6-Chloro-2,3-diaminopyridine supplier

Name
6-Chloro-2,3-diaminopyridine
EINECS 214-589-6
CAS No. 40851-95-4
Article Data34
CAS DataBase
Density 1.448 g/cm³
Solubility
Melting Point 132.0 to 136.0 °C
Formula C₅H₆ClN₃
Boiling Point 360.216 °C at 760 mmHg
Molecular Weight 143.576
Flash Point 171.653 °C
Transport Information
Appearance
Safety 22-36/37-45-37-28
Risk Codes 22-36/37/38-42/43-33-23/24/25
Molecular Structure
Hazard Symbols Xn
Synonyms Pyridine,2,3-diamino-6-chloro- (6CI,7CI);2,3-Diamino-6-chloropyridine;6-Chloropyridine-2,3-diamine;
PSA 64.93000
LogP 2.06180

Synthetic route

: 146015-42-1
6-chloro-2-nitropyridine-3-amine

: 40851-95-4
6-chloropyridine-2,3-diamine

Conditions

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;

: 27048-04-0
2-amino-6-chloro-3-nitropyridine

: 40851-95-4
6-chloropyridine-2,3-diamine

Conditions

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

A: 452-58-4
2,3-Diaminopyridine

B: 40851-95-4
6-chloropyridine-2,3-diamine

Conditions

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%

: 27048-04-0
2-amino-6-chloro-3-nitropyridine

: 75-65-0
tert-butyl alcohol

A: 40851-95-4
6-chloropyridine-2,3-diamine

B: 1426845-56-8
N3-(tert-butyl)-6-chloropyridine-2,3-diamine

Conditions

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%

...Expand

: 4214-75-9
2-amino-3-nitropyridine

A: 452-58-4
2,3-Diaminopyridine

B: 40851-95-4
6-chloropyridine-2,3-diamine

Conditions

Conditions	Yield
With hydrogenchloride; tin

: 139087-01-7
ethyl (2-acetamido-6-chloro-3-pyridyl)aminomethylenemalonate

: 40851-95-4
6-chloropyridine-2,3-diamine

Conditions

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

: 7647-01-0
hydrogenchloride

: 4214-75-9
2-amino-3-nitropyridine

tin: tin

A: 452-58-4
2,3-Diaminopyridine

B: 40851-95-4
6-chloropyridine-2,3-diamine

...Expand

: 4214-75-9
2-amino-3-nitropyridine

A: 40851-95-4
6-chloropyridine-2,3-diamine

B 2,3-diamino-pyridine: 2,3-diamino-pyridine

Conditions

Conditions	Yield
With hydrogenchloride; tin

: 16013-85-7
2,6-dicholoro-3-nitropyridine

: 40851-95-4
6-chloropyridine-2,3-diamine

Conditions

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

: 139086-98-9
2-acetamido-3-amino-6-chloropyridine

: 40851-95-4
6-chloropyridine-2,3-diamine

Conditions

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

: 139086-97-8
2-acetamido-6-chloro-3-nitropyridine

: 40851-95-4
6-chloropyridine-2,3-diamine

Conditions

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

: 27048-04-0
2-amino-6-chloro-3-nitropyridine

: 75-65-0
tert-butyl alcohol

: 40851-95-4
6-chloropyridine-2,3-diamine

Conditions

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

...Expand

: tin(II)chloride dihydrate

: 6945-68-2
5-bromo-3-nitro-pyridin-2-ylamine

: 75-65-0
tert-butyl alcohol

: 40851-95-4
6-chloropyridine-2,3-diamine

Conditions

Conditions	Yield
With sodium borohydrid In ethyl acetate

...Expand

: tin(II)chloride dihydrate

: 5409-39-2
2-amino-5-chloro-3-nitropyridine

: 75-65-0
tert-butyl alcohol

: 40851-95-4
6-chloropyridine-2,3-diamine

Conditions

Conditions	Yield
With sodium borohydrid In ethyl acetate

...Expand

: 40851-95-4
6-chloropyridine-2,3-diamine

: 131543-46-9
Glyoxal

: 68236-03-3
6-chloropyrido[2,3-b]pyrazine

Conditions

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

: 40851-95-4
6-chloropyridine-2,3-diamine

: 105-07-7
4-cyanobenzaldehyde

: 5-chloro-2-(4-cyanophenyl)-4-azabenzimidazole

Conditions

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

: 40851-95-4
6-chloropyridine-2,3-diamine

: 149-73-5
trimethyl orthoformate

: 52090-89-8
5-Chloro-3H-imidazo<4,5-b>pyridine

Conditions

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

: 40851-95-4
6-chloropyridine-2,3-diamine

: 95-92-1
oxalic acid diethyl ester

: 173930-57-9
6-chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione

Conditions

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

: 40851-95-4
6-chloropyridine-2,3-diamine

: 122-51-0
orthoformic acid triethyl ester

: 52090-89-8
5-chloro-1H-imidazo[4,5-b]pyridine

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 79-14-1
glycolic Acid

: 172648-09-8
(5-chloro-1H-imidazo[4,5-b]pyridin-2-yl)methanol

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 144-62-7
oxalic acid

: 173930-57-9
6-chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione

Conditions

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

: 40851-95-4
6-chloropyridine-2,3-diamine

: 79-14-1
glycolic Acid

: 172648-09-8
(5-chloro-3H-imidazo[4,5-b]pyridin-2-yl)methanol

Conditions

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

: 40851-95-4
6-chloropyridine-2,3-diamine

: 42287-94-5
(4-cyanophenyl)propionic acid

: 1541988-43-5
N-(2-amino-6-chloropyridin-3-yl)-3-(4-cyanophenyl)propanamide

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 21678-37-5
N,N,2-trimethylpropionamide

: 5-chloro-2-isopropyl-1H-imidazo[4,5-b]pyridine

Conditions

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

: 40851-95-4
6-chloropyridine-2,3-diamine

: 530-62-1
1,1'-carbonyldiimidazole

: 40851-98-7
5-chloro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Conditions

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

: 40851-95-4
6-chloropyridine-2,3-diamine

: 4397-53-9
p-benzyloxybenzaldehyde

: 2-(4-(benzyloxy)phenyl)-5-chloro-3H-imidazo[4,5-b]pyridine

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 406-87-1
4,4,4-trifluorobutanal

: 1383051-41-9
6-chloro-N3-(4,4,4-trifluorobutyl)-pyridine-2,3-diamine

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 1878-82-6
(4-cyanophenoxy)acetic acid

: 1541988-03-7
N-(2-amino-6-chloropyridin-3-yl)-2-(4-cyanophenoxy)acetamide

Conditions

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%

: 75-15-0
carbon disulfide

: 40851-95-4
6-chloropyridine-2,3-diamine

: 40851-97-6
5-chloro-1,3-dihydro-2H-imidazo[4,5-b]pyridine-2-thione

Conditions

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℃;

: 40851-95-4
6-chloropyridine-2,3-diamine

: 590-86-3
isovaleraldehyde

: 1383050-89-2
6-chloro-N3-isopentylpyridine-2,3-diamine

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 1119-16-0
isocaproic aldehyde

: 1383050-89-2
6-chloro-N3-isopentylpyridine-2,3-diamine

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 42288-26-6
(4-cyanophenyl)glycine

: 1541988-45-7
N-(2-amino-6-chloropyridin-3-yl)-2-[(4-cyanophenyl)amino]acetamide

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 7304-32-7
2-fluoro-5-nitrobenzoic acid

: 1533399-36-8
5-chloro-2-(2-fluoro-5-nitrophenyl)-3H-imidazo[4,5-b]pyridine

Conditions

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

: 40851-95-4
6-chloropyridine-2,3-diamine

: 706819-66-1
2-bromo-1-(1-methyl-1H-pyrazol-4-yl)ethan-1-one

: 1431872-99-9
C11H8ClN5

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 1095985-13-9
(R)-4-(1-phenylethoxy)benzaldehyde

: C20H16ClN3O

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 600-22-6
pyruvic acid methyl ester

: 6-chloro-3-methylpyrido[2,3-b]pyrazin-2(1H)-one

Conditions

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

: 40851-95-4
6-chloropyridine-2,3-diamine

: 105-36-2
ethyl bromoacetate

: 1350925-19-7
ethyl 2-(2-amino-6-chloropyridin-3-ylamino)acetate

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 32315-10-9
bis(trichloromethyl) carbonate

: 40851-98-7
5-chloro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Conditions

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%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 24424-99-5
di-tert-butyl dicarbonate

: tert-butyl (2-amino-6-chloropyridin-3-yl)carbamate

Conditions

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

: 40851-95-4
6-chloropyridine-2,3-diamine

: 456-22-4
4-Fluorobenzoic acid

: 337902-77-9
5-Chloro-2-(4-fluorophenyl)imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
In PPA	44%

: 40851-95-4
6-chloropyridine-2,3-diamine

: 1075-06-5
2,2-dihydroxy-1-phenyl-ethanone

A: 7-chloro-2-phenylpyrido[3,4-b]pyrazine

B: 7-chloro-3-phenylpyrido[3,4-b]pyrazine

Conditions

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

...Expand

6-Chloro-2,3-diaminopyridine Specification

The 6-Chloro-2,3-diaminopyridine is an organic compound with the formula C₅H₆ClN₃. The systematic name of this chemical is 6-chloropyridine-2,3-diamine. With the CAS registry number 40851-95-4, it is also named as 2,3-pyridinediamine, 6-chloro-.

Physical properties about 6-Chloro-2,3-diaminopyridine are: (1)ACD/LogP: 0.92; (2)ACD/LogD (pH 5.5): 1; (3)ACD/LogD (pH 7.4): 1; (4)ACD/BCF (pH 5.5): 7; (5)ACD/BCF (pH 7.4): 7; (6)ACD/KOC (pH 5.5): 146; (7)ACD/KOC (pH 7.4): 146; (8)#H bond acceptors: 3; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 64.93 Å²; (12)Index of Refraction: 1.685; (13)Molar Refractivity: 37.711 cm³; (14)Molar Volume: 99.168 cm³; (15)Polarizability: 14.95×10^-24cm³; (16)Surface Tension: 72.085 dyne/cm; (17)Density: 1.448 g/cm³; (18)Flash Point: 171.653 °C; (19)Enthalpy of Vaporization: 60.59 kJ/mol; (20)Boiling Point: 360.216 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1nc(N)c(N)cc1
(2)InChI: InChI=1/C5H6ClN3/c6-4-2-1-3(7)5(8)9-4/h1-2H,7H2,(H2,8,9)
(3)InChIKey: QEIRYIILFUVXAM-UHFFFAOYAE
(4)Std. InChI: InChI=1S/C5H6ClN3/c6-4-2-1-3(7)5(8)9-4/h1-2H,7H2,(H2,8,9)
(5)Std. InChIKey: QEIRYIILFUVXAM-UHFFFAOYSA-N

Product Name

6-Chloro-2,3-diaminopyridine

Synthetic route

6-Chloro-2,3-diaminopyridine Specification

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