40851-95-4

Basic information

• Product Name: 6-Chloro-2,3-diaminopyridine
• Synonyms: 6-Chloro-2,3-diaminopyridine;2,3-Diamino-6-chloropyridine ,97%;6-chloro-2,3-PyridinediaMine;2,3-PyridinediaMine, 6-chloro-;6-chloro-pyridine-2,3-diyldiamine;2,3-Diamino-6-chloropyridine
• CAS NO: 40851-95-4
• Molecular Formula: C₅H₆ClN₃
• Molecular Weight: 143.57
• EINECS: 214-589-6
• Product Categories: Heterocycle-Pyridine series
• Mol File: 40851-95-4.mol
• Article Data: 32

Chemical Properties

• Melting Point: 132.0 to 136.0 °C
• Boiling Point: 360.216 °C at 760 mmHg
• Flash Point: 171.653 °C
• Appearance: /
• Density: 1.448 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.685
• Storage Temp.: 2-8°C
• PKA: 2.69±0.50(Predicted)
• CAS DataBase Reference: 6-Chloro-2,3-diaminopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-2,3-diaminopyridine(40851-95-4)
• EPA Substance Registry System: 6-Chloro-2,3-diaminopyridine(40851-95-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-42/43-33-23/24/25
• Safety Statements: 22-36/37-45-37-28
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1
• Hazardous Substances Data: 40851-95-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H6ClN3/c6-4-2-1-3(7)5(8)9-4/h1-2H,7H2,(H2,8,9)

Synthetic route

6-chloro-2-nitropyridine-3-amine (146015-42-1) → 6-chloropyridine-2,3-diamine (40851-95-4)

Conditions	Yield
With hydrogen; Raney nickel In methanol at 20℃; for 24h;	95.6%
With hydrogen In methanol at 20℃; for 24h;	95.6%
With methanol at 20℃; for 24h;
With Raney nickel In methanol at 20℃; for 24h;
With Raney Nickel In methanol at 20℃; for 24h;

2-amino-6-chloro-3-nitropyridine (27048-04-0) → 6-chloropyridine-2,3-diamine (40851-95-4)

Conditions	Yield
With iron; ammonium chloride In water; ethyl acetate at 20℃; for 24h;	93.7%
With iron; ammonium chloride In water; isopropyl alcohol at 90℃; for 1h;	91%
With sodium tetrahydroborate In ethanol; water at 20℃; for 4h; chemoselective reaction;	91%

2-amino-3-benzyloxycarbonylamino-6-chloro-pyridine → 2,3-Diaminopyridine (452-58-4) + 6-chloropyridine-2,3-diamine (40851-95-4)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate In methanol at 20℃; under 760.051 Torr; for 2h; Sealed tube; Overall yield = 87 %Spectr.; chemoselective reaction;	A 45% B 42%

2-amino-6-chloro-3-nitropyridine (27048-04-0) + tert-butyl alcohol (75-65-0) → 6-chloropyridine-2,3-diamine (40851-95-4) + N3-(tert-butyl)-6-chloropyridine-2,3-diamine (1426845-56-8)

Conditions	Yield
Stage #1: 2-amino-6-chloro-3-nitropyridine; tert-butyl alcohol With tin(II) chloride dihdyrate In ethyl acetate at 60℃; for 1h; Stage #2: With sodium tetrahydroborate In ethyl acetate at 60℃; for 3h;	A 43% B 30%

2-amino-3-nitropyridine (4214-75-9) → 2,3-Diaminopyridine (452-58-4) + 6-chloropyridine-2,3-diamine (40851-95-4)

Conditions	Yield
With hydrogenchloride; tin

ethyl (2-acetamido-6-chloro-3-pyridyl)aminomethylenemalonate (139087-01-7) → 6-chloropyridine-2,3-diamine (40851-95-4)

Conditions	Yield
With PPA at 80℃; for 0.166667h;

hydrogenchloride (7647-01-0) + 2-amino-3-nitropyridine (4214-75-9) + tin → 2,3-Diaminopyridine (452-58-4) + 6-chloropyridine-2,3-diamine (40851-95-4)

2-amino-3-nitropyridine (4214-75-9) → 6-chloropyridine-2,3-diamine (40851-95-4) + 2,3-diamino-pyridine

Conditions	Yield
With hydrogenchloride; tin

2,6-dicholoro-3-nitropyridine (16013-85-7) → 6-chloropyridine-2,3-diamine (40851-95-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: 75 percent / NH3 / ethanol 2: 92 percent / acetic acid, conc. H2SO4 / 2 h / Heating 3: aluminum amalgam, water / ethanol / 4 h / 40 °C 4: 52 percent / 2 h / 100 °C 5: 85percent polyphosphoric acid / 0.17 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: 75 percent / NH3 / ethanol 2: aluminum amalgam, water / ethanol / 4 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: ammonia / ethanol / 0 - 20 °C 2: ammonium chloride; iron / ethyl acetate; water / 24 h / 20 °C View Scheme

2-acetamido-3-amino-6-chloropyridine (139086-98-9) → 6-chloropyridine-2,3-diamine (40851-95-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 52 percent / 2 h / 100 °C 2: 85percent polyphosphoric acid / 0.17 h / 80 °C View Scheme

2-acetamido-6-chloro-3-nitropyridine (139086-97-8) → 6-chloropyridine-2,3-diamine (40851-95-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum amalgam, water / ethanol / 4 h / 40 °C 2: 52 percent / 2 h / 100 °C 3: 85percent polyphosphoric acid / 0.17 h / 80 °C View Scheme

tin(II)chloride dihydrate + 2-amino-6-chloro-3-nitropyridine (27048-04-0) + tert-butyl alcohol (75-65-0) → 6-chloropyridine-2,3-diamine (40851-95-4)

Conditions	Yield
With sodium borohydrid; sodium chloride; potassium carbonate In hexane; ethyl acetate

tin(II)chloride dihydrate + 5-bromo-3-nitro-pyridin-2-ylamine (6945-68-2) + tert-butyl alcohol (75-65-0) → 6-chloropyridine-2,3-diamine (40851-95-4)

Conditions	Yield
With sodium borohydrid In ethyl acetate

tin(II)chloride dihydrate + 2-amino-5-chloro-3-nitropyridine (5409-39-2) + tert-butyl alcohol (75-65-0) → 6-chloropyridine-2,3-diamine (40851-95-4)

Conditions	Yield
With sodium borohydrid In ethyl acetate

6-chloropyridine-2,3-diamine (40851-95-4) + Glyoxal (131543-46-9) → 6-chloropyrido[2,3-b]pyrazine (68236-03-3)

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h;	100%
With acetic acid In methanol; water at 50℃; for 4h;

6-chloropyridine-2,3-diamine (40851-95-4) + 4-cyanobenzaldehyde (105-07-7) → 5-chloro-2-(4-cyanophenyl)-4-azabenzimidazole

Conditions	Yield
With sodium metabisulfite; dimethyl sulfoxide at 165℃; for 0.25h; Inert atmosphere; Sealed tube;	99%

6-chloropyridine-2,3-diamine (40851-95-4) + trimethyl orthoformate (149-73-5) → 5-Chloro-3H-imidazo<4,5-b>pyridine (52090-89-8)

Conditions	Yield
With hydrogenchloride In water at 20℃;	98%
With hydrogenchloride In water at 20℃;

6-chloropyridine-2,3-diamine (40851-95-4) + oxalic acid diethyl ester (95-92-1) → 6-chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione (173930-57-9)

Conditions	Yield
at 130℃; for 15h;	96%

6-chloropyridine-2,3-diamine (40851-95-4) + orthoformic acid triethyl ester (122-51-0) → 5-chloro-1H-imidazo[4,5-b]pyridine (52090-89-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 140℃; for 4h;	95%
With toluene-4-sulfonic acid for 5h; Reflux;	59%
In methanol for 3h; Reflux;	58%

6-chloropyridine-2,3-diamine (40851-95-4) + glycolic Acid (79-14-1) → (5-chloro-1H-imidazo[4,5-b]pyridin-2-yl)methanol (172648-09-8)

Conditions	Yield
Stage #1: 6-chloropyridine-2,3-diamine; glycolic Acid at 150℃; for 4h; Stage #2: With hydrogenchloride In water at 60℃;	94%
In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 4h;	86%

6-chloropyridine-2,3-diamine (40851-95-4) + oxalic acid (144-62-7) → 6-chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione (173930-57-9)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 6h;	90.6%
With hydrogenchloride Heating; Yield given;

6-chloropyridine-2,3-diamine (40851-95-4) + glycolic Acid (79-14-1) → (5-chloro-3H-imidazo[4,5-b]pyridin-2-yl)methanol (172648-09-8)

Conditions	Yield
at 150℃; for 4h; Cyclization;	83%
With hydrogenchloride; ammonium hydroxide

6-chloropyridine-2,3-diamine (40851-95-4) + (4-cyanophenyl)propionic acid (42287-94-5) → N-(2-amino-6-chloropyridin-3-yl)-3-(4-cyanophenyl)propanamide (1541988-43-5)

Conditions	Yield
Stage #1: (4-cyanophenyl)propionic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 50℃; for 0.5h; Stage #2: 6-chloropyridine-2,3-diamine In tetrahydrofuran at 50℃; for 6h;	83%

6-chloropyridine-2,3-diamine (40851-95-4) + N,N,2-trimethylpropionamide (21678-37-5) → 5-chloro-2-isopropyl-1H-imidazo[4,5-b]pyridine

Conditions	Yield
With acetic acid at 135℃; for 12h;	77%

6-chloropyridine-2,3-diamine (40851-95-4) + 1,1'-carbonyldiimidazole (530-62-1) → 5-chloro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (40851-98-7)

Conditions	Yield
In chloroform for 5h; Heating;	76%

6-chloropyridine-2,3-diamine (40851-95-4) + p-benzyloxybenzaldehyde (4397-53-9) → 2-(4-(benzyloxy)phenyl)-5-chloro-3H-imidazo[4,5-b]pyridine

Conditions	Yield
Stage #1: 6-chloropyridine-2,3-diamine; p-benzyloxybenzaldehyde In methanol at 120℃; for 0.25h; Microwave irradiation; Stage #2: With [bis(acetoxy)iodo]benzene In tetrahydrofuran at 20℃; for 18h;	73%

6-chloropyridine-2,3-diamine (40851-95-4) + 4,4,4-trifluorobutanal (406-87-1) → 6-chloro-N3-(4,4,4-trifluorobutyl)-pyridine-2,3-diamine (1383051-41-9)

Conditions	Yield
Stage #1: 6-chloropyridine-2,3-diamine; 4,4,4-trifluorobutanal In dichloromethane; acetic acid for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane; acetic acid at 20℃;	70%
Stage #1: 6-chloropyridine-2,3-diamine; 4,4,4-trifluorobutanal With acetic acid In dichloromethane for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	70%
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;	70%
Stage #1: 6-chloropyridine-2,3-diamine; 4,4,4-trifluorobutanal With acetic acid In dichloromethane for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	70%

6-chloropyridine-2,3-diamine (40851-95-4) + (4-cyanophenoxy)acetic acid (1878-82-6) → N-(2-amino-6-chloropyridin-3-yl)-2-(4-cyanophenoxy)acetamide (1541988-03-7)

Conditions	Yield
Stage #1: (4-cyanophenoxy)acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 50℃; for 0.5h; Stage #2: 6-chloropyridine-2,3-diamine In tetrahydrofuran at 50℃; for 6h;	70%

carbon disulfide (75-15-0) + 6-chloropyridine-2,3-diamine (40851-95-4) → 5-chloro-1,3-dihydro-2H-imidazo[4,5-b]pyridine-2-thione (40851-97-6)

Conditions	Yield
Stage #1: carbon disulfide; 6-chloropyridine-2,3-diamine With sodium hydroxide In ethanol Reflux; Stage #2: With hydrogenchloride In ethanol	67%
With pyridine In ethanol at 40℃;
With pyridine In ethanol at 40℃;

6-chloropyridine-2,3-diamine (40851-95-4) + isovaleraldehyde (590-86-3) → 6-chloro-N3-isopentylpyridine-2,3-diamine (1383050-89-2)

Conditions	Yield
Stage #1: 6-chloropyridine-2,3-diamine; isovaleraldehyde With acetic acid In dichloromethane for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	65%
Stage #1: 6-chloropyridine-2,3-diamine; isovaleraldehyde With acetic acid In dichloromethane for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	65%

6-chloropyridine-2,3-diamine (40851-95-4) + isocaproic aldehyde (1119-16-0) → 6-chloro-N3-isopentylpyridine-2,3-diamine (1383050-89-2)

Conditions	Yield
Stage #1: 6-chloropyridine-2,3-diamine; isocaproic aldehyde With acetic acid In dichloromethane for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	65%

6-chloropyridine-2,3-diamine (40851-95-4) + (4-cyanophenyl)glycine (42288-26-6) → N-(2-amino-6-chloropyridin-3-yl)-2-[(4-cyanophenyl)amino]acetamide (1541988-45-7)

Conditions	Yield
Stage #1: (4-cyanophenyl)glycine With 1,1'-carbonyldiimidazole In tetrahydrofuran at 50℃; for 0.5h; Stage #2: 6-chloropyridine-2,3-diamine In tetrahydrofuran at 50℃; for 6h;	65%

6-chloropyridine-2,3-diamine (40851-95-4) + 2-fluoro-5-nitrobenzoic acid (7304-32-7) → 5-chloro-2-(2-fluoro-5-nitrophenyl)-3H-imidazo[4,5-b]pyridine (1533399-36-8)

Conditions	Yield
With polyphosphoric acid at 158 - 160℃; for 5h;	62%

6-chloropyridine-2,3-diamine (40851-95-4) + 2-bromo-1-(1-methyl-1H-pyrazol-4-yl)ethan-1-one (706819-66-1) → C11H8ClN5 (1431872-99-9)

Conditions	Yield
Stage #1: 6-chloropyridine-2,3-diamine; 2-bromo-1-(1-methyl-1H-pyrazol-4-yl)ethan-1-one With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃; for 18h; Stage #2: With manganese(IV) oxide In acetonitrile at 20℃; for 15h;	61%
Stage #1: 6-chloropyridine-2,3-diamine; 2-bromo-1-(1-methyl-1H-pyrazol-4-yl)ethan-1-one With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃; for 18h; Stage #2: With manganese(IV) oxide In acetonitrile at 20℃; for 0.25h;	61%

6-chloropyridine-2,3-diamine (40851-95-4) + (R)-4-(1-phenylethoxy)benzaldehyde (1095985-13-9) → C20H16ClN3O

Conditions	Yield
Stage #1: 6-chloropyridine-2,3-diamine; 4-[(1R)-1-phenylethoxy]benzaldehyde In methanol at 90℃; for 0.5h; Stage #2: With [bis(acetoxy)iodo]benzene In tetrahydrofuran at 20℃;	58%

6-chloropyridine-2,3-diamine (40851-95-4) + pyruvic acid methyl ester (600-22-6) → 6-chloro-3-methylpyrido[2,3-b]pyrazin-2(1H)-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 96h;	53%

6-chloropyridine-2,3-diamine (40851-95-4) + ethyl bromoacetate (105-36-2) → ethyl 2-(2-amino-6-chloropyridin-3-ylamino)acetate (1350925-19-7)

Conditions	Yield
Stage #1: 6-chloropyridine-2,3-diamine With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 60 - 70℃; for 3h;	50.5%
Stage #1: 6-chloropyridine-2,3-diamine With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 60 - 70℃; for 3h;	50.5%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 3h;	39%

6-chloropyridine-2,3-diamine (40851-95-4) + bis(trichloromethyl) carbonate (32315-10-9) → 5-chloro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (40851-98-7)

Conditions	Yield
Stage #1: 6-chloropyridine-2,3-diamine; bis(trichloromethyl) carbonate With sodium hydroxide In dichloromethane; water Stage #2: With hydrogenchloride In dichloromethane; water	47%

6-chloropyridine-2,3-diamine (40851-95-4) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (2-amino-6-chloropyridin-3-yl)carbamate

Conditions	Yield
In tetrahydrofuran at 45℃; for 18h;	47%

6-chloropyridine-2,3-diamine (40851-95-4) + 4-Fluorobenzoic acid (456-22-4) → 5-Chloro-2-(4-fluorophenyl)imidazo[4,5-b]pyridine (337902-77-9)

Conditions	Yield
In PPA	44%

6-chloropyridine-2,3-diamine (40851-95-4) + 2,2-dihydroxy-1-phenyl-ethanone (1075-06-5) → 7-chloro-2-phenylpyrido[3,4-b]pyrazine + 7-chloro-3-phenylpyrido[3,4-b]pyrazine

Conditions	Yield
In 1,4-dioxane for 6h; Reflux;	A 44% B 14%

Upstream product

• 7647-01-0 hydrogenchloride 
• 4214-75-9 2-amino-3-nitropyridine 
• 27048-04-0 2-amino-6-chloro-3-nitropyridine 
• 75-65-0 tert-butyl alcohol 
• 5409-39-2 2-amino-5-chloro-3-nitropyridine 
• 6945-68-2 5-bromo-3-nitro-pyridin-2-ylamine 
• 139086-98-9 2-acetamido-3-amino-6-chloropyridine 
• 139087-01-7 ethyl (2-acetamido-6-chloro-3-pyridyl)aminomethylenemalonate 
• 139086-97-8 2-acetamido-6-chloro-3-nitropyridine 
• 16013-85-7 2,6-dicholoro-3-nitropyridine 
• 146015-42-1 6-chloro-2-nitropyridine-3-amine 

Downstream Products

• 68236-03-3 6-Chlor-pyrido<2,3-b>pyrazin 
• 1350925-20-0 6-chloro-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one 
• 1350925-21-1 6-chloropyrido[2,3-b]pyrazin-3(4H)-one 
• 1350925-22-2 3,6-dichloropyrido[2,3-b]pyrazine 

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