[ CAS No. 53174-98-4 ]

Name: 53174-98-4|Thieno[2,3-b]pyridine-2-carbaldehyde|97%
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Product Details of [ 53174-98-4 ]

CAS No. :	53174-98-4	MDL No. :	MFCD07772791
Formula :	C₈H₅NOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HGZQKYOLRLVMHZ-UHFFFAOYSA-N
M.W :	163.20 g/mol	Pubchem ID :	289925
Synonyms :

Safety of [ 53174-98-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 53174-98-4 ]

* 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 [ 53174-98-4 ]
Downstream synthetic route of [ 53174-98-4 ]

[ 53174-98-4 ] Synthesis Path-Upstream 1~4

1
[ 272-23-1 ]
[ 68-12-2 ]
[ 53174-98-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 20℃; for 19 h; Inert atmosphere; Cooling with ethanol-dry ice Stage #2: for 1 h; Cooling with ice; Inert atmosphere	Thieno[2,3-b]pyridine-2-carbaldehyde: In an atmosphere of argon a mixture of 1.3 mL (2.08 mmol) of 0.8 M n-butyllithium in hexane and 0.3 mL (3.3 mmol) of N,N,N’,N’-tetramethylethylenediamine was stirred magnetically at room temperature for 30 minutes, diluted with 5 mL of hexane, cooled in a bath of dry ice-ethanol, and treated (with vigorous stirring) dropwise (from a syringe with a small needle) with 0.23 g (1.7 mmol) of thieno[2,3-b] pyridine. The mixture was stirred in the bath for 7 h longer and then for 12 h while it warmed to room temperature. It was cooled in ice, treated with 0.15 g (2.1 mmol) of dimethylformamide, stirred for one hour, and then treated successively with 1 mL of ethanol, 3 mL of saturated aqueous ammonium chloride solution, and 4 mL of water. The layers were separated. The organic layer (plus chloroform extracts of the aqueous layer) was dried (magnesium sulfate) and evaporated. The residue was triturated with hexane to give 0.18 g (66percent) of brown solid; m.p. 131.5-132.5 °C. Recrystallizations from ethanol (once with charcoal) gave white needles. ¹H NMR (300 MHz, CDCl₃) ppm 7.41 (dd, J = 4.5 Hz, 8.1 Hz, 1 H), 7.99 (s, 1 H), 8.24 (dd, J = 1.8 Hz, 8.1 Hz, 1 H), 8.73 (dd, J = 1.8 Hz, 4.5 Hz, 1 H), 10.12 (s, 1 H). ¹³C NMR (75 MHz, CDCl₃) ppm 120.7, 131.8, 132.3, 134.0, 143.2, 150.5, 163.8, 185.0. IR (CHCl₃, cm^-1) 1682 (C=O). MS (EI, 70 eV): m/z [percent] = 162[M]⁺ (100), 134[M-CO]⁺ (26). HRMS (FAB⁺) calculated for C₈H₆NOS [M+1] 164.0170, found 164.0167.

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 20, p. 1952 - 1956
[2] Tetrahedron Letters, 1994, vol. 35, # 7, p. 1011 - 1014
[3] Journal of Heterocyclic Chemistry, 1974, vol. 11, p. 355 - 361

2
[ 131337-81-0 ]
[ 53174-98-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With manganese(IV) oxide In dichloromethane at 20℃;	To a solution of compound B-131 (4.0 g, 24 mmol) in dichloromethane (40 mL) was added manganese dioxide (21 g, 24 mmol) at room temperature. The mixture was stirred at room temperature overnight. On completion, the mixture was filtered, and the filtrate was concentrated in vacuo to give compound B-132 (3.4 g, 85percent yield) as a yellow solid. LCMS: (ES⁺) m/z (M+H)⁺ = 164.1, tR=0.537.

Reference： [1] Patent: WO2015/66371, 2015, A1, . Location in patent: Paragraph 00264-00265

3
[ 36404-88-3 ]
[ 53174-98-4 ]

Reference： [1] Patent: WO2015/66371, 2015, A1,

4
[ 154650-88-1 ]
[ 53174-98-4 ]

Reference： [1] Patent: WO2015/66371, 2015, A1,

[ 53174-98-4 ] Synthesis Path-Downstream 1~43

1
[ 272-23-1 ]
[ 68-12-2 ]
[ 53174-98-4 ]

Yield	Reaction Conditions	Operation in experiment
66%		Thieno[2,3-b]pyridine-2-carbaldehyde: In an atmosphere of argon a mixture of 1.3 mL (2.08 mmol) of 0.8 M n-butyllithium in hexane and 0.3 mL (3.3 mmol) of N,N,N?,N?-tetramethylethylenediamine was stirred magnetically at room temperature for 30 minutes, diluted with 5 mL of hexane, cooled in a bath of dry ice-ethanol, and treated (with vigorous stirring) dropwise (from a syringe with a small needle) with 0.23 g (1.7 mmol) of thieno[2,3-b] pyridine. The mixture was stirred in the bath for 7 h longer and then for 12 h while it warmed to room temperature. It was cooled in ice, treated with 0.15 g (2.1 mmol) of dimethylformamide, stirred for one hour, and then treated successively with 1 mL of ethanol, 3 mL of saturated aqueous ammonium chloride solution, and 4 mL of water. The layers were separated. The organic layer (plus chloroform extracts of the aqueous layer) was dried (magnesium sulfate) and evaporated. The residue was triturated with hexane to give 0.18 g (66%) of brown solid; m.p. 131.5-132.5 C. Recrystallizations from ethanol (once with charcoal) gave white needles. 1H NMR (300 MHz, CDCl3) ppm 7.41 (dd, J = 4.5 Hz, 8.1 Hz, 1 H), 7.99 (s, 1 H), 8.24 (dd, J = 1.8 Hz, 8.1 Hz, 1 H), 8.73 (dd, J = 1.8 Hz, 4.5 Hz, 1 H), 10.12 (s, 1 H). 13C NMR (75 MHz, CDCl3) ppm 120.7, 131.8, 132.3, 134.0, 143.2, 150.5, 163.8, 185.0. IR (CHCl3, cm-1) 1682 (C=O). MS (EI, 70 eV): m/z [%] = 162[M]+ (100), 134[M-CO]+ (26). HRMS (FAB+) calculated for C8H6NOS [M+1] 164.0170, found 164.0167.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 1952 - 1956
[2]Tetrahedron Letters,1994,vol. 35,p. 1011 - 1014
[3]Journal of Heterocyclic Chemistry,1974,vol. 11,p. 355 - 361

2
[ 75-52-5 ]
[ 53174-98-4 ]
[ 53175-07-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1974,vol. 11,p. 355 - 361

3
[ 7306-64-1 ]
[ 53174-98-4 ]
[ 156736-78-6 ]