78607-32-6

Basic information

• Product Name: 2,5-Dichloropyridin-3-amine
• Synonyms: TIMTEC-BB SBB005503;BUTTPARK 43\57-86;2,5-DICHLOROPYRIDIN-3-AMINE;2,5-DICHLORO-PYRIDIN-3-YLAMINE;2,5-DICHLORO-3-AMINOPYRIDINE;3-AMINO-2,5-DICHLOROPYRIDINE;2,5-Dichloro-3-pyridinamine;2,5-Dichloropyridin-3-amine, 95+%
• CAS NO: 78607-32-6
• Molecular Formula: C₅H₄Cl₂N₂
• Molecular Weight: 163
• Product Categories: pharmacetical;Amines;Pyridines;Pyridine;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Amino-pyridine series;Aromatics;Heterocycles;Building Blocks;C5;C5 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-Pyridine series
• Mol File: 78607-32-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 124 °C
• Boiling Point: 287.009 °C at 760 mmHg
• Flash Point: 127.379 °C
• Appearance: /
• Density: 1.498 g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol
• PKA: 0.03±0.10(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 2,5-Dichloropyridin-3-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dichloropyridin-3-amine(78607-32-6)
• EPA Substance Registry System: 2,5-Dichloropyridin-3-amine(78607-32-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-37/39-36-39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 78607-32-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Pale Beige Solid

InChI:InChI=1/C5H4Cl2N2/c6-3-1-4(8)5(7)9-2-3/h1-2H,8H2

Synthetic route

2,5-dichloro-3-nitropyridine (21427-62-3) → 3-amino-2,5-dichloropyridine (78607-32-6)

Conditions	Yield
With formic acid; triethylamine for 24h; chemoselective reaction;	95%
With hydrogen In tetrahydrofuran; water at 120℃; under 37503.8 Torr; for 15h; chemoselective reaction;	94%
With chlorobis(cyclooctene)rhodium(I) dimer In N,N-dimethyl-formamide at 120℃; for 12h; pH=2.25; Inert atmosphere;	86%

2-bromo-3-amino-5-chloropyridine (90902-83-3) → 3-amino-2,5-dichloropyridine (78607-32-6)

Conditions	Yield
With hydrogenchloride

2-bromo-5-chloro-3-nitropyridine (75806-86-9) → 3-amino-2,5-dichloropyridine (78607-32-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: iron-turnings; acetic acid 2: aqueous HCl View Scheme

2-amino-5-chloro-3-nitropyridine (5409-39-2) → 3-amino-2,5-dichloropyridine (78607-32-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated aqueous hydrochloric acid / -10 °C / anschliessend Behandeln mit wss. Natriumnitrit-Loesung 2: iron-turnings; acetic acid View Scheme

5-chloro-3-nitropyridin-2-ol (21427-61-2) → 3-amino-2,5-dichloropyridine (78607-32-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphoryl chloride; phosphorus (V)-chloride 2: iron-turnings; acetic acid View Scheme
Multi-step reaction with 3 steps 1: bromine; phosphorus (III)-bromide 2: iron-turnings; acetic acid 3: aqueous HCl View Scheme

3-amino-2,5-dichloropyridine (78607-32-6) + C26H35ClN4O3Si → C31H38Cl2N6O3Si

Conditions	Yield
With chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-t-butyl ether adduct; caesium carbonate In tetrahydrofuran at 95℃; for 18h; Inert atmosphere;	100%

3-amino-2,5-dichloropyridine (78607-32-6) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(2,5-dichloro-pyridin-3-yl)-acetamide (1256478-40-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; Inert atmosphere;	96%

3-amino-2,5-dichloropyridine (78607-32-6) + 3-chlorobenzoate (535-80-8) → 2,5-dichloro-N-(3-chloro-phenyl)-nicotinamide (1314530-64-7)

Conditions	Yield
In acetonitrile at 20℃;	90%

3-amino-2,5-dichloropyridine (78607-32-6) + 4,5-dichloro-1,2,3-dithiazolium chloride (75318-43-3) → (Z)-2,5-dichloro-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)pyridin-3-amine (1417816-48-8)

Conditions	Yield
Stage #1: 3-amino-2,5-dichloropyridine; 4,5-dichloro-1,2,3-dithiazolium chloride In dichloromethane at 20℃; for 1h; Stage #2: With 2,6-dimethylpyridine In dichloromethane at 20℃; for 2h;	82%

3-amino-2,5-dichloropyridine (78607-32-6) + 1,3,5-trimethyl-benzene (108-67-8) → 2,5-dichloro-N-mesityl-3-aminopyridine

Conditions	Yield
With I,I-bis(acetoxy)iodobenzene at 20℃; regioselective reaction;	82%

3-amino-2,5-dichloropyridine (78607-32-6) → 2,5-dichloropyridine-3-sulfonyl chloride

Conditions	Yield
Stage #1: 3-amino-2,5-dichloropyridine With tetrafluoroboric acid; thionyl chloride In acetonitrile at 0℃; for 0.166667h; Stage #2: With tert.-butylnitrite In acetonitrile at 0℃; for 1h; Further stages;	81.7%
Stage #1: 3-amino-2,5-dichloropyridine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: With thionyl chloride; copper(l) chloride In water at 0℃; for 1h; Sandmeyer Reaction;	1.85 g

3-amino-2,5-dichloropyridine (78607-32-6) + 5-chlorosalicyclaldehyde (635-93-8) → 2,8-Dichloro-5-oxa-4,11-diaza-dibenzo[a,d]cycloheptene (96830-44-3)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 110 - 120℃; for 4h;	81%

3-amino-2,5-dichloropyridine (78607-32-6) + 5-bromosalicyclaldehyde (1761-61-1) → 8-Bromo-2-chloro-5-oxa-4,11-diaza-dibenzo[a,d]cycloheptene (96830-47-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 110 - 120℃; for 4h;	81%

3-amino-2,5-dichloropyridine (78607-32-6) + 2,6-dichloro-3,5-dinitrotoluene (51676-76-7) → 2,5-dichloro-N-(3-chloro-2-methyl-4,6-dinitrophenyl)pyridin-3-amine

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide at 25℃;	78%

3-amino-2,5-dichloropyridine (78607-32-6) + salicylaldehyde (90-02-8) → 2-Chloro-5-oxa-4,11-diaza-dibenzo[a,d]cycloheptene (96830-45-4)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 110 - 120℃; for 4h;	71%

3-amino-2,5-dichloropyridine (78607-32-6) → bis(3-amino-5-chloro-2-pyridyl) diselenide

Conditions	Yield
With selenium; sodium tetrahydroborate; toluene-4-sulfonic acid at 50℃; for 20h; Inert atmosphere;	66%

3-amino-2,5-dichloropyridine (78607-32-6) + acetyl chloride (75-36-5) → N-(2,5-dichloro-pyridin-3-yl)-acetamide (1256478-46-2)

Conditions	Yield
Stage #1: 3-amino-2,5-dichloropyridine; acetyl chloride In dichloromethane at 0℃; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Inert atmosphere;	65%

2-Picolinic acid (98-98-6) + 3-amino-2,5-dichloropyridine (78607-32-6) → N-(2,5-dichloropyridin-3-yl)picolinamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 70℃; for 12h;	65%

3-amino-2,5-dichloropyridine (78607-32-6) + ethyl acrylate (140-88-5) → ethyl (E)-3-(3-amino-5-chloropyridin-2-yl)prop-2-enoate (959616-22-9)

Conditions	Yield
With tetrabutylammomium bromide; palladium diacetate; N-ethyl-N,N-diisopropylamine; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 140℃; for 30h;	52%
With tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine; palladium diacetate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 140℃; for 30h; Heck Reaction;
With tetrabutylammomium bromide; palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 140℃; for 30h;

3-amino-2,5-dichloropyridine (78607-32-6) + Benzyloxyacetyl chloride (19810-31-2) → 2-(benzyloxy)-N-(2,5-dichloropyridin-3-yl)acetamide (1227628-86-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	46%

3-amino-2,5-dichloropyridine (78607-32-6) + aniline (62-53-3) → 5-chloro-N2-phenylpyridine-2,3-diamine (6604-46-2)

Conditions	Yield
Stage #1: 3-amino-2,5-dichloropyridine; aniline With hydrogen bromide In water; diethylene glycol at 80℃; for 2.5h; Microwave irradiation; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	17%

morpholine (110-91-8) + 3-amino-2,5-dichloropyridine (78607-32-6) → di-morpholin-4-yl-phosphinic acid 2,5-dichloro-pyridin-3-ylamide (35980-84-8)

Conditions	Yield
(i) PCl5, benzene, (ii) HCO2H, (iii) /BRN= 102549/, Et3N; Multistep reaction;

2-Chloronicotinoyl chloride (49609-84-9) + 3-amino-2,5-dichloropyridine (78607-32-6) → 2-Chloro-N-(2,5-dichloro-pyridin-3-yl)-nicotinamide (866422-00-6)

Conditions	Yield
With pyridine In 1,4-dioxane; cyclohexane Ambient temperature;

3-amino-2,5-dichloropyridine (78607-32-6) → 8-Chloro-5-ethyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one (134698-38-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / cyclohexane; dioxane / Ambient temperature 2: xylene / Heating 3: NaH / various solvent(s) / Heating View Scheme

3-amino-2,5-dichloropyridine (78607-32-6) → N-(2,5-Dichloro-pyridin-3-yl)-2-ethylamino-nicotinamide

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / cyclohexane; dioxane / Ambient temperature 2: xylene / Heating View Scheme

3-amino-2,5-dichloropyridine (78607-32-6) → 8-Chloro-5-ethyl-10-methyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one (133627-14-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / cyclohexane; dioxane / Ambient temperature 2: xylene / Heating 3: NaH / various solvent(s) / Heating 4: 1.) NaH / 1.) DMSO, 2.) DMSO View Scheme

3-amino-2,5-dichloropyridine (78607-32-6) → 8-Chloro-5-ethyl-10-methyl-7-nitro-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one (133627-28-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine / cyclohexane; dioxane / Ambient temperature 2: xylene / Heating 3: NaH / various solvent(s) / Heating 4: 1.) NaH / 1.) DMSO, 2.) DMSO 5: nitronium tetrafluoroborate / acetonitrile View Scheme

3-amino-2,5-dichloropyridine (78607-32-6) → 8-Chloro-5-ethyl-10-methyl-2,7-dinitro-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one (135794-93-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine / cyclohexane; dioxane / Ambient temperature 2: xylene / Heating 3: NaH / various solvent(s) / Heating 4: 1.) NaH / 1.) DMSO, 2.) DMSO 5: nitronium tetrafluoroborate / acetonitrile View Scheme

3-amino-2,5-dichloropyridine (78607-32-6) → 2-Chloro-10,11-dihydro-5-oxa-4,11-diaza-dibenzo[a,d]cycloheptene (96830-57-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / NaH / dimethylformamide / 4 h / 110 - 120 °C 2: 87 percent / NaBH4 / ethanol View Scheme

3-amino-2,5-dichloropyridine (78607-32-6) → 2,8-Dichloro-10,11-dihydro-5-oxa-4,11-diaza-dibenzo[a,d]cycloheptene (96830-56-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / NaH / dimethylformamide / 4 h / 110 - 120 °C 2: 99 percent / NaBH4 / ethanol View Scheme

Upstream product

• 90902-83-3 3-amino-2-bromo-5-chloropyridine 
• 21427-61-2 5-chloro-3-nitropyridin-2-ol 
• 5409-39-2 2-amino-5-chloro-3-nitropyridine 
• 75806-86-9 2-bromo-5-chloro-3-nitropyridine 
• 21427-62-3 2,5-dichloro-3-nitropyridine 

Downstream Products

• 103999-77-5 2,5-dichloro-3-fluoropyridine 
• 89402-43-7 5-chloro-2,3-difluoropyridine 
• 1227628-86-5 2-(benzyloxy)-N-(2,5-dichloropyridin-3-yl)acetamide 
• 89639-36-1 5-chloro-2-methylpyridin-3-amine 
• 1211530-05-0 6-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid 
• 1083196-33-1 methyl 6-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate 
• 1416422-14-4 C₁₃H₃Cl₅N₄ 

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