91-15-6

Basic information

• Product Name: Phthalonitrile
• Synonyms: o-pdn[qr];o-phthalodinitrile[qr];ortho-dicyanobenzene[qr];Phthalic acid dinitrile;phthalicacid,dinitrile[qr];phthalicaciddinitrile;USAF nd-09;usafnd-09
• CAS NO: 91-15-6
• Molecular Formula: C₈H₄N₂
• Molecular Weight: 128.13
• 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;Building Blocks;C8 to C9;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Pharmaceutical intermediates
• Mol File: 91-15-6.mol
• Article Data: 78

Chemical Properties

• Melting Point: 137-139 °C(lit.)
• Boiling Point: 227.54°C (rough estimate)
• Flash Point: 162°C
• Appearance: White to beige/Crystals or Crystalline Powder
• Density: 1.24
• Vapor Pressure: 0.000865mmHg at 25°C
• Refractive Index: 1.6231 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: benzene: 50 mg/mL, clear
• Water Solubility: 0.56 g/L (25 ºC)
• Stability: Stable. Incompatible with strong bases, strong acids, strong oxidizing agents, strong reducing agents.
• BRN: 775028
• CAS DataBase Reference: Phthalonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Phthalonitrile(91-15-6)
• EPA Substance Registry System: Phthalonitrile(91-15-6)

Safety Data

• Hazard Codes: T
• Statements: 25-23/24/25
• Safety Statements: 36/37/39-45-28A
• RIDADR: UN 3439 6.1/PG 2
• WGK Germany: 1
• RTECS: TI8575000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 91-15-6(Hazardous Substances Data)

Usage

Chemical Properties

Phthalonitrile is a crystalline powder having a faint grayish yellow color and a slighty aromatic odor, similar to benzonitrile. Phthalonitrile was first described in 1896 when it was isolated during the diazotization of 2-aminobenzonitrile. The compound is sparingly soluble in water (ca. 1 g/L) and soluble in acetone, nitrobenzene, and benzonitrile. It cannot be distilled and polymerizes if heated above the melting point. It is not explosive and is difficult to ignite, but the dust can explode.

uses

Phthalonitrile is used as a starting material for producing phthalocyanine pigments (→ Phthalocyanines), fluorescent brightners, and photographic sensitizers.

Uses

Phthalonitrile is used as an intermediate for chemical synthesis in the production of building blocks for colorants and coatings, life science and agricultural chemicals.?And also used as a precursor to phthalocyanine and other pigments, fluorescent brighteners, and photographic sensitizers.

Preparation

Phthalonitrile can be produced from phthalic acid, phthalic anhydride, phthalamide, or phthalimide by reaction with ammonia and elimination of water at 300–500°C in the gas phase in the presence of a catalyst. In a single-stage continuous process, o-xylene is converted to phthalonitrile by reaction with ammonia and oxygen in the gas phase in a fluidized-bed reactor. Generally, metal oxide mixtures containing vanadium, antimony, chromium, and molybdenum, with further active components such as iron, tungsten, and alkali-metal oxides, on an alumina or silica support are used as catalysts.

Reactions

The route from o-phthalodinitrile can be represented 4C8H4N2 +M → MPc, where M is a bivalent metal, metal halide, metal alcoholate, or an equivalent amount of metal of valence other than two in a 4:1 molar ratio.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by ingestion, subcutaneous, and intraperitoneal routes. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits toxic fumes of CN- and NOx. See also NITRILES.

Purification Methods

Crystallise the nitrile from EtOH, toluene or *benzene. It has also been distilled under high vacuum. It is steam volatile. [Beilstein 9 H 815, 9 II 602, 9 III 4199, 9 IV 3268.]

InChI:InChI=1/C8H4N2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H

Synthetic route

N,N'-o-phthaloylbis(P,P,P-triphenylphospha-λ5-azene) (112069-03-1) → phthalonitrile (91-15-6)

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

nitroacetic acid ethyl ester (626-35-7) + 2-iodobenzonitrile (4387-36-4) → phthalonitrile (91-15-6)

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%

2-iodobenzonitrile (4387-36-4) → phthalonitrile (91-15-6)

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

1,2-benzenedimethanamine (17300-02-6) → phthalonitrile (91-15-6)

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%

2-iodobenzonitrile (4387-36-4) + potassium ferrocyanide → phthalonitrile (91-15-6)

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 + o-cyanobromobenzene (2042-37-7) → phthalonitrile (91-15-6)

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 + 2-iodobenzonitrile (4387-36-4) → phthalonitrile (91-15-6)

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 (89942-45-0) → phthalonitrile (91-15-6)

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 (13506-83-7) + 4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide → 4-bromo-benzenesulfonic acid-(4-chloro-anilide) (6295-97-2) + phthalonitrile (91-15-6)

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 (13506-83-7) + N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide → 4-nitro-N-(4-chlorophenyl)benzenesulfonamide (16937-03-4) + phthalonitrile (91-15-6)

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%

o-phthalic dicarboxaldehyde (643-79-8) → phthalonitrile (91-15-6)

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 + 1-Bromo-2-iodobenzene (583-55-1) → phthalonitrile (91-15-6)

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%

benzoimidazole (51-17-2) + chloroform (67-66-3) → 2-chloroquinoxaline (1448-87-9) + phthalonitrile (91-15-6)

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

[2-(dihydroxyboranyl)phenyl]boronic acid (13506-83-7) + N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide (119986-58-2) → 4-methyl-N-(4-chlorophenyl)benzenesulfonamide (2903-34-6) + phthalonitrile (91-15-6)

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 (1044569-46-1) → phthalonitrile (91-15-6)

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

potassiumhexacyanoferrate(II) trihydrate + 1,2-dibromobenzene (583-53-9) → phthalonitrile (91-15-6)

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%

nitroacetic acid ethyl ester (626-35-7) + o-cyanobromobenzene (2042-37-7) → phthalonitrile (91-15-6)

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%

2,3-dicyano-1,4-hydroquinone (4733-50-0) + Chloromethyltrimethylsilane (2344-80-1) → phthalonitrile (91-15-6)

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

1,2-Bis(nonaflyl)benzene (41694-39-7) + dicyanozinc (557-21-1) → phthalonitrile (91-15-6)

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

zinc(II) cyanide (557-21-1) + 2-Chlorobenzonitrile (873-32-5) → phthalonitrile (91-15-6)

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%

o-formylbenzonitrile (7468-67-9) → phthalonitrile (91-15-6)

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 + 1,2-dibromobenzene (583-53-9) → phthalonitrile (91-15-6)

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) + 1,2-dibromobenzene (583-53-9) → phthalonitrile (91-15-6)

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

(1-chloroethyl)trimethylsilane (7787-87-3) + 4-hydroxy-1,2-benzenedicarbonitrile (30757-50-7) → phthalonitrile (91-15-6)

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

3-nitrobenzene-1,2-dicarbonitrile (51762-67-5) + Chloromethyltrimethylsilane (2344-80-1) → phthalonitrile (91-15-6)

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

3-hydroxylphthalonitrile (116039-49-7) + Chloromethyltrimethylsilane (2344-80-1) → phthalonitrile (91-15-6)

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

(3-chloropropyl)trimethylsilane (2344-83-4) + 3-hydroxylphthalonitrile (116039-49-7) → phthalonitrile (91-15-6)

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

tetra-n-butylammonium cyanide (10442-39-4) + C13H9N3S (114650-54-3) → 2-(phenylthio)benzonitrile (91804-55-6) + phthalonitrile (91-15-6)

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

C13H9N3S (114650-54-3) → 2-(phenylthio)benzonitrile (91804-55-6) + phthalonitrile (91-15-6)

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

phthalonitrile (91-15-6) → isoindole-1,3-diylidenediamine (160956-25-2, 160956-26-3, 160956-27-4, 160956-28-5, 160956-29-6)

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%

phthalonitrile (91-15-6) → 29H,31H-Phthalocyanine (574-93-6)

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 (2026-48-4) + phthalonitrile (91-15-6) → 1,2-bis[(4S)-(4-isopropyl-Δ2-1,3-oxazolin-2-yl)]benzene (131380-80-8)

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 (91-15-6) + /PBGZJ115-1120/ → 2-(4-Methoxy-phenyl)-3-[(Z)-4-methoxy-phenylimino]-2,3-dihydro-isoindol-1-one

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

phthalonitrile (91-15-6) → phthalimide (136918-14-4)

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.

nickel (7440-02-0) + phthalonitrile (91-15-6) → nickel(II) phthalocyanine (14055-02-8)

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%

phthalonitrile (91-15-6) + zinc (7440-66-6) → zinc(II) phthalocyanine (14320-04-8)

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 + phthalonitrile (91-15-6) → chloro(phthalodinitile)phthalocyaninato(2-)iridate(III) (14096-14-1, 187386-26-1)

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 (7446-70-0, 7784-13-6) + urea (57-13-6) + phthalonitrile (91-15-6) → chloroaluminum phthalocyanine (14154-42-8, 62905-77-5)

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

methylamine (74-89-5) + phthalonitrile (91-15-6) → 1,3-bis(methylimino)-isoindoline (88988-76-5, 89130-82-5, 93698-08-9, 93698-09-0)

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

phthalonitrile (91-15-6) → 5-(2-cyanophenyl)tetrazole (71515-74-7)

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 (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) + phthalonitrile (91-15-6) → copper phthalocyanine (147-14-8)

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%

4-(2-cyanoacetyl)benzoic acid (122545-30-6) + phthalonitrile (91-15-6) → C28H15N3O6

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 + phthalonitrile (91-15-6) → C112H112Au2N4O12P2(2+)*2F6Sb(1-)

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

aluminum (III) chloride (7446-70-0, 7784-13-6) + phthalonitrile (91-15-6) → chloroaluminum phthalocyanine (14154-42-8)

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 (380896-89-9) + indium(III) chloride + phthalonitrile (91-15-6) → 2-[4-(pyridyloxy)phthalocyaninato]chloroindium(III)

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

benzylamine (100-46-9) + phthalonitrile (91-15-6) → 1,3-Bis-[(Z)-benzylimino]-2,3-dihydro-1H-isoindole (32313-76-1)

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

(2S)-2-phenylglycinol (20989-17-7) + phthalonitrile (91-15-6) → 1,2-bis<(4S)-4-phenyl-2-oxazolin-2-yl>benzene (131380-82-0)

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

phthalonitrile (91-15-6) → copper phthalocyanine (147-14-8)

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 + phthalonitrile (91-15-6) → N'-(3-amino-1H-isoindol-1-ylidene)-4-butylcyclohexanecarbohydrazide

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

Trimethylenediamine (109-76-2) + phthalonitrile (91-15-6) → 2-(1,4,5,6-tetrahydropyrimidin-2-yl)benzonitrile (1476807-78-9)

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 + phthalonitrile (91-15-6) → 2-(3-(trifluoromethyl)benzyl)benzonitrile (670-74-6)

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

propylamine (107-10-8) + phthalonitrile (91-15-6) → 1,3-Bis-[(Z)-propylimino]-2,3-dihydro-1H-isoindole (93423-55-3)

Conditions	Yield
sulfur for 2h; Heating;	96%

isobutyric acid hydrazide (3619-17-8) + phthalonitrile (91-15-6) → N'-(3-amino-1H-isoindol-1-ylidene)-2-methytlpropanohydrazide

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

phthalonitrile (91-15-6) + tin(ll) chloride → phthalocyanine tin(IV) dichloride (18253-54-8)

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 (1603-40-3) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) + phthalonitrile (91-15-6) → Co(3-MeBPI)2 (79062-08-1)

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 (1393596-93-4) + phthalonitrile (91-15-6) → (Et2B)2(1,2-(NHC(CHC5H4N))2C6H4) (1393596-99-0)

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%

thiosemicarbazide (79-19-6) + phthalonitrile (91-15-6) → 3-amino-1H-isoindol-1-one thiosemicarbazone

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

phthalonitrile (91-15-6) → zinc phthalocyanine (14320-04-8)

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%

Upstream product

• 85-44-9 phthalic anhydride 
• 88-96-0 phthalamide 
• 108-24-7 acetic anhydride 
• 615-42-9 1,2-Diiodobenzene 
• 95-47-6 o-xylene 
• 64148-19-2 2-dichloromethyl-benzonitrile 
• 15187-16-3 lead(II) phthalocyanine 
• 1033995-63-9 oxonium 
• 583-53-9 2,3-dibromobenzene 
• 80-05-7 BPA 
• 31643-49-9 4-Nitrophthalonitrile 
• 108-46-3 recorcinol 
• 92-88-6 4,4'-Dihydroxybiphenyl 
• 620-92-8 bis-(4-hydroxyphenyl)methane 

Downstream Products

• 21517-30-6 6-hydrazinyl-[1,2,4]triazolo[3,4-a]phthalazine 
• 32313-77-2 1,3-bis(phenylimino)isoindoline 
• 861382-24-3 3,3-dibenzyl-isoindolin-1-one-imine 
• 496-12-8 isoindoline 
• 4741-70-2 Phthalimid-dioxim 
• 484-23-1 1,4-bis(hydrazino)phthalazine 
• 6876-33-1 2,4,6-tris(o-cyanophenyl)-1,3,5-triazine 
• 574-93-6 29H,31H-Phthalocyanine 
• 14352-51-3 3-iminoisoindolinone 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 2510-55-6 9-cyanophenanthrene 
• 56666-55-8 9-(9,10-dihydro)phenanthrenecarbonitrile 
• 92756-78-0 3-(2-cyanophenyl)-2-methoxy-2,3-dimethybutane 
• 92756-69-9 1-(2-cyanophenyl)-2,3-dimethyl-2-butene 

Relevant articles and documents

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A Versatile VMPO Catalyst Prepared In Situ for Oxidative Ammonolysis of Isomeric Picolines and Xylenes

Abstract: The V2O5–MoO3–P2O5 (VMPO) catalyst has been prepared in situ by thermal decomposition of vanado-molybdophosphoric acid (PMoV) on TiO2 support at 475°C. The TiO2 supported VMPO catalysts are characterized by FT–IR, XRD, BET surface area, NH3–TPD, and H2–TPR. Morphology of the catalyst has been studied by TEM. The accumulated data indicate decomposition of PMoV and presence of phosphate and pyrophosphate phases of molybdenum and vanadium after calcination. TPD and TPR studies exhibit the moderate acidity and presence of V4+ in the material, respectively. The VMPO catalyst has been used for ammoxidation of six different compounds including three isomeric picolines and three isomeric xylenes to the corresponding nitriles with the yield of 90–96%.