3,3'-dinitro-2,2'-hydrazobipyridine
2,3-Diaminopyridine
Conditions | Yield |
---|---|
With hydrogen; nickel In ethanol under 3102.9 Torr; for 3h; Ambient temperature; | 92% |
Conditions | Yield |
---|---|
With sulfur; sodium hydroxide In methanol; water at 80℃; for 16h; Green chemistry; | 89% |
With hydrogen; palladium on activated charcoal In ethyl acetate at 20 - 35℃; under 3102.9 Torr; other solvent; | 80% |
With hydrogenchloride; ethanol; iron |
2-Hydrazino-3-nitropyridine
2,3-Diaminopyridine
Conditions | Yield |
---|---|
With hydrogen; nickel In tetrahydrofuran; ethanol at 65℃; under 3102.9 Torr; for 16h; | 70% |
Multi-step reaction with 2 steps 1: 31 percent / (C2H5)3N / ethanol / 96 h / Heating 2: 92 percent / H2 / Raney Ni / ethanol / 3 h / 3102.9 Torr / Ambient temperature View Scheme |
2-amino-3-nitropyridine 1-oxide
2,3-Diaminopyridine
Conditions | Yield |
---|---|
With sulfur; sodium hydroxide In methanol; water at 80℃; for 16h; Green chemistry; | 68% |
Conditions | Yield |
---|---|
With zinc ammonium chloride at 220℃; for 5h; Autoclave; | 60% |
With ammonium hydroxide; copper(II) sulfate at 130℃; under 13239.1 Torr; |
2-nitro-3-azidopyridine
2,3-Diaminopyridine
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol for 0.5h; | 50% |
With hydrazine hydrate In ethanol for 0.5h; Mechanism; | 50% |
A
2,3-Diaminopyridine
B
6-chloropyridine-2,3-diamine
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% |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol at 80℃; under 3102.9 Torr; for 18h; | 41% |
2-amino-3-azidopyridine
isobutyraldehyde
A
2,3-Diaminopyridine
B
2-(1-methylethyl)imidazo[4,5-b]pyridine
Conditions | Yield |
---|---|
In ethanol for 24h; Heating; | A 33% B 8% |
Conditions | Yield |
---|---|
With sulfuric acid; zinc In methanol; water at 90℃; for 48h; | 20% |
With sodium hydroxide; aluminum nickel |
Conditions | Yield |
---|---|
With 4-methylisopropylbenzene; sodium amide at 210℃; | |
Multi-step reaction with 2 steps 1: concentrated aqueous HCl 2: CuSO4; aqueous NH3 / 130 °C / 13239.1 Torr View Scheme |
5-bromo-pyridine-2,3-diamine
2,3-Diaminopyridine
Conditions | Yield |
---|---|
With sodium hydroxide; Pd/SrCO3 Hydrogenation; |
3-amino-2-nitropyridine
2,3-Diaminopyridine
Conditions | Yield |
---|---|
With methanol; nickel Hydrogenation; | |
With sodium hydroxide; aluminum nickel |
2-amino-3-nitropyridine
A
2,3-Diaminopyridine
B
6-chloropyridine-2,3-diamine
Conditions | Yield |
---|---|
With hydrogenchloride; tin |
Conditions | Yield |
---|---|
With sodium hydroxide; aluminum nickel |
Conditions | Yield |
---|---|
at 210℃; |
hydrogenchloride
2-amino-3-nitropyridine
A
2,3-Diaminopyridine
B
6-chloropyridine-2,3-diamine
3-amino-2-phthalimidopyridine
2,3-Diaminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: HCl; sodium nitrite / H2O / 3.5 h / cooling 1.2: 60 percent / sodium azide / H2O; diethyl ether / 2 h / 0 °C 2.1: 96 percent / hydrazine hydrate / ethanol; tetrahydrofuran; H2O / 26 h / 20 °C 3.1: 33 percent / ethanol / 24 h / Heating View Scheme |
3-azido-2-phthalimidopyridine
2,3-Diaminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 percent / hydrazine hydrate / ethanol; tetrahydrofuran; H2O / 26 h / 20 °C 2: 33 percent / ethanol / 24 h / Heating View Scheme |
3-nitro-2-phthalimidopyridine
2,3-Diaminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 50 percent / hydrogen / Pd/C / ethanol / 15 h / 60 °C / 3040 Torr 2.1: HCl; sodium nitrite / H2O / 3.5 h / cooling 2.2: 60 percent / sodium azide / H2O; diethyl ether / 2 h / 0 °C 3.1: 96 percent / hydrazine hydrate / ethanol; tetrahydrofuran; H2O / 26 h / 20 °C 4.1: 33 percent / ethanol / 24 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86 percent / ethanol / 3 h / Heating 2: 41 percent / H2 / 5percent Pd/C / ethanol / 18 h / 80 °C / 3102.9 Torr View Scheme | |
Multi-step reaction with 2 steps 1: 65 percent / CH3COONH4 / bis-(2-methoxy-ethyl) ether / 12 h / Heating 2: 80 percent / H2 / 5percent Pd/C / ethyl acetate / 20 - 35 °C / 3102.9 Torr / other solvent View Scheme | |
Multi-step reaction with 3 steps 1: 78 percent / N2H4 / acetonitrile / 1 h / Heating 2: 31 percent / (C2H5)3N / ethanol / 96 h / Heating 3: 92 percent / H2 / Raney Ni / ethanol / 3 h / 3102.9 Torr / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: 78 percent / N2H4 / acetonitrile / 1 h / Heating 2: 70 percent / H2 / Raney Ni / ethanol; tetrahydrofuran / 16 h / 65 °C / 3102.9 Torr View Scheme | |
Multi-step reaction with 2 steps 1: iron; acetic acid 2: CuSO4; aqueous NH3 / 130 °C / 13239.1 Torr View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: concentrated H2SO4; HNO3 2: aqueous NaOH 3: nickel-aluminium-alloy; aq.-ethanolic NaOH View Scheme |
ethyl N-(2-nitro-3-pyridyl)carbamate
2,3-Diaminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH 2: nickel-aluminium-alloy; aq.-ethanolic NaOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; ammonium acetate / acetonitrile / 0.25 h 2: nitric acid; sulfuric acid / 4 h / 0 - 50 °C 3: sulfuric acid; zinc / water; methanol / 48 h / 90 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 4 h / 0 - 50 °C 2: sulfuric acid; zinc / water; methanol / 48 h / 90 °C View Scheme |
Conditions | Yield |
---|---|
With sodium hypochlorite; potassium hydroxide In water at 5 - 100℃; for 5h; Reagent/catalyst; |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethanol at 25℃; for 2h; |
Conditions | Yield |
---|---|
With zirconium(IV) chloride In methanol at 20℃; for 0.0833333h; | 100% |
With silica-supported stannous chloride In methanol at 20℃; for 0.166667h; | 95% |
With acetic acid In ethanol at 70℃; for 16h; | 95% |
2,3-Diaminopyridine
4-benzoyl-3-hydroxy-2,5-dihydrofuran-2-one
2-aminopyrido-3-ammonium 4-benzoyl-2(5H)-furanone-3-oxide
Conditions | Yield |
---|---|
In chloroform Ambient temperature; | 100% |
2,3-Diaminopyridine
Conditions | Yield |
---|---|
Stage #1: (7aSR,9RS,11aRS)-11a-ethyl-9-hydroxy-9-propyl-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: 2,3-Diaminopyridine In N,N-dimethyl-formamide at 20℃; for 18h; | 100% |
Conditions | Yield |
---|---|
With polyphosphoric acid at 180℃; for 16h; | 100% |
2,3-Diaminopyridine
orthoformic acid triethyl ester
3H-imidazo[4,5-b]pyridine
Conditions | Yield |
---|---|
Stage #1: 2,3-Diaminopyridine; orthoformic acid triethyl ester at 145℃; for 3h; Stage #2: With formic acid at 110℃; for 2h; | 99% |
Stage #1: 2,3-Diaminopyridine; orthoformic acid triethyl ester for 3.5h; Reflux; Stage #2: With hydrogenchloride In water for 1h; Reflux; | 83% |
With H-Y-zeolite In ethanol for 10h; Heating; | 81% |
2,3-Diaminopyridine
acenaphthene quinone
acenaphtho[1,2-b]pyrido[2,3-e]pyrazine
Conditions | Yield |
---|---|
With zirconium oxide salicylaldehyde-(3-aminopropyl)trimethoxysilane imine complex modified SBA-15 In water for 2h; Reflux; | 99% |
With Cu(II)-Schiff base/SBA-15 In water for 2h; Reflux; | 98% |
With SBA-15 mesoporous silica supported Fe(III)-Schiff base In water for 2h; Reflux; | 98% |
Conditions | Yield |
---|---|
Stage #1: 2,3-Diaminopyridine With orthoformic acid triethyl ester at 145℃; for 3h; Stage #2: formic acid at 110℃; for 2h; Stage #3: In methanol at 20℃; | 99% |
at 170℃; for 48h; | 30% |
Conditions | Yield |
---|---|
With silica-supported bismuth(III) chloride In methanol at 20℃; for 0.5h; Catalytic behavior; | 98% |
In methanol; acetic acid at 160℃; for 0.0833333h; Irradiation; | 97% |
With zirconium(IV) chloride In methanol at 20℃; for 1h; | 96% |
Conditions | Yield |
---|---|
at 140℃; for 5h; | 98% |
at 130 - 140℃; |
carbon disulfide
2,3-Diaminopyridine
1,3-dihydro-2H-imidazo[4,5-b]pyridine-2-thione
Conditions | Yield |
---|---|
In pyridine for 5h; Heating; | 98% |
With sodium hydroxide | 76% |
With potassium hydroxide In ethanol; water at 80℃; | 69% |
2,3-Diaminopyridine
6-methylnicotinic acid
2-(6-Methyl-pyridin-3-yl)-1H-imidazo[4,5-b]pyridine
Conditions | Yield |
---|---|
With PPA at 210℃; for 2h; | 98% |
2,3-Diaminopyridine
4-methylnicotinic acid
2-(4-Methyl-pyridin-3-yl)-1H-imidazo[4,5-b]pyridine
Conditions | Yield |
---|---|
With PPA at 210℃; for 2h; | 98% |
2,3-Diaminopyridine
carbon monoxide
1,3-dihydro-imidazo[4,5-b]pyridin-2-one
Conditions | Yield |
---|---|
With selenium In tetrahydrofuran at 100℃; under 22800.7 Torr; for 20h; | 98% |
2,3-Diaminopyridine
C11H12N2OS3
(3H-Imidazo[4,5-b]pyridin-2-yl)-(6-methoxy-benzothiazol-2-yl)-amine
Conditions | Yield |
---|---|
In various solvent(s) Heating; | 98% |
Conditions | Yield |
---|---|
With PPA for 3h; Heating; | 98% |
With polyphosphoric acid at 100℃; for 5h; | 80% |
With PPA at 100℃; for 5h; | 62% |
2,3-Diaminopyridine
2-methyl-1H-imidazo[4,5-c]pyridine
2-(1H-Imidazo[4,5-c]pyridin-2-yl)-3H-imidazo[4,5-b]pyridine
Conditions | Yield |
---|---|
With sulfur at 200 - 210℃; for 4h; | 98% |
Conditions | Yield |
---|---|
With silica-supported bismuth(III) chloride In methanol at 20℃; for 0.166667h; Catalytic behavior; regioselective reaction; | 98% |
With bismuth(lll) trifluoromethanesulfonate In water at 20℃; for 0.0833333h; | 92% |
With (2,3,4,5,6-pentafluorophenyl)ammonium triflate In water at 20℃; for 1h; Green chemistry; | 92% |
In ethanol Heating; | 77% |
2,3-Diaminopyridine
2-methyl-benzyl alcohol
N,N′-bis(salicyliden)-2,3-diaminopyridine
Conditions | Yield |
---|---|
for 0.0333333h; microwave irradiation; | 98% |
2,3-Diaminopyridine
zinc(II) acetate dihydrate
salicylaldehyde
[N,N′-bis(salicylidene)-2,3-diiminopyridine]zinc(II)
Conditions | Yield |
---|---|
In methanol at 70℃; for 4h; | 98% |
In methanol under N2; salicylaldehyde in MeOH treated with Zn salt, mixt. stirred atroom temp., 2,3-diaminopyridine added, mixt. stirred; ppt. filtered off, washed with MeOH; elem. anal.; | 77% |
2,3-Diaminopyridine
zinc(II) acetate dihydrate
[N,N-bis(4-hexadecyloxy-2-hydroxybenzylidene)-2,3-pyridinediaminato]zinc(II)
Conditions | Yield |
---|---|
In ethanol under N2; to a soln. of 4-alcoxy-2-hydroxybenzaldehyde (1.00 mmol) in ethanol, diamine (0.500 mmol) was added under stirring; mixt. was heated at reflux with stirring for 1 h; Zn-contg. compd. (0.500 mmol) addn.; heating at reflux with stirring for 1 h; after cooling, the ppt was collected by filtration, washed with ethanol and dried; elem. anal.; | 98% |
Conditions | Yield |
---|---|
at 100℃; | 98% |
In water at 60℃; for 2h; | 81% |
for 4h; Reflux; | 75% |
2,3-Diaminopyridine
Dimethyl N-(4-chloro-2-benzothiazolyl)-dithiocarbonimidate
(4-Chloro-benzothiazol-2-yl)-(3H-imidazo[4,5-b]pyridin-2-yl)-amine
Conditions | Yield |
---|---|
In various solvent(s) Heating; | 97% |
2,3-Diaminopyridine
ethyl 2-cyanoacetate
2-(3H-imidazo[4,5-b]pyridin-2-yl)acetonitrile
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 110℃; Microwave irradiation; | 97% |
at 180℃; for 2h; | 75% |
at 110 - 115℃; for 14h; Neat (no solvent); | 70% |
2,3-Diaminopyridine
trifluoroacetic acid
2-Trifluoromethyl-3H-imidazo<4,5-b>pyridine
Conditions | Yield |
---|---|
for 48h; Heating; | 97% |
Conditions | Yield |
---|---|
With acetic acid In ethanol Reflux; | 97% |
With zirconium(IV) chloride In methanol at 20℃; for 4h; | 95% |
With SBA-15 mesoporous silica supported Fe(III)-Schiff base In water for 2h; Reflux; | 95% |
2,3-Diaminopyridine
Thiazole-4-carboxylic acid
4-(1H-imidazo[4,5-b]pyridin-2-yl)thiazole
Conditions | Yield |
---|---|
With PPA at 180℃; for 2h; | 97% |
2,3-Diaminopyridine
di(2-azulenyl)ethanedione
2,3-di(2-azulenyl)-5.azaquinoxaline
Conditions | Yield |
---|---|
In ethanol for 20h; Reflux; | 97% |
2,3-Diaminopyridine
1,2-bis(4-fluorophenyl)ethane-1,2-dione
2,3-bis(4-fluorophenyl)pyrido[2,3-b]pyrazine
Conditions | Yield |
---|---|
With SBA-15 mesoporous silica supported Fe(III)-Schiff base In water for 2h; Reflux; | 97% |
With Cu(II)-Schiff base/SBA-15 In water for 2h; Reflux; | 96% |
With zirconium oxide salicylaldehyde-(3-aminopropyl)trimethoxysilane imine complex modified SBA-15 In water for 2h; Reflux; | 96% |
Conditions | Yield |
---|---|
In ethylene glycol at 80℃; for 0.2h; Microwave irradiation; Green chemistry; chemoselective reaction; | 97% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 110℃; Microwave irradiation; | 97% |
The 2,3-diaminopyridine, with the cas registry number 452-58-4, has the IUPAC name of pyridine-2,3-diamine. This is a kind of brown power and is sensitive to air. Besides, its product categories are various, including pyridines, pyrimidines, purines and pteredines; amines; pyridines derivates; highly purified reagents; other categories; refined products by sublimation; boronic acid; c5; heterocyclic building blocks.
The characteristics of this kind of chemical are as follows: (1)ACD/LogP: 0.27; (2)ACD/LogD (pH 5.5): -0.55; (3) ACD/LogD (pH 7.4): 0.24; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 5.06; (7)ACD/KOC (pH 7.4): 31.19; (8)#H bond acceptors: 3; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 19.37; (12)Index of Refraction: 1.676; (13)Molar Refractivity: 32.81 cm3; (14)Molar Volume: 87.2 cm3; (15)Polarizability: 13 ×10-24 cm3; (16)Surface Tension: 70.9 dyne/cm; (17)Density: 1.251 g/cm3; (18)Flash Point: 167.7 °C; (19)Enthalpy of Vaporization: 55.22 kJ/mol; (20)Boiling Point: 311.3 °C at 760 mmHg; (21)Vapour Pressure: 0.00057 mmHg at 25°C; (22)Exact Mass: 109.063997; (23)MonoIsotopic Mass:109.063997; (24)Topological Polar Surface Area: 64.9; (25)Heavy Atom Count: 8; (26)Formal Charge: 0; (27)Complexity: 74.1.
The production method of this chemical is as below: 3-nitro-pyridin-2-ylamine could react to produce 2,3-diaminopyridine, with the following condition: reagent: iron; concentrated aqueous HCl; ethanol.
The use of this chemical is as below: 2,3-diaminopyridine could react with 2-oxo-propionic acid ethyl ester to produce 2-methyl-4H-pyrido[2,3-b]pyrazin-3-one, with the following condition: reagent: benzene.
When you are dealing with this chemical, you should be very careful and then take some measures to protect yourself. For being a kind of irritant chemical, it is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. Then it is a kind of toxic chemical which may cause damage to health. Therefore, you should take the following instructions. Wear suitable gloves and eye/face protection and protective clothing. If in case of contacting with eyes, rinse immediately with plenty of WATER and seek medical advice, and if in case of accident or if you feel unwell, seek medical advice immediately (show label where possible). Besides, after contacting with skin, wash immediately with plenty of ... (to be specified by the manufacturer).
Additionally, the following datas could be converted into the molecular structure:
(1)Canonical SMILES: C1=CC(=C(N=C1)N)N
(2)InChI: InChI=1S/C5H7N3/c6-4-2-1-3-8-5(4)7/h1-3H,6H2,(H2,7,8)
(3)InChIKey: ZZYXNRREDYWPLN-UHFFFAOYSA-N
Below are the toxicity information of this chemical:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 25mg/kg (25mg/kg) | Journal of Medicinal Chemistry. Vol. 8, Pg. 296, 1965. |
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