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Basic Information
CAS No.: 527-72-0
Name: 2-Thiophenecarboxylic acid
Article Data: 279
Molecular Structure:
Molecular Structure of 527-72-0 (2-Thiophenecarboxylic acid)
Formula: C5H4O2S
Molecular Weight: 128.152
Synonyms: 2-Carboxythiophene;2-Thenoic acid;2-Thiophenecarboxylicacid;2-Thiophenic acid;NSC 2188;a-Thiophenecarboxylic acid;
EINECS: 208-423-4
Density: 1.401 g/cm3
Melting Point: 125-127 °C(lit.)
Boiling Point: 260 °C at 760 mmHg
Flash Point: 117.8 °C
Solubility: water: 80 g/L (20 °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: 1.44630
Synthetic route
5380-42-7

thiophene-2-carboxylic acid methyl ester

527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With sodium; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 90℃; for 0.25h;100%
With hydrogenchloride In 1,4-dioxane for 1h; Heating;97%
With potassium carbonate; thiophenol In 1-methyl-pyrrolidin-2-one at 190℃; for 0.166667h; Substitution;75%
188290-36-0

thiophene

108-24-7

acetic anhydride

527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
Stage #1: thiophene; acetic anhydride at 30℃; for 0.333333h;
Stage #2: With oxygen; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate; acetic acid; sodium bromide at 90 - 125℃; under 1654.92 Torr; for 4.75h; Reagent/catalyst;
100%
98-03-3

thiophene-2-carbaldehyde

527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; under 760.051 Torr; for 12h; Sealed tube;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;99%
With C20H25N2(1+)*Cl(1-); water; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 3.5h; Schlenk technique;96%

thiophene-2-carboxylic acid benzyl ester

108-88-3

toluene

A

527-72-0

2-thiophenylcarboxylic acid

B

620-47-3

1-methyl-3-(phenylmethyl)-benzene

C

620-83-7

1-methyl-4-(phenylmethyl)benzene

D

713-36-0

2-benzyltoluene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; water at 80℃; for 2h; regioselective reaction;A 99%
B n/a
C n/a
D n/a
326-91-0

1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione

527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation;99%
98-03-3

thiophene-2-carbaldehyde

A

527-72-0

2-thiophenylcarboxylic acid

B

636-72-6

2-thiophenemethanol

Conditions
ConditionsYield
Stage #1: thiophene-2-carbaldehyde With potassium hydroxide for 0.0833333h; Cannizzaro Reaction; Milling; Inert atmosphere; Sealed tube; Green chemistry;
Stage #2: With hydrogenchloride In water for 0.0833333h; Green chemistry;
A 98%
B 98%
With aluminum oxide; water; sodium hydroxide at 100℃; for 0.0333333h; Cannizzaro Reaction; Microwave irradiation;A 47%
B 47%
With aluminum oxide; sodium hydroxide; water for 0.00416667h; Irradiation; Yield given; Yields of byproduct given;
62521-42-0

4,4-dimethyl-2-(2-thienyl)oxazoline

527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide; sodium hypochlorite; tetra-tert-butylammonium hydrogen sulfate 1.) ethyl acetate, water, 20 deg C, 12 h; 2.) MeOH, water, 12 h, 20 deg C;97%
With potassium hydroxide; sodium hypochlorite; tetra-tert-butylammonium hydrogen sulfate Product distribution; multistep.: 1.) ethyl acetate-water, 20 deg C, 12 h; 2.) MeOH-water, 20 deg C, 12 h; transformation of oxazoline derivatives into carboxylic functions;97%
Multi-step reaction with 3 steps
1: 85 percent / CH2Cl2 / 0.25 h / 0 °C
2: 98 percent / diethyl ether / Ambient temperature
3: 92 percent / 2.0M KOH / dimethylsulfoxide-d6 / 4 h / 110 °C
View Scheme
1003-09-4

2-bromothiophene

201230-82-2

carbon monoxide

527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; cobalt(II) acetate In ethanol at 30℃; under 1520 Torr; for 20h; Irradiation;96.9%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide; bis(benzonitrile)palladium(II) dichloride; triphenylphosphine In xylene at 90℃; for 4h; Carbonylation;18%
13679-77-1

(thiophen-2-yl)methyl acetate

A

98-03-3

thiophene-2-carbaldehyde

B

527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 100℃; for 1.66667h; Product distribution; Rate constant; dependence on temperatures and concentrations of reagent and catalysts;A n/a
B 96.5%
124-38-9

carbon dioxide

52770-33-9

2-thienylmagnesium chloride

527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; 2-thienylmagnesium chloride In tetrahydrofuran at 20℃; under 3000.3 Torr; gas-liquid flow reactor assembly;
Stage #2: With polymer-supported sulfonic acid In tetrahydrofuran
95%
In tetrahydrofuran at 1℃; for 0.0833333h;82%
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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

ASSAY: 98.0% min
WATER: 0.5% max

Specification

The 2-Thiophenecarboxylic acid, with the cas registry number527-72-0, has the systematic name of thiophene-2-carboxylic acid. This is a kind of white to light yellow crystal powder, and is soluble in hot water, ethanol, ethyl ether, and slightly soluble in chloroform. Its product categories are various, including thiophenes; aromatic carboxylic acids, amides, anilides, anhydrides & salts; thiophene&benzothiophene; organic acids; heterocyclic compounds; miscellaneous; building blocks; heterocyclic building blocks. As to its usage, it could be used as the intermediate of analgesics anti-inflammatory and the organic synthesis reagents.

The characteristics of this chemical are as follows: (1)ACD/LogP: 1.57; (2)ACD/LogD (pH 5.5): -0.39; (3)ACD/LogD (pH 7.4): -1.5; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1.85; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 54.54; (12)Index of Refraction: 1.606; (13)Molar Refractivity: 31.56 cm3; (14)Molar Volume: 91.4 cm3; (15)Polarizability: 12.51 ×10-24 cm3; (16)Surface Tension: 58.1 dyne/cm; (17)Density: 1.401 g/cm3; (18)Flash Point: 117.8 °C; (19)Enthalpy of Vaporization: 52.58 kJ/mol; (20)Boiling Point: 260 °C at 760 mmHg; (21)Vapour Pressure: 0.00639 mmHg at 25°C.

Production method of 2-Thiophenecarboxylic acid is as below: thiophene could react to produce 2-Thiophenecarboxylic acid, with the following condition: reagent: mercury diethyl and sodium; other condition: unter Durchleiten von Kohlendioxyd.

Use of 2-Thiophenecarboxylic acid: 2-Thiophenecarboxylic acid reacts to produce thiophene-2-carbonyl chloride, with the following condition: reagent: thionyl chloride; reaction time: 3 hours; other condition: heating.

While dealing with this chemical, you should be very cautious. This is irritating to eyes, respiratory system and skin, and may cause inflammation to the skin or other mucous membranes. You should take the following instructions. Wear suitable protective clothing, gloves and eye/face protection, and ig in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Additionally, the following datas could be converted into the molecular structure:
(1)SMILES:O=C(O)c1sccc1
(2)InChI:InChI=1/C5H4O2S/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7)