[ CAS No. 4282-31-9 ]

Name: 4282-31-9|Thiophene-2,5-dicarboxylic acid|97%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 4282-31-9 ]

CAS No. :	4282-31-9	MDL No. :	MFCD00016896
Formula :	C₆H₄O₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	172.16 g/mol	Pubchem ID :	20273
Synonyms :

Calculated chemistry of of [ 4282-31-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	38.24
TPSA :	102.84 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.66
Log Po/w (XLOGP3) :	1.32
Log Po/w (WLOGP) :	1.14
Log Po/w (MLOGP) :	0.16
Log Po/w (SILICOS-IT) :	1.31
Consensus Log Po/w :	0.92

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.94
Solubility :	1.96 mg/ml ; 0.0114 mol/l
Class :	Very soluble
Log S (Ali) :	-3.08
Solubility :	0.143 mg/ml ; 0.000831 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.41
Solubility :	67.1 mg/ml ; 0.39 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.2

Safety of [ 4282-31-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4282-31-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 4282-31-9 ]
Downstream synthetic route of [ 4282-31-9 ]

[ 4282-31-9 ] Synthesis Path-Upstream 1~6

1
[ 13679-74-8 ]
[ 1918-79-2 ]
[ 4282-31-9 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1932, vol. 51, p. 1134,1141

2
[ 3141-27-3 ]
[ 124-38-9 ]
[ 7311-63-9 ]
[ 4282-31-9 ]

Reference： [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 21, p. 4562 - 4570

3
[ 4282-31-9 ]
[ 74-88-4 ]
[ 50340-79-9 ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	Thiophene-2,5-dicarboxylic acid (1.72 g, 10 mmol) and sodium carbonate (3.18 g, 30 mmol) suspended in dimethylformamide (25 mL) were stirred with methyl iodide (623 uL) at room temperature overnight. The sodium salt of the desired product was extracted with water, and 12 M hydrochloric acid was added to the combined aqueous layer. The desired product was extracted with ethyl acetate, and the combined organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to give 0.49 g of the desired product as a colorless solid (yield 28percent). ^XH-NMR (ppm in CDC1₃)d 3.93 (s, 3H), 7.77 (d, J = 4.2 Hz, 1H), 7.83 (d, J = 4.2 Hz, 1H).LC/MS(ESI) 186(M⁺).

Reference： [1] Patent: WO2004/108683, 2004, A1, . Location in patent: Page 548

4
[ 4282-31-9 ]
[ 50340-79-9 ]

Reference： [1] Chemistry - A European Journal, 2016, vol. 22, # 33, p. 11785 - 11794

5
[ 4282-31-9 ]
[ 7128-64-5 ]

Reference： [1] Helvetica Chimica Acta, 1980, vol. 63, # 2, p. 413 - 419

6
[ 4282-31-9 ]
[ 112887-68-0 ]

Reference： [1] Synthetic Communications, 2003, vol. 33, # 20, p. 3519 - 3526

[ 4282-31-9 ] Synthesis Path-Downstream 1~43

1
[ 13679-74-8 ]
[ 1918-79-2 ]
[ 4282-31-9 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1932,vol. 51,p. 1134,1141

2
[ 13679-74-8 ]
[ 4282-31-9 ]

Reference： [1]Chemische Berichte,1885,vol. 18,p. 3026
Chemische Berichte,1886,vol. 19,p. 680
[2]Tetrahedron,1999,vol. 55,p. 11039 - 11050

3
[ 67-56-1 ]
[ 4282-31-9 ]
[ 4282-34-2 ]

Yield	Reaction Conditions	Operation in experiment
99.9%	With thionyl chloride; at 0 - 20℃; for 3h;Heating / reflux;	2,5-Thiophenedicarboxylic acid (5 g, 29 mmol), which is compound 22 and commercial, was dissolved in methanol (300 ml) and thionyl chloride (SOC12) was slowly added dropwise thereto at 0C. The reaction vessel was warmed up to room temperature, followed by reflux for 3hours. After confirming the disappearance of the starting material using TLC, methanol was removed under reduced pressure. The residue was dissolved in 200 ml of chloroform and the solution was slowly added to 300ml of chloroform saturated with NH3. The formed white solid was filtered and then recrystallized in methanol to obtain the desirable compound 23 (5.75 g, 99.9%). HNMR (300MHZ, CDC13) 7. 71 (s, 2H), 3.89 (s, 6H). 13C NMR (300MHZ, CDC13) 161.96, 133. 99, 130. 84,51. 96.
99%	With thionyl chloride;Reflux;	Example 1; Lambda^lJ-Benzodioxol-5-ylmethyl)-3-[5,6-bis(methyloxy)-2-pyridinyll-2,4-dioxo-l,2,3,4- tetrahydrothieno[3,2-</\|pyrimidine-6-carboxamide Ia) Dimethyl 2,5-thiophenedicarboxylateTo a stirred solution of thiophene-2,5-dicarboxylic acid (25g, 145 mmol) in 500 mLCH3OH, was added SOCl2 (42.4 mL, 581 mmol ) dropwise over a period of 2h (the reaction generated some heat and the starting.material was gradually dissolved), then the mixture was refluxed in the reflux work station for 19h. The reaction was monitored by TLC and LC-MS. After the reaction was completed (19h), the reaction mixture was concentrated. The crude diester product was obtained as white powder (28.7g, 99%). LC-MS showed 100% of purity (rt=0.92min, MH+ = 201). IH NMR confirmed the structure [400 MHz, DMSO-<i6, delta ppm 3.88 (s, 6 H) 7.82 (s, 2 H)]. The crude product was used for next step without further purification.
99%	With thionyl chloride;Reflux;	Ia) Dimethyl 2,5-thiophenedicarboxylate; To a stirred solution of thiophene-2,5-dicarboxylic acid (25g, 145 mmol) in 500 mL CH3OH, was added SOCl2 (42.4 mL, 581 mmol ) dropwise over a period of 2h (the reaction generated some heat and the s.m. was gradually dissolved), then the mixture was refluxed in the reflux work station for 19h. The reaction was monitored by TLC and LC-MS. After the reaction was completed (19h), the reaction mixture was concentrated. The crude diester product was obtained as white powder (28.7g, 99%). LC-MS showed 100% of purity (rt=0.92min, MH+ = 201). IH NMR confirmed the structure [400 MHz, DMSO-^6, delta ppm 3.88 (s, 6 H) 7.82 (s, 2 H)]. The crude product was used for next step without further purification.

96.6%	sulfuric acid; for 48h;Heating / reflux;	Dimethyl thiophene-2,5-dicarboxylate To a stirred suspension of thiophene- 2,5-dicarboxylic acid (6.886g, 40mmol) in 40 ml_ of dry methanol was added 1 mL of sulfuric acid, and the reaction was refluxed for 48 hours. After cooled to room temperature, the reaction mixture was put in refrigerator overnight. The solid was collected by suction filtration, washed with methanol, and dried under vacuum. 7.737g (96.6 %) of product was obtained as a white solid, mp 146.0 - 148.0 C [lit. EPO <DP n="25"/>mp: 148-149 0C (Nippon Kagaku Kaishi 1987, (7), 1424-9), 142-146 0C (Khimiya Geterotsiklicheskikh Soedinenii 1986, (6), 826-36)].
91%	sulfuric acid; In 1,2-dichloro-ethane; for 40h;Heating / reflux;	(1). 3,5-Thiophenedicarboxylic acid (21.2 g, 123 mmol) was dissolved in methanol (70 mL, anhydrous) and dichloroethane (70 mL, anhydrous). c.H2SO4 (10.6 mL) was added and the reaction mixture was heated at reflux for 40 h. Solvent was removed in vacuo and the solid was suspended in EtOAc, washed with saturated NaHCO3 (2×200 nL) and brine and dried over MgSO4. Solvent was removed in vacuo to yield 1 as a white powder (22.4 g, 91%).
88%	In thionyl chloride; for 18h;Reflux; Inert atmosphere;	To a solution of 2,5-Thiophenedicarboxylic acid (2.50 g, 14.5 mmol) in dry MeOH (50 mL) was added thionyl chloride (4.43 mL, 61.0 mmol) over 10 min and the resulting solution heated at reflux for 18 h under a nitrogen atmosphere. The solution was cooled and the resulting precipitate was filtered, washed with MeOH (3x 10 mL) and air dried to afford dimethyl thiophene-2,5-dicarboxylate as an off-white solid (2.52 g, 88%). Experimental data as per literature. ADDIN EN.CITE Khusnutdinov2008802808017Khusnutdinov, R. I.Shchadneva, N. A.Baiguzina, A. R.Mukminov, R. R. Mayakova, Yu. Yu.Smirnov, A. A.Dzhemilev, U. M. Synthesis of 2-thiophenecarboxylic and 2,5-thiophenedicarboxylic acid esters via the reaction of thiophenes with the CCl4-ROH reagent in the presence of vanadium, iron, and molybdenum catalystsPetroleum ChemistryPetroleum ChemistryPet. Chem.471-47848620082 1H NMR (500 MHz, CDCl3) delta3.93 (s, 6H), 7.74 (s, 2H). 13C NMR (125 MHz, CDCl3) delta 55.2, 135.7, 141.5, 164.7.
86%	sulfuric acid;Heating / reflux;	A mixture of concentrated sulfuric acid (150 [P. L)] and of 2, 5-thiophenedicarboxylic acid (1.0 g, 5.81 mmol) in of methanol (15 [MI)] were heated to reflux under nitrogen over night. The reaction mixture was cooled to room temperature and a white crystalline solid was filtered and [DRIED (MGS04)] to give [THIOPHENE-2, 5-DICARBOXYLIC] acid dimethyl ester [(0.] 995 g, 4.97 mmol, 86% [YIELD).'H] NMR [(CD30D) 8H] 7.73 (s, 2H), 3.87 (s, [6H).]
81.7%	sulfuric acid;Heating / reflux;	<strong>[4282-31-9]Thiophene-2,5-dicarboxylic acid</strong> (4 g, 23.3 mmol) was dissolved in methanol (300ml). Catalytic amount of sulfuric acid was slowly added therein. The reaction mixture was refluxed to give 3.8 g (yield: 81. 7%, white solid) of thiophene-2,5-dicarboxylic acid dimethylester.

Reference： [1]Patent: WO2004/37808,2004,A1 .Location in patent: Page 14-15; 92-92
[2]Patent: WO2010/59555,2010,A1 .Location in patent: Page/Page column 15
[3]Patent: WO2010/22308,2010,A1 .Location in patent: Page/Page column 14
[4]Angewandte Chemie - International Edition,2016,vol. 55,p. 3290 - 3294
Angew. Chem.,2016,vol. 128,p. 3350 - 3355,6
[5]Journal of Medicinal Chemistry,2017,vol. 60,p. 2099 - 2118
[6]Chemistry - A European Journal,2016,vol. 22,p. 11785 - 11794
[7]Patent: WO2006/92059,2006,A1 .Location in patent: Page/Page column 22-23; 15/21
[8]Journal of Heterocyclic Chemistry,2020
[9]Patent: US2004/116425,2004,A1 .Location in patent: Page 88
[10]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 396 - 399
[11]Patent: WO2004/817,2003,A2 .Location in patent: Page 99
[12]Patent: WO2004/113281,2004,A1 .Location in patent: Page 58
[13]Journal of the American Chemical Society,1948,vol. 70,p. 3416,3418
[14]Journal of Organic Chemistry,2005,vol. 70,p. 7996 - 8000

4
[ 4282-31-9 ]
[ 3857-36-1 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In tetrahydrofuran; for 4h;Inert atmosphere; Reflux;	The solution of thiophene-2,5-dicarboxylic acid (1.0g, 6.0mmol) and 2.0mL of thionyl chloride (0.016mol) was gently refluxed in dry THF for 4h under nitrogen atmosphere. The excess of thionyl chloride was removed under reduced vacuum. The compound prepared was then used directly for the following step. The solution of 4-(octyloxy)benzohydrazide (3.2g, 0.012mol) dissolved in 60mL of THF was dropwise added 0.14mL of triethylamine (1.0mmol) at ice bath. The solution was stirred at rt for 24h. The solution was extracted twice with 100mL of CH2Cl2/H2O. The organic layers were combined and concentrated to give white solids. The products, isolated as white solids were obtained after recrystallization from THF/MeOH. Yield 83%, 1H NMR (300MHz, CDCl3): delta 0.86 (t, 6H, -CH3, J=6.3Hz), 1.27-1.42 (m, 20H, -CH2), 1.70-1.75 (m, 4H, -CH2), 4.04 (t, 4H, -OCH2, J=6Hz), 7.04 (d, 4H, Ar-H, J=8.4Hz), 7.87 (d, 4H, Ar-H, J=9Hz), 7.90 (s, 2H, thiophene-H), 10.4 (s, 2H, N-H), 10.7 (s, 2H, N-H). 13C NMR (75MHz, CDCl3): delta 13.99, 22.11, 25.49, 28.58, 28.68, 28.74, 31.26, 67.77, 106.52, 114.23, 124.26, 129.41, 141.34, 160.33, 161.63, 165.41.

Reference： [1]Tetrahedron,1999,vol. 55,p. 11039 - 11050
[2]Synthesis,2004,p. 568 - 572
[3]Angewandte Chemie - International Edition,2011,vol. 50,p. 6552 - 6556
[4]Journal of the American Chemical Society,1948,vol. 70,p. 3416,3418
[5]Helvetica Chimica Acta,1980,vol. 63,p. 413 - 419
[6]Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie,1983,vol. 38,p. 1669 - 1677
[7]Collection of Czechoslovak Chemical Communications,2003,vol. 68,p. 1467 - 1487
[8]Collection of Czechoslovak Chemical Communications,2004,vol. 69,p. 1301 - 1308
[9]Journal of Heterocyclic Chemistry,2004,vol. 41,p. 899 - 908
[10]Tetrahedron Letters,2004,vol. 45,p. 5649 - 5652
[11]European Journal of Medicinal Chemistry,2008,vol. 43,p. 19 - 24
[12]Journal of Medicinal Chemistry,2010,vol. 53,p. 2418 - 2432
[13]Chemical Biology and Drug Design,2012,vol. 80,p. 479 - 488
[14]Journal of Chemical Sciences,2013,vol. 125,p. 29 - 40
[15]Journal of Nanoscience and Nanotechnology,2013,vol. 13,p. 1295 - 1299
[16]Tetrahedron,2015,vol. 71,p. 4352 - 4361
[17]Langmuir,2015,vol. 31,p. 10831 - 10842
[18]Macromolecules,2015,vol. 48,p. 8480 - 8488
[19]European Journal of Organic Chemistry,2014,vol. 2014,p. 5487 - 5500
[20]New Journal of Chemistry,2016,vol. 40,p. 9494 - 9499
[21]Chemistry - A European Journal,2016,vol. 22,p. 17843 - 17856
[22]Chemical Communications,2017,vol. 53,p. 3030 - 3033
[23]Polyhedron,2020,vol. 186

5
[ 131543-46-9 ]
[ 925-47-3 ]
[ 4282-31-9 ]

Reference： [1]Chemische Berichte,1912,vol. 45,p. 2417

6
[ 3141-27-3 ]
[ 124-38-9 ]
[ 4282-31-9 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 5250 - 5253
[2]Patent: CN107445939,2017,A .Location in patent: Paragraph 0020; 0021; 0022; 0023; 0024; 0025; 0026

7
[ 4282-31-9 ]
[ 100-21-0 ]
[ 16523-31-2 ]
poly[p-phenylenebenzobisoxazole-co-2,5-thienylbenzobisoxazole], feed molar content of 2,5-thiophene-dicarboxylic acid 30% from total feed content of terephthalic acid and 2,5-thiophene-dicarboxylic acid [ No CAS ]