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13602-11-4

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13602-11-4 Usage

Uses

Methyl 6-Methylpyridine-2-carboxylate is a reagent used in the sunthesis of antitumor agents based upon the dihydropyrrolopyrazole compounds. Also used in the synthesis of quinazolinone TGF-β inhibitors.

Check Digit Verification of cas no

The CAS Registry Mumber 13602-11-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,6,0 and 2 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 13602-11:
(7*1)+(6*3)+(5*6)+(4*0)+(3*2)+(2*1)+(1*1)=64
64 % 10 = 4
So 13602-11-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO2/c1-6-4-3-5-7(9-6)8(10)11-2/h3-5H,1-2H3

13602-11-4 Well-known Company Product Price

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  • Alfa Aesar

  • (H33571)  Methyl 6-methylpyridine-2-carboxylate, 96%   

  • 13602-11-4

  • 250mg

  • 450.0CNY

  • Detail
  • Alfa Aesar

  • (H33571)  Methyl 6-methylpyridine-2-carboxylate, 96%   

  • 13602-11-4

  • 1g

  • 1254.0CNY

  • Detail

13602-11-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl 6-methylpyridine-2-carboxylate

1.2 Other means of identification

Product number -
Other names Methyl 6-Methylpicolinate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13602-11-4 SDS

13602-11-4Synthetic route

methanol
67-56-1

methanol

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

6-methyl-2-pyridinecarboxylic acid

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

Conditions
ConditionsYield
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%
6-methyl-2-pyridinecarboxylic acid
934-60-1

6-methyl-2-pyridinecarboxylic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

Conditions
ConditionsYield
In methanol; diethyl ether; dichloromethane at 20℃; for 0.5h;91%
2-bromo-6-methylpyridine
5315-25-3

2-bromo-6-methylpyridine

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; palladium diacetate at 65℃;60%
6-methyl-2-pyridinecarboxylic acid
934-60-1

6-methyl-2-pyridinecarboxylic acid

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

methanol
67-56-1

methanol

6-methyl-picolinic acid

6-methyl-picolinic acid

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid
methanol
67-56-1

methanol

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

6-methyl-pyridine-2-carbonyl chloride

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

Conditions
ConditionsYield
With sodium methylate for 4h; Inert atmosphere; Reflux;
6-methyl-2-pyridinecarboxylic acid
934-60-1

6-methyl-2-pyridinecarboxylic acid

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 1 h / Inert atmosphere; Reflux
2: sodium methylate / 4 h / Inert atmosphere; Reflux
View Scheme
carbon dioxide
124-38-9

carbon dioxide

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

2-methyl-6-(trimethylsilyl)-pyridine

methyl iodide
74-88-4

methyl iodide

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

Conditions
ConditionsYield
With tetrabutylammonium triphenyldifluorosilicate In tetrahydrofuran-d8 at 20℃; under 750.075 Torr; for 18h; Inert atmosphere; Schlenk technique;> 97 %Spectr.
2-bromo-6-methylpyridine
5315-25-3

2-bromo-6-methylpyridine

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

Conditions
ConditionsYield
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
2,6-dimethylpyridine
108-48-5

2,6-dimethylpyridine

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

Conditions
ConditionsYield
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
6-hydroxy-2-methylpyridine
3279-76-3

6-hydroxy-2-methylpyridine

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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
6-methylpyridin-2-yl fluorosulfate

6-methylpyridin-2-yl fluorosulfate

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

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

Conditions
ConditionsYield
With platinum(IV) oxide; palladium 10% on activated carbon; hydrogen; acetic acid at 20℃; for 24h;97%
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

6-methyl-2-picolinic acid hydrazide

Conditions
ConditionsYield
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%
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

methylamine
74-89-5

methylamine

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

N,6-dimethylpyridine-2-carboxamide

Conditions
ConditionsYield
In methanol at 20℃; for 72h;92%
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

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

Conditions
ConditionsYield
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%
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

4-methylquinoline-6-carbonitrile

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

4-(2-(6-methylpyridin-2-yl)-2-oxoethyl)quinoline-6-carbonitrile

Conditions
ConditionsYield
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%
methanol
67-56-1

methanol

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

4,6-dimethyl-pyridine-2-carboxylic acid methyl ester

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;81%
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

3,5-dimethyl-4-nitro-1H-pyrazole

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

methyl 6-(bromomethyl)picolinate

Conditions
ConditionsYield
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%
2-methyl-[1,5]naphthyridine
7675-32-3

2-methyl-[1,5]naphthyridine

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

1-(6-methylpyridin-2-yl)-2-(1,5-naphthyridin-2-yl)ethan-1-one

Conditions
ConditionsYield
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%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

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

Conditions
ConditionsYield
With sodium ethanolate In toluene75%
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

acetophenone
98-86-2

acetophenone

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

2-methyl-6-(5-phenyl-1H-pyrazol-3-yl)pyridine

Conditions
ConditionsYield
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%
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

4-methyl-6-bromoquinoline

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

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

Conditions
ConditionsYield
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%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

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

Conditions
ConditionsYield
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%
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

4-methyl-6-(trifluoromethoxy)quinoline

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

1-(6-methylpyridin-2-yl)-2-(6-(trifluoromethoxy)quinolin-4-yl)ethanone

Conditions
ConditionsYield
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%
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
With sodium ethanolate In ethyl acetate Acidic conditions;68%
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

methyl 6-(bromomethyl)picolinate

Conditions
ConditionsYield
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%
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

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

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

Conditions
ConditionsYield
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%

13602-11-4Relevant articles and documents

A two-in-one pincer ligand and its diiron(II) complex showing spin state switching in solution through reversible ligand exchange

Samanta, Subhas,Demesko, Serhiy,Dechert, Sebastian,Meyer, Franc

, p. 583 - 587 (2015)

A novel pyrazolate-bridged ligand providing two {PNN} pincer-type compartments has been synthesized. Its diiron(II) complex LFe2(OTf)3(CH3CN) (1; Tf=triflate) features, in solid state, two bridging triflate ligands, with a terminal triflate and a MeCN ligand completing the octahedral coordination spheres of the two high-spin metalions. In MeCN solution, 1 is shown to undergo a sequential, reversible, and complete spin transition to the low-spin state upon cooling. Detailed UV/Vis and 19F NMR spectroscopic studies as well as magnetic measurements have unraveled that spin state switching correlates with a rapid multistep triflate/MeCN ligand exchange equilibrium. The spin transition temperature can be continuously tuned by varying the triflate concentration in solution.

Nickel-catalyzed carboxylation of aryl and heteroaryl fluorosulfates using carbon dioxide

Ma, Cong,Zhao, Chuan-Qi,Xu, Xue-Tao,Li, Zhao-Ming,Wang, Xiang-Yang,Zhang, Kun,Mei, Tian-Sheng

, p. 2464 - 2467 (2019/04/10)

The development of efficient and practical methods to construct carboxylic acids using CO2 as a C1 synthon is of great importance. Nickel-catalyzed carboxylation of aryl fluorosulfates and heteroaryl fluorosulfates with CO2 is described, affording arene carboxylic acids with good to excellent yields under mild conditions. In addition, a one-pot phenol fluorosulfation/carboxylation is developed.

Polysubstituted pyridine medical intermediate and synthetic method thereof

-

, (2016/10/08)

The invention belongs to the field of medicine intermediate technology, and specifically relates to a polysubstituted pyridine medical intermediate and a synthetic method thereof. The polysubstituted pyridine medical intermediate is a key intermediate in pharmaceutical synthesis, and has a huge market potential. The synthetic method has simple synthetic route, simple and easily available staring material, and has great meaning in synthesis of pyridine intermediate, development of pyridine medicament and research and development of novel medicament, and the product is cheap.

CO2 Conversion into Esters by Fluoride-Mediated Carboxylation of Organosilanes and Halide Derivatives

Frogneux, Xavier,Von Wolff, Niklas,Thuéry, Pierre,Lefèvre, Guillaume,Cantat, Thibault

, p. 2930 - 2934 (2016/03/25)

A one-step conversion of CO2 into heteroaromatic esters is presented under metal-free conditions. Using fluoride anions as promoters for the C-Si bond activation, pyridyl, furanyl, and thienyl organosilanes are successfully carboxylated with CO2 in the presence of an electrophile. The mechanism of this unprecedented reaction has been elucidated based on experimental and computational results, which show a unique catalytic influence of CO2 in the C-Si bond activation of pyridylsilanes. The methodology is applied to 18 different esters, and it has enabled the incorporation of CO2 into a polyester material for the first time. Metal free! A novel methodology is described to convert CO2 into heteroaromatic esters in the presence of organosilanes and organic halides using fluoride anions as promoters for the C-Si bond activation (see scheme). CO2 exhibits a unique catalytic influence in the C-Si bond cleavage of pyridylsilanes, serving as a traceless activator.

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