopropyl alcohol at 65℃; for 10h; Irradiation; | 42% |
With tri-tert-butyl phosphine; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 24h; Reagent/catalyst; Inert atmosphere; | 75 %Chromat. |
Conditions | Yield |
---|---|
With dichloro(2,2-bis(diphenylphosphino)diphenyl ether)palladium(II); potassium acetate In 1,4-dioxane; water at 90℃; for 1.33333h; Sealed tube; | 91% |
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere; | 91% |
With sodium acetate In N,N-dimethyl-formamide; isopropyl alcohol at 55℃; Irradiation; Sealed tube; |
2-(hydroxymethyl)benzenecorbonitrile
phthalonitrile
Conditions | Yield |
---|---|
With ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water for 24h; Reflux; Green chemistry; | 90% |
[2-(dihydroxyboranyl)phenyl]boronic acid
A
4-bromo-benzenesulfonic acid-(4-chloro-anilide)
B
phthalonitrile
Conditions | Yield |
---|---|
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 15h; Catalytic behavior; Reflux; | A n/a B 90% |
[2-(dihydroxyboranyl)phenyl]boronic acid
A
4-nitro-N-(4-chlorophenyl)benzenesulfonamide
B
phthalonitrile
Conditions | Yield |
---|---|
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 14h; Catalytic behavior; Reflux; | A n/a B 90% |
Conditions | Yield |
---|---|
With ammonium hydroxide; sodium persulfate; sodium iodide; iron(II) chloride In 1,2-dichloro-ethane at 20 - 50℃; for 16h; | 89% |
With O-(diphenylphosphinyl)hydroxylamine In toluene at 20 - 85℃; chemoselective reaction; | 78% |
With formic acid; hydroxylamine hydrochloride; silica gel for 0.0333333h; Irradiation; | 72 % Chromat. |
With K2Co4[WZn3(H2O)2][ZnW9O34]2*53H2O; ammonia; dihydrogen peroxide In water at 20℃; for 6h; | 100 %Spectr. |
Conditions | Yield |
---|---|
With palladium diacetate; sodium carbonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In N,N-dimethyl acetamide at 120℃; for 3h; | 89% |
Conditions | Yield |
---|---|
at 390 - 400℃; | A 12% B 88% |
[2-(dihydroxyboranyl)phenyl]boronic acid
N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide
A
4-methyl-N-(4-chlorophenyl)benzenesulfonamide
B
phthalonitrile
Conditions | Yield |
---|---|
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 16h; Catalytic behavior; Reflux; | A n/a B 88% |
1-hydrazinophthalazine
phthalonitrile
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate In methanol at 20℃; | 87% |
Conditions | Yield |
---|---|
With palladium diacetate; sodium carbonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In N,N-dimethyl acetamide at 120℃; for 10h; | 86% |
Conditions | Yield |
---|---|
With potassium phenolate; palladium diacetate; potassium carbonate; dimethyl cis-but-2-ene-1,4-dioate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 24h; Schlenk technique; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide | 84.8% |
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide Substitution; | 83% |
Conditions | Yield |
---|---|
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6h; Schlenk technique; Inert atmosphere; Sealed tube; | 83% |
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6h; Inert atmosphere; Sealed tube; | 83% |
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride In glycerol at 90℃; for 9.5h; Green chemistry; | 83% |
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium carbonate / methanol; water / Reflux 2: fluorosulfonyl fluoride; triethylamine / acetonitrile / 0.25 h / 20 °C / Schlenk technique View Scheme |
Conditions | Yield |
---|---|
With copper(l) iodide; potassium iodide at 80℃; for 1h; Inert atmosphere; Sonication; | 80% |
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; | 65% |
With 1-Butylimidazole; copper(l) iodide In toluene at 160℃; for 16h; Inert atmosphere; | 78 %Chromat. |
Conditions | Yield |
---|---|
With 1-Butylimidazole; copper(l) iodide In toluene at 160℃; for 16h; | 78% |
(1-chloroethyl)trimethylsilane
4-hydroxy-1,2-benzenedicarbonitrile
phthalonitrile
Conditions | Yield |
---|---|
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide | 77% |
3-nitrobenzene-1,2-dicarbonitrile
Chloromethyltrimethylsilane
phthalonitrile
Conditions | Yield |
---|---|
With hydrogenchloride; potassium carbonate; sodium nitrite In 1-methyl-pyrrolidin-2-one; N,N-dimethyl acetamide | 74.7% |
Conditions | Yield |
---|---|
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide | 73% |
(3-chloropropyl)trimethylsilane
3-hydroxylphthalonitrile
phthalonitrile
Conditions | Yield |
---|---|
With hydrogenchloride; potassium carbonate In N,N-dimethyl acetamide; dimethyl sulfoxide | 71.2% |
tetra-n-butylammonium cyanide
C13H9N3S
A
2-(phenylthio)benzonitrile
B
phthalonitrile
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 25℃; for 0.75h; Irradiation; | A 13% B 63% |
Conditions | Yield |
---|---|
With tetra-n-butylammonium cyanide In dimethyl sulfoxide at 25℃; for 1h; Irradiation; | A 13% B 63% |
phthalonitrile
isoindole-1,3-diylidenediamine
Conditions | Yield |
---|---|
With ammonia; sulfur at 100℃; for 6h; titanium autoclave; var. cat.: sodium hydrosulfide, benzenethiol; add of MeOH; | 100% |
With ammonia; sodium methylate In methanol 1 h then reflux, 3 h; | 90% |
With ammonia for 5h; Heating; | 52% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]-undecen-7-ene In ethylene glycol at 35 - 40℃; for 3h; Product distribution; Further Variations:; Temperatures; Solvents; Reagents; UV-irradiation; | 100% |
With sodium methylate; blue zeolite In methanol at 40℃; for 72h; | 76% |
With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In N,N-dimethyl-formamide at 150℃; for 24h; | 72% |
(S)-valinol
phthalonitrile
1,2-bis[(4S)-(4-isopropyl-Δ2-1,3-oxazolin-2-yl)]benzene
Conditions | Yield |
---|---|
In neat (no solvent) at 150℃; for 1h; Microwave irradiation; | 100% |
With zinc(II) chloride In toluene for 96h; Heating; | 92% |
With zinc(II) chloride In chlorobenzene for 24h; Heating; | 89% |
With polyvinylpyrrolidone capped poly [Zn(2,6-bis(2H-1,2,3,4-tetrazol-2-id-5-yl)pyridine)H2O] nanocrystal In chlorobenzene for 15h; Reflux; | 84% |
phthalonitrile
Conditions | Yield |
---|---|
In tetrahydrofuran at 55℃; for 1h; | 100% |
phthalonitrile
phthalimide
Conditions | Yield |
---|---|
With manganese(IV) oxide; silica gel In chlorobenzene for 5h; Heating; | 100% |
With 1,3-dimethyl-1H-imidazol-3-ium hydrogen carbonate; water In ethanol at 80℃; for 4h; Catalytic behavior; Green chemistry; chemoselective reaction; | 90% |
With copper(II) acetate monohydrate In water; acetic acid Reflux; | 71% |
With sodium tetrahydroborate In ethanol; water at 80℃; for 4h; regioselective reaction; | 94 %Chromat. |
Conditions | Yield |
---|---|
With sodium methylate In methanol pyrophoric Ni under water layer added to a methanol soln. containing an equivalent quantity of phthalonitrile and 5 drops of 30% soln of CH3ONa in methanol; flask maintained at 25°C for 24-72 h; blue product separated from unreacted metal by shaking and decanting with the solvent, washed with ethanol in Soxhlet equipment and dried in air; purity of 95-97%; elem. anal.; | 100% |
With sodium methylate In methanol; water pyrophoric metal:phthalonitrile=1:4 and few drops of CH3ONa under water layer treated for 24 h at 25°C; septd., washed (ethanol), dried in air, elem. anal.; | 100% |
With sodium methylate In ethanol pyrophoric Ni under water layer added to an ethanol soln. containing an equivalent quantity of phthalonitrile and 5 drops of 30% soln of CH3ONa in methanol; flask maintained at 25°C for 24-72 h; blue product separated from unreacted metal by shaking and decanting with the solvent, washed with ethanol in Soxhlet equipment and dried in air; purity of 95-97%; elem. anal.; | 100% |
Conditions | Yield |
---|---|
With sodium methylate In methanol Sonication; Zn added to a methanol soln. containing an equivalent quantity of phthalonitrile and 5 drops of 30% soln of CH3ONa in methanol; flask put into an ultrasonic cleaner and maintained at 50°C for 24-72 h; blue product separated from unreacted metal by shaking and decanting with the solvent, washed with ethanol in Soxhlet equipment and dried in air; purity of 95-97%; elem. anal.; | 100% |
With sodium methylate In further solvent(s) Sonication; Zn added to an 1-octanol soln. containing an equivalent quantity of phthalonitrile and 5 drops of 30% soln of CH3ONa in methanol; flask put intoan ultrasonic cleaner and maintained at 50°C for 24-72 h; blue product separated from unreacted metal by shaking and decanting with the solvent, washed with ethanol in Soxhlet equipment and dried in air; purity of 95-97%; elem. anal.; | 100% |
With sodium methylate In methanol Sonication; Zn added to a methanol soln. containing an equivalent quantity of phthalonitrile and 5 drops of 30% soln of CH3ONa in methanol; flask put into an ultrasonic cleaner and maintained at 40°C for 24-72 h; blue product separated from unreacted metal by shaking and decanting with the solvent, washed with ethanol in Soxhlet equipment and dried in air; purity of 95-97%; elem. anal.; | 85% |
phthalonitrile
chloro(phthalodinitile)phthalocyaninato(2-)iridate(III)
Conditions | Yield |
---|---|
With NH4I In neat (no solvent) byproducts: [IrI(PDN)Pc(2-)]; boiling (10 min); extraction (acetone), pptn. (HCl, boiling), centrifugation, washing (H2O), drying (vac.); | 100% |
aluminum (III) chloride
urea
phthalonitrile
chloroaluminum phthalocyanine
Conditions | Yield |
---|---|
With ammonium molybdate at 200℃; for 12h; | 99.26% |
methylamine
phthalonitrile
1,3-bis(methylimino)-isoindoline
Conditions | Yield |
---|---|
sulfur at 40℃; for 3h; titanium autoclave; | 99% |
sulfur at 40℃; for 3h; titanium autoclave; var. primary amines; | 99% |
phthalonitrile
5-(2-cyanophenyl)tetrazole
Conditions | Yield |
---|---|
With sodium azide In water at 100℃; for 0.666667h; Reagent/catalyst; | 99% |
With sodium azide at 120℃; for 0.583333h; Reagent/catalyst; | 99% |
With sodium azide at 120℃; for 0.0833333h; | 97% |
copper
phthalonitrile
copper phthalocyanine
Conditions | Yield |
---|---|
With sodium methylate In methanol Sonication; Cu added to a methanol soln. containing an equivalent quantity of phthalonitrile and 5 drops of 30% soln of CH3ONa in methanol; flask put into an ultrasonic cleaner and maintained at 50°C for 24-72 h; blue product separated from unreacted metal by shaking and decanting with the solvent, washed with ethanol in Soxhlet equipment and dried in air; purity of 95-97%; elem. anal.; | 99% |
With sodium methylate In ethanol Sonication; Cu added to an ethanol soln. containing an equivalent quantity of phthalonitrile and 5 drops of 30% soln of CH3ONa in methanol; flask put into an ultrasonic cleaner and maintained at 50°C for 24-72 h; blue product separated from unreacted metal by shaking and decanting with the solvent, washed with ethanol in Soxhlet equipment and dried in air; purity of 95-97%; elem. anal.; | 99% |
With sodium methylate In methanol Sonication; Cu added to a methanol soln. containing an equivalent quantity of phthalonitrile and 5 drops of 30% soln of CH3ONa in methanol; flask put into an ultrasonic cleaner and maintained at 25°C for 24-72 h; blue product separated from unreacted metal by shaking and decanting with the solvent, washed with ethanol in Soxhlet equipment and dried in air; purity of 95-97%; elem. anal.; | 60% |
Conditions | Yield |
---|---|
Stage #1: phthalonitrile With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene at 5℃; for 6.5h; Stage #2: 4-(2-cyanoacetyl)benzoic acid With acetic acid In 5,5-dimethyl-1,3-cyclohexadiene at 5 - 45℃; for 26h; Solvent; | 99% |
Stage #1: phthalonitrile With sodium methylate In methanol at 5℃; for 13.5h; Stage #2: 4-(2-cyanoacetyl)benzoic acid With acetic acid In methanol at 20 - 40℃; for 100h; |
phthalonitrile
Conditions | Yield |
---|---|
In dichloromethane at 23℃; for 1h; Inert atmosphere; | 99% |
aluminum (III) chloride
phthalonitrile
chloroaluminum phthalocyanine
Conditions | Yield |
---|---|
With ammonium chloride at 200℃; for 10.5h; Reagent/catalyst; Concentration; | 98.4% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol at 136℃; for 5h; Inert atmosphere; | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol at 136℃; for 5h; |
1-(pyridine-4-oxy) 3,4-dicyanobenzene
phthalonitrile
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol for 18h; Inert atmosphere; Reflux; | 98.2% |
benzylamine
phthalonitrile
1,3-Bis-[(Z)-benzylimino]-2,3-dihydro-1H-isoindole
Conditions | Yield |
---|---|
sulfur at 40℃; for 1h; | 98% |
(2S)-2-phenylglycinol
phthalonitrile
1,2-bis<(4S)-4-phenyl-2-oxazolin-2-yl>benzene
Conditions | Yield |
---|---|
at 150℃; for 1h; Microwave irradiation; | 98% |
With zinc(II) chloride In chlorobenzene for 24h; Heating; | 66% |
Conditions | Yield |
---|---|
With CuCl2*2H2O for 0.166667h; microwave irradiation; | 98% |
With CuCl2*2H2O at 190 - 210℃; for 0.25h; microwave irradiation; | 88% |
With copper diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 140℃; for 0.0833333h; | 76% |
With 1,1,1,3,3,3-hexamethyl-disilazane; copper(ll) bromide In N,N-dimethyl-formamide at 100℃; for 10h; | 74% |
phthalonitrile
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 5h; Heating; | 98% |
Trimethylenediamine
phthalonitrile
2-(1,4,5,6-tetrahydropyrimidin-2-yl)benzonitrile
Conditions | Yield |
---|---|
With bis(2-hydroxy-κO-2-phenylacetato)copper(II); iodine; sodium acetate In toluene at 90℃; for 0.333333h; Time; Microwave irradiation; chemoselective reaction; | 97% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 40℃; for 0.5h; Reagent/catalyst; Inert atmosphere; Microwave irradiation; | 97% |
propylamine
phthalonitrile
1,3-Bis-[(Z)-propylimino]-2,3-dihydro-1H-isoindole
Conditions | Yield |
---|---|
sulfur for 2h; Heating; | 96% |
Conditions | Yield |
---|---|
In methanol for 5h; Heating; | 96% |
Conditions | Yield |
---|---|
In further solvent(s) SnCl2 and phthalonitrile were added to 1-chloronaphthalene (solvent); brought to reflux over a period of 1 h; was allowed to reflux for 3 h; cooled slowly to room temperature; filtered; washed in benzene in a Soxhlet extractor for 24 h; elem. anal.; | 96% |
3-methylpyridin-2-ylamine
cobalt(II) acetate
phthalonitrile
Co(3-MeBPI)2
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; toluene 1,2-dicyanobenzene and 2-amino-3-methylpyridine heated in oil bath to 210°C for 3 h, mixt. cooled to ambient temp., toluene added, temp.increased to 90°C, NaOH in methanol added, Co(OAc)2 in methanol added and mixt. heated for 1 h; mixt. cooled to 40°C, product filtered, washed with methanol, diethyl ether and dried; | 96% |
With sodium hydroxide In methanol; toluene 1,2-dicyanobenzene and 2-amino-3-methylpyridine heated in oil bath to 210°C for 4 h, mixt. cooled to 210°C., toluene added, NaOH in methanol added and stirred for 5 min, Co(OAc)2 in methanol added and mixt. stirredd for 45 min; mixt. cooled to 40°C, product filtered, washed with methanol, diethyl ether and dried in vacuo at 80°C; |
(2-picolyl)diethylborane dimer
phthalonitrile
(Et2B)2(1,2-(NHC(CHC5H4N))2C6H4)
Conditions | Yield |
---|---|
In toluene (inert atm.); reaction of boron compd. and 1 equiv. of dicyanobenzene intoluene at 70°C for 4 h; | 96% |
In toluene at 70℃; for 4h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With sodium hydroxide for 2h; Reflux; | 96% |
phthalonitrile
zinc phthalocyanine
Conditions | Yield |
---|---|
With zinc acetate dihydrate; N,N-dimethyl-formamide at 200℃; for 0.166667h; Microwave irradiation; Sealed tube; | 95% |
With N-ethyl-N-hydroxy-ethanamine; zinc(II) chloride at 80℃; for 0.25h; | 45% |
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