Production Method 1

61341-26-2

81452-54-2

Reaction Conditions

1.1 Solvents: Methanol ;  4 h, rt → 45 °C

Reference

Development of potential manufacturing routes for substituted thiophenes - preparation of halogenated 2-thiophenecarboxylic acid derivatives as building blocks for a new family of 2,6-dihaloaryl 1,2,4-triazole insecticides

Hull, John W. Jr.; et al, Beilstein Journal of Organic Chemistry, 2007, 3,

Production Method 2

26137-08-6

80-48-8

81452-54-2

Reaction Conditions

1.1 Reagents: Tetrabutylammonium iodide ,  Zinc ,  Magnesium chloride Catalysts: 4,4′-Dimethyl-2,2′-bipyridine ,  Nickel iodide (NiI2) Solvents: Dimethylacetamide ;  12 h, rt

Reference

Nickel-catalyzed methylation of aryl halides/tosylates with methyl tosylate

Wang, Jiawang; et al, Chemical Communications (Cambridge, 2017, 53(73), 10180-10183

Production Method 3

181226-89-1

80-48-8

81452-54-2

Reaction Conditions

1.1 Reagents: Tetrabutylammonium iodide ,  Zinc ,  Magnesium chloride Catalysts: Triphenylphosphine ,  Dichloro[1,2-di(methoxy-κO)ethane]nickel Solvents: Dimethylacetamide ;  12 h, 25 °C

Reference

Nickel-catalyzed methylation of aryl halides/tosylates with methyl tosylate

Wang, Jiawang; et al, Chemical Communications (Cambridge, 2017, 53(73), 10180-10183

Production Method 4

14282-76-9

81452-54-2

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Tetrahydrofuran ;  < 40 °C; 60 min, 25 °C
1.2 0.1 h, 25 °C; 4 h, 25 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Development of potential manufacturing routes for substituted thiophenes - preparation of halogenated 2-thiophenecarboxylic acid derivatives as building blocks for a new family of 2,6-dihaloaryl 1,2,4-triazole insecticides

Hull, John W. Jr.; et al, Beilstein Journal of Organic Chemistry, 2007, 3,

Production Method 5

16494-40-9

81452-54-2

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Diethyl ether

Reference

A new synthesis of benzo[b]thiophenes and benzo[c]thiophenes by annulation of disubstituted thiophenes

Terpstra, Jan W.; et al, Journal of Organic Chemistry, 1986, 51(2), 230-8

Production Method 6

13679-72-6

81452-54-2

Reaction Conditions

1.1 Catalysts: Sodium hypobromite
2.1 Solvents: Methanol

Reference

Synthesis and properties of methyl 3,4-dihydro-4-oxo-1H-2-benzothiopyran-3-carboxylate and related thiopyrano compounds

Scrowston, Richard M.; et al, Journal of the Chemical Society, 1976, (7), 749-54

Production Method 7

23806-24-8

81452-54-2

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Dimethylformamide ,  1,2-Dichloroethane ;  2 h, reflux
2.1 Solvents: Methanol ;  4 h, rt → 45 °C

Reference

Development of potential manufacturing routes for substituted thiophenes - preparation of halogenated 2-thiophenecarboxylic acid derivatives as building blocks for a new family of 2,6-dihaloaryl 1,2,4-triazole insecticides

Hull, John W. Jr.; et al, Beilstein Journal of Organic Chemistry, 2007, 3,

Production Method 8

59201-85-3

62353-77-9

51202-29-0

81452-54-2

Reaction Conditions

1.1 Catalysts: Di-μ-chlorobis(η3-2-propenyl)dipalladium Solvents: Dimethylformamide

Reference

A convenient synthesis of substituted heteroaromatic compounds via the palladium-catalyzed cross-coupling reaction of organosilicon compounds

Hatanaka, Yasuo; et al, Heterocycles, 1990, 30(1), 303-6

Production Method 9

5834-16-2

81452-54-2

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Catalysts: Perchloric acid, iron(3+) salt, hydrate Solvents: Methanol ,  Water ;  4 h, 0 °C; 1 h, 0 °C; 0 °C → rt; 15 h, rt

Reference

Iron-catalyzed one-pot oxidative esterification of aldehydes

Wu, Xiao-Feng; et al, European Journal of Organic Chemistry, 2009, (8), 1144-1147

Production Method 10

81452-54-2

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Chloro(triphenylphosphine)gold ,  [1,1,1-Trifluoro-N-[(trifluoromethyl)sulfonyl-κO]methanesulfonamidato-κO]silver Solvents: Dichloromethane ;  10 min, 1 atm, rt
1.2 Reagents: Methanol ,  Oxygen Solvents: Dichloromethane ;  24 h, 1 atm, 25 °C

Reference

Gold-catalyzed oxidative cleavage of aryl-substituted alkynyl ethers using molecular oxygen. Simultaneous degradation of C-H and single and triple carbon-carbon bonds under ambient conditions

Das, Arindam; et al, Chemical Communications (Cambridge, 2009, (27), 4046-4048

Production Method 11

5118-06-9

81452-54-2

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  15 min, 0 °C; 0 °C → rt; 2 h, rt
2.1 Reagents: Tetrabutylammonium iodide ,  Zinc ,  Magnesium chloride Catalysts: Triphenylphosphine ,  Dichloro[1,2-di(methoxy-κO)ethane]nickel Solvents: Dimethylacetamide ;  12 h, 25 °C

Reference

Nickel-catalyzed methylation of aryl halides/tosylates with methyl tosylate

Wang, Jiawang; et al, Chemical Communications (Cambridge, 2017, 53(73), 10180-10183

Production Method 12

81452-54-2

Reaction Conditions

1.1 Reagents: Acetic anhydride ,  N-Bromosuccinimide Solvents: Acetic acid ;  rt → 44 °C; 20 min, rt
1.2 Reagents: Sodium bisulfite Solvents: Water ;  0 °C
2.1 Reagents: Magnesium Solvents: Tetrahydrofuran ;  < 40 °C; 60 min, 25 °C
2.2 0.1 h, 25 °C; 4 h, 25 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Development of potential manufacturing routes for substituted thiophenes - preparation of halogenated 2-thiophenecarboxylic acid derivatives as building blocks for a new family of 2,6-dihaloaryl 1,2,4-triazole insecticides

Hull, John W. Jr.; et al, Beilstein Journal of Organic Chemistry, 2007, 3,

Production Method 13

14282-78-1

23806-24-8

81452-54-2

28686-90-0

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Methanol

Reference

Synthesis of N-(methoxycarbonylthienylmethyl)thioureas and evaluation of their interaction with inducible and neuronal nitric oxide synthase

Suaifan, Ghadeer A. R. Y.; et al, Molecules, 2010, 15, 3121-3134

Production Method 14

81452-54-2

28686-90-0

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether ,  Hexane ;  0 °C; 3 h, 0 °C
1.2 Solvents: Diethyl ether ;  0 °C; 16 h, 0 °C
1.3 Reagents: Water ;  cooled

Reference

Synthesis of N-(methoxycarbonylthienylmethyl)thioureas and evaluation of their interaction with inducible and neuronal nitric oxide synthase

Suaifan, Ghadeer A. R. Y.; et al, Molecules, 2010, 15, 3121-3134

Methyl 3-methylthiophene-2-carboxylate Raw materials

• Methyl 3-bromothiophene-2-carboxylate
• 3-methylthiophene-2-carbaldehyde
• 2-iodo-3-methylthiophene
• Ethanaminium, N-[bis(diethylamino)-λ4-sulfanylidene]-N-ethyl-
• Methyl 3-Oodothiophene-2-carboxylate
• Methyl 3-{(4-Methylphenyl)sulfonyloxy}-2-thiophenecarboxylate
• 3-Hydroxy-2-thiophenecarboxylic Acid Methyl Ester
• 3-Methylthiophene-2-carbonyl chloride
• methyl 4-methylbenzene-1-sulfonate
• 2-Acetyl-3-methylthiophene
• 2-Bromo-3-methylthiophene
• 4-Methylthiophene-2-carboxylic acid
• 3-Methylthiophene-2-carboxylic acid
• Silicate(1-), difluorotrimethyl-

Methyl 3-methylthiophene-2-carboxylate Preparation Products

• Methyl 3-methylthiophene-2-carboxylate (81452-54-2)
• Methyl 4-methylthiophene-2-carboxylate (28686-90-0)

• 1. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130
• 2. Evolution of dealloying induced strain in nanoporous gold crystals?
  Ross Harder,David C. Dunand,Ian McNulty Nanoscale, 2017,9, 5686-5693
• 3. Dissociative dynamics of O2 on Ag(110)?
  Ivor Lon?ari? Phys. Chem. Chem. Phys., 2015,17, 9436-9445
• 4. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409
• 5. Excimer–monomer switch: a reaction-based approach for selective detection of fluoride?
  Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi Cao Analyst, 2014,139, 3588-3592

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Thiophenes Thiophene carboxylic acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 391936-75-7(2-Thiophenecarboxylicacid, 5-formyl-4-methyl-, methyl ester)
• 21676-89-1(3-Phenylthiophene-2-carboxylic Acid Methyl Ester)
• 57041-28-8(2-Thiophenecarboxylic acid, 3,5-dimethyl-, methyl ester)
• 14300-68-6(dimethyl thiophene-2,3-dicarboxylate)
• 22099-17-8(2-Thiophenecarboxylic acid, 3,4-diphenyl-, methyl ester)
• 23806-22-6(2-Thiophenecarboxylic acid, 3,4-dimethyl-, ethyl ester)
• 33668-06-3(2-Thiophenecarboxylic acid, 3,4-dimethyl-, methyl ester)
• 168850-69-9(Methyl 4,5-dimethylthiophene-2-carboxylate)
• 14300-64-2(Ethyl 3-methylthiophene-2-carboxylate)
• 115777-72-5(2-(Methoxycarbonyl)thiophene-3-carboxylic acid)