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5470-70-2

Basic Information
CAS No.: 5470-70-2
Name: Methyl 6-methylnicotinate
Molecular Structure:
Molecular Structure of 5470-70-2 (Methyl 6-methylnicotinate)
Formula: C8H9NO2
Molecular Weight: 151.16
Synonyms: 3-pyridinecarboxylic acid, 6-methyl-, methyl ester;3-(Methoxycarbonyl)-6-methylpyridine;5-Methoxycarbonyl-2-methylpyridine;6-Methyl-3-pyridinecarboxylic acid methylester;6-Methylnicotinic acid methyl ester;Methyl6-methyl-3-pyridinecarboxylate;Methyl 6-methylaminonicotinate;6-Methyl nicotinic acid methyl ester;methyl 6-methylpyridine-3-carboxylate;
EINECS: 1308068-626-2
Density: 1.104 g/cm3
Melting Point: 34-37 °C(lit.)
Boiling Point: 228.4 °C at 760 mmHg
Flash Point: 80.6 °C
Solubility:
Appearance: Brown Solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26
Transport Information:
PSA: 39.19000
LogP: 1.17660
Synthetic route
49668-89-5

5-(methoxycarbonyl)-2-methylpyridine 1-oxide

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
With indium; cobalt(II) chloride In methanol at 20℃; for 2h; sonication;80%
67-56-1

methanol

3222-47-7

6-methylnicotinic acid

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
With sulfuric acid for 17h; Reflux;75%
With sulfuric acid for 21h; Heating; Yield given;
With sulfuryl dichloride
922-67-8

propynoic acid methyl ester

C-ethoxy-N-isopropenylmethanimine

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
In benzene for 5h; Heating;41%
646-06-0

1,3-DIOXOLANE

93-60-7

methyl 3-pyridinecarboxylate

A

5470-70-2

Methyl 6-methylnicotinate

B

69971-44-4

Methyl 4,6-Dimethylnicotinate

Conditions
ConditionsYield
With sulfuric acid for 7h; Irradiation;A 21%
B 5%
1211000-51-9

(+/-)-(E)-methyl 3-(but-3-yn-2-yloxy)acrylate

593-56-6

N-methoxylamine hydrochloride

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
With sodium acetate In ethanol at 150℃; for 3h; Inert atmosphere; Microwave irradiation;14%
67-56-1

methanol

93-60-7

methyl 3-pyridinecarboxylate

A

33402-75-4

4-methylnicotinic acid methyl ester

B

5470-70-2

Methyl 6-methylnicotinate

C

67367-26-4

2-methoxynicotinic acid methyl ester

D

26218-80-4

6-methoxy-nicotinic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid for 1h; Product distribution; Mechanism; Irradiation; effect of additives; variation of temp., acid concn.; further alcohol;A 7.1%
B 9.5%
C 8.8%
D 3.8%
With sulfuric acid for 1h; Irradiation;A 7.1%
B 9.5%
C 8.8%
D 3.8%
With sulfuric acid at 32℃; for 0.833333h; Product distribution; Mechanism; Irradiation; var. reagent, acid concentration and time;
67-56-1

methanol

51598-76-6

6-methyl-nicotinoyl chloride

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
In dichloromethane Ambient temperature;
With triethylamine for 3h;
93-60-7

methyl 3-pyridinecarboxylate

676-58-4

methylmagnesium chloride

1885-14-9

phenyl chloroformate

A

33402-75-4

4-methylnicotinic acid methyl ester

B

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
With sulfur Yield given. Multistep reaction;
With sulfur Yield given. Multistep reaction;
6-methyl-nicotinic acid-hydrochloride

6-methyl-nicotinic acid-hydrochloride

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
With hydrogenchloride
3222-47-7

6-methylnicotinic acid

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / 2 h / Heating
2: CH2Cl2 / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
2: triethylamine / 3 h
View Scheme
3222-47-7

6-methylnicotinic acid

144-55-8

sodium hydrogencarbonate

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
In methanol
67-56-1

methanol

34107-46-5

6-methyl-3-pyridinemethanol

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
With oxygen; potassium carbonate at 60℃; under 750.075 Torr; for 24h; Schlenk technique; Green chemistry;92%Chromat.
104-90-5

5-ethyl-2-methyl-pyridine

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 150℃;
1121-78-4

5-Hydroxy-2-methylpyridine

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: fluorosulfonyl fluoride; triethylamine / dichloromethane / 24 h / 20 °C / 760.05 Torr
2: bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline; manganese / N,N-dimethyl-formamide / 20 h / 20 °C / 760.05 Torr / Schlenk technique; Inert atmosphere; Glovebox
3: methanol
View Scheme
3222-47-7

6-methylnicotinic acid

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
In methanol54.2 mg

6-methylpyridin-3-yl sulfurofluoridate

5470-70-2

Methyl 6-methylnicotinate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline; manganese / N,N-dimethyl-formamide / 20 h / 20 °C / 760.05 Torr / Schlenk technique; Inert atmosphere; Glovebox
2: methanol
View Scheme
5470-70-2

Methyl 6-methylnicotinate

34107-46-5

6-methyl-3-pyridinemethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at -5 - 23℃; for 2h;100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h;98%
Stage #1: Methyl 6-methylnicotinate With lithium aluminium tetrahydride In diethyl ether at 55℃; for 1.5h; Heating / reflux;
Stage #2: With water In diethyl ether at 0℃; for 1h;
97%
5470-70-2

Methyl 6-methylnicotinate

49668-89-5

5-(methoxycarbonyl)-2-methylpyridine 1-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; Inert atmosphere;100%
With dihydrogen peroxide; sodium tungstate In water at 60 - 80℃; for 5.66667h;98%
Stage #1: Methyl 6-methylnicotinate With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at 24℃; for 6h;
Stage #2: manganese(IV) oxide In dichloromethane; water
91%
5470-70-2

Methyl 6-methylnicotinate

1009376-74-2

methyl 6-methylpiperidine-3-carboxylate.hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In methanol; water at 80℃; under 3102.97 Torr; for 21h;100%
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol at 75℃; under 2844.39 Torr;100%
5470-70-2

Methyl 6-methylnicotinate

3222-47-7

6-methylnicotinic acid

Conditions
ConditionsYield
100%
5470-70-2

Methyl 6-methylnicotinate

908245-03-4

6-methyl-3-piperidinecarboxylic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; 1% Pd/C In methanol; water at 80℃; under 3102.97 Torr; for 21h; Inert atmosphere;100%
With hydrogenchloride; platinum(IV) oxide; hydrogen In methanol; water at 50℃; under 2585.81 Torr; for 15h;96.15%
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In methanol; water under 2534.09 Torr; for 24h;
5470-70-2

Methyl 6-methylnicotinate

64-19-7

acetic acid

methyl 6-methylpiperidine-3-carboxylate acetic acid

Conditions
ConditionsYield
With platinum(IV) oxide; hydrogen at 60℃; under 7500.75 Torr; Autoclave;100%
5470-70-2

Methyl 6-methylnicotinate

197079-25-7

6-methylpyridine-3-carbohydrazide

Conditions
ConditionsYield
With hydrazine In methanol at 20℃; for 2h;98%
With hydrazine hydrate In ethanol for 2h; Reflux;90%
With hydrazine hydrate In ethanol at 20℃; for 2h;90%
5470-70-2

Methyl 6-methylnicotinate

10213-10-2

sodium tungstate (VI) dihydrate

49668-89-5

5-(methoxycarbonyl)-2-methylpyridine 1-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In methanol; water98%
5470-70-2

Methyl 6-methylnicotinate

25015-63-8

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

C14H22BNO4

Conditions
ConditionsYield
With 1,3-di-tert-butyl-2-(neopentyloxy)-2,3-dihydro-1H-1,3,2-diazaphosphole In diethyl ether at 20℃; for 12h;96%
5470-70-2

Methyl 6-methylnicotinate

1117-97-1

N,0-dimethylhydroxylamine

221615-71-0

N-methoxy-N-methyl-6-methylnicotinamide

Conditions
ConditionsYield
With isopropylmagnesium chloride In tetrahydrofuran at -10 - 5℃; for 2.5h;94.3%
With isopropylmagnesium chloride In tetrahydrofuran; toluene at -10℃; for 0.5h;
5470-70-2

Methyl 6-methylnicotinate

598-31-2

1-bromoacetone

207791-84-2

methyl 2-methyl-indolizine-6-carboxylate

Conditions
ConditionsYield
Stage #1: Methyl 6-methylnicotinate; 1-bromoacetone In acetone Heating;
Stage #2: With sodium carbonate In ethanol for 3h; Heating;
93%
5470-70-2

Methyl 6-methylnicotinate

6960-22-1

6-methylnicotinamide

Conditions
ConditionsYield
With ammonia In ethanol at 80℃; for 72h;91%
With ammonia; water at 20℃; for 4h;72%
5470-70-2

Methyl 6-methylnicotinate

lithium 4-(methylthio)phenylacetate

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h; Reagent/catalyst; Temperature;87.7%
5470-70-2

Methyl 6-methylnicotinate

358-23-6

trifluoromethylsulfonic anhydride

603-35-0

triphenylphosphine

(5-(methoxycarbonyl)-2-methylpyridin-4-yl)triphenylphosphonium trifluoromethanesulfonate

Conditions
ConditionsYield
Stage #1: Methyl 6-methylnicotinate; trifluoromethylsulfonic anhydride In dichloromethane at -78℃; for 1h; Inert atmosphere;
Stage #2: triphenylphosphine With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -78 - 20℃;
83%
at -78 - 20℃; Alkaline conditions;83%
67-56-1

methanol

5470-70-2

Methyl 6-methylnicotinate

69971-44-4

Methyl 4,6-Dimethylnicotinate

Conditions
ConditionsYield
With Ethyl 2-mercaptopropionate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; toluene-4-sulfonic acid In dimethyl sulfoxide at 23℃; UV-irradiation;82%
5470-70-2

Methyl 6-methylnicotinate

39657-45-9

isoxazolidine hydrochloride

isoxazolidine-2-yl-(6-methylpyridin-3-yl)methanone

Conditions
ConditionsYield
With isopropylmagnesium chloride In tetrahydrofuran; toluene at -20 - -10℃; for 0.5h; Reagent/catalyst; Inert atmosphere;80%
5470-70-2

Methyl 6-methylnicotinate

107-12-0

propiononitrile

2-methyl-3-(6-methylpyridin-3-yl)-3-oxopropanenitrile

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran at 20℃;80%
5470-70-2

Methyl 6-methylnicotinate

676-58-4

methylmagnesium chloride

40472-90-0

2-(6-methylpyridin-3-yl)propan-2-ol

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 12h;80%
5470-70-2

Methyl 6-methylnicotinate

sodium 4-(methylthio)phenylacetate

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h;78.5%
5470-70-2

Methyl 6-methylnicotinate

1421227-96-4

lithium (4-methylsulfonylphenyl)acetate

A

1421227-97-5

1-(6-methylpyridin-3-yl)-2-({4-[2-(6-methylpyridin-3-yl)-2-oxoethyl]phenyl}sulfonyl)ethanone

B

221615-75-4

1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1.5h;A n/a
B 78%
5470-70-2

Methyl 6-methylnicotinate

141-78-6

ethyl acetate

21683-58-9

ethyl 3-(2-methyl-5-pyridinyl)-3-oxopropanoate

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran at -50℃; for 0.5h;76%
With sodium hydride In N,N-dimethyl-formamide; toluene at 80℃; for 2.5h;
5470-70-2

Methyl 6-methylnicotinate

454-89-7

3-Trifluoromethylbenzaldehyde

methyl 6-{(E)-2-[3-(trifluoromethyl)phenyl]ethenyl}nicotinate

Conditions
ConditionsYield
With zinc(II) chloride In acetic anhydride at 140℃; for 12h;76%
5470-70-2

Methyl 6-methylnicotinate

5-Bromo-3,3-dihydroxy-1,3-dihydro-indol-2-one

6-(5-Bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-ylmethyl)-nicotinic acid methyl ester

Conditions
ConditionsYield
at 120℃; for 4h;75.9%
5470-70-2

Methyl 6-methylnicotinate

1001200-43-6

methyl 6-(dibromomethyl)pyridine-3-carboxylate

Conditions
ConditionsYield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Heating;75%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Heating;75%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Heating / reflux;19.4%
5470-70-2

Methyl 6-methylnicotinate

25015-63-8

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

1360145-70-5

methyl 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-methyl-1,2-dihydropyridine-3-carboxylate

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tricyclohexylphosphine In benzene-d6 at 50℃; for 24h; Inert atmosphere; regioselective reaction;75%
With P(C6H11)3; chloro(1,5-cyclooctadiene)rhodium(I) dimer In benzene-d6 ligand reacted with pinacolborane in C6D6 at 50°C for 24 h in presence of (Rh(C8H12)Cl)2 and P(C6H11)3; distilled;75%
5470-70-2

Methyl 6-methylnicotinate

100-10-7

4-dimethylamino-benzaldehyde

6-[(E)-2-(4-Dimethylamino-phenyl)-vinyl]-nicotinic acid methyl ester

Conditions
ConditionsYield
With piperidine; acetic acid In toluene for 72h; Knoevenagel reaction; Heating;74%
924-44-7

glyoxylic acid ethyl ester

5470-70-2

Methyl 6-methylnicotinate

1620675-63-9

(E)-methyl 6-(3-ethoxy-3-oxoprop-1-en-1-yl)nicotinate

Conditions
ConditionsYield
In acetic anhydride at 130℃; for 48h;73%
With acetic anhydride at 130℃; for 48h; Reflux;73%
In acetic anhydride at 130℃; for 48h;73%
With acetic anhydride at 130℃; for 48h;57 g
5470-70-2

Methyl 6-methylnicotinate

16188-55-9

2-(4-(methylthio)phenyl)acetic acid

221615-72-1

1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h;72%
Stage #1: 2-(4-(methylthio)phenyl)acetic acid With tert-butylmagnesium chloride In tetrahydrofuran at 60℃; for 1h; Flow reactor;
Stage #2: Methyl 6-methylnicotinate In tetrahydrofuran at 60℃; for 1h; Flow reactor;
Stage #3: With hydrogenchloride In water; toluene Temperature; Flow reactor;
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Chemistry

Molecular Structure of Methyl 6-methylnicotinate (CAS NO.5470-70-2):

IUPAC Name: methyl 6-methylpyridine-3-carboxylate
BRN: 122940
Empirical Formula: C8H9NO2
Molecular Weight: 151.1626
Packaging: 1.10 g in glass btl
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 2
Polar Surface Area: 39.19 Å2
Index of Refraction: 1.51
Molar Refractivity: 40.94 cm3
Molar Volume: 136.8 cm3
Surface Tension: 39.9 dyne/cm
Density: 1.104 g/cm3
Flash Point: 80.6 °C
Enthalpy of Vaporization: 46.5 kJ/mol
Boiling Point: 228.4 °C at 760 mmHg
Vapour Pressure: 0.0736 mmHg at 25°C
Melting point: 34-37 °C(lit.)
Product Categories: Carboxylicester; Acids and Derivatives; Heterocycles; Esters; Pyridines; Organic acids; Nicotine Derivatives; Pyridine

Safety Profile

Hazard Codes:  Xi
Risk Statements information :
36/37/38: Irritating to eyes, respiratory system and skin 
The Safety Statements information of Methyl-6-methylnictinate (CAS NO.5470-70-2):
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
WGK Germany: 3
Hazard Note: Irritant

Specification

  Methyl 6-methylnicotinate , with CAS number of 5470-70-2, can be called 3-pyridinecarboxylic acid, 6-methyl-, methyl ester ; 3-(Methoxycarbonyl)-6-methylpyridine ; 5-Methoxycarbonyl-2-methylpyridine ; 6-Methyl-3-pyridinecarboxylic acid methylester ; 6-Methylnicotinic acid methyl ester ; Methyl6-methyl-3-pyridinecarboxylate ; Methyl 6-methylaminonicotinate ; 6-Methyl nicotinic acid methyl ester . It is a brown solid.