Methyl pyrazine-2-carboxylate supplier

Name
METHYL PYRAZINE-2-CARBOXYLATE
EINECS 228-198-6
CAS No. 6164-79-0
Article Data66
CAS DataBase
Density 1.213 g/cm³
Solubility
Melting Point 57-61 °C(lit.)
Formula C₆H₆N₂O₂
Boiling Point 220.4 °C at 760 mmHg
Molecular Weight 138.126
Flash Point 87.1 °C
Transport Information
Appearance white powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Pyrazinecarboxylicacid, methyl ester (7CI,8CI,9CI);Pyrazinoic acid methyl ester (6CI);2-Methoxycarbonylpyrazine;Methyl 2-pyrazinecarboxylate;Methylpyrazinecarboxylate;Methyl pyrazinoate;NSC 32337;Pyrazine-2-carboxylic acid,methyl ester;
PSA 52.08000
LogP 0.26320

Synthetic route

: 186581-53-3, 908094-01-9
diazomethane

: 98-97-5
2-pyrazylcarboxylic acid

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
In diethyl ether; dichloromethane at 20℃; for 0.25h;	100%

: 14508-49-7
2-chloropyrazin

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
With dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II); triethylamine at 100℃; under 2585.74 Torr; for 4h;	99%
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In acetonitrile at 180℃; under 25502.6 Torr; Flow reactor;	61%
With triethylamine; palladium bis(dibenzylideneacetone)palladium(0); triphenylphosphine at 120℃; under 29420.3 Torr; for 16h; other chloropyrazines;	93 % Chromat.
With ethyl azide; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) at 120℃; under 29420.3 Torr; for 16h;	93 % Chromat.

...Expand

: 67-56-1
methanol

: 98-97-5
2-pyrazylcarboxylic acid

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
With sulfuric acid for 2h; Reflux;	98%
With sulfuric acid for 48h; Heating;	95%
With sulfuric acid at 80 - 85℃; for 5h;	94.8%

: 290-37-9
1,4-pyrazine

: 600-23-7
oxalic acid monomethyl ester

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
With sodium persulfate; sulfuric acid; silver nitrate In dichloromethane; water for 1.5h; Heating;	93%

: 770-00-3
methylester of pyrazinecarboxylic acid 4-oxide

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
With Eosin Y; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 5h; Inert atmosphere; Irradiation; chemoselective reaction;	88%

: 98-97-5
2-pyrazylcarboxylic acid

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 2-pyrazylcarboxylic acid With sulfuric acid In methanol at 20℃; for 5h; Reflux; Stage #2: With sodium hydrogencarbonate In methanol pH=8.5;	63.63%
Multi-step reaction with 2 steps 1: 74 percent / SOCl2 / benzene / 2 h / Heating 2: pyridine / CH2Cl2 / a) 0 deg C, 1 h, b) RT, overnight View Scheme
With thionyl chloride; sodium bicarbonate In methanol; di-isopropyl ether; water
With sulfuric acid; sodium hydrogencarbonate In methanol; toluene

: 98-97-5
2-pyrazylcarboxylic acid

: 74-88-4
methyl iodide

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 72h;	8%

: 73763-86-7
3-[(methyloxy)carbonyl]-2-pyrazinecarboxylic acid

: 6164-79-0
methyl pyrazine-2-carboxylate

: 67-56-1
methanol

: 19847-10-0
pyrazinoyl chloride

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
With pyridine In dichloromethane a) 0 deg C, 1 h, b) RT, overnight;

: 13925-00-3
2-ethylpyrazine

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium permanganate / H2O / 20 °C 2: HCl View Scheme

: 4744-50-7
2,3-pyrazinedicarboxylic anhydride

: 6164-79-0
methyl pyrazine-2-carboxylate

: 89-01-0
2,3-dicarboxypyrazine

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 210 °C / 3 - 4 Torr 2: HCl View Scheme

: 98-97-5
2-pyrazylcarboxylic acid

: 75-36-5
acetyl chloride

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
In methanol

: 67-56-1
methanol

: 1254073-95-4
4-[(3-chloro-2-methylphenyl)carbonyl]-2-piperazinone

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
With thionyl chloride at 20℃; Reflux;

: methyl pyrazine-2-carboxylate hydrochloride

: 6164-79-0
methyl pyrazine-2-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane for 5h;	37 g

: 6164-79-0
methyl pyrazine-2-carboxylate

: 768-05-8
pyrazine-2-carbohydrazide

Conditions

Conditions	Yield
With hydrazine In ethanol for 2h; Heating / reflux;	100%
With hydrazine In ethanol for 2h; Heating / reflux;	100%
With hydrazine In ethanol for 2h; Reflux;	99%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 5780-66-5
pyrazinecarboxaldehyde

Conditions

Conditions	Yield
Stage #1: methyl pyrazine-2-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 72℃; for 0.333333h; Stage #2: With hydrogenchloride; water	100%
With lithium aluminium tetrahydride In tetrahydrofuran at -83℃; for 2h;	68%
With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 1.83333h; Inert atmosphere; Schlenk technique;	53.4%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 554-12-1
propanoic acid methyl ester

: 324737-10-2
methyl 2-methyl-3-(pyrazin-2-yl)-3-oxopropionate

Conditions

Conditions	Yield
Stage #1: methyl pyrazine-2-carboxylate With sodium hydride In toluene at 15 - 25℃; for 0.5h; Industrial scale; Stage #2: propanoic acid methyl ester In methanol; toluene at 15 - 40℃; Temperature; Solvent; Reagent/catalyst; Industrial scale;	100%
Stage #1: propanoic acid methyl ester With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: methyl pyrazine-2-carboxylate In tetrahydrofuran at 0 - 25℃; for 3.5h; Stage #3: With ammonium chloride In tetrahydrofuran for 0.5h;	89%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 5h; Inert atmosphere;	79%
With NaH; ammonium chloride In toluene

: 6164-79-0
methyl pyrazine-2-carboxylate

: 75-05-8
acetonitrile

: sodium 2-cyano-1-(pyrazin-2-yl)ethenolate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil for 20h; Reflux;	96%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 6705-33-5
pyrazin-2-ylmethanol

Conditions

Conditions	Yield
With sodium tetrahydroborate; sodium methylate In methanol at 25℃; for 3h; Inert atmosphere;	95%
Stage #1: methyl pyrazine-2-carboxylate With sodium tetrahydroborate In water for 0.5h; Stage #2: With water; potassium carbonate In ethanol for 0.5h;	80%
With sodium tetrahydroborate; calcium chloride In ethanol at 25℃; for 5h;	75%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 74-88-4
methyl iodide

: 3-methoxycarbonyl-1-methylpyrazinium iodide

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 12h;	94%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 73183-34-3
bis(pinacol)diborane

: 1393720-91-6
methyl 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dihydropyrazine-2-carboxylate

Conditions

Conditions	Yield
In pentane N2; ligand and B compd. (1.1:1 molar ratio) stirred at room temp. for 2 h;	93%
In pentane at 20℃; for 2h; Inert atmosphere;	93%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 60-34-4
methylhydrazine

: 80364-57-4
pyrazine-2-carboxylic acid N'-methylhydrazide

Conditions

Conditions	Yield
In ethanol Heating;	90%
In ethanol Heating;	81.1%
In ethanol for 1.5h; Heating;	68%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 100-46-9
benzylamine

: 347368-07-4
pyrazine-2-carboxylic acid benzylamide

Conditions

Conditions	Yield
With niobium(V) oxide In neat (no solvent) at 140℃; for 30h; Molecular sieve; Inert atmosphere;	90%
for 2h; Heating;	70%
With potassium phosphate; 2,2,2-trifluoroethanol In tetrahydrofuran at 90℃; for 22h; Sealed tube;	64%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 62-53-3
aniline

: 34067-83-9
N-(phenyl)pyrazine-2-carboxamide

Conditions

Conditions	Yield
With sodium t-butanolate In neat (no solvent) at 20℃; for 1h; Inert atmosphere; Schlenk technique; Green chemistry;	90%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 358-23-6
trifluoromethylsulfonic anhydride

: 31469-25-7
1,1-bis(trimethylsiloxy)-2-methylprop-1-ene

: methyl 7,7-dimethyl-6-oxo-1,4-bis(trifluoromethanesulfonyl)-1,4,4a,6,7,7a-hexahydrofuro[2,3-b]pyrazine-3-carboxylate

Conditions

Conditions	Yield
Stage #1: methyl pyrazine-2-carboxylate; trifluoromethylsulfonic anhydride In dichloromethane at -30℃; Inert atmosphere; Stage #2: 1,1-bis(trimethylsiloxy)-2-methylprop-1-ene In dichloromethane at -30 - 20℃; for 12h; Inert atmosphere;	89%

...Expand

: 6164-79-0
methyl pyrazine-2-carboxylate

: C5H4N3O2(1-)*Na(1+)

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In methanol for 24h; Inert atmosphere; Schlenk technique; Cooling with ice;	89%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 171504-79-3
methyl 1,4,5,6-tetrahydropyrazine-2-carboxylate

Conditions

Conditions	Yield
palladium-carbon In methanol	86%
With hydrogen; palladium on activated charcoal

: 6164-79-0
methyl pyrazine-2-carboxylate

: 768-06-9
pyrazine‑2‑hydroxamic acid

Conditions

Conditions	Yield
With hydroxylamine In methanol at 20℃; for 72h;	85%
With hydroxylamine

: 6164-79-0
methyl pyrazine-2-carboxylate

: 358-23-6
trifluoromethylsulfonic anhydride

: 40348-04-7
(Bis-trimethylsilanyloxy-methylene)-cyclohexane

: C15H16F6N2O8S2

Conditions

Conditions	Yield
Stage #1: methyl pyrazine-2-carboxylate; trifluoromethylsulfonic anhydride In dichloromethane at -30℃; Inert atmosphere; Stage #2: (Bis-trimethylsilanyloxy-methylene)-cyclohexane In dichloromethane at -30 - 20℃; for 12h; Inert atmosphere;	84%

...Expand

: 6164-79-0
methyl pyrazine-2-carboxylate

: 20010-99-5
2-aminomethylpyrazine

: (2-pyrazylmethyl)-2-pyrazinecarboxamide

Conditions

Conditions	Yield
In methanol for 168h; Reflux;	83%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 401-78-5
3-bromo-1-trifluoromethylbenzene

: 2-pyrazinyl(3-trifluoromethylphenyl)methanone

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane -80 deg C to rt;	80%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 368-39-8
triethyloxonium fluoroborate

: 3-(methoxycarbonyl)-1-ethylpyrazinium tetrafluoroborate

Conditions

Conditions	Yield
In chloroform at 5℃; for 24h; Inert atmosphere;	78%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 120068-79-3
5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

: 315208-01-6
N-[3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole-5-yl]pyrazine-2-carboxamide

Conditions

Conditions	Yield
With hydrogenchloride; CH3ONa In methanol; water; ethyl acetate; acetonitrile	77%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 56-40-6
glycine

: 57229-37-5
(pyrazine-2-carbonyl)glycine

Conditions

Conditions	Yield
With sodium methylate In N,N-dimethyl-formamide for 2.5h; Heating;	76%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 624-24-8
methyl valerate

: methyl 2-(pyrazine-2-carbonyl)pentanoate

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 5h; Inert atmosphere;	75%

: 3731-51-9
(2-aminomethylpyridine)

: 6164-79-0
methyl pyrazine-2-carboxylate

: 549493-17-6
pyrazine-2-carboxylic acid (pyridine-2-ylmethyl)-amide

Conditions

Conditions	Yield
In methanol for 120h; Reflux;	73%

: 6164-79-0
methyl pyrazine-2-carboxylate

: 23611-75-8
6-chloro-pyrazine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With N-chloro-succinimide In N,N-dimethyl-formamide at 80℃;	72%
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / 1,2-dichloro-ethane / 16 h / 60 °C 2: thionyl chloride / 8 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / 1,2-dichloro-ethane / 60 °C 2: thionyl chloride / 85 °C View Scheme
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / 1,2-dichloro-ethane / 60 °C 2: thionyl chloride / 85 °C View Scheme
Stage #1: methyl pyrazine-2-carboxylate With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 60℃; for 16h; Stage #2: With thionyl chloride at 75℃; for 8h;

: 6164-79-0
methyl pyrazine-2-carboxylate

: 770-00-3
methylester of pyrazinecarboxylic acid 4-oxide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 60℃; for 16h;	64%
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 60℃; for 16h;	64%
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 60℃; for 16h;	64%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 48h;	22%

Methyl pyrazine-2-carboxylate Specification

The IUPAC name of 2-Pyrazinecarboxylic acid, methyl ester is methyl pyrazine-2-carboxylate. With the CAS registry number 6164-79-0 and EINECS 228-198-6, it is also named as Pyrazinoic acid methyl ester. The product's categories are Heterocycles; Pharmacetical; Piperazine Series; Esters; Pyrazines, Pyrimidines & Pyridazines; Pyrazine; Building Blocks; Heterocyclic Building Blocks. It is powder which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.32; (4)ACD/LogD (pH 7.4): -0.32; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 15.89; (8)ACD/KOC (pH 7.4): 15.89; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 52.08 Å²; (13)Index of Refraction: 1.513; (14)Molar Refractivity: 34.2 cm³; (15)Molar Volume: 113.7 cm³; (16)Polarizability: 13.56×10^-24 cm³; (17)Surface Tension: 48.6 dyne/cm; (18)Enthalpy of Vaporization: 45.68 kJ/mol; (19)Vapour Pressure: 0.113 mmHg at 25°C; (20)Rotatable Bond Count: 2; (21)Exact Mass: 138.042927; (22)MonoIsotopic Mass: 138.042927; (23)Topological Polar Surface Area: 52.1; (24)Heavy Atom Count: 10; (25)Complexity: 127.

Preparation of 2-Pyrazinecarboxylic acid, methyl ester: It can be obtained by pyrazine-2-carboxylic acid and methanol. This reaction needs reagent conc. H₂SO₄ by heating. The reaction time is 48 hours. The yield is 95%.

Uses of 2-Pyrazinecarboxylic acid, methyl ester: It can react with methylhydrazine to get pyrazine-2-carboxylic acid-(N'-methyl-hydrazide). This reaction needs solvent ethanol by heating. The yield is 81.1%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OC)c1nccnc1
2. InChI:InChI=1/C6H6N2O2/c1-10-6(9)5-4-7-2-3-8-5/h2-4H,1H3
3. InChIKey:TWIIRMSFZNYMQE-UHFFFAOYAU

Product Name

METHYL PYRAZINE-2-CARBOXYLATE

Synthetic route

Methyl pyrazine-2-carboxylate Specification

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