36157-41-2

Usage

Uses

Used in Pharmaceutical Industry:
2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID is used as an intermediate in the synthesis of pharmaceuticals for its ability to be modified to create biologically active molecules, contributing to the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID is utilized as a precursor in the production of agrochemicals, playing a role in the creation of compounds that can enhance crop protection and yield.
Used in Organic Electronic Devices:
2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID is used as a precursor in the synthesis of materials for organic electronic devices, leveraging its chemical properties to develop functional components in electronic systems.
Used in Functional Polymers:
2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID is also employed in the synthesis of functional polymers, where its unique structure allows for the creation of polymers with specific properties for various applications in materials science.

InChI:InChI=1/C5H2Cl2O2S/c6-3-1-2(5(8)9)4(7)10-3/h1H,(H,8,9)/p-1

Synthetic route

2,5-diclorothiophene (3172-52-9) → 2,5-dichlorothiophene-3-carboxylic acid (36157-41-2)

Conditions	Yield
With palladium diacetate; sodium persulfate In acetic acid at 70 - 80℃; for 7h;	1.6%

2,5-dichlorothiophene-4-carboxaldehyde (61200-60-0) → 2,5-dichlorothiophene-3-carboxylic acid (36157-41-2)

Conditions	Yield
With silver(l) oxide

2-chlorothiophene-4-carboxylic acid (36157-42-3) → 2,5-dichlorothiophene-3-carboxylic acid (36157-41-2)

Conditions	Yield
With chlorine; acetic acid

2-chlorothiophene-3-carboxylic acid (53935-71-0) → 2,5-dichlorothiophene-3-carboxylic acid (36157-41-2)

Conditions	Yield
With chlorine; acetic acid

3-acetyl-2,5-dichlorothiophene (36157-40-1) → 2,5-dichlorothiophene-3-carboxylic acid (36157-41-2)

Conditions	Yield
With sodium hypochlorite
With sodium hypochlorite In water at 55℃;

3-Thiophene carboxylic acid (88-13-1) → 2,5-dichlorothiophene-3-carboxylic acid (36157-41-2)

Conditions	Yield
With chlorine; acetic acid
Multi-step reaction with 2 steps 1: acetic acid; chlorine 2: acetic acid; chlorine View Scheme

thiophene-3-carboxylic acid ethyl ester (5751-80-4) + ethyl 2,5-dichlorothiophene-3-carboxylate (130562-95-7) + sodium thiosulfate → 2,5-dichlorothiophene-3-carboxylic acid (36157-41-2)

Conditions	Yield
With sodium hydroxide; sulfuryl dichloride In tetrahydrofuran; ethanol; acetonitrile

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → 2,5-dichlorothiophene-3-carbonyl chloride (57248-14-3)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2.5h;	100%
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2.5h;	100%
With thionyl chloride In chloroform for 2h; Heating;
With thionyl chloride In benzene for 6h; Reflux;
With thionyl chloride at 60℃; for 1h;

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) + 4-chloro-aniline (106-47-8) → 2,5-dichloro-N-(4-chlorophenyl)thiophene-3-carboxamide

Conditions	Yield
Stage #1: 2,5-dichlorothiophene-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: 4-chloro-aniline In N,N-dimethyl-formamide at 20℃;	95%

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) + 4-fluoroaniline (371-40-4) → 2,5-dichloro-N-(4-fluorophenyl)thiophene-3-carboxamide

Conditions	Yield
Stage #1: 2,5-dichlorothiophene-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: 4-fluoroaniline In N,N-dimethyl-formamide at 20℃;	91%

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) + 4-(N,N-diethylaminosulfonyl)aniline (1709-39-3) → 2,5-dichloro-N-(4-(N,N-diethylsulfamoyl)phenyl)thiophene-3-carboxamide

Conditions	Yield
Stage #1: 2,5-dichlorothiophene-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: 4-(N,N-diethylaminosulfonyl)aniline In N,N-dimethyl-formamide at 20℃;	87%

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → 3-carboxy-2,5-dichlorothiophene 1,1-dioxide

Conditions	Yield
With trifluoroacetyl peroxide In acetonitrile for 4h;	80%

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) + aniline (62-53-3) → 2,5-dichloro-N-phenylthiophene-3-carboxamide

Conditions	Yield
Stage #1: 2,5-dichlorothiophene-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: aniline In N,N-dimethyl-formamide at 20℃;	80%

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) + 2-Chloroaniline (95-51-2) → 2,5-dichloro-N-(2-chlorophenyl)thiophene-3-carboxamide

Conditions	Yield
Stage #1: 2,5-dichlorothiophene-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: o-chloroaniline In N,N-dimethyl-formamide at 20℃;	67%

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) + N-(2-(pyridin-2-yl)propan-2-yl)benzamide → 2-(2,5-dichlorothiophen-3-yl)-N-(2-(pyridin-2-yl)propan-2-yl)benzamide

Conditions	Yield
With copper (I) acetate; lithium carbonate; silver nitrate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Sealed tube;	66%

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → 2,5-dichloro-4-nitrothiophene-3-carboxylic acid

Conditions	Yield
With sulfuric acid; nitric acid at -10 - 20℃; for 3h;	66%

N-methyl-N-(3-pyridyl)amine (18364-47-1) + 2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → 2,5-dichlorothiophene-3-carboxylic acid methylpyridin-3-yl-amide (1366573-63-8)

Conditions	Yield
Stage #1: 2,5-dichlorothiophene-3-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 4h; Stage #2: N-methyl-N-(3-pyridyl)amine With triethylamine In dichloromethane at 20℃;	65%

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → 2,5-diclorothiophene (3172-52-9) + 2,2',5,5'-tetrachloro-3,3'-bithiophene (57308-99-3)

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 16h; Inert atmosphere;	A n/a B 57%

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) + tert-butyl alcohol (75-65-0) → tert‐butyl N‐(2,5‐dichlorothiophen‐3‐yl)carbamate

Conditions	Yield
With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine at 90℃; for 12h;	56%

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) + sulphaacetamide (144-80-9) → N-(4-(N-acetylsulfamoyl)phenyl)-2,5-dichlorothiophene-3-carboxamide

Conditions	Yield
Stage #1: 2,5-dichlorothiophene-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: sulphaacetamide In N,N-dimethyl-formamide at 20℃;	50%

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → 3-hydroxymethyl-thiophene (71637-34-8)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → 2,5-dichloro-thiophene-3-carboxylic acid amide

Conditions	Yield
With thionyl chloride Behandeln des erhaltenen Saeurechlorids mit wss. Ammoniak;

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → 3-Thiophene carboxylic acid (88-13-1)

Conditions	Yield
With palladium on activated charcoal Hydrogenation;

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) + 5-n-butyl-2,4-dihydro-4-<(2'-sulfamoylbiphenyl-4-yl)methyl>-2-<2-(trifluoromethyl)phenyl>-3H-1,2,4-triazol-3-one (147776-47-4) → 4'-[3-Butyl-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid (2,5-dichloro-thiophene-3-carbonyl)-amide

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole 1.) THF, 55 deg C, 2 h, 2.) THF, 55 deg C, overnight; Yield given. Multistep reaction;

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) + diethyl ether (60-29-7) + lithium alanate → 3-hydroxymethyl-thiophene (71637-34-8)

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → 2,5-dichloro-thiophene-3-carboxylic acid methoxy-methyl-amide (210097-99-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / CHCl3 / 2 h / Heating 2: Et3N / CHCl3 / 0 - 20 °C View Scheme

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → 4-(2,5-dichloro-thiophen-3-ylmethyl)-1H-imidazole

Conditions	Yield
Multi-step reaction with 5 steps 1: SOCl2 / CHCl3 / 2 h / Heating 2: Et3N / CHCl3 / 0 - 20 °C 3: CH2Cl2 / 20 °C 4: NaBH4 / propan-2-ol / 2 h / Heating 5: NaBH4; TFA / 0 - 20 °C View Scheme

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → (2,5-dichloro-thiophen-3-yl)-(1-trityl-1H-imidazol-4-yl)-methanol (334918-23-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2 / CHCl3 / 2 h / Heating 2: Et3N / CHCl3 / 0 - 20 °C 3: CH2Cl2 / 20 °C 4: NaBH4 / propan-2-ol / 2 h / Heating View Scheme

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → (2,5-dichloro-thiophen-3-yl)-(1-trityl-1H-imidazol-4-yl)-methanone (334918-28-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 / CHCl3 / 2 h / Heating 2: Et3N / CHCl3 / 0 - 20 °C 3: CH2Cl2 / 20 °C View Scheme

2,5-dichlorothiophene-3-carboxylic acid (36157-41-2) → [1]naphthyl-carbamic acid-[3]thienylmethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium alanate; diethyl ether View Scheme

Upstream product

• 61200-60-0 2,5-dichlorothiophene-4-carboxaldehyde 
• 36157-42-3 2-chlorothiophene-4-carboxylic acid 
• 53935-71-0 2-chlorothiophene-3-carboxylic acid 
• 36157-40-1 3-acetyl-2,5-dichlorothiophene 
• 88-13-1 3-Thiophene carboxylic acid 
• 3172-52-9 2,5-diclorothiophene 
• 5751-80-4 thiophene-3-carboxylic acid ethyl ester 
• 130562-95-7 ethyl 2,5-dichlorothiophene-3-carboxylate 

Downstream Products

• 3172-52-9 2,5-diclorothiophene 
• 57308-99-3 2,2',5,5'-tetrachloro-3,3'-bithiophene 
• 1418130-85-4 2,5-dichloro-N-(2-hydroxy-4-methyl-phenyl)thiophene-3-carboxamide 
• 334918-28-4 (2,5-dichloro-thiophen-3-yl)-(1-trityl-1H-imidazol-4-yl)-methanone 

Relevant academic research and scientific papers

Facile synthesis of 2-(substituted amino)-4H-thieno[3,2-e]-1,3-thiazin-4- ones

Interaction between 2,5-dichlorothiophene-3-carbonyl isothiocyanate, accessible via 2,5-dichlorothiophene-3-carbonyl chloride, and model heterocyclic amines produced the respective 2,5-dichloro-N-(substituted aminocarbonothioyl) thiophene-3-carboxamides. Upon heating, the deprotonated form of the latter underwent intramolecular cyclization to deliver the corresponding 2-(substituted amino)-4H-thieno[3,2-e]-1,3-thiazin-4-ones. The structures of these new bicyclic derivatives and their acyclic precursors are based on microanalytical and spectral (IR, MS, and NMR) data.

Phosphorylamides, their preparation and use

A phosphorylamide derivative represented by the general formula (I): STR1 wherein R represents an amino group that may be substituted, or a salt thereof, possesses potent antibacterial activity against Helicobacter bacterium, especially Helicobacter pylori, and is useful for prevention or treatment of digestive diseases caused by Helicobacter bacterium, solely or in combination with an antacid or an acid secretion inhibitor.

CARBOXYLATION OF 1,3-DIMETHYLURACIL AND THIOPHENES WITH CARBON MONOXIDE AND PALLADIUM(II) ACETATE IN THE PRESENCE OF SODIUM PEROXODISULFATE

Treatments of 1,3-dimethyluracil and of thiophenes with palladium(II) acetate and sodium peroxodisulfate under a carbon monoxide atmosphere gave 1,3-dimethyluracil-5-carboxylic acid and the corresponding thiophene-2-carboxylic acids, respectively.