Product Name

  • Name

    Methyl nicotinate

  • EINECS 202-261-8
  • CAS No. 93-60-7
  • Article Data131
  • CAS DataBase
  • Density 1.137 g/cm3
  • Solubility NEGLIGIBLE
  • Melting Point 42-44 °C(lit.)
  • Formula C7H7NO2
  • Boiling Point 209 °C at 760 mmHg
  • Molecular Weight 137.138
  • Flash Point 95.6 °C
  • Transport Information
  • Appearance white to brownish crystals or crystalline powder
  • Safety 26-36-37/39
  • Risk Codes 36/37/38-36/38
  • Molecular Structure Molecular Structure of 93-60-7 (Methyl nicotinate)
  • Hazard Symbols IrritantXi
  • Synonyms 3-(Carbomethoxy)pyridine;m-(Methoxycarbonyl)pyridine;3-Pyridinecarboxylic acid, methyl ester;Methyl 3-pyridinecarboxylate;Methyl-nicotinate;Methylnicotinate;methyl pyridine-3-carboxylate;Nicotinic acid, methyl ester;3-Carbomethoxypyridine;Nicometh;Nicotinic acid methyl ester;Nikomet;3-(Methoxycarbonyl)pyridine;3-Picolinic Acid Methyl Ester;
  • PSA 39.19000
  • LogP 0.86820

Synthetic route

1-oxy-nicotinic acid methyl ester
15905-18-7

1-oxy-nicotinic acid methyl ester

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

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 1.5h;98%
With (4,4′-di-tert-butyl-2,2′-bipyridine)bis[(2-pyridinyl)phenyl]iridium(III) hexafluorophosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 1.5h; Inert atmosphere; Irradiation; chemoselective reaction;98%
3-iodopyridine
1120-90-7

3-iodopyridine

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With triethylamine at 100℃; for 1.5h; Inert atmosphere;98%
...Expand
nicotinic acid
59-67-6

nicotinic acid

methanol
67-56-1

methanol

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With phosphotungstic acid for 6h; Reflux;96%
With sulfuric acid at 65℃; for 18h;89%
With sulfuric acid for 14h; Heating / reflux;88%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

methanol
67-56-1

methanol

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With oxygen; potassium carbonate at 60℃; under 750.075 Torr; for 20h;95%
With iodine; potassium carbonate for 24h; Heating;82%
With dibromamine-T; potassium carbonate In acetonitrile at 20℃; for 2h;78%
3-Bromopyridine
626-55-1

3-Bromopyridine

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With C57H43IP2Pd; triethylamine at 130℃; under 3750.38 Torr; for 24h; Autoclave;94%
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 61h; Irradiation;70%
With sodium methylate; C2H5OOCCH2Co(CO)4 In diethyl ether at 25 - 35℃;57%
...Expand
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

methanol
67-56-1

methanol

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With 4-ethyl-1-methyl-4H-[1,2,4]-triazol-1-ium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 0.333333h;93%
With potassium carbonate In water at 20℃; for 2h;92%
With oxygen at 70℃; under 750.075 Torr; for 16h;87%
methanol
67-56-1

methanol

nicotinamide
98-92-0

nicotinamide

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With N,N-dimethyl-formamide dimethyl acetal at 25℃; for 2h;92%
With sulfuric acid at 100℃; for 0.5h; Temperature; Sealed tube;
nicotinic acid
59-67-6

nicotinic acid

dimethyl dicarbonate
4525-33-1

dimethyl dicarbonate

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
magnesium(II) perchlorate In nitromethane at 40℃; for 16h;92%
C38H48N2O8

C38H48N2O8

A

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

B

methyl hexanoate
106-70-7

methyl hexanoate

C

C20H32O5

C20H32O5

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 8h;A n/a
B n/a
C 90%
...Expand
nicotinic acid
59-67-6

nicotinic acid

Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
microwave irradiation;88%
In toluene at 110℃; for 24h;77%
nicotinic acid
59-67-6

nicotinic acid

methyl salicylate
119-36-8

methyl salicylate

A

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

B

salicylic acid
69-72-7

salicylic acid

Conditions
ConditionsYield
Stage #1: nicotinic acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h;
Stage #2: methyl salicylate at 110℃; for 24h;		A 81%
B n/a
...Expand
methanol
67-56-1

methanol

N-acetyl-N-methylnicotinamide
114951-31-4

N-acetyl-N-methylnicotinamide

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
for 1h; Heating;80%
Acetic acid (4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-pyridin-3-yl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

Acetic acid (4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-pyridin-3-yl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

sodium methoxide

sodium methoxide

A

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

B

(4aS,5S,6aR,7R,10aS,10bR)-5,8-Dihydroxy-7-hydroxymethyl-3,4a,7,10a-tetramethyl-1-oxo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester

(4aS,5S,6aR,7R,10aS,10bR)-5,8-Dihydroxy-7-hydroxymethyl-3,4a,7,10a-tetramethyl-1-oxo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
In methanol; water at 25℃; for 18h; Ring cleavage; in 70 percent MeOH; evapn.; purification by ODS column chromy.;A n/a
B 80%
...Expand
nicotinic acid
59-67-6

nicotinic acid

trimethylphosphane
594-09-2

trimethylphosphane

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With 1,3-diazido-propane In neat (no solvent) at 20℃; for 0.333333h;75%
3-Chloropyridine
626-60-8

3-Chloropyridine

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

lithium methanolate
865-34-9

lithium methanolate

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; 5 mol% Pd/C; sodium fluoride In 1,4-dioxane at 150℃; Inert atmosphere;75%
...Expand
methanol
67-56-1

methanol

pyridin-3-yl trifluoromethanesulfonate
107658-27-5

pyridin-3-yl trifluoromethanesulfonate

CO

CO

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate In dimethyl sulfoxide at 70℃; for 2h;72%
...Expand
nicotinic acid
59-67-6

nicotinic acid

methyl iodide
74-88-4

methyl iodide

A

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

B

3-methoxycarbonyl-1-methyl-pyridinium
18899-18-8

3-methoxycarbonyl-1-methyl-pyridinium

Conditions
ConditionsYield
Stage #1: nicotinic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 0.166667h;
Stage #2: methyl iodide In acetonitrile at 20℃; for 4h;		A 72%
B n/a
...Expand
6-Chloronicotinic acid methyl ester
73781-91-6

6-Chloronicotinic acid methyl ester

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 2h; Reagent/catalyst; Inert atmosphere; chemoselective reaction;62%
pyridine-2,5-dicarboxylic acid 5-methyl ester
17874-79-2

pyridine-2,5-dicarboxylic acid 5-methyl ester

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With methanol at 40℃; for 48h; Schlenk technique; Irradiation; Inert atmosphere;62%
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

methanol
67-56-1

methanol

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With iron(III) chloride for 32h; Heating;61.3%
With boron trifluoride diethyl etherate for 168h; Heating;43%
nicotinic acid
59-67-6

nicotinic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With sulfuric acid for 22h; Neat (no solvent); Reflux;54.7%
trans-bromo(3-pyridylcarbonyl)bis(triphenylphosphine)palladium(II)

trans-bromo(3-pyridylcarbonyl)bis(triphenylphosphine)palladium(II)

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

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;48%
methanol
67-56-1

methanol

1-(pyridin-3-yl)propan-1-one
1570-48-5

1-(pyridin-3-yl)propan-1-one

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With N,N-dimethyl-formamide dimethyl acetal for 16h; Heating;40%
1-oxy-nicotinic acid methyl ester
15905-18-7

1-oxy-nicotinic acid methyl ester

N,N-Dimethylthiocarbamoyl chloride
16420-13-6

N,N-Dimethylthiocarbamoyl chloride

A

methyl 2-[[(dimethylamino)carbonyl]thio]-3-pyridine carboxylate

methyl 2-[[(dimethylamino)carbonyl]thio]-3-pyridine carboxylate

B

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
In acetonitrile at 81℃; for 4h;A 10%
B 36%
...Expand
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

methyl methoxyacetate
6290-49-9

methyl methoxyacetate

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

C

methyl α-methoxy-β-(β-pyridyl)acrylate
136138-66-4

methyl α-methoxy-β-(β-pyridyl)acrylate

Conditions
ConditionsYield
With sodium methylate In toluene for 2h; Heating;A n/a
B 10%
C 31%
...Expand
methyl-3-pyridylketone
350-03-8

methyl-3-pyridylketone

methanol
67-56-1

methanol

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With N,N-dimethyl-formamide dimethyl acetal for 16h; Heating;26%
1-(3-methyl-2-butenyl)-3-carbomethoxypyridinium perchlorate

1-(3-methyl-2-butenyl)-3-carbomethoxypyridinium perchlorate

A

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

B

methyl 6-isopropylnicotinate
84625-02-5

methyl 6-isopropylnicotinate

Conditions
ConditionsYield
In methanol for 1.5h; Irradiation;A 6.5%
B 4%
In methanol for 1.5h; Mechanism; Irradiation; intramolecular electron-transfer-induced photochemical cyclization;A 6.5%
B 4%
diazomethane
186581-53-3, 908094-01-9

diazomethane

nicotinic acid
59-67-6

nicotinic acid

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With diethyl ether; water
In diethyl ether
quinoline
91-22-5

quinoline

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With selenium; sulfuric acid at 300℃; Erwaermen des Reaktionsgemisches mit Methanol;
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

methyl 1,4,5,6-tetrahydro-3-pyridinecarboxylate
14997-05-8

methyl 1,4,5,6-tetrahydro-3-pyridinecarboxylate

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; triethylamine In methanol at 23℃; for 48h;100%
With palladium 10% on activated carbon; hydrogen; triethylamine In methanol under 879.175 Torr; for 12h;10.1 g
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

nipecotic acid
498-95-3

nipecotic acid

Conditions
ConditionsYield
With hydrogen In water at 120℃; under 11251.1 Torr; for 1h;100%
1,4-bis(bromomethyl)benzene
623-24-5

1,4-bis(bromomethyl)benzene

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

α,α'-bis(3-methoxycarbonylpyridiniumyl)-p-xylene dibromide

α,α'-bis(3-methoxycarbonylpyridiniumyl)-p-xylene dibromide

Conditions
ConditionsYield
In acetone for 10h; Substitution; Heating;99.6%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

Nicotinic acid hydrazide
553-53-7

Nicotinic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate for 5h; Heating;99%
With hydrazine hydrate In ethanol at 20℃; for 3h;93.2%
With hydrazine hydrate In methanol at 100℃; for 24h;85%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

prenyl tributylstannane
104108-29-4

prenyl tributylstannane

methyl chloroformate
79-22-1

methyl chloroformate

1,3-bis(methoxycarbonyl)-4-(1,1-dimethyl-2-propenyl)-1,4-dihydropyridine
115119-35-2

1,3-bis(methoxycarbonyl)-4-(1,1-dimethyl-2-propenyl)-1,4-dihydropyridine

Conditions
ConditionsYield
In dichloromethane at 0℃;99%
...Expand
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

benzyl alcohol
100-51-6

benzyl alcohol

benzyl nicotinate
94-44-0

benzyl nicotinate

Conditions
ConditionsYield
With lanthanum(III) isopropoxide; 2-(2-methoxyethoxy)ethyl alcohol at 110℃; for 6h; Reagent/catalyst; Molecular sieve;99%
With N,N'-biscyclohexyl-imidazol-2-ylidene; 4 A molecular sieve In tetrahydrofuran at 20℃; for 0.25h;96%
With lanthanum (III) nitrate * water; 1,1,1-trioctyl-1-methylphosphonium methylcarbonate In hexane for 1h; Molecular sieve; Reflux;92%
With platinum; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20 - 60℃; for 2h; Inert atmosphere; Electrochemical reaction; Green chemistry;62%
With 3,5-bistrifluoromethylphenylisothiocyanate; 4-pyrrolidin-1-ylpyridine In n-heptane for 24h; Reflux;
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

lithio dimethyl (2-oxo-2-pyridin-3-ylethyl)phosphonate

lithio dimethyl (2-oxo-2-pyridin-3-ylethyl)phosphonate

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran Barbier reaction; Cooling with ice; Inert atmosphere;99%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

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

(Bis-trimethylsilanyloxy-methylene)-cyclohexane

1-{3-(methoxycarbonyl)-1-[(trifluoromethyl)sulfonyl]-1,4-dihydropyridin-4-yl}cyclohexanecarboxylic acid
1570044-75-5

1-{3-(methoxycarbonyl)-1-[(trifluoromethyl)sulfonyl]-1,4-dihydropyridin-4-yl}cyclohexanecarboxylic acid

Conditions
ConditionsYield
Stage #1: methyl 3-pyridinecarboxylate With trifluoromethylsulfonic anhydride In dichloromethane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: (Bis-trimethylsilanyloxy-methylene)-cyclohexane In dichloromethane at -78 - 20℃;		99%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

ethanolamine
141-43-5

ethanolamine

N-(2-hydroxyethyl)nicotinamide
6265-73-2

N-(2-hydroxyethyl)nicotinamide

Conditions
ConditionsYield
at 150 - 160℃; for 3h; Condensation;98%
at 50℃; for 0.5h;71%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; potassium tert-butylate; hydrogen In tetrahydrofuran at 50℃; under 7500.75 Torr; for 5h; Schlenk technique; Inert atmosphere;98%
With sodium tetrahydroborate; sodium methylate In methanol at 25℃; for 3h; Reagent/catalyst; Inert atmosphere;98%
With 2-(Aminomethyl)pyridine; 1,3-bis-(diphenylphosphino)propane; potassium tert-butylate; hydrogen In 2-methyltetrahydrofuran at 100℃; under 37503.8 Torr; for 16h; Reagent/catalyst; Autoclave;95%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

1-oxy-nicotinic acid methyl ester
15905-18-7

1-oxy-nicotinic acid methyl ester

Conditions
ConditionsYield
With phthalic anhydride; urea-hydrogen peroxide In dichloromethane for 4h; Ambient temperature;98%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 24h; Inert atmosphere;98%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 24h;98%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

(1R)-endo-(+)-fenchol
2217-02-9

(1R)-endo-(+)-fenchol

Nicotinic acid (1R,2R,4S)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Nicotinic acid (1R,2R,4S)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane for 0.2h;98%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

methyl iodide
74-88-4

methyl iodide

3-(methoxycarbonyl)-1-methylpyridinium iodide
4685-10-3

3-(methoxycarbonyl)-1-methylpyridinium iodide

Conditions
ConditionsYield
In acetonitrile at 90℃; for 1h; Sealed tube;97%
In benzene for 3h; Heating;
In ethyl acetate
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

phenyl chloroformate
1885-14-9

phenyl chloroformate

2H-pyridine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl ester
323201-15-6

2H-pyridine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at -78℃; for 3h; Fowler reduction;97%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

6-methoxy-tryptophyl bromide
68104-24-5

6-methoxy-tryptophyl bromide

1-[2-[3-(6-methoxyindolyl)]ethyl]-3-carbomethoxypyridinium bromide

1-[2-[3-(6-methoxyindolyl)]ethyl]-3-carbomethoxypyridinium bromide

Conditions
ConditionsYield
In methanol; diethyl ether at 100℃; for 1h;97%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

2-(Diethylamino)ethanol
100-37-8

2-(Diethylamino)ethanol

nicametate
3099-52-3

nicametate

Conditions
ConditionsYield
With N,N'-biscyclohexyl-imidazol-2-ylidene; 4 A molecular sieve In tetrahydrofuran at 20℃; for 2h;97%
With tetraethylammonium bicarbonate at 60℃; for 2h;84%
With platinum; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20 - 60℃; for 2h; Inert atmosphere; Electrochemical reaction; Green chemistry;62%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

1,3-dioxoisoindoline-2-yl-2-acetylamino-3-methylbutyrate

1,3-dioxoisoindoline-2-yl-2-acetylamino-3-methylbutyrate

C13H18N2O3

C13H18N2O3

Conditions
ConditionsYield
With (Ra)-4-hydroxy-2,6-bis(2,4,6-tricyclohexylphenyl)dinaphtho-[1,3,2]dioxaphosphepine 4-oxide; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In 1,4-dioxane for 14h; Minisci Aromatic Substitution; Irradiation; enantioselective reaction;97%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

nickel(II) sulfate hexahydrate

nickel(II) sulfate hexahydrate

naphthalene-2-sulfonate
120-18-3

naphthalene-2-sulfonate

water
7732-18-5

water

C14H22N2NiO8(2+)*2C10H7O3S(1-)

C14H22N2NiO8(2+)*2C10H7O3S(1-)

Conditions
ConditionsYield
Stage #1: nickel(II) sulfate hexahydrate; naphthalene-2-sulfonate In hexane at 40℃; for 0.5h;
Stage #2: methyl 3-pyridinecarboxylate; water In methanol; ethanol at 40℃; for 2h;		96.6%
...Expand
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

1-phenyl-1-trimethylsiloxypropene
37471-46-8

1-phenyl-1-trimethylsiloxypropene

methyl chloroformate
79-22-1

methyl chloroformate

1,3-bis(methoxycarbonyl)-4-(1-methyl-2-oxo-2-phenylethyl)-1,4-dihydropyridine
105619-05-4, 105619-06-5

1,3-bis(methoxycarbonyl)-4-(1-methyl-2-oxo-2-phenylethyl)-1,4-dihydropyridine

Conditions
ConditionsYield
In dichloromethane Ambient temperature;96%
...Expand
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

benzylamine
100-46-9

benzylamine

N-benzylnicotinamide
2503-55-1

N-benzylnicotinamide

Conditions
ConditionsYield
With 14C2H2F3O(1-)*6C4H8O*La2Na8(14+) at 80℃; for 6h; Inert atmosphere;96%
With silica gel In neat (no solvent) at 100℃; for 12h; Inert atmosphere; Sealed tube;87%
With bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct In tetrahydrofuran at 130℃; for 0.133333h; Concentration; Solvent; Inert atmosphere; Microwave irradiation;80%
With potassium phosphate; 2,2,2-trifluoroethanol In tetrahydrofuran at 90℃; for 22h; Sealed tube;67%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

(phenylmethoxy)methylphosphonic acid diethyl ester
89268-01-9

(phenylmethoxy)methylphosphonic acid diethyl ester

diethyl [1-benzyloxy-2-oxo-2-(pyridin-3-yl)ethyl]phosphonate
1574232-82-8

diethyl [1-benzyloxy-2-oxo-2-(pyridin-3-yl)ethyl]phosphonate

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -5 - 0℃; for 0.75h; Inert atmosphere;95.9%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

benzyl bromide
100-39-0

benzyl bromide

1-benzyl-3-(methoxycarbonyl)pyridinium bromide
6516-41-2

1-benzyl-3-(methoxycarbonyl)pyridinium bromide

Conditions
ConditionsYield
In isopropyl alcohol at 20℃; for 18h;95%
In isopropyl alcohol at 20℃; for 18h; Inert atmosphere;93%
With methanol
Alkylation;
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

tris(methylthio)methane
5418-86-0

tris(methylthio)methane

A

tetrathioorthocarbonic acid tetramethyl ester
6156-25-8

tetrathioorthocarbonic acid tetramethyl ester

B

2,2-Bis-methylsulfanyl-1-pyridin-3-yl-ethanone

2,2-Bis-methylsulfanyl-1-pyridin-3-yl-ethanone

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane 1.) -95 deg C, 2 h, 2.) -78 deg C, 30 min;A n/a
B 95%
...Expand
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

bromoacetic acid
79-08-3

bromoacetic acid

1-carboxymethyl-3-methoxycarbonyl-pyridinium; bromide

1-carboxymethyl-3-methoxycarbonyl-pyridinium; bromide

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 3h; Substitution;95%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

tert-butyl (Z)-(1-(((chloro(phenyl)methylene)amino)oxy)-1-oxo-3-phenylpropan-2-yl)carbamate

tert-butyl (Z)-(1-(((chloro(phenyl)methylene)amino)oxy)-1-oxo-3-phenylpropan-2-yl)carbamate

methyl 6-(1-((tert-butoxycarbonyl)amino)-2-phenylethyl)nicotinate

methyl 6-(1-((tert-butoxycarbonyl)amino)-2-phenylethyl)nicotinate

Conditions
ConditionsYield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In acetonitrile at 20℃; for 12h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation;95%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

cholesterol
57-88-5

cholesterol

(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl nicotinate
71437-79-1

(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl nicotinate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane for 18h; Ambient temperature;94%

Methyl nicotinate Chemical Properties


IUPAC Name: Methyl pyridine-3-carboxylate
Canonical SMILES: COC(=O)C1=CN=CC=C1
InChI: InChI=1S/C7H7NO2/c1-10-7(9)6-3-2-4-8-5-6/h2-5H,1H3
InChIKey: YNBADRVTZLEFNH-UHFFFAOYSA-N
Molecular Weight: 137.13598 [g/mol]
Molecular Formula: C7H7NO2
XLogP3: 0.8
H-Bond Donor: 0
H-Bond Acceptor: 3 
solubility: H2O: 0.1 g/mL, clear
Water Solubility: NEGLIGIBLE 
Appearance: white to brownish crystals or crystalline powder
Melting Point: 42-44 °C(lit.)
EINECS: 202-261-8 
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: 95.6 °C
Enthalpy of Vaporization: 44.53 kJ/mol
Boiling Point: 209 °C at 760 mmHg
Vapour Pressure: 0.208 mmHg at 25 °C
Product Categories of Methyl nicotinate (CAS NO.93-60-7): Heterocyclic Compounds; Pharmaceutical Intermediates

Methyl nicotinate Uses

 Methyl nicotinate (CAS NO.93-60-7) is used in the preparation of rubefacient. Nicotinic acid methyl ester(93-60-7) is available for biochemical study.

Methyl nicotinate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD subcutaneous > 1gm/kg (1000mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 428, 1948.
mouse LDLo parenteral 2gm/kg (2000mg/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 7, Pg. 691, 1955.

Methyl nicotinate Consensus Reports

Reported in EPA TSCA Inventory.

Methyl nicotinate Safety Profile

Moderately toxic by parenteral route. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38-36/38
36/37/38: Irritating to eyes, respiratory system and skin 
36/38: Irritating to eyes and skin 
Safety Statements: 26-36-37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36: Wear suitable protective clothing 
37/39: Wear suitable gloves and eye/face protection 
WGK Germany: 3
RTECS: QT1925000

Methyl nicotinate Specification

  Methyl nicotinate (CAS NO.93-60-7), its Synonyms are 3-(Carbomethoxy)pyridine ; 3-(Methoxycarbonyl)pyridine ; 3-Pyridinecarboxylic acid, methyl ester ; Methyl 3-pyridinecarboxylate ; Methyl-nicotinate ; Nicometh ; Nicotinic acid, methyl ester ; Nikomet ; m-(Methoxycarbonyl)pyridine .

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