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Basic Information
CAS No.: 24065-33-6
Name: 5-Chlorothiophene-2-carboxylic acid
Article Data: 32
Molecular Structure:
Molecular Structure of 24065-33-6 (5-Chlorothiophene-2-carboxylic acid)
Formula: C5H3ClO2S
Molecular Weight: 162.597
Synonyms: 2-Chlorothiophene-5-Formic Acid;5-18-06-00177 (Beilstein Handbook Reference);2-Thiophenecarboxylic acid, 5-chloro-;5-Chloro-2-thiophenecarboxylic acid;5-chlorothiophene-2-carboxylate;
EINECS: -0
Density: 1.572 g/cm3
Melting Point: 154-158 °C(lit.)
Boiling Point: 287 °C at 760 mmHg
Flash Point: 127.4 °C
Appearance: White to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
PSA: 65.54000
LogP: 2.09970
Synthetic route
7283-96-7

5-Chloro-2-thiophenecarboxaldehyde

24065-33-6

5-Chlorothiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-Chloro-2-thiophenecarboxaldehyde With sodium hydroxide at -5 - 0℃; for 2h; Large scale;
Stage #2: With chlorine at 15 - 30℃; for 8h; Large scale;
98.8%
With tert.-butylhydroperoxide In dichloromethane at 35 - 40℃; for 4h; Reagent/catalyst; Temperature;96%
With 1,4-dithio-D,L-threitol; recombinant aldehyde dehydrogenase from bovine lens; water‐forming NADH oxidase from Streptococcus mutans; NAD In aq. phosphate buffer at 40℃; for 4h; pH=8.5; Reagent/catalyst; Green chemistry; Enzymatic reaction; chemoselective reaction;
2873-18-9

5-bromo-2-chlorothiophene

124-38-9

carbon dioxide

24065-33-6

5-Chlorothiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-bromo-2-chlorothiophene With iodine; magnesium In tetrahydrofuran at 22 - 28℃; Inert atmosphere;
Stage #2: carbon dioxide With hydrogenchloride In water at -15℃; for 1.5h;
96.7%
Multistep reaction;

5-chloro-2-trichloroacetylthiophene

24065-33-6

5-Chlorothiophene-2-carboxylic acid

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In toluene at 20℃; for 2h; Reagent/catalyst; Solvent;95%
6310-09-4

2-acetyl-5-chlorothiophene

24065-33-6

5-Chlorothiophene-2-carboxylic acid

Conditions
ConditionsYield
With sodium chlorite; potassium dihydrogenphosphate In water; acetone at 0 - 30℃; for 22h;84.9%
With bromine; sodium hydroxide In 1,4-dioxane; water at 0 - 20℃;76.1%
With sodium hydroxide; potassium permanganate; water
527-72-0

2-thiophenylcarboxylic acid

24065-33-6

5-Chlorothiophene-2-carboxylic acid

Conditions
ConditionsYield
With trichloroisocyanuric acid; sulfuric acid at -5 - 5℃; for 4h; Reagent/catalyst; Temperature;82.2%
With chlorine; acetic acid
96-43-5

2-thienyl chloride

124-38-9

carbon dioxide

24065-33-6

5-Chlorothiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 2-thienyl chloride With lithium diisopropyl amide In tetrahydrofuran at 20℃; for 0.000833333h; Flow reactor;
Stage #2: carbon dioxide In tetrahydrofuran at 20℃; for 0.000138889h; Flow reactor;
Stage #3: With water; acetic acid In tetrahydrofuran at 20℃; under 7500.75 Torr; Flow reactor;
77%
With ethylaluminum dichloride In hexane; chlorobenzene at 100℃; under 22502.3 Torr; for 3h; Autoclave; Inert atmosphere; regioselective reaction;41%
Stage #1: 2-thienyl chloride With n-butyllithium In tetrahydrofuran; hexane at 0℃;
Stage #2: carbon dioxide In tetrahydrofuran; hexane
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 0℃;
> 70 %Chromat.
96-43-5

2-thienyl chloride

24065-33-6

5-Chlorothiophene-2-carboxylic acid

Conditions
ConditionsYield
With palladium diacetate; sodium persulfate In acetic acid for 7h; Heating;19.6%
With n-butyllithium; diethyl ether anschliessend Behandeln mit festem Kohlendioxid;
141-97-9

ethyl acetoacetate

(5-chlorothiophen-2-yl)boronic acid

24065-33-6

5-Chlorothiophene-2-carboxylic acid

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;3%
96-43-5

2-thienyl chloride

60-29-7

diethyl ether

24065-33-6

5-Chlorothiophene-2-carboxylic acid

Conditions
ConditionsYield
With sodium amalgam Behandeln der Reaktionsloesung mit festem Kohlendioxid;
With sodium Behandeln der Reaktionsloesung mit festem Kohlendioxid;
3172-52-9

2,5-diclorothiophene

24065-33-6

5-Chlorothiophene-2-carboxylic acid

Conditions
ConditionsYield
With n-butyllithium; diethyl ether anschliessend Behandeln mit festem Kohlendioxid;
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    Name: 5-Chlorothiophene-2-carboxylic acid Synonyms: 5-Chloro-2-thiophenecarboxylic acid CAS:24065-33-6 MF: C5H2ClO2S Appearance: White To Brown Powder Storage:Store in cool and dry place, away from sun light. Package: 25kgs/drum Application:Interm

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    24065-33-6

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  • 5-Chlorothiophene-2-carboxylic acid / C5H3ClO2S CAS 24065-33-6

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    24065-33-6

    5-Chlorothiophene-2-carboxylic acid / C5H3ClO2S CAS 24065-33-6

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Analytical Methods

The compounds of formula according to the invention having a free carboxylic radical or a free amino radical may be converted in usual manner into their pharmaceutically acceptable salts. E.g. the compound of formula  is dissolved in its free form in a solvent, e.g. an alcohol or WATER, an adequate amount of hydrochlorid acid or Sodium hydroxide is added to the solution, the mixture is agitated at room temperature for an adequate period, then the solvent is distilled off, the residue is recrystallized and the salt of the compound of formula is obtained. Suitable examples for such pharmaceutically acceptable salts additionally to the salt of hydrochloric acid are the salts of SULFURIC ACID, nitric acid, phosphoric acid, sulfonic acid, benzoic acid, SUCCINIC ACID, Tartaric acid and citric acid. Examples for pharmaceutically acceptable addition salts of bases additionally to the sodium salt are the POTASSIUM salt, the calcium salt and the MAGNESIUM salt.
 

Specification

5-Chloro-2-thiophenecarboxylic acid, with the CAS Registry Number 24065-33-6, has the Molecular Formula of C5H3ClO2S and Molecular weight of 162.594.  It is also called 2-Thiophenecarboxylic acid, 5-chloro-; 5-CHLORO-THIOPHENE-2-CARBOXILIC ACID.

Physical properties about 5-Chloro-2-thiophenecarboxylic acid are: (1)ACD/LogP: 2.87; (2)ACD/LogD (pH 5.5): 0.73; (3)ACD/LogD (pH 7.4): -0.23; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 6.29; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.623; (12)Molar Refractivity: 36.462 cm3; (13)Molar Volume: 103.393 cm3; (14)Polarizability: 14.455 10-24cm3; (15)Surface Tension: 60.5610008239746 dyne/cm; (16)Density: 1.573 g/cm3; (17)Flash Point: 127.364 °C; (18)Enthalpy of Vaporization: 55.568 kJ/mol; (19)Boiling Point: 286.984 °C at 760 mmHg; (20)Vapour Pressure: 0.00100000004749745 mmHg at 25°C

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. Wear suitable gloves and eye/face protection;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C5H3ClO2S/c6-4-2-1-3(9-4)5(7)8/h1-2H,(H,7,8);
(2)InChIKey=QZLSBOVWPHXCLT-UHFFFAOYSA-N;
(3)Smilesc1(sc(Cl)cc1)C(=O)O

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03275,