5-Methyl-2-pyrazinecarboxylic acid supplier

Name
5-Methyl-2-pyrazinecarboxylic acid
EINECS 413-260-9
CAS No. 5521-55-1
Article Data17
CAS DataBase
Density 1.319 g/cm³
Solubility
Melting Point 167-171 °C(lit.)
Formula C₆H₆N₂O₂
Boiling Point 316.5 °C at 760 mmHg
Molecular Weight 138.126
Flash Point 145.2 °C
Transport Information
Appearance Pale Brown Powder
Safety 26-39-36
Risk Codes 41-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Pyrazinecarboxylicacid, 5-methyl-;Pyrazinecarboxylic acid, 5-methyl- (7CI,8CI,9CI);2-Methylpyrazine-5-carboxylic acid;5-Methyl-2-pyrazinoic acid;5-Methylpyrazine carboxylic acid;5-Methylpyrazine-2-Carboxylic Acid;
PSA 63.08000
LogP 0.48320

Synthetic route

: 123-32-0
2,5-dimethyl-pyrazine

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

Conditions

Conditions	Yield
at 30℃; for 16h; Pseudomonas putida ATCC 33015;	90%
With potassium permanganate In water at 76 - 82℃; for 5.7h; Temperature; Industrial scale;	81.6%
With sodium tungstate; oxygen; cobalt(II) nitrate; manganese(ll) chloride In water	75.6%

: 3-bromo-5-methylpyrazine-2-carboxylic acid

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; sodium hydroxide In methanol at 60℃; under 15001.5 Torr; for 12h; Autoclave; Inert atmosphere;	68%

: 3-chloro-5-methylpyrazine-2-carboxylic acid

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; sodium hydroxide In methanol at 60℃; under 15001.5 Torr; for 12h; Reagent/catalyst; Autoclave; Inert atmosphere;	71%

: 128229-06-1
2-(chloromethyl)-5-methylpyrazine hydrochloride

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

Conditions

Conditions	Yield
With potassium carbonate In water; tert-butyl alcohol at 60℃; Ni-anode, 12 mA/cm2;	82%
Multi-step reaction with 2 steps 1: 74 percent / KOAc, KHCO3 / ethanol / 6 h / Heating 2: 93 percent / 1 N aq. NaOH / 40 °C / Ni-anode, 12 mA/cm2 View Scheme
Multi-step reaction with 2 steps 1: 65 percent / KOAc / ethanol / 6 h / Heating 2: 87 percent / 1 N aq.NaOH / 40 °C / Ni-anode, 12 mA/cm2 View Scheme

: 61892-95-3
2-Hydroxymethyl-5-methylpyrazine

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide at 40℃; Ni-anode, 12 mA/cm2;	93%
With potassium permanganate for 0.5h; Oxidation;

: 98006-89-4
2-Acetoxymethyl-5-methylpyrazine

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide at 40℃; Ni-anode, 12 mA/cm2;	87%
Multi-step reaction with 2 steps 1: 85 percent / NaOH / ethanol / 0.17 h 2: aq. KMnO4 / 0.5 h View Scheme

: 5521-60-8
5-methyl-pyrazine-2,3-dicarboxylic acid

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

Conditions

Conditions	Yield
at 175 - 185℃; under 2 Torr;	71%

: 123-32-0
2,5-dimethyl-pyrazine

A: 5521-55-1
2-methylpyrazin-5-carboxylic acid

B: 122-05-4
2,5-pyrazinedicarboxylic acid

Conditions

Conditions	Yield
With chromium(III) nitrate In water Ambient temperature; electrochemical oxidation on activated nickel hydroxide anode;	A 40% B 20%

: 81831-68-7
2-methyl-5-pyrazinylmethyl chloride

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent Chromat. / ethanol / Heating 2: 85 percent / NaOH / ethanol / 0.17 h 3: aq. KMnO4 / 0.5 h View Scheme

: 88394-05-2
3-carboxamido-2-hydroxy-6-methylpyrazine

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 12 h / 100 °C 2: thionyl chloride / 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide / 6 h / 80 °C 3: palladium 10% on activated carbon; hydrogen; sodium hydroxide / methanol / 12 h / 60 °C / 15001.5 Torr / Autoclave; Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 12 h / 100 °C 2: dibromo sulfoxide / 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide / 6 h / 80 °C 3: palladium 10% on activated carbon; hydrogen; sodium hydroxide / methanol / 12 h / 60 °C / 15001.5 Torr / Autoclave; Inert atmosphere View Scheme

: 120992-57-6
2-Hydroxy-6-methylpyrazine-3-carboxylic acid

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide / 6 h / 80 °C 2: palladium 10% on activated carbon; hydrogen; sodium hydroxide / methanol / 12 h / 60 °C / 15001.5 Torr / Autoclave; Inert atmosphere View Scheme

: 123-32-0
2,5-dimethyl-pyrazine

A: 5521-55-1
2-methylpyrazin-5-carboxylic acid

B: 103150-78-3
diethyl pyrazine-2,5-dicarboxylate

Conditions

Conditions	Yield
With potassium permanganate

: CP290

A: 5521-55-1
2-methylpyrazin-5-carboxylic acid

B: 3-hydroxy-1-(3-hydroxypropyl)-2-methylpyridin-4(1H)-one

Conditions

Conditions	Yield
With water In acetonitrile at 37℃; for 0.166667h; pH=2.0; Kinetics; Further Variations:; pH-values; reaction time; Acid hydrolysis;

: 123-32-0
2,5-dimethyl-pyrazine

A: 98-97-5
2-pyrazylcarboxylic acid

B: 5521-55-1
2-methylpyrazin-5-carboxylic acid

C: 122-05-4
2,5-pyrazinedicarboxylic acid

Conditions

Conditions	Yield
With cobalt(II) nitrate In water Ambient temperature; electrochemical oxidation on activated nickel hydroxide anode;	A 2% B 42% C 3%
In water Ambient temperature; electrochemical oxidation on activated nickel hydroxide anode;	A 12% B 22% C 5%
With chromium(III) nitrate In diethyl ether Product distribution; Ambient temperature; electrochemical oxidation; var. additives, var. reaction time vs. conversion;

...Expand

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: copper(II) choride dihydrate

: [Cu(2-methylpyrazine-5-carboxylate)2(H2O)]*3H2O

Conditions

Conditions	Yield
With NaOH In water ligand was added to aq. soln. of NaOH, stirred at room temp. for 10 min, CuCl2*2H2O was added slowly, stirred at room temp. for 2 h; filtered, washed with water, dried in air; elem. anal.;	99%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 51037-30-0
acipimox

Conditions

Conditions	Yield
Stage #1: 2-methylpyrazin-5-carboxylic acid With hydrogenchloride In water for 0.5h; Stage #2: With peracetic acid In water at 20℃; for 3h; Reagent/catalyst; Temperature;	98.5%
With sodium tungstate; dihydrogen peroxide; sodium hydroxide In water at 45℃; for 12h; pH=9; Concentration; pH-value; Reagent/catalyst; Temperature;	94.5%
Stage #1: 2-methylpyrazin-5-carboxylic acid With sulfuric acid at 60℃; for 1h; Large scale; Stage #2: With disodium tungstate dihydrate; dihydrogen peroxide In water for 8h; Heating; Large scale;	77.3%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 31858-85-2
1-<sulfonyl>-3-cyclohexyl-2-iminoimidazolidine

: 85390-02-9
5-Methyl-pyrazine-2-carboxylic acid {2-[4-(3-cyclohexyl-2-imino-imidazolidine-1-sulfonyl)-phenyl]-ethyl}-amide

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran; acetonitrile for 12h; Ambient temperature;	97%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: copper dichloride

: Cu(2-methylpyrazine-5-carboxylate)2 hydrate

Conditions

Conditions	Yield
With NaOH; H2O In water acid was added to a soln. of NaOH in water and stirred at room temp. for10 min, CuCl2 was added slowly, the mixt. was stirred at room temp. for 2 h; filtered, ppt. was washed with water and dried in air;	97%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 75-65-0
tert-butyl alcohol

: 1151655-02-5
t-butyl 5-methylpyrazine-2-carboxylate

Conditions

Conditions	Yield
With dmap; di-tert-butyl dicarbonate at 60℃; for 18h;	95%
Stage #1: 2-methylpyrazin-5-carboxylic acid; tert-butyl alcohol With di-tert-butyl dicarbonate In tert-butyl alcohol at 55℃; for 0.25h; Stage #2: With dmap at 55℃; for 17h;	86%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 2015-16-9
N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea

: 33288-71-0
N-[2-[4-(amino-sulfonyl)phenyl]ethyl]-5-methylpyrazinecarboxamide

Conditions

Conditions	Yield
Stage #1: 2-methylpyrazin-5-carboxylic acid With triethylamine In acetone at 0℃; for 1h; Stage #2: With chloroformic acid ethyl ester In acetone for 1h; Stage #3: N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea With triethylamine In acetone at 20℃; for 3h;	93.4%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 100-51-6
benzyl alcohol

: 1033418-57-3
benzyl-5-methylpyrazin-2-yl carbamate

Conditions

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In acetonitrile at 120℃;	87%
Stage #1: 2-methylpyrazin-5-carboxylic acid With N-ethyl-N,N-diisopropylamine In toluene at 50℃; Inert atmosphere; Stage #2: With diphenyl phosphoryl azide In toluene at 15℃; Stage #3: benzyl alcohol In toluene at 85 - 90℃; for 3h;	85%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 818-08-6
di(n-butyl)tin oxide

: 931099-35-3
[((n-Bu)2Sn(2-methylpyrazine-5-acid(-1H)))2O]2

Conditions

Conditions	Yield
In methanol; benzene (N2); acid was added to soln. of Sn compd. in C6H6/MeOH (5/1) in Schlenkflask; refluxed for 10 h; solvent evapd. (vac. ); recrystd. (MeOH); elem. anal.;	86%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: C71H69F17N8O7

: C77H73F17N10O8

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran; N,N-dimethyl-formamide	86%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 1019453-85-0
2-(2,4-dimethylphenylsulphanyl)benzeneamine

: N-(2-(2,4-dimethylphenylthio)phenyl)-5-methylpyrazine-2-carboxamide

Conditions

Conditions	Yield
With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 1h;	85%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: tert-butyl N-(1-amino-3-bicyclo[1.1.1]pentanyl)carbamate

: 76-05-1
trifluoroacetic acid

: N-(3-aminobicyclo[1.1.1]pentan-1-yl)-5-methylpyrazine-2-carboxamide bis(2,2,2-trifluoroacetate)

Conditions

Conditions	Yield
Stage #1: 2-methylpyrazin-5-carboxylic acid; tert-butyl N-(1-amino-3-bicyclo[1.1.1]pentanyl)carbamate With pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: trifluoroacetic acid In acetonitrile at 20℃; for 1h;	83%

...Expand

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 2273-51-0
diphenyltin(IV) oxide

: 931099-36-4
[(Ph2Sn(2-methylpyrazine-5-acid(-1H)))3O2(Ph2Sn(OCH3))]

Conditions

Conditions	Yield
In methanol; benzene (N2); acid was added to soln. of Sn compd. in C6H6/MeOH (5/1) in Schlenkflask; refluxed for 10 h; solvent evapd. (vac. ); recrystd. (MeOH); elem. anal.;	82%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 954584-43-1
7-(5-aminopyridin-2-yloxy)-4-methyl-2H-chromen-2-one

: 1420161-33-6
5-methyl-N-(6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)pyridin-3-yl)pyrazine-2-carboxamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	81.9%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 212773-15-4
3-aminolup-20(29)-en-28-oic acid

: C36H53N3O3

Conditions

Conditions	Yield
Stage #1: 2-methylpyrazin-5-carboxylic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 2h; Stage #2: 3-aminolup-20(29)-en-28-oic acid With dmap In dichloromethane at 20℃; for 8h;	81%
Stage #1: 2-methylpyrazin-5-carboxylic acid With dmap; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: 3-aminolup-20(29)-en-28-oic acid In dichloromethane at 20℃; for 8h; Inert atmosphere;	81%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 753-73-1
dimethyltin dichloride

: [(CH3)2Cl2Sn(2-methylpyrazine-5-acid(-1H))Sn(CH3)2(2-methylpyrazine-5-acid(-1H))]

Conditions

Conditions	Yield
With C2H5ONa In benzene byproducts: NaCl; (N2); acid was added to soln. of Sn compd. in C6H6 in Schlenk flask; stirred for 0.5 h; EtONa was added; stirred at 50°C for 12 h; filtered; solvent evapd. (vac. ); recrystd. (MeOH); elem. anal.;	80%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: C38H48N6O7S2*ClH

: C44H52N8O8S2

Conditions

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 30℃; for 6h; Inert atmosphere;	80%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 4-[5-(naphtho[2,1-b]furan-2-yl)-1,3,4-oxadiazol-2-yl]aniline

: 5-methyl-N-(4-(5-(naphtho[2,1-b]furan-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)pyrazine-2 carboxamide

Conditions

Conditions	Yield
Stage #1: 4-[5-(naphtho[2,1-b]furan-2-yl)-1,3,4-oxadiazol-2-yl]aniline With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; Inert atmosphere; Stage #2: 2-methylpyrazin-5-carboxylic acid In dichloromethane at 20℃; Inert atmosphere;	80%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 931099-37-5
(2,4-Cl2C6H3CH2)3SnCl

: 931099-32-0
[(2,4-Cl2C6H3CH2)2Sn(2-methylpyrazine-5-acid(-1H))2ClSn(CH2C6H3Cl2-2,4)3]2

Conditions

Conditions	Yield
With C2H5ONa In benzene byproducts: NaCl; (N2); acid was added to soln. of Sn compd. in C6H6 in Schlenk flask; stirred for 0.5 h; EtONa was added; stirred at 50°C for 12 h; filtered; solvent evapd. (vac. ); recrystd. (MeOH); elem. anal.;	79%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 4-(3,5-dichlorophenoxy)-2-(piperazin-1-yl)pyrimidine

: (4-(4-(3,5-dichlorophenoxy)pyrimidin-2-yl)piperazin-1-yl)(5-methylpyrazin-2-yl)methanone

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 10h;	79%

: 5521-55-1
2-methylpyrazin-5-carboxylic acid

: 1245730-97-5
di[bis[9-(2-(2-methoxyethoxy)ethyl)-3-(4-phenylquinolin-2-yl)-9H-carbazolato-N,C2']iridium(III) chloride]

: 1310041-69-0
bis[9-(2-(2-methoxyethoxy)ethyl)-3-(4-phenylquinolin-2-yl)-9H-carbazolato-N,C2']iridium(III)(5-methyl-2-pyridinecarboxylate)

Conditions

Conditions	Yield
With Na2CO3 In 2-ethoxy-ethanol Ir complex and 5-methyl-2-pyridinecarboxylic acid (5 equiv.) mixed with Na2CO3 (10 equiv.) in 2-ethoxyethanol, refluxed for 12 h (N2); cooled ro room temp., poured into H2O, extd.(EtOAc), dried (MgSO3), evapd.(vac.), chromy.(silica gel - hexane/EtOAc 1:4), recrystd twice (CH2Cl2/hexane), elem. anal.;	78%

5-Methyl-2-pyrazinecarboxylic acid Chemical Properties

Molecular Structure of 5-Methyl-2-pyrazinecarboxylic acid (CAS NO.5521-55-1):

IUPAC Name: 5-methylpyrazine-2-carboxylic acid
Empirical Formula: C₆H₆N₂O₂
Molecular Weight: 138.124
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 52.08 Å²
Molar Refractivity: 34.19 cm³
Molar Volume: 104.6 cm³
Index of Refraction: 1.566
Surface Tension: 63.3 dyne/cm
Density: 1.319 g/cm³
Flash Point: 145.2 °C
Enthalpy of Vaporization: 58.9 kJ/mol
Boiling Point: 316.5 °C at 760 mmHg
Vapour Pressure: 0.000172 mmHg at 25°C
Melting Point: 167-171 °C(lit.)
Synonyms of 5-Methyl-2-pyrazinecarboxylic acid (CAS NO.5521-55-1): 2-pyrazinecarboxylic acid, 5-methyl- ; 5-Methylpyrazine-2-Carboxylic Acid ; 5-Methylpyrazinecarboxylic acid ; Pyrazinecarboxylic acid, 5-methyl-

5-Methyl-2-pyrazinecarboxylic acid Uses

5-Methyl-2-Pyrazinecarboxylic acid (CAS NO.5521-55-1) is used as an intermediate in the synthesis of glipizide.

5-Methyl-2-pyrazinecarboxylic acid Safety Profile

Hazard Codes: : Irritant Xi
Risk Statements: 41-36/37/38
R41:Risk of serious damage to the eyes.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S39:Wear eye / face protection.
S36:Wear suitable protective clothing.
WGK Germany: 1
Hazard Note: Irritant

5-Methyl-2-pyrazinecarboxylic acid Specification

5-Methyl-2-pyrazinecarboxylic acid (CAS NO.5521-55-1) is a pale brown powder, it can be made by 2,5-2-methyl or 2-methyl-5-(substituted) methyl pyrazine electrolytic oxidation .Preparation Products are Acipimox , raw material is 2-Methylpyrazine .

Product Name

5-Methyl-2-pyrazinecarboxylic acid

Synthetic route

5-Methyl-2-pyrazinecarboxylic acid Chemical Properties

5-Methyl-2-pyrazinecarboxylic acid Uses

5-Methyl-2-pyrazinecarboxylic acid Safety Profile

5-Methyl-2-pyrazinecarboxylic acid Specification

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