Product Name

  • Name

    Methyl isonicotinate

  • EINECS 219-546-8
  • CAS No. 2459-09-8
  • Article Data96
  • CAS DataBase
  • Density 1.137 g/cm3
  • Solubility Slightly soluble in water.
  • Melting Point 8-8.5 °C(lit.)
  • Formula C7H7NO2
  • Boiling Point 205.1 °C at 760 mmHg
  • Molecular Weight 137.138
  • Flash Point 77.8 °C
  • Transport Information
  • Appearance clear orange to brown liquid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 2459-09-8 (Methyl isonicotinate)
  • Hazard Symbols IrritantXi
  • Synonyms Isonicotinicacid, methyl ester (6CI,7CI,8CI);4-Carbomethoxypyridine;4-Methoxycarbonylpyridine;Methyl 4-pyridinecarboxylate;4-Pyridinecarboxylicacid, methyl ester;
  • PSA 39.19000
  • LogP 0.86820

Synthetic route

methyl isonicotinate N-oxide
3783-38-8

methyl isonicotinate N-oxide

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol for 0.0166667h; Ambient temperature;98%
With sodium hypophosphite; palladium on activated charcoal In acetic acid at 60℃; for 1h;98%
With ammonium formate; silica gel; zinc In methanol at 20℃; for 0.166667h; chemoselective reaction;97%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

methanol
67-56-1

methanol

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With water; iodine; sodium nitrite at 20 - 70℃; chemoselective reaction;96%
With potassium carbonate In water at 20℃; for 2h;89%
With dibromamine-T; potassium carbonate at 20℃; for 1h;83%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

methanol
67-56-1

methanol

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With sulfuric acid for 24h; Heating;95%
With sulfuric acid for 72h; Reflux;92%
With sulfuric acid Reflux;80%
methanol
67-56-1

methanol

isonicotinic acid ethylester
1570-45-2

isonicotinic acid ethylester

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With lanthanum complex grafted upon hydrotalcite for 4h; pH=10; Reflux;95%
methanol
67-56-1

methanol

potassium pyridine-4-carboxylate
25108-37-6

potassium pyridine-4-carboxylate

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With tetrachloromethane; triphenylphosphine at 55 - 60℃;91%
4-Chloropyridine
626-61-9

4-Chloropyridine

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

lithium methanolate
865-34-9

lithium methanolate

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; 5 mol% Pd/C; sodium fluoride In 1,4-dioxane at 150℃; Inert atmosphere;88%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

methyl iodide
74-88-4

methyl iodide

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h;85%
picoline
108-89-4

picoline

methanol
67-56-1

methanol

A

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

B

4-trichloromethyl-pyridine
22796-40-3

4-trichloromethyl-pyridine

Conditions
ConditionsYield
Stage #1: picoline With thionyl chloride for 3h; Reflux;
Stage #2: methanol In water
A 18%
B 82%
methanol
67-56-1

methanol

1-(4-pyridyl)-1-propanone
1701-69-5

1-(4-pyridyl)-1-propanone

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With N,N-dimethyl-formamide dimethyl acetal for 16h; Heating;71%
isoniazid
54-85-3

isoniazid

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With methanol; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In chloroform at 20℃; for 1h;70%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With sulfuric acid for 17h; Neat (no solvent); Reflux;67.5%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

methanol
67-56-1

methanol

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With boron trifluoride diethyl etherate for 108h; Heating;63%
With iron(III) chloride for 32h; Heating;59%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

methyl iodide
74-88-4

methyl iodide

A

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

B

4-methoxycarbonyl-1-methylpyridinium cation
38117-49-6

4-methoxycarbonyl-1-methylpyridinium cation

Conditions
ConditionsYield
Stage #1: pyridine-4-carboxylic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone for 0.166667h;
Stage #2: methyl iodide In acetone at 20℃; for 4h;
A 62%
B n/a
pyridine-4-methanol
586-95-8

pyridine-4-methanol

methanol
67-56-1

methanol

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With manganese(IV) oxide; sodium cyanide; acetic acid In tetrahydrofuran at 20℃; for 72h;55%
Stage #1: methanol With sodium tetrachloroaurate(III) dihyrate; potassium carbonate at 20℃; for 0.0166667h; Green chemistry;
Stage #2: pyridine-4-methanol at 20℃; for 0.0333333h; Green chemistry;
Stage #3: With oxygen at 80℃; under 760.051 Torr; Autoclave; Green chemistry;
2 %Chromat.
trans-bromo(4-pyridylcarbonyl)bis(triphenylphosphine)palladium(II)

trans-bromo(4-pyridylcarbonyl)bis(triphenylphosphine)palladium(II)

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With CH3OH In dichloromethane MeOH added under N2 to soln. of Pd complex in CH2Cl2, kept for 24 h; evapd. under reduced pressure, extd. with Et2O, evapd., dissolved in CD2Cl2; identified by NMR;54%
methyl 3-(methylsulfonyloxy)-1-tosyl-1,2,3,6-tetrahydropyridine-4-carboxylate
1196959-81-5

methyl 3-(methylsulfonyloxy)-1-tosyl-1,2,3,6-tetrahydropyridine-4-carboxylate

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With potassium hexamethylsilazane In tetrahydrofuran at -78 - 0℃;53%
N-benzyl-4-(carbomethoxy)pyridinyl
94983-57-0, 62010-19-9

N-benzyl-4-(carbomethoxy)pyridinyl

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
In acetonitrile Product distribution; Quantum yield; Irradiation;51%
methyl (4-pyridyl) ketone
1122-54-9

methyl (4-pyridyl) ketone

methanol
67-56-1

methanol

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With N,N-dimethyl-formamide dimethyl acetal for 16h; Heating;42%
methanol
67-56-1

methanol

isoniazid
54-85-3

isoniazid

A

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

B

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene at 10℃; for 6h;A n/a
B 40%
methyl isonicotinate N-oxide
3783-38-8

methyl isonicotinate N-oxide

N,N-Dimethylthiocarbamoyl chloride
16420-13-6

N,N-Dimethylthiocarbamoyl chloride

A

C10H12N2O3S

C10H12N2O3S

B

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
In acetonitrile at 81℃; for 4h;A 30%
B 35%
methanol
67-56-1

methanol

isonicotinoyl chloride hydrochloride
39178-35-3

isonicotinoyl chloride hydrochloride

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
In diethyl ether
1,2-Dimethyl-4-oxo-8-(pyridine-4-carbonyl)-1,8-diaza-spiro[4.5]deca-2,6,9-triene-3-carboxylic acid ethyl ester
74578-59-9

1,2-Dimethyl-4-oxo-8-(pyridine-4-carbonyl)-1,8-diaza-spiro[4.5]deca-2,6,9-triene-3-carboxylic acid ethyl ester

A

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

B

(E)-3-Methylamino-2-(pyridine-4-carbonyl)-but-2-enoic acid ethyl ester

(E)-3-Methylamino-2-(pyridine-4-carbonyl)-but-2-enoic acid ethyl ester

Conditions
ConditionsYield
With methanol Ambient temperature;
n-propyl isonicotinate
90610-01-8

n-propyl isonicotinate

methyl iodide
74-88-4

methyl iodide

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
1) Et4NBF4, electrolysis; Yield given. Multistep reaction;
silver salt of pyridine-dicarboxylic acid-(3.4)-methyl ester-(4)

silver salt of pyridine-dicarboxylic acid-(3.4)-methyl ester-(4)

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
durch Destillation im Wasserstoffstrom;
1-Iodo-4-methoxycarbonyl-pyridinium

1-Iodo-4-methoxycarbonyl-pyridinium

A

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

B

I(1+)

I(1+)

Conditions
ConditionsYield
at 59.9℃; Thermodynamic data; gas-phase;
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With sulfuric acid; sodium carbonate In methanol
Multi-step reaction with 2 steps
1.1: thionyl chloride / 0.17 h / 0 - 20 °C / Inert atmosphere
2.1: 0.17 h / 0 - 20 °C
2.2: pH ~ 6
View Scheme
1H-benzimidazol-2-amine
934-32-7

1H-benzimidazol-2-amine

3-pyridinecarboxylic acid methyl ester (methyl nicotinate)

3-pyridinecarboxylic acid methyl ester (methyl nicotinate)

A

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

B

N-(1H-benzoimidazol-2-yl)-nicotinamide
27111-31-5

N-(1H-benzoimidazol-2-yl)-nicotinamide

Conditions
ConditionsYield
In methanol
3-methyl-4-cyanopyridine
7584-05-6

3-methyl-4-cyanopyridine

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

3-(2-oxo-2-pyridin-4-yl-ethyl)isonicotinonitrile
1071017-66-7

3-(2-oxo-2-pyridin-4-yl-ethyl)isonicotinonitrile

Conditions
ConditionsYield
With sodium hydride In 1,2-dimethoxyethane at 95℃; for 16h;100%
With sodium hydride In 1,2-dimethoxyethane at 95℃;100%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

C60H84O8Rh2*0.19H2O*0.5CHCl3

C60H84O8Rh2*0.19H2O*0.5CHCl3

C67H91NO10Rh2

C67H91NO10Rh2

Conditions
ConditionsYield
In chloroform for 0.0833333h;100%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

mesitylenesulfonylhydroxylamine
36016-40-7

mesitylenesulfonylhydroxylamine

1-amino-4-(methoxycarbonyl)pyridin-1-ium 2,4,6-trimethylbenzene-1-sulfonate
59247-63-1

1-amino-4-(methoxycarbonyl)pyridin-1-ium 2,4,6-trimethylbenzene-1-sulfonate

Conditions
ConditionsYield
Stage #1: 4-pyridinecarboxylic acid, methyl ester; mesitylenesulfonylhydroxylamine In acetonitrile at 30℃; for 0.0166667h; Flow reactor;
Stage #2: With sodium hydroxide In N,N-dimethyl-formamide at 30℃; for 0.0433333h; Flow reactor;
100%
In dichloromethane at 0 - 20℃; for 21h; Inert atmosphere;72%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

benzyl bromide
100-39-0

benzyl bromide

1-benzyl-4-(methoxycarbonyl)pyridin-1-ium
94983-57-0

1-benzyl-4-(methoxycarbonyl)pyridin-1-ium

Conditions
ConditionsYield
In methanol at 80℃; for 2h; Inert atmosphere;100%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

methyl isonicotinate N-oxide
3783-38-8

methyl isonicotinate N-oxide

Conditions
ConditionsYield
Stage #1: 4-pyridinecarboxylic acid, methyl ester With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at 20℃; for 18h;
Stage #2: With manganese(IV) oxide In dichloromethane at 20℃; for 2h;
99%
With bis-trimethylsilanyl peroxide; per-rhenic acid In dichloromethane; water at 24℃; for 6h;98%
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at 24℃; for 17h;98%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

4-(((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)methyl)pyridine

4-(((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)methyl)pyridine

Conditions
ConditionsYield
With {Cp'2Th(μ-H)H}2 at 70℃; for 24h;99%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

4-pyridinecarbohydroxamic acid
4427-22-9

4-pyridinecarbohydroxamic acid

Conditions
ConditionsYield
With hydroxylamine In methanol at 20℃; for 72h;98%
Stage #1: 4-pyridinecarboxylic acid, methyl ester With hydroxylamine hydrochloride; potassium hydroxide In methanol; water at 40℃; for 72h;
Stage #2: With hydrogenchloride In methanol; water pH=5.5;
93%
With hydrogenchloride; methanol; hydroxylamine; sodium methylate
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

pyridine-4-methanol
586-95-8

pyridine-4-methanol

Conditions
ConditionsYield
With sodium tetrahydroborate; sodium methylate In methanol at 25℃; for 3h; Inert atmosphere;98%
Stage #1: 4-pyridinecarboxylic acid, methyl ester With sodium tetrahydroborate In tetrahydrofuran at 70℃; for 0.25h;
Stage #2: In tetrahydrofuran; methanol at 70℃; for 1h;
52%
With lithium aluminium tetrahydride In diethyl ether for 0.5h;38%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

acetonitrile
75-05-8

acetonitrile

1-cyano-2-oxo-2-(pyridin-4-yl)ethane sodium salt

1-cyano-2-oxo-2-(pyridin-4-yl)ethane sodium salt

Conditions
ConditionsYield
Stage #1: 4-pyridinecarboxylic acid, methyl ester With sodium hydroxide In toluene at 0℃; for 0.166667h;
Stage #2: acetonitrile In toluene at 80℃; for 4h;
98%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

methyl trifluoromethyl propiolate

methyl trifluoromethyl propiolate

α-bromoacetophenone
70-11-1

α-bromoacetophenone

dimethyl 3-benzoyl-2-(trifluoromethyl)indolizine-1,7-dicarboxylate

dimethyl 3-benzoyl-2-(trifluoromethyl)indolizine-1,7-dicarboxylate

Conditions
ConditionsYield
Stage #1: 4-pyridinecarboxylic acid, methyl ester; α-bromoacetophenone In acetonitrile at 40℃; for 4h;
Stage #2: methyl trifluoromethyl propiolate With N-ethyl-N,N-diisopropylamine In acetonitrile for 7h;
98%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

methyl iodide
74-88-4

methyl iodide

4-(methoxycarbonyl)-1-methylpyridinium iodide
7630-02-6

4-(methoxycarbonyl)-1-methylpyridinium iodide

Conditions
ConditionsYield
In methanol97.2%
Methylation;95%
In dichloromethane at 30℃;87%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

triethyloxonium fluoroborate
368-39-8

triethyloxonium fluoroborate

N-ethyl methyl isonicotinate tetrafluoroborate

N-ethyl methyl isonicotinate tetrafluoroborate

Conditions
ConditionsYield
In dichloromethane at 20℃; Glovebox;97%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

2,2-difluoro-2-(4-methoxyphenyl)acetic acid
1027513-97-8

2,2-difluoro-2-(4-methoxyphenyl)acetic acid

methyl 2-(difluoro(4-methoxyphenyl)methyl)isonicotinate

methyl 2-(difluoro(4-methoxyphenyl)methyl)isonicotinate

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate In dichloromethane; water at 50℃; for 24h; Minisci Aromatic Substitution; Inert atmosphere; Sealed tube; regioselective reaction;97%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

cobalt(II) sulphate heptahydrate

cobalt(II) sulphate heptahydrate

naphthalene-2-sulfonate
120-18-3

naphthalene-2-sulfonate

water
7732-18-5

water

C14H22CoN2O8(2+)*2C10H7O3S(1-)

C14H22CoN2O8(2+)*2C10H7O3S(1-)

Conditions
ConditionsYield
Stage #1: cobalt(II) sulphate heptahydrate; naphthalene-2-sulfonate In hexane at 40℃; for 0.5h;
Stage #2: 4-pyridinecarboxylic acid, methyl ester; water In methanol; ethanol at 40℃; for 2h;
96.6%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

2,4-dinitrophenyl 4-methylbenzenesulfonate
742-25-6

2,4-dinitrophenyl 4-methylbenzenesulfonate

1-(2,4-dinitrophenyl)-4-(methoxycarbonyl)pyridin-1-ium p-toluenesulfonate

1-(2,4-dinitrophenyl)-4-(methoxycarbonyl)pyridin-1-ium p-toluenesulfonate

Conditions
ConditionsYield
In toluene for 16h; Reflux;96%
In toluene for 48h; Reflux;25%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

N-methylaniline
100-61-8

N-methylaniline

N-methyl-N-phenyl-4-pyridinecarboxamide
252930-65-7

N-methyl-N-phenyl-4-pyridinecarboxamide

Conditions
ConditionsYield
With [(Me3Si)2N]3La(μ-Cl)Li(THF)3 In tetrahydrofuran at 30℃; for 0.333333h; Inert atmosphere; Schlenk technique;96%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine hydrate In methanol at 70℃; for 0.00111111h;95.6%
With hydrazine hydrate In ethanol at 20℃; for 3h;94.1%
With hydrazine hydrate In ethanol at 23℃; for 16h;86%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

potassium tetrachloroaurate(III) dihydrate

potassium tetrachloroaurate(III) dihydrate

trichloro(methyl isonicotinate)gold(III)
129915-44-2

trichloro(methyl isonicotinate)gold(III)

Conditions
ConditionsYield
In water KAuCl4*2H2O in H2O treated dropwise with stoich. amount of nitrogen donor base in H2O under stirring, pptd.; ppt. filtered off, washed (H2O) 3 times, dried (vac.), elem. anal.;95%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

methyl 2‐carbamoylpyridine‐4‐carboxylate

methyl 2‐carbamoylpyridine‐4‐carboxylate

Conditions
ConditionsYield
With dipotassium peroxodisulfate; oxygen; sodium formate; silver nitrate at 80℃; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Schlenk technique; regioselective reaction;95%
With dipotassium peroxodisulfate; oxygen; sodium acetate; silver nitrate In water at 80℃; for 4h; Green chemistry;95%
With iron(III) sulfate; sulfuric acid; dihydrogen peroxide at 10 - 20℃; for 8h; Temperature;80.4%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

copper(ll) sulfate pentahydrate

copper(ll) sulfate pentahydrate

isobutyric Acid
79-31-2

isobutyric Acid

C30H42Cu2N2O12

C30H42Cu2N2O12

Conditions
ConditionsYield
Stage #1: copper(ll) sulfate pentahydrate; isobutyric Acid In hexane at 39℃; for 0.583333h;
Stage #2: 4-pyridinecarboxylic acid, methyl ester In methanol; ethanol; water at 39℃; for 2.16667h;
95%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

benzyl chloride
100-44-7

benzyl chloride

1-Benzyl-4-methoxycarbonyl-pyridinium; iodide
1216-01-9

1-Benzyl-4-methoxycarbonyl-pyridinium; iodide

Conditions
ConditionsYield
In methanol for 24h; Heating;94%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

di-μ-chloro-bis[bis(cyclo-octene)rhodium]

di-μ-chloro-bis[bis(cyclo-octene)rhodium]

1-diphenylphosphinomethyl-1,2-dicarba-closo-dodecaborane
36989-07-8

1-diphenylphosphinomethyl-1,2-dicarba-closo-dodecaborane

hydridochlorobis{4-(methoxycarbonyl)pyridine}{1-{(diphenylphosphino)methyl}-o-carbaboranyl-B3(6),P}rhodium

hydridochlorobis{4-(methoxycarbonyl)pyridine}{1-{(diphenylphosphino)methyl}-o-carbaboranyl-B3(6),P}rhodium

Conditions
ConditionsYield
In hexane Ar-atmosphere, to a stirred suspn. of Rh-compd. the pyridine-base is added,after 5-10 min. a soln. of the B-compd. added and the mixt. boiled for 1h; after cooling ppt. filtered off, washed with hexane and dried, elem. anal.;94%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium
12092-47-6

di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium

1-diphenylphosphinomethyl-1,2-dicarba-closo-dodecaborane
36989-07-8

1-diphenylphosphinomethyl-1,2-dicarba-closo-dodecaborane

hydridochlorobis{4-(methoxycarbonyl)pyridine}{1-{(diphenylphosphino)methyl}-o-carbaboranyl-B3(6),P}rhodium

hydridochlorobis{4-(methoxycarbonyl)pyridine}{1-{(diphenylphosphino)methyl}-o-carbaboranyl-B3(6),P}rhodium

Conditions
ConditionsYield
In hexane Ar-atmosphere, to a stirred suspn. of Rh-compd. the pyridine-base is added,after 5-10 min. a soln. of the B-compd. added and the mixt. boiled for 1h; after cooling ppt. filtered off, washed with hexane and dried, elem. anal.;94%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

di(rhodium)tetracarbonyl dichloride

di(rhodium)tetracarbonyl dichloride

1-diphenylphosphinomethyl-1,2-dicarba-closo-dodecaborane
36989-07-8

1-diphenylphosphinomethyl-1,2-dicarba-closo-dodecaborane

hydridochlorobis{4-(methoxycarbonyl)pyridine}{1-{(diphenylphosphino)methyl}-o-carbaboranyl-B3(6),P}rhodium

hydridochlorobis{4-(methoxycarbonyl)pyridine}{1-{(diphenylphosphino)methyl}-o-carbaboranyl-B3(6),P}rhodium

Conditions
ConditionsYield
In hexane Ar-atmosphere, to a stirred suspn. of Rh-compd. the pyridine-base is added,after 5-10 min. a soln. of the B-compd. added and the mixt. boiled for 1h; after cooling ppt. filtered off, washed with hexane and dried, elem. anal.;94%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

di(rhodium)tetracarbonyl dichloride

di(rhodium)tetracarbonyl dichloride

cis-[Rh(CO)2Cl(methyl isonicotinate)]
1005760-23-5

cis-[Rh(CO)2Cl(methyl isonicotinate)]

Conditions
ConditionsYield
In dichloromethane (Rh(CO)2Cl)2 dissolved in CH2Cl2, methyl isonicotinate added, stirred atroom temp. for 10 min; evapn. under vac., washing (diethyl ether), elem. anal.;94%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

methyl trifluoromethyl propiolate

methyl trifluoromethyl propiolate

4-(bromoacetyl)toluene
619-41-0

4-(bromoacetyl)toluene

dimethyl 3-(4-methoxybenzoyl)-2-(trifluoromethyl)indolizine-1,7-dicarboxylate

dimethyl 3-(4-methoxybenzoyl)-2-(trifluoromethyl)indolizine-1,7-dicarboxylate

Conditions
ConditionsYield
Stage #1: 4-pyridinecarboxylic acid, methyl ester; 4-(bromoacetyl)toluene In acetonitrile at 40℃; for 4h;
Stage #2: methyl trifluoromethyl propiolate With N-ethyl-N,N-diisopropylamine In acetonitrile for 7h;
94%

Methyl isonicotinate Chemical Properties


IUPAC Name: Methyl pyridine-4-carboxylate
Canonical SMILES: COC(=O)C1=CC=NC=C1
InChI: InChI=1S/C7H7NO2/c1-10-7(9)6-2-4-8-5-3-6/h2-5H,1H3
InChIKey: OLXYLDUSSBULGU-UHFFFAOYSA-N
Molecular Weight: 137.13598 [g/mol]
Molecular Formula: C7H7NO2
XLogP3: 0.9
H-Bond Donor: 0
H-Bond Acceptor: 3 
EINECS: 219-546-8 
storage temp. 2-8 °C
Appearance: clear orange to brown liquid
Melting Point: 8-8.5 °C(lit.)
Index of Refraction: 1.511
Molar Refractivity: 36.11 cm3
Molar Volume: 120.5 cm3
Surface Tension: 41.6 dyne/cm
Density: 1.137 g/cm3
Flash Point: 77.8 °C
Enthalpy of Vaporization: 44.13 kJ/mol
Boiling Point: 205.1 °C at 760 mmHg
Vapour Pressure: 0.255 mmHg at 25 °C 
Product Categories of Methyl isonicotinate (CAS NO.2459-09-8): C7 and C8; Heterocyclic Building Blocks; Pyridines

Methyl isonicotinate Uses

 Methyl isonicotinate (CAS NO.2459-09-8) is used for pharmaceutical intermediates.

Methyl isonicotinate Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
F: 10
Hazard Note of Methyl isonicotinate (CAS NO.2459-09-8): Irritant

Methyl isonicotinate Specification

 Methyl isonicotinate (CAS NO.2459-09-8), its Synonyms are 4-Methoxycarbonylpyridine ; Isonicotinic acid methyl ester ; Methyl 4-pyridinecarboxylate ; N-Methylisonicotinate ; Isonicotinic acid, methyl ester (8CI) .

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