13134-31-1

Basic information

• Product Name: 2,3-PYRAZINEDIAMINE
• Synonyms: 2,3-PYRAZINEDIAMINE;2,3-DIAMINOPYRAZINE;PYRAZINE-2,3-DIAMINE;Nsc139902;2,3- twoaMinopiperazine;SA017326
• CAS NO: 13134-31-1
• Molecular Formula: C₄H₆N₄
• Molecular Weight: 110.12
• Product Categories: Piperazine series
• Mol File: 13134-31-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 205.6 °C
• Boiling Point: 351.6 °C at 760 mmHg
• Flash Point: 193.5 °C
• Appearance: /
• Density: 1.368 g/cm³
• Vapor Pressure: 4.05E-05mmHg at 25°C
• Refractive Index: 1.694
• Storage Temp.: 2-8°C(protect from light)
• PKA: 4.58±0.10(Predicted)
• CAS DataBase Reference: 2,3-PYRAZINEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-PYRAZINEDIAMINE(13134-31-1)
• EPA Substance Registry System: 2,3-PYRAZINEDIAMINE(13134-31-1)

Safety Data

• Hazardous Substances Data: 13134-31-1(Hazardous Substances Data)

Usage

General Description

2,3-Pyrazinediamine, also known as Amidol, is a chemical compound with the formula C4H6N4. It is a derivative of pyrazine, which belongs to a class of organic compounds known as diamines. Diamines are organic compounds containing two amine groups. 2,3-Pyrazinediamine is an important chemical reagent often used in the synthesis of other complex organic compounds. It is a white crystalline solid that is soluble in water and has a slightly pungent smell. It is advised to handle this chemical with care as it is a potential eye irritant and may be harmful if inhaled or swallowed.

InChI:InChI=1/C4H6N4/c5-3-4(6)8-2-1-7-3/h1-2H,(H2,5,7)(H2,6,8)

Synthetic route

2-amino-3-azidopyrazine (156331-25-8) → pyrazine-2,3-diamine (13134-31-1)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In methanol at 60℃; for 2h;	87%
With hydrogenchloride; tin(ll) chloride In methanol at 60℃;	70%

[1,2,5]thiadiazolo[3,4-b]pyrazine (51097-07-5) → pyrazine-2,3-diamine (13134-31-1)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride for 1h; Ambient temperature;	83%

3-chloropyrazin-2-amine (6863-73-6) → pyrazine-2,3-diamine (13134-31-1)

Conditions	Yield
With ammonia In water at 130℃; Sealed tube;	11%
With ammonia; water; copper

3-bromo-pyrazine-2-amine (21943-12-4) → pyrazine-2,3-diamine (13134-31-1)

Conditions	Yield
With ammonia; copper In ethanol at 140℃; for 20h;	2.05 g

2,3-diamino-5-bromopyrazine (89123-58-0) → pyrazine-2,3-diamine (13134-31-1)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol under 2068.65 Torr; for 8h;

pyrazine-2,3-diamine (13134-31-1) + 2,3-dihydroxyanthracene (64817-81-8) → 5,14-dihydro-1,4,5,14-tetraazapentacene (1356380-51-2)

Conditions	Yield
at 205 - 215℃; for 3h; Inert atmosphere;	98%

pyrazine-2,3-diamine (13134-31-1) + 1,1'-carbonyldiimidazole (530-62-1) → 1H-imidazo<4,5-b>pyrazin-2(3H)-one (16328-63-5)

Conditions	Yield
In tetrahydrofuran at 80℃; for 4h; Inert atmosphere;	92%

pyrazine-2,3-diamine (13134-31-1) + bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] (12354-84-6, 12354-85-7) + potassium oxalate monohydrate (6487-48-5) → C34H49Cl4Ir3N4

Conditions	Yield
In methanol at 20℃; for 3h;	85%

pyrazine-2,3-diamine (13134-31-1) + C22H15NO2 → C26H17N5

Conditions	Yield
With acetic acid Reflux;	82%

pyrazine-2,3-diamine (13134-31-1) + urea (57-13-6) → 1H-Imidazo<4,5-b>pyrazin-2-ol (16328-63-5)

Conditions	Yield
In diphenylether at 240℃; for 5h;	57%

pyrazine-2,3-diamine (13134-31-1) + 1,2-Cyclohexanediol (931-17-9) → 1,2,3,4,6,7,8,9-octahydropyrazino[2,3-b]quinoxaline

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; potassium tert-butylate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tert-Amyl alcohol at 130℃; for 10h; Inert atmosphere; Schlenk technique; Sealed tube;	56%

pyrazine-2,3-diamine (13134-31-1) + trifluoroacetic acid (76-05-1) → 2-(trifluoromethyl)-1H-imidazo[4.5-b]pyrazine (58885-00-0)

Conditions	Yield
at 120℃; for 16h;	54%

pyrazine-2,3-diamine (13134-31-1) + 2-methoxy-4-(methylsulfanyl)benzoic acid (72856-73-6) → 2-(2-methoxy-4-methylthiophenyl)-1H-imidazo<4,5-b>pyrazine (99454-75-8)

Conditions	Yield
With trichlorophosphate for 4h; Heating;	45%

pyrazine-2,3-diamine (13134-31-1) + 1,2-diphenyl-1,2-ethanediol (492-70-6, 655-48-1, 2325-10-2, 38270-73-4, 52340-78-0, 579-43-1) → 6,7-diphenyl-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; potassium tert-butylate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tert-Amyl alcohol at 130℃; for 10h; Inert atmosphere; Schlenk technique; Sealed tube;	43%

pyrazine-2,3-diamine (13134-31-1) + ethyl 3-oxo-3-phenylpropionate (94-02-0) → ethyl 3-phenylpyrazino[2,3-b]pyrazine-2-carboxylate

Conditions	Yield
Stage #1: ethyl 3-oxo-3-phenylpropionate With copper nitrate hemi(pentahydrate) In acetonitrile at 50℃; for 1h; Stage #2: pyrazine-2,3-diamine In methanol; acetonitrile at 20℃; for 2h;	33%

pyrazine-2,3-diamine (13134-31-1) + 2-(cyclopropanecarbonylamino)-3-(cyclopropylmethylcarbamoyl)-4,5,6,7-tetrahydrobenzothiophene-5-carboxylic acid → 2-(cyclopropanecarbonylamino)-N-(cyclopropylmethyl)-5-(1H-imidazo[4,5-b]pyrazin-2-yl)-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide

Conditions	Yield
With pyridine; triphenylphosphine at 220℃; for 1h; Microwave irradiation;	26%

pyrazine-2,3-diamine (13134-31-1) + 9,10-bis((triisopropylsilyl)ethynyl)anthracene-2,3-diol (1356380-54-5) → 7,12-bis((triisopropylsilyl)ethynyl)-5,14-dihydro-1,4,5,14-tetraazapentacene (1356380-52-3)

Conditions	Yield
at 205 - 215℃; for 0.5h; Inert atmosphere;	25%

pyrazine-2,3-diamine (13134-31-1) + 3-carbomethoxyphenyl isothiocyanate (3125-66-4) → methyl 3-(1H-imidazo[4,5-b]pyrazin-2-ylamino)benzoate

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 2h;	5%

pyrazine-2,3-diamine (13134-31-1) + ethoxy-1 formyl-2 butene-1 (30989-75-4) → 5,14-dihydro-7,16-diethyldipyrazo<1,4,8,11>tetraazacyclotetradecine (120757-21-3)

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Heating;	3%

pyrazine-2,3-diamine (13134-31-1) + glycolic Acid (79-14-1) → (1H-imidazo[4,5-b]pyrazin-2-yl)-methanol (55635-81-9)

Conditions	Yield
at 140 - 150℃;

Upstream product

• 6863-73-6 3-chloropyrazin-2-amine 
• 51097-07-5 [1,2,5]thiadiazolo[3,4-b]pyrazine 
• 89123-58-0 5-bromopyrazine-2,3-diamine 
• 156331-25-8 2-amino-3-azidopyrazine 
• 21943-12-4 3-bromo-pyrazine-2-amine 

Downstream Products

• 38956-46-6 2-methyl-1H-imidazo[4,5-b]pyrazine 
• 6499-39-4 2,3-Dimethyl-1,4,5,8-tetraaza-naphthalin 
• 16328-63-5 1H-imidazo<4,5-b>pyrazin-2(3H)-one 
• 79100-21-3 1H-imidazo<4,5-b>-pyrazine-2(3H)-thione 
• 99454-75-8 2-(2-methoxy-4-methylthiophenyl)-1H-imidazo<4,5-b>pyrazine 
• 16328-63-5 1H-Imidazo<4,5-b>pyrazin-2-ol 

Relevant articles and documents

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Imidazopyridine- and purine-thioacetamide derivatives: Potent inhibitors of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)

Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1) belongs to the family of ecto-nucleotidases, which control extracellular nucleotide, nucleoside, and (di)phosphate levels. To study the (patho)physiological roles of NPP1 potent and selective inhibitors with drug-like properties are required. Therefore, a compound library was screened for NPP1 inhibitors using a colorimetric assay with p-nitrophenyl 5′-thymidine monophosphate (p-Nph-5′-TMP) as an artificial substrate. This led to the discovery of 2-(3H-imidazo[4,5-b]pyridin-2-ylthio)-N-(3,4-dimethoxyphenyl)acetamide (5a) as a hit compound with a Ki value of 217 nM. Subsequent structure-activity relationship studies led to the development of purine and imidazo[4,5-b]pyridine analogues with high inhibitory potency (Ki values of 5.00 nM and 29.6 nM, respectively) when assayed with p-Nph-5′-TMP as a substrate. Surprisingly, the compounds were significantly less potent when tested versus ATP as a substrate, with Ki values in the low micromolar range. A prototypic inhibitor was investigated for its mechanism of inhibition and found to be competitive versus both substrates.

Studies on Pyrazines. Part 33.1 Synthesis of 2,3-Diaminopyrazines via [1,2,5]Thiadiazolo[3,4-b] pyrazines

The syntheses of [1,2,5]thiadiazolo[3,4-b]pyrazine (3) and its methyl and/or phenyl derivatives as well as their reduction to 2,3-diaminopyrazines 4 are described.