Methyl 6-methyl-2-pyridinecarboxylate supplier

Name
methyl 6-methylpyridine-2-carboxylate
EINECS 237-085-0
CAS No. 13602-11-4
Article Data24
CAS DataBase
Density 1.105 g/cm³
Solubility
Melting Point 18 °C
Formula C₈H₉NO₂
Boiling Point 242.053 °C at 760 mmHg
Molecular Weight 151.165
Flash Point 100.19 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Picolinicacid, 6-methyl-, methyl ester (7CI,8CI);6-Methylpicolinic acid methyl ester;6-Methylpyridin-2-carboxylic acid methyl ester;6-Methylpyridine-2-carboxylicacid methyl ester;Methyl6-methylpicolinate;NSC 109151;
PSA 39.19000
LogP 1.17660

Synthetic route

: 67-56-1
methanol

: 934-60-1
6-methyl-2-pyridinecarboxylic acid

: 13602-11-4
6-methylpicolinic acid methyl ester

Conditions

Conditions	Yield
Stage #1: methanol In thionyl chloride at -10 - 20℃; for 1h; Stage #2: 6-methyl-2-pyridinecarboxylic acid In thionyl chloride at 80℃; for 5h; Time;	93%
Stage #1: methanol; 6-methyl-2-pyridinecarboxylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Stage #2: at 20℃; for 6h;	92%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6h;	92%

: 934-60-1
6-methyl-2-pyridinecarboxylic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 13602-11-4
6-methylpicolinic acid methyl ester

Conditions

Conditions	Yield
In methanol; diethyl ether; dichloromethane at 20℃; for 0.5h;	91%

: 5315-25-3
2-bromo-6-methylpyridine

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 13602-11-4
6-methylpicolinic acid methyl ester

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; palladium diacetate at 65℃;	60%

...Expand

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

: 934-60-1
6-methyl-2-pyridinecarboxylic acid

: 13602-11-4
6-methylpicolinic acid methyl ester

: 67-56-1
methanol

6-methyl-picolinic acid: 6-methyl-picolinic acid

: 13602-11-4
6-methylpicolinic acid methyl ester

Conditions

Conditions	Yield
With sulfuric acid

: 67-56-1
methanol

: 126125-54-0
6-methyl-pyridine-2-carbonyl chloride

: 13602-11-4
6-methylpicolinic acid methyl ester

Conditions

Conditions	Yield
With sodium methylate for 4h; Inert atmosphere; Reflux;

: 934-60-1
6-methyl-2-pyridinecarboxylic acid

: 13602-11-4
6-methylpicolinic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 1 h / Inert atmosphere; Reflux 2: sodium methylate / 4 h / Inert atmosphere; Reflux View Scheme

: 124-38-9
carbon dioxide

: 13737-10-5
2-methyl-6-(trimethylsilyl)-pyridine

: 74-88-4
methyl iodide

: 13602-11-4
6-methylpicolinic acid methyl ester

Conditions

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate In tetrahydrofuran-d8 at 20℃; under 750.075 Torr; for 18h; Inert atmosphere; Schlenk technique;	> 97 %Spectr.

...Expand

: 5315-25-3
2-bromo-6-methylpyridine

: 13602-11-4
6-methylpicolinic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / diethyl ether; hexane / 1 h / -78 °C / Inert atmosphere; Schlenk technique 1.2: 18 h / -78 - 20 °C / Inert atmosphere; Schlenk technique 2.1: tetrabutylammonium triphenyldifluorosilicate / tetrahydrofuran-d8 / 18 h / 20 °C / 750.08 Torr / Inert atmosphere; Schlenk technique View Scheme

: 108-48-5
2,6-dimethylpyridine

: 13602-11-4
6-methylpicolinic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium permanganate / water-d2 / 5 h / 20 - 60 °C 2.1: thionyl chloride / 1 h / -10 - 20 °C 2.2: 5 h / 80 °C View Scheme

: 3279-76-3
6-hydroxy-2-methylpyridine

: 13602-11-4
6-methylpicolinic acid methyl ester

Conditions

Conditions	Yield
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

: 6-methylpyridin-2-yl fluorosulfate

: 13602-11-4
6-methylpicolinic acid methyl ester

Conditions

Conditions	Yield
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

: 13602-11-4
6-methylpicolinic acid methyl ester

: methyl (2R*,6R*)-6-methylpiperidine-2-carboxylate

Conditions

Conditions	Yield
With platinum(IV) oxide; palladium 10% on activated carbon; hydrogen; acetic acid at 20℃; for 24h;	97%

: 13602-11-4
6-methylpicolinic acid methyl ester

: 98547-86-5
6-methyl-2-picolinic acid hydrazide

Conditions

Conditions	Yield
With hydrazine In methanol at 20℃; for 0.5h;	94%
With hydrazine In methanol at 20℃; for 18h;	93%
With hydrazine hydrate In ethanol for 1.5h; Reflux;	71%

: 13602-11-4
6-methylpicolinic acid methyl ester

: 74-89-5
methylamine

: 107427-69-0
N,6-dimethylpyridine-2-carboxamide

Conditions

Conditions	Yield
In methanol at 20℃; for 72h;	92%

: 75-97-8
3,3-dimethyl-butan-2-one

: 13602-11-4
6-methylpicolinic acid methyl ester

: 2‐(5‐(tert‐butyl)‐1H‐pyrazol‐3‐yl)‐6‐methylpyridine

Conditions

Conditions	Yield
Stage #1: 3,3-dimethyl-butan-2-one With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; Schlenk technique; Reflux; Stage #2: 6-methylpicolinic acid methyl ester In tetrahydrofuran; mineral oil for 4h; Reflux; Inert atmosphere; Schlenk technique; Further stages;	85%

: 13602-11-4
6-methylpicolinic acid methyl ester

: 924962-08-3
4-methylquinoline-6-carbonitrile

: 924898-11-3
4-(2-(6-methylpyridin-2-yl)-2-oxoethyl)quinoline-6-carbonitrile

Conditions

Conditions	Yield
Stage #1: 4-methylquinoline-6-carbonitrile With sodium t-butanolate In tetrahydrofuran at 5 - 25℃; for 0.5h; Stage #2: 6-methylpicolinic acid methyl ester In tetrahydrofuran at 20 - 25℃; for 2.33333 - 2.66667h; Product distribution / selectivity;	81%

: 67-56-1
methanol

: 13602-11-4
6-methylpicolinic acid methyl ester

: 69971-38-6
4,6-dimethyl-pyridine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
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;	81%

: 13602-11-4
6-methylpicolinic acid methyl ester

: 14531-55-6
3,5-dimethyl-4-nitro-1H-pyrazole

: 146462-25-1
methyl 6-(bromomethyl)picolinate

Conditions

Conditions	Yield
Stage #1: 6-methylpicolinic acid methyl ester With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 70℃; for 2h; Stage #2: 3,5-dimethyl-4-nitro-1H-pyrazole With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 12h;	79%

: 7675-32-3
2-methyl-[1,5]naphthyridine

: 13602-11-4
6-methylpicolinic acid methyl ester

: 446297-56-9
1-(6-methylpyridin-2-yl)-2-(1,5-naphthyridin-2-yl)ethan-1-one

Conditions

Conditions	Yield
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78 - 20℃; for 21h;	76%
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78 - 21℃; for 21h; Inert atmosphere;	30.5%
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78 - 21℃; for 21h; Inert atmosphere;	30.5%
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78 - 21℃; for 21h; Inert atmosphere;	30.5%
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78 - 21℃; for 21.0833h; Inert atmosphere;	30.5%

: 6940-57-4
2-acetyl-6-methylpyridine

: 13602-11-4
6-methylpicolinic acid methyl ester

: 93733-12-1
1,3-bis-(6-methyl-pyridin-2-yl)-propane-1,3-dione

Conditions

Conditions	Yield
With sodium ethanolate In toluene	75%

: 13602-11-4
6-methylpicolinic acid methyl ester

: 98-86-2
acetophenone

: 284490-39-7
2-methyl-6-(5-phenyl-1H-pyrazol-3-yl)pyridine

Conditions

Conditions	Yield
Stage #1: acetophenone With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; Schlenk technique; Reflux; Stage #2: 6-methylpicolinic acid methyl ester In tetrahydrofuran; mineral oil for 4h; Reflux; Inert atmosphere; Schlenk technique; Further stages;	75%

: 13602-11-4
6-methylpicolinic acid methyl ester

: 41037-28-9
4-methyl-6-bromoquinoline

: 2-(6-bromoquinolin-4-yl)-1-(6-methylpyridin-2-yl)ethan-1-one

Conditions

Conditions	Yield
Stage #1: 6-bromo-4-methylquinoline With potassium hexamethylsilazane In tetrahydrofuran at -70 - -65℃; for 3h; Stage #2: 6-methylpicolinic acid methyl ester In tetrahydrofuran at -70 - 20℃; for 7h;	73.8%
Stage #1: 6-bromo-4-methylquinoline With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 3h; Inert atmosphere; Stage #2: 6-methylpicolinic acid methyl ester In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	53%
Stage #1: 6-bromo-4-methylquinoline With potassium hexamethylsilazane In tetrahydrofuran at -65 - -60℃; Stage #2: 6-methylpicolinic acid methyl ester In tetrahydrofuran at -65 - -60℃; Further stages.;	50%

: 4926-28-7
2-Bromo-4-picoline

: 13602-11-4
6-methylpicolinic acid methyl ester

: 446880-80-4
2-(2-bromopyridin-4-yl)-1-(6-methylpyridin-2-yl)ethan-1-one

Conditions

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran at -30 - 20℃;	70%
Stage #1: 2-Bromo-4-picoline With sodium hexamethyldisilazane In tetrahydrofuran at -30℃; for 1h; Stage #2: 6-methylpicolinic acid methyl ester In tetrahydrofuran at 20℃;	70%
Stage #1: 2-Bromo-4-picoline With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: 6-methylpicolinic acid methyl ester In tetrahydrofuran at 21℃; for 16h; Inert atmosphere;	65.4%

: 13602-11-4
6-methylpicolinic acid methyl ester

: 476471-93-9
4-methyl-6-(trifluoromethoxy)quinoline

: 476472-32-9
1-(6-methylpyridin-2-yl)-2-(6-(trifluoromethoxy)quinolin-4-yl)ethanone

Conditions

Conditions	Yield
Stage #1: 4-methyl-6-(trifluoromethoxy)quinoline With potassium hexamethylsilazane In tetrahydrofuran at -65 - -60℃; Stage #2: 6-methylpicolinic acid methyl ester In tetrahydrofuran at -65 - -60℃; Further stages.;	69%

: 13602-11-4
6-methylpicolinic acid methyl ester

: 6940-57-4
2-acetyl-6-methylpyridine

Conditions

Conditions	Yield
With sodium ethanolate In ethyl acetate Acidic conditions;	68%

: 13602-11-4
6-methylpicolinic acid methyl ester

: 146462-25-1
methyl 6-(bromomethyl)picolinate

Conditions

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 5h; Reflux;	66%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 48℃; for 5h; Wohl-Ziegler Bromination;	66%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 12h; Inert atmosphere; Reflux;	51.3%

: 13602-11-4
6-methylpicolinic acid methyl ester

: 2-(7-bromo-quinolin-4-yl)-1-(6-methyl-pyridin-2-yl)-ethanone

Conditions

Conditions	Yield
Stage #1: 7-bromo-4-methylquinoline With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: 6-methylpicolinic acid methyl ester In tetrahydrofuran at -78℃; for 2h; Stage #3: at 0 - 20℃; for 2h;	66%

Methyl 6-methyl-2-pyridinecarboxylate Specification

The 2-Pyridinecarboxylicacid, 6-methyl-, methyl ester is an organic compound with the formula C₈H₉NO₂. The IUPAC name of this chemical is methyl 6-methylpyridine-2-carboxylate. With the CAS registry number 13602-11-4, it is also named as 6-Methyl-pyridine-2-carboxylic acid methyl ester. The product's categories are Carboxylicester; Glycinescaffold.

Physical properties about 2-Pyridinecarboxylicacid, 6-methyl-, methyl ester are: (1)ACD/LogP: 1.01; (2)ACD/LogD (pH 5.5): 1.006; (3)ACD/LogD (pH 7.4): 1.007; (4)ACD/BCF (pH 5.5): 3.427; (5)ACD/BCF (pH 7.4): 3.427; (6)ACD/KOC (pH 5.5): 84.032; (7)ACD/KOC (pH 7.4): 84.055; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 39.19 Å²; (11)Index of Refraction: 1.51; (12)Molar Refractivity: 40.942 cm³; (13)Molar Volume: 136.825 cm³; (14)Polarizability: 16.231×10^-24cm³; (15)Surface Tension: 39.916 dyne/cm; (16)Density: 1.105 g/cm³; (17)Flash Point: 100.19 °C; (18)Enthalpy of Vaporization: 47.902 kJ/mol; (19)Boiling Point: 242.053 °C at 760 mmHg; (20)Vapour Pressure: 0.035 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc1cccc(n1)C(=O)OC
(2)InChI: InChI=1/C8H9NO2/c1-6-4-3-5-7(9-6)8(10)11-2/h3-5H,1-2H3
(3)InChIKey: CYWIZMOZBTXFIL-UHFFFAOYAU
(4)Std. InChI: InChI=1S/C8H9NO2/c1-6-4-3-5-7(9-6)8(10)11-2/h3-5H,1-2H3
(5)Std. InChIKey: CYWIZMOZBTXFIL-UHFFFAOYSA-N

Product Name

methyl 6-methylpyridine-2-carboxylate

Synthetic route

Methyl 6-methyl-2-pyridinecarboxylate Specification

Related Products

Hot Products