174623-07-5|4-(5-Formyl-thiophen-2-yl)-benzoic acid| Ambeed

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Quality Control of [ 174623-07-5 ] Purity: 95+% SDS Specification

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Product Details of [ 174623-07-5 ]

CAS No. :	174623-07-5
Formula :	C₁₂H₈O₃S
M.W :	232.26
SMILES Code :	O=C(O)C1=CC=C(C2=CC=C(C=O)S2)C=C1
MDL No. :	MFCD06740281

Safety of [ 174623-07-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 174623-07-5 ]

* 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.

Downstream synthetic route of [ 174623-07-5 ]

[ 174623-07-5 ] Synthesis Path-Downstream 1~35

1
[ 98-03-3 ]
[ 150-13-0 ]
[ 174623-07-5 ]

References: [1]Molecules,2003,vol. 8,p. 342 - 349.
[2]Monatshefte fur Chemie,1995,vol. 126,p. 1375 - 1382.

2
[ 137-07-5 ]
[ 174623-07-5 ]
[ 174623-09-7 ]

References: [1]Monatshefte fur Chemie,1995,vol. 126,p. 1375 - 1382.

3
[ 174623-07-5 ]
[ 174658-22-1 ]
[ 618913-75-0 ]

References: [1]Molecules,2003,vol. 8,p. 342 - 349.

4
[ 174623-07-5 ]
[ 618913-79-4 ]

References: [1]Molecules,2003,vol. 8,p. 342 - 349.

5
[ 174623-07-5 ]
[ 174623-12-2 ]

References: [1]Monatshefte fur Chemie,1995,vol. 126,p. 1375 - 1382.

6
[ 174623-07-5 ]
2-(2'-benzothiazolyl)-5-[4"-(2'"-benzothiazolyl)phenyl]thiophene [ No CAS ]

References: [1]Monatshefte fur Chemie,1995,vol. 126,p. 1375 - 1382.

7
[ 110-89-4 ]
[ 6322-62-9 ]
[ 174623-07-5 ]
4-[5-(4-Oxo-3-thiophen-2-ylmethyl-2-thioxo-thiazolidin-5-ylidenemethyl)-thiophen-2-yl]-benzoic Acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	In ethanol;	B. 4-[5-(4-Oxo-3-thiophen-2-ylmethyl-2-thioxo-thiazolidin-5-ylidenemethyl)-thiophen-2-yl]-benzoic Acid Piperidine (1 drop) was added to a solution of <strong>[174623-07-5]4-(5-formyl-thiophene-2-yl)-benzoic acid</strong> (23.2 mg, 0.1 mmol) and 3-thiophen-2-ylmethyl-2-thioxo-thiazolidin-4-one (22.9 mg, 0.1 mmol) in ethanol (5 ml) and the mixture was heated under reflux for 60 minutes. After cooling to room temperature, the solid was filtered, washed with cold ethanol (2*5 ml), and dried under vacuum to give the title compound (25 mg, 56% yield).

References: [1]Patent: US2004/2526,2004,A1 .

8
[ 639816-37-8 ]
[ 174623-07-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With water; lithium hydroxide; In tetrahydrofuran; at 20℃; for 8h;	To a solution of methyl 4-(5-formylthiophen-2-yl)benzoate (25.2, 1.50 g, 6.0 mmol) in THF (15 mL), LiOH (0.439 g, 18.2 mmol) dissolved in water (2.0 mL) was added at room temperature and stirred for 8 h. After completion, THF was removed under reduced pressure, water (30 mL) was added and pH was adjusted to 7 by addition of citric acid solution. The precipitated solid was collected by filtration and the product was purified by washings with diethyl ether and pentane to afford 4-(5-formylthiophen-2-yl)benzoic acid (25.1) as yellow solid.Yield: 1.10 g, 78.0%.
53%	With hydrogenchloride; lithium hydroxide; In methanol; water;	B. 4-(5-Formyl-thiophene-2-yl)-benzoic Acid To a solution of 4-(5-formyl-thiophene-2-yl)-benzoic acid methyl ester (369 mg, 1.5 mmol) in methanol (50 ml) and water (10 ml) was added lithium hydroxide (205 mg, 5 mmol). After stirring at room temperature for 24 hours, the solution was acidified to pH 2 by addition of 0.1 M hydrochloric acid and extracted with ethyl acetate (4*20 ml). The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluding with 10% methanol-dichloromethane to provide 4-(5-formyl-thiophene-2-yl)-benzoic acid (185 mg, 53% yield).

References: [1]Patent: WO2018/126072,2018,A1 .Location in patent: Paragraph 0291; 0293.
[2]Patent: US2004/2526,2004,A1 .

9
[ 74-89-5 ]
[ 174623-07-5 ]
[ 1313398-23-0 ]

Yield	Reaction Conditions	Operation in experiment
80%		4-(5-Formylthiophen-2-yl)benzoic acid (85 mg, 0.67 mmol) was dissolved in THF (5 mL), to which was added pyridine (289 mg, 3.66 mmol) and pentafluorophenyl trifluoroacetate (512 mg, 1.83 mmol). This mixture was stirred for 2 h. at R.T. The solvent was removed under reduced pressure to give a crude solid which was dissolved in EtOAc (50 mL) and washed with 1 M HCl (2x50 mL), water (50 mL), sat. NaHC03 (2x50 mL), brine (50 mL) and dried (Na2S04). The solvent was removed under reduced pressure and the resulting solid purified by filtration through a plug of silica gel (20% EtOAc/hexanes as eluant). The resulting yellow solid. was dissolved in THF (5 mL), to which was added methylamine solution (0.8 mL of a 2 M solution in methanol). Complete reaction of the ester was observed by TLC after 1 h. at R.T., then 1 M HCl (5 mL) was added to hydrolyze any imine. After stirring at R.T. for an additional hour, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2x20 mL). The combined organic extracts were dried (Na2S04) and the solvent removed under reduced pressure to afford a crude product which was purified by trituration with Et20, giving the title compound as a pale yellow solid (72 mg, 80%). NMR [400 MHz, (CD3)2SO] delta 9.93 (s, 1 H), 8.47-8.53 (br m, 1 H), 8.07 (d, J = 4.0 Hz, 1 H), 7.93 (d, J = 8.7 Hz, 2 H), 7.89 (d, J = 8.7 Hz, 2 H), 7.84 (d, J = 4.0 Hz, 1 H), 2.80 (d, J = 4.5 Hz, 3 H). LRMS (APCI+) calcd for C,3Hl2N02S 246 (MH+), found 246.

References: [1]Patent: WO2011/75784,2011,A1 .Location in patent: Page/Page column 74-75.

10
[ 174623-07-5 ]
[ 1313398-23-0 ]