Phthalonitrile supplier | CasNO.91-15-6

Name
Phthalonitrile
EINECS 202-044-8
CAS No. 91-15-6
Article Data122
CAS DataBase
Density 1.24 g/cm³
Solubility 50 mg/mL, clear in benzene, 0.56 g/L (25 °C) in water
Melting Point 137-139 °C(lit.)
Formula C₈H₄N₂
Boiling Point 304.6 °C at 760 mmHg
Molecular Weight 128.133
Flash Point 153.3 °C
Transport Information UN 3439 6.1/PG 2
Appearance off-white to tan powder
Safety 36/37/39-45-28A
Risk Codes 25-23/24/25
Molecular Structure
Hazard Symbols T
Synonyms Phthalonitrile(8CI);1,2-Benzodinitrile;1,2-Bis(cyano)benzene;1,2-Dicyanobenzene;NSC17562;o-Benzenedicarbonitrile;o-Benzenedinitrile;o-Cyanobenzonitrile;o-Dicyanobenzene;
PSA 47.58000
LogP 1.42996

Synthetic route

: 112069-03-1
N,N'-o-phthaloylbis(P,P,P-triphenylphospha-λ5-azene)

: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
In dimethyl sulfoxide at 140℃; intramolecular aza-Wittig reaction;	100%

: 626-35-7
nitroacetic acid ethyl ester

: 4387-36-4
2-iodobenzonitrile

: 91-15-6
phthalonitrile

Conditions

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%

: 4387-36-4
2-iodobenzonitrile

: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
With sodium carbonate; potassium ferrocyanide In N,N-dimethyl-formamide at 120℃; for 5h;	93%

: 17300-02-6
1,2-benzenedimethanamine

: 91-15-6
phthalonitrile

Conditions

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%

: 4387-36-4
2-iodobenzonitrile

: potassium ferrocyanide

: 91-15-6
phthalonitrile

Conditions

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.

: potassium hexacyanoferrate(II) trihydrate

: 2042-37-7
o-cyanobromobenzene

: 91-15-6
phthalonitrile

Conditions

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%

: potassiumhexacyanoferrate(II) trihydrate

: 4387-36-4
2-iodobenzonitrile

: 91-15-6
phthalonitrile

Conditions

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;

: 89942-45-0
2-(hydroxymethyl)benzenecorbonitrile

: 91-15-6
phthalonitrile

Conditions

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%

: 13506-83-7
[2-(dihydroxyboranyl)phenyl]boronic acid

: 4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide

A: 6295-97-2
4-bromo-benzenesulfonic acid-(4-chloro-anilide)

B: 91-15-6
phthalonitrile

Conditions

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%

...Expand

: 13506-83-7
[2-(dihydroxyboranyl)phenyl]boronic acid

: N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide

A: 16937-03-4
4-nitro-N-(4-chlorophenyl)benzenesulfonamide

B: 91-15-6
phthalonitrile

Conditions

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%

...Expand

: 643-79-8
o-phthalic dicarboxaldehyde

: 91-15-6
phthalonitrile

Conditions

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.

: potassiumhexacyanoferrate(II) trihydrate

: 583-55-1
1-Bromo-2-iodobenzene

: 91-15-6
phthalonitrile

Conditions

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%

: 51-17-2
benzoimidazole

: 67-66-3
chloroform

A: 1448-87-9
2-chloroquinoxaline

B: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
at 390 - 400℃;	A 12% B 88%

...Expand

: 13506-83-7
[2-(dihydroxyboranyl)phenyl]boronic acid

: 119986-58-2
N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide

A: 2903-34-6
4-methyl-N-(4-chlorophenyl)benzenesulfonamide

B: 91-15-6
phthalonitrile

Conditions

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%

...Expand

: 1044569-46-1
1-hydrazinophthalazine

: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate In methanol at 20℃;	87%

: potassiumhexacyanoferrate(II) trihydrate

: 583-53-9
1,2-dibromobenzene

: 91-15-6
phthalonitrile

Conditions

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%

: 626-35-7
nitroacetic acid ethyl ester

: 2042-37-7
o-cyanobromobenzene

: 91-15-6
phthalonitrile

Conditions

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%

: 4733-50-0
2,3-dicyano-1,4-hydroquinone

: 2344-80-1
Chloromethyltrimethylsilane

: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide	84.8%

: 41694-39-7
1,2-Bis(nonaflyl)benzene

: 557-21-1
dicyanozinc

: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide Substitution;	83%

: 557-21-1
zinc(II) cyanide

: 873-32-5
2-Chlorobenzonitrile

: 91-15-6
phthalonitrile

Conditions

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%

: 7468-67-9
o-formylbenzonitrile

: 91-15-6
phthalonitrile

Conditions

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

: potassium ferrocyanide

: 583-53-9
1,2-dibromobenzene

: 91-15-6
phthalonitrile

Conditions

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.

: potassium hexacyanoferrate(II)

: 583-53-9
1,2-dibromobenzene

: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
With 1-Butylimidazole; copper(l) iodide In toluene at 160℃; for 16h;	78%

: 7787-87-3
(1-chloroethyl)trimethylsilane

: 30757-50-7
4-hydroxy-1,2-benzenedicarbonitrile

: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide	77%

: 51762-67-5
3-nitrobenzene-1,2-dicarbonitrile

: 2344-80-1
Chloromethyltrimethylsilane

: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
With hydrogenchloride; potassium carbonate; sodium nitrite In 1-methyl-pyrrolidin-2-one; N,N-dimethyl acetamide	74.7%

: 116039-49-7
3-hydroxylphthalonitrile

: 2344-80-1
Chloromethyltrimethylsilane

: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide	73%

: 2344-83-4
(3-chloropropyl)trimethylsilane

: 116039-49-7
3-hydroxylphthalonitrile

: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
With hydrogenchloride; potassium carbonate In N,N-dimethyl acetamide; dimethyl sulfoxide	71.2%

: 10442-39-4
tetra-n-butylammonium cyanide

: 114650-54-3
C13H9N3S

A: 91804-55-6
2-(phenylthio)benzonitrile

B: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
In dimethyl sulfoxide at 25℃; for 0.75h; Irradiation;	A 13% B 63%

...Expand

: 114650-54-3
C13H9N3S

A: 91804-55-6
2-(phenylthio)benzonitrile

B: 91-15-6
phthalonitrile

Conditions

Conditions	Yield
With tetra-n-butylammonium cyanide In dimethyl sulfoxide at 25℃; for 1h; Irradiation;	A 13% B 63%

: 91-15-6
phthalonitrile

: 160956-25-2, 160956-26-3, 160956-27-4, 160956-28-5, 160956-29-6
isoindole-1,3-diylidenediamine

Conditions

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%

: 91-15-6
phthalonitrile

: 574-93-6
29H,31H-Phthalocyanine

Conditions

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%

: 2026-48-4
(S)-valinol

: 91-15-6
phthalonitrile

: 131380-80-8
1,2-bis[(4S)-(4-isopropyl-Δ2-1,3-oxazolin-2-yl)]benzene

Conditions

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%

: 91-15-6
phthalonitrile

/PBGZJ115-1120/: /PBGZJ115-1120/

: 2-(4-Methoxy-phenyl)-3-[(Z)-4-methoxy-phenylimino]-2,3-dihydro-isoindol-1-one

Conditions

Conditions	Yield
In tetrahydrofuran at 55℃; for 1h;	100%

: 91-15-6
phthalonitrile

: 136918-14-4
phthalimide

Conditions

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.

: 7440-02-0
nickel

: 91-15-6
phthalonitrile

: 14055-02-8
nickel(II) phthalocyanine

Conditions

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%

: 91-15-6
phthalonitrile

: 7440-66-6
zinc

: 14320-04-8
zinc(II) phthalocyanine

Conditions

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%

: sodium hexachloroiridate

: 91-15-6
phthalonitrile

: 14096-14-1, 187386-26-1
chloro(phthalodinitile)phthalocyaninato(2-)iridate(III)

Conditions

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%

: 7446-70-0, 7784-13-6
aluminum (III) chloride

: 57-13-6
urea

: 91-15-6
phthalonitrile

: 14154-42-8, 62905-77-5
chloroaluminum phthalocyanine

Conditions

Conditions	Yield
With ammonium molybdate at 200℃; for 12h;	99.26%

...Expand

: 74-89-5
methylamine

: 91-15-6
phthalonitrile

: 88988-76-5, 89130-82-5, 93698-08-9, 93698-09-0
1,3-bis(methylimino)-isoindoline

Conditions

Conditions	Yield
sulfur at 40℃; for 3h; titanium autoclave;	99%
sulfur at 40℃; for 3h; titanium autoclave; var. primary amines;	99%

: 91-15-6
phthalonitrile

: 71515-74-7
5-(2-cyanophenyl)tetrazole

Conditions

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%

: 12775-96-1, 15158-11-9, 15721-63-8, 16941-75-6, 17493-86-6, 19498-52-3, 20499-83-6, 20499-84-7, 20499-85-8, 20499-86-9, 20573-10-8, 20573-11-9, 21595-51-7, 21595-52-8, 22206-52-6, 26445-28-3, 28959-95-7, 37362-93-9, 39417-05-5, 54603-16-6, 54603-23-5, 54603-32-6, 54603-40-6, 54603-48-4, 54603-81-5, 54603-89-3, 56316-56-4, 95985-91-4, 122297-32-9, 7440-50-8
copper

: 91-15-6
phthalonitrile

: 147-14-8
copper phthalocyanine

Conditions

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%

: 122545-30-6
4-(2-cyanoacetyl)benzoic acid

: 91-15-6
phthalonitrile

: C28H15N3O6

Conditions

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;

: silver hexafluoroantimonate

: C104H108Au2Cl2N2O12P2

: 91-15-6
phthalonitrile

: C112H112Au2N4O12P2(2+)*2F6Sb(1-)

Conditions

Conditions	Yield
In dichloromethane at 23℃; for 1h; Inert atmosphere;	99%

...Expand

: 7446-70-0, 7784-13-6
aluminum (III) chloride

: 91-15-6
phthalonitrile

: 14154-42-8
chloroaluminum phthalocyanine

Conditions

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;

: 380896-89-9
1-(pyridine-4-oxy) 3,4-dicyanobenzene

: indium(III) chloride

: 91-15-6
phthalonitrile

: 2-[4-(pyridyloxy)phthalocyaninato]chloroindium(III)

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol for 18h; Inert atmosphere; Reflux;	98.2%

...Expand

: 100-46-9
benzylamine

: 91-15-6
phthalonitrile

: 32313-76-1
1,3-Bis-[(Z)-benzylimino]-2,3-dihydro-1H-isoindole

Conditions

Conditions	Yield
sulfur at 40℃; for 1h;	98%

: 20989-17-7
(2S)-2-phenylglycinol

: 91-15-6
phthalonitrile

: 131380-82-0
1,2-bis<(4S)-4-phenyl-2-oxazolin-2-yl>benzene

Conditions

Conditions	Yield
at 150℃; for 1h; Microwave irradiation;	98%
With zinc(II) chloride In chlorobenzene for 24h; Heating;	66%

: 91-15-6
phthalonitrile

: 147-14-8
copper phthalocyanine

Conditions

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%

: 4-Butyl-cyclohexanecarboxylic acid hydrazide

: 91-15-6
phthalonitrile

: N'-(3-amino-1H-isoindol-1-ylidene)-4-butylcyclohexanecarbohydrazide

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 5h; Heating;	98%

: 109-76-2
Trimethylenediamine

: 91-15-6
phthalonitrile

: 1476807-78-9
2-(1,4,5,6-tetrahydropyrimidin-2-yl)benzonitrile

Conditions

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%

: (3-(trifluoromethyl)benzyl)zinc chloride * lithium chloride

: 91-15-6
phthalonitrile

: 670-74-6
2-(3-(trifluoromethyl)benzyl)benzonitrile

Conditions

Conditions	Yield
In tetrahydrofuran at 40℃; for 0.5h; Reagent/catalyst; Inert atmosphere; Microwave irradiation;	97%

: 107-10-8
propylamine

: 91-15-6
phthalonitrile

: 93423-55-3
1,3-Bis-[(Z)-propylimino]-2,3-dihydro-1H-isoindole

Conditions

Conditions	Yield
sulfur for 2h; Heating;	96%

: 3619-17-8
isobutyric acid hydrazide

: 91-15-6
phthalonitrile

: N'-(3-amino-1H-isoindol-1-ylidene)-2-methytlpropanohydrazide

Conditions

Conditions	Yield
In methanol for 5h; Heating;	96%

: 91-15-6
phthalonitrile

: tin(ll) chloride

: 18253-54-8
phthalocyanine tin(IV) dichloride

Conditions

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%

: 1603-40-3
3-methylpyridin-2-ylamine

: 71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7
cobalt(II) acetate

: 91-15-6
phthalonitrile

: 79062-08-1
Co(3-MeBPI)2

Conditions

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;

...Expand

: 1393596-93-4
(2-picolyl)diethylborane dimer

: 91-15-6
phthalonitrile

: 1393596-99-0
(Et2B)2(1,2-(NHC(CHC5H4N))2C6H4)

Conditions

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%

: 79-19-6
thiosemicarbazide

: 91-15-6
phthalonitrile

: 3-amino-1H-isoindol-1-one thiosemicarbazone

Conditions

Conditions	Yield
With sodium hydroxide for 2h; Reflux;	96%

: 91-15-6
phthalonitrile

: 14320-04-8
zinc phthalocyanine

Conditions

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%

Phthalonitrile Chemical Properties

Molecule structure of 1,2-Benzenedicarbonitrile (CAS NO.91-15-6):

IUPAC Name: Benzene-1,2-dicarbonitrile
Molecular Weight: 128.13076 g/mol
Molecular Formula: C₈H₄N₂
Density: 1.24 g/cm³
Melting Point: 137-139 °C(lit.)
Boiling Point: 304.6 °C at 760 mmHg
Flash Point: 153.3 °C
Index of Refraction: 1.565
Molar Refractivity: 35.88 cm³
Molar Volume: 110 cm³
Polarizability: 14.22×10^-24 cm³
Surface Tension: 55.6 dyne/cm
Enthalpy of Vaporization: 54.5 kJ/mol
Vapour Pressure: 0.000865 mmHg at 25 °C
Solubility Benzene: 50 mg/mL, clear
Water Solubility: 0.56 g/L (25 °C)
XLogP3: 1
H-Bond Acceptor: 2
Exact Mass: 128.037448
MonoIsotopic Mass: 128.037448
Topological Polar Surface Area: 47.6
Heavy Atom Count: 10
Complexity: 178
Canonical SMILES: C1=CC=C(C(=C1)C#N)C#N
InChI: InChI=1S/C8H4N2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H
InChIKey: XQZYPMVTSDWCCE-UHFFFAOYSA-N
EINECS: 202-044-8
Product Categories: Industrial/Fine Chemicals; Organics; Functional Materials; Phthalonitriles & Naphthalonitriles; Phthalonitriles (Building Blocks for Phthalocyanines); C8 to C9; Cyanides/Nitriles; Nitrogen Compounds

Phthalonitrile History

In 1896, the first formation of 1,2-Benzenedicarbonitrile was reported by Johannes Pinnow. It was noted to be a byproduct of the reaction between orthamidobenzonitrile hydrochloride, sodium nitrite, and hydrochloric acid to synthesize orthodicyanodiazoamidobenzene. In 1907, the first intentional method derived for the synthesis of 1,2-Benzenedicarbonitrile appeared, when 1,2-Benzenedicarbonitrile was boiled with acetic anhydride. While initial yields were small, it was a precursor that eventually to the contemporary large-scale synthesis seen today.

Phthalonitrile Uses

1,2-Benzenedicarbonitrile (CAS NO.91-15-6) is widely used for the sythesis of phthalein sulfonamide durgs, phthalocyanine pigments and dyes, high-resistance polyamide fiber, xylyl, di-isocyanate plastic and desulfuration catalyst. It is also used for dyes, pigments and other organic synthesis.

Phthalonitrile Production

1,2-Benzenedicarbonitrile is made by the ammoxidation of o-xylene in the presence of a vanadium oxide-antimony-oxide catalyst over heat (480 °C). This process passes a gaseous mixture of ammonia, oxygen, ando-xylene through a distributor plate into a fluidized bed reactor, containing the catalyst.

Phthalonitrile Toxicity Data With Reference

1.	orl-rat TDLo:7425 mg/kg/66W-I:ETA	VOONAW Voprosy Onkologii. Problems of Onkology. 18 (1)(1972),81.
2.	ipr-rat LD50:62 mg/kg	KJMDA6 Kobe Journal of the Medical Sciences. 11 (1965),63.
3.	orl-mus LD50:65 mg/kg	INHEAO Industrial Health. 4 (1966),11.
4.	ipr-mus LD50:25 mg/kg	NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .
5.	scu-mus LD50:46 mg/kg	INHEAO Industrial Health. 4 (1966),11.

Phthalonitrile Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

Phthalonitrile Safety Profile

Hazard Codes: Toxic T
Risk Statements: 25-23/24/25
R25 :Toxic if swallowed.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 36/37/39-45-28A
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S28:After contact with skin, wash immediately with plenty of soap-suds.
RIDADR: UN 3439 6.1/PG 2
WGK Germany: 1
RTECS: TI8575000
HazardClass: 6.1
PackingGroup: II
HS Code: 29269095
Hazardous Substances Data: 91-15-6(Hazardous Substances Data)
Poison by ingestion, subcutaneous, and intraperitoneal routes. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits toxic fumes of CN⁻ and NO_x.

Phthalonitrile Specification

1,2-Benzenedicarbonitrile (CAS NO.91-15-6) is also named as 1,2-Benzodinitrile ; 1,2-Dicyanobenzene ; AI3-00049 ; CCRIS 8898 ; Ftalodinitril ; Ftalodinitril [Czech] ; Ftalonitril ; Ftalonitril [Czech] ; HSDB 5273 ; NSC 17562 ; Phthalic acid dinitrile ; Phthalodinitrile ; Phthalonitrile ; USAF ND-09 ; o-Benzenedicarbonitrile ; o-Benzenedinitrile ; o-Cyanobenzonitrile ; o-Dicyanobenzene ; o-Pdn ; o-Phthalodinitrile ; ortho-Dicyanobenzene . 1,2-Benzenedicarbonitrile (CAS NO.91-15-6) is off-white to tan powder. It is soluble in alcohol, ether, chloroform and benzene, insoluble in oil. It can be volatile with steam. 1,2-Benzenedicarbonitrile is stable and incompatible with strong bases, strong acids, strong oxidizing agents, strong reducing agents.

Product Name

Phthalonitrile

Synthetic route

Phthalonitrile Chemical Properties

Phthalonitrile History

Phthalonitrile Uses

Phthalonitrile Production

Phthalonitrile Toxicity Data With Reference

Phthalonitrile Consensus Reports

Phthalonitrile Safety Profile

Phthalonitrile Specification

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