14346-13-5

Basic information

• Product Name: 2,5-Diaminobenzonitrile
• Synonyms: 2-CYANO-1,4-PHENYLENE DIAMINE;2-Cyano-1,4-diaminobenzene;5-AMINOANTHRANILONITRILE ---TAN POWDER---;TIMTEC-BB SBB008419;5-AMINOANTHRANILONITRILE;2,5-DIAMINOBENZONITRILE;2-cyano-p-phenylenediamine
• CAS NO: 14346-13-5
• Molecular Formula: C₇H₇N₃
• Molecular Weight: 133.15
• Product Categories: Aromatic Nitriles
• Mol File: 14346-13-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 90-92 °C
• Boiling Point: 371°C
• Flash Point: 178°C
• Appearance: /
• Density: 1.24
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.05±0.10(Predicted)
• CAS DataBase Reference: 2,5-Diaminobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diaminobenzonitrile(14346-13-5)
• EPA Substance Registry System: 2,5-Diaminobenzonitrile(14346-13-5)

Safety Data

• Hazardous Substances Data: 14346-13-5(Hazardous Substances Data)

Usage

General Description

2,5-Diaminobenzonitrile is an organic compound with the molecular formula C7H7N3. It is a colorless to pale yellow solid that is primarily used in the synthesis of pharmaceuticals and organic compounds. This chemical is used as a building block in the production of dyes, pharmaceuticals, and other organic compounds. It possesses two amino groups and a nitrile group, making it a versatile molecule for use in a variety of chemical reactions. Despite its potential uses, 2,5-Diaminobenzonitrile is not widely used in industry and has limited commercial availability.

InChI:InChI=1/C7H7N3/c8-4-5-3-6(9)1-2-7(5)10/h1-3H,9-10H2

Synthetic route

5-nitroanthranilonitrile (17420-30-3) → 2-cyano-1,4-phenylenediamine (14346-13-5)

Conditions	Yield
With 3 % platinum on carbon; ammonia; hydrogen In ethanol at 50℃; under 12001.2 Torr; Solvent; Reagent/catalyst; Temperature; Pressure; Autoclave;	98%
With hydrazine hydrate In ethanol at 80℃; for 1h; Inert atmosphere; chemoselective reaction;	89%
With palladium diacetate; hydrazine hydrate; potassium hydroxide In water at 50℃; for 8h; Inert atmosphere; Green chemistry; chemoselective reaction;	82%

tin(II)chloride dihydrate + 5-nitroanthranilonitrile (17420-30-3) → 2-cyano-1,4-phenylenediamine (14346-13-5)

Conditions	Yield
With sodium hydroxide In hydrogenchloride

5-amino-2-nitrobenzonitrile (72115-08-3) → 2-cyano-1,4-phenylenediamine (14346-13-5)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In methanol at 120℃; under 15001.5 Torr; Temperature; Solvent;

2-cyano-1,4-phenylenediamine (14346-13-5) → 5-nitroanthranilonitrile (17420-30-3)

Conditions	Yield
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h;	90%

2-cyano-1,4-phenylenediamine (14346-13-5) + cyclohexanone (108-94-1) → 7,9-diamino-1,2,3,4-tetrahydroacridine (244219-97-4)

Conditions	Yield
With silica gel; toluene-4-sulfonic acid microwave irradiation;	75%

formaldehyd (50-00-0) + 2-cyano-1,4-phenylenediamine (14346-13-5) → 2-amino-5-(dimethylamino)benzonitrile (141400-26-2)

Conditions	Yield
Stage #1: formaldehyd; 2-cyano-1,4-phenylenediamine With acetic acid for 0.25h; Inert atmosphere; Stage #2: With sodium cyanoborohydride at 20℃; for 16h; Inert atmosphere; stereoselective reaction;	49%

ethyl 2-[5-(4-methylpiperazinyl)benzimidazol-2-yl]acetate + 2-cyano-1,4-phenylenediamine (14346-13-5) → 4,6-diamino-3-(5-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one (668428-98-6)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 5h;	45%

2-cyano-1,4-phenylenediamine (14346-13-5) + benzenesulfenyl chloride (931-59-9) → C19H13N3S2

Conditions	Yield
With pyridine In dichloromethane	36%

4-methoxybenzenesulfenyl chloride (1950-65-8) + 2-cyano-1,4-phenylenediamine (14346-13-5) → C21H17N3O2S2

Conditions	Yield
With pyridine In dichloromethane	22%

phthalic anhydride (85-44-9) + 2-cyano-1,4-phenylenediamine (14346-13-5) → N,N'-2-cyano-p-phenylenebisphthalimide

Conditions	Yield
In various solvent(s)

1,3-Dicarbomethoxy-S-methylisothiourea (34840-23-8) + 2-cyano-1,4-phenylenediamine (14346-13-5) → C12H13N5O4 (104479-12-1)

Conditions	Yield
With toluene-4-sulfonic acid In methanol Heating;

2-cyano-1,4-phenylenediamine (14346-13-5) → C14H15N5O5

Conditions	Yield
Multi-step reaction with 2 steps 1: p-TsOH / methanol / Heating 2: acetic acid / 1 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: p-TsOH / methanol / Heating 2: N,N-dimethylaniline / acetonitrile / 30 °C View Scheme

2-cyano-1,4-phenylenediamine (14346-13-5) + Ethyl oxalyl chloride (4755-77-5) → N,N'-(cyano-p-phenylene)dioxamic acid, diethyl ester (53325-61-4)

Conditions	Yield
With triethylamine In N-methyl-acetamide; water

(S)-N-[1-(2-chloro-6-propylpyrimidin-4-yl)pyrrolidin-3-yl]acetamide (1394321-80-2) + 2-cyano-1,4-phenylenediamine (14346-13-5) → (S)-N-{1-[2-(4-amino-3-cyanophenylamino)-6-propylpyrimidin-4-yl]pyrrolidin-3-yl}acetamide hydrochloride (1394316-97-2)

Conditions	Yield
In butan-1-ol for 0.666667h; Microwave irradiation;
In butan-1-ol for 0.666667h; Microwave irradiation;	17.1 mg

2-cyano-1,4-phenylenediamine (14346-13-5) + (S)-N-{1-(2-chloro-8-methoxyquinazolin-4-yl)pyrrolidin-3-yl}acetamide → (S)-N-[1-{2-(4-amino-3-cyanophenylamino)-8-methoxyquinazolin-4-yl}pyrrolidin-3-yl]acetamide

Conditions	Yield
for 0.666667h; Microwave irradiation;	1.4 mg

2-cyano-1,4-phenylenediamine (14346-13-5) → C11H12N4O2

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite 2: sodium acetate View Scheme

2-cyano-1,4-phenylenediamine (14346-13-5) → C11H9N3O2

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride; sodium nitrite 2: sodium acetate 3: polyphosphoric acid / 70 °C View Scheme

2-cyano-1,4-phenylenediamine (14346-13-5) → C10H7N3O2

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride; sodium nitrite 2: sodium acetate 3: polyphosphoric acid / 70 °C 4: sodium hydroxide / tetrahydrofuran; methanol; water View Scheme

2-cyano-1,4-phenylenediamine (14346-13-5) → C10H8N4O

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogenchloride; sodium nitrite 2: sodium acetate 3: polyphosphoric acid / 70 °C 4: sodium hydroxide / tetrahydrofuran; methanol; water 5: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ammonium chloride; triethylamine / N,N-dimethyl-formamide View Scheme

2-cyano-1,4-phenylenediamine (14346-13-5) → C10H8N4S

Conditions	Yield
Multi-step reaction with 6 steps 1: hydrogenchloride; sodium nitrite 2: sodium acetate 3: polyphosphoric acid / 70 °C 4: sodium hydroxide / tetrahydrofuran; methanol; water 5: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ammonium chloride; triethylamine / N,N-dimethyl-formamide 6: Lawessons reagent / tetrahydrofuran / Reflux View Scheme

2-cyano-1,4-phenylenediamine (14346-13-5) → C16H14N4O2S

Conditions	Yield
Multi-step reaction with 7 steps 1: hydrogenchloride; sodium nitrite 2: sodium acetate 3: polyphosphoric acid / 70 °C 4: sodium hydroxide / tetrahydrofuran; methanol; water 5: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ammonium chloride; triethylamine / N,N-dimethyl-formamide 6: Lawessons reagent / tetrahydrofuran / Reflux 7: pyridine / ethanol / Reflux View Scheme

2-cyano-1,4-phenylenediamine (14346-13-5) → C14H10N4O2S

Conditions

Yield

Multi-step reaction with 8 steps 1: hydrogenchloride; sodium nitrite 2: sodium acetate 3: polyphosphoric acid / 70 °C 4: sodium hydroxide / tetrahydrofuran; methanol; water 5: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ammonium chloride; triethylamine / N,N-dimethyl-formamide 6: Lawessons reagent / tetrahydrofuran / Reflux 7: pyridine / ethanol / Reflux 8: sodium hydroxide / tetrahydrofuran; methanol; water View Scheme

2-cyano-1,4-phenylenediamine (14346-13-5) → C7H8N4

Conditions	Yield
With hydrogenchloride; sodium nitrite

Upstream product

• 17420-30-3 5-nitroanthranilonitrile 
• 72115-08-3 5-amino-2-nitrobenzonitrile 

Downstream Products

• 141400-26-2 2-amino-5-(dimethylamino)benzonitrile 
• 17420-30-3 5-nitroanthranilonitrile 
• 1394316-97-2 (S)-N-{1-[2-(4-amino-3-cyanophenylamino)-6-propylpyrimidin-4-yl]pyrrolidin-3-yl}acetamide hydrochloride 
• 53325-61-4 N,N'-(cyano-p-phenylene)dioxamic acid, diethyl ester 
• 104479-12-1 C₁₂H₁₃N₅O₄ 

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