36157-41-2

Basic information

• Product Name: 2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID
• Synonyms: AKOS 90171;2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID;2,5-DICHLORO-3-THIOPHENEFORMIC ACID;RARECHEM AL BE 1205;2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID, 98+%;3-Thiophenecarboxylicacid, 2,5-dichloro-;2,5-Dichlorothiophene-3-carboxylic acid 97%
• CAS NO: 36157-41-2
• Molecular Formula: C₅H₂Cl₂O₂S
• Molecular Weight: 197.04
• Product Categories: Halogenated Heterocycles;Heterocyclic Building Blocks;Thiophenes;ThiophenesBuilding Blocks
• Mol File: 36157-41-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 147-151 °C(lit.)
• Boiling Point: 296.6 °C at 760 mmHg
• Flash Point: 133.2 °C
• Appearance: /
• Density: 1.708 g/cm³
• Vapor Pressure: 0.000641mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 3.36±0.30(Predicted)
• BRN: 127865
• CAS DataBase Reference: 2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID(36157-41-2)
• EPA Substance Registry System: 2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID(36157-41-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 36157-41-2(Hazardous Substances Data)

Usage

General Description

2,5-Dichlorothiophene-3-carboxylic acid is a chemical compound with the molecular formula C6H3Cl2O2S. It is a derivative of thiophene, which is a heterocyclic compound containing a five-membered ring with four carbon atoms and one sulfur atom. 2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID is commonly used in the production of pharmaceuticals, agrochemicals, and other specialty chemicals. It is known for its potential as an intermediate in the synthesis of various biologically active molecules, and its structural nature allows it to be modified for specific applications. Additionally, 2,5-dichlorothiophene-3-carboxylic acid is also used as a precursor in the synthesis of materials for organic electronic devices and functional polymers.

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

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 articles and documents

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.

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.