[ CAS No. 71605-72-6 ] {[proInfo.proName]}

Name: 71605-72-6|Benzo[c][1,2,5]thiadiazole-5-carbaldehyde|97%
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Quality Control of [ 71605-72-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 71605-72-6 ]

Product Details of [ 71605-72-6 ]

CAS No. :	71605-72-6	MDL No. :	MFCD00457949
Formula :	C₇H₄N₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GEFIFDVQYCPLHC-UHFFFAOYSA-N
M.W :	164.18	Pubchem ID :	2776290
Synonyms :

Safety of [ 71605-72-6 ]

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 [ 71605-72-6 ]

* 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 [ 71605-72-6 ]
Downstream synthetic route of [ 71605-72-6 ]

[ 71605-72-6 ] Synthesis Path-Upstream 1~7

1
[ 89795-51-7 ]
[ 71605-72-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With manganese(IV) oxide In chloroform at 20℃; Inert atmosphere	Benzo[1,2,5]thiadiazol-5-ylmethanol 6 (115 mg, 0.69 mmol) and MnO₂ (241 mg, 2.8 mmol) in CHCl₃ (10 mL) were stirred at room temperature overnight. The reaction mixture was filtered on a plug of Celite and the filtrate evaporated to provide 111 mg of pure 2,1,3-benzothiadiazole-5-carboxaldehyde 7 (98 percent): ¹H NMR (300 MHz, CDCl₃) δ 10.19(s, 1H), 8.49 (s, 1H), 8.09 (s, 2H).
1.9 g	With manganese(IV) oxide In chloroform at 25℃;	The 5-Hydroxy-methylbenzo-2,1,3-thiadiazole (2,6 g, 16 mmol) and MnO₂(5.6 g, 64.41 mmol) in CHCl₃(150 mL) were stirred at room temperature (approximately 25° C.) overnight. The reaction mixture was filtered and the filtrate evaporated. Crude residue was submitted to the chromatograph on silica gel (EtOAc/Hexane, 7/3, v/v) to provide 1.9 g of 2,1,3-benzothiadiazole-5-carboxaldehyde. m.p. 93° C. ESI-MS (M_w164.18): 165.2 (M+H⁺). ¹H-NMR (DMSO-d6): 10.21 (s, 1H), 8.78 (d, 1H), 8.19 (d, 1H), 8.04 (s, 1H).

Reference： [1] Medicinal Chemistry Research, 2015, vol. 24, # 8, p. 3143 - 3156
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 12, p. 3163 - 3179
[3] Patent: US6593335, 2003, B1,
[4] Patent: US2016/75702, 2016, A1, . Location in patent: Paragraph 0126-0129

2
[ 65858-50-6 ]
[ 71605-72-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 12, p. 3163 - 3179
[2] Bulletin of the Chemical Society of Japan, 1959, vol. 32, p. 551
[3] Pharmaceutical Chemistry Journal, 1979, vol. 13, # 6, p. 591 - 598[4] Khimiko-Farmatsevticheskii Zhurnal, 1979, vol. 13, # 6, p. 33 - 41

3
[ 1457-93-8 ]
[ 71605-72-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 12, p. 3163 - 3179
[2] Bulletin of the Chemical Society of Japan, 1959, vol. 32, p. 551

4
[ 71605-71-5 ]
[ 71605-72-6 ]

Reference： [1] Pharmaceutical Chemistry Journal, 1979, vol. 13, # 6, p. 591 - 598[2] Khimiko-Farmatsevticheskii Zhurnal, 1979, vol. 13, # 6, p. 33 - 41

5
[ 71764-94-8 ]
[ 71605-72-6 ]

Reference： [1] Pharmaceutical Chemistry Journal, 1979, vol. 13, # 6, p. 591 - 598[2] Khimiko-Farmatsevticheskii Zhurnal, 1979, vol. 13, # 6, p. 33 - 41

6
[ 619-05-6 ]
[ 71605-72-6 ]

Reference： [1] Medicinal Chemistry Research, 2015, vol. 24, # 8, p. 3143 - 3156

7
[ 36692-49-6 ]
[ 71605-72-6 ]

Reference： [1] Medicinal Chemistry Research, 2015, vol. 24, # 8, p. 3143 - 3156

[ 71605-72-6 ] Synthesis Path-Downstream 1~5

1
[ 17115-51-4 ]
[ 5220-49-5 ]
[ 71605-72-6 ]
[ 315187-64-5 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3163 - 3179

2
[ 89795-51-7 ]
[ 71605-72-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With manganese(IV) oxide; In chloroform; at 20℃;Inert atmosphere;	Benzo[1,2,5]thiadiazol-5-ylmethanol 6 (115 mg, 0.69 mmol) and MnO2 (241 mg, 2.8 mmol) in CHCl3 (10 mL) were stirred at room temperature overnight. The reaction mixture was filtered on a plug of Celite and the filtrate evaporated to provide 111 mg of pure 2,1,3-benzothiadiazole-5-carboxaldehyde 7 (98 %): 1H NMR (300 MHz, CDCl3) delta 10.19(s, 1H), 8.49 (s, 1H), 8.09 (s, 2H).
	With manganese dioxide; In chloroform;	EXAMPLE 214C 2,1,3-benzothiadiazole-5-carboxaldehyde 5-Hydroxymethylbenzo-2, 1,3-thiadiazole (2.6 g, 16 mmol) and manganese dioxide (6.0 g, 64 mmol) in chloroform (150 mL) were stirred at room temperature overnight. The reaction mixture was filtered off and the filtrate was evaporated to provide 1.9 g of the title compound. 1H NMR (CDC13) 8.12 (s, 2H), 8.51 (m, 1H), 10. 21 (s, 1H).
1.9 g	With manganese(IV) oxide; In chloroform; at 25℃;	The 5-Hydroxy-methylbenzo-2,1,3-thiadiazole (2,6 g, 16 mmol) and MnO2 (5.6 g, 64.41 mmol) in CHCl3 (150 mL) were stirred at room temperature (approximately 25 C.) overnight. The reaction mixture was filtered and the filtrate evaporated. Crude residue was submitted to the chromatograph on silica gel (EtOAc/Hexane, 7/3, v/v) to provide 1.9 g of 2,1,3-benzothiadiazole-5-carboxaldehyde. m.p. 93 C. ESI-MS (Mw 164.18): 165.2 (M+H+). 1H-NMR (DMSO-d6): 10.21 (s, 1H), 8.78 (d, 1H), 8.19 (d, 1H), 8.04 (s, 1H).

Reference： [1]Medicinal Chemistry Research,2015,vol. 24,p. 3143 - 3156
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 3163 - 3179
[3]Patent: US6593335,2003,B1
[4]Patent: US2016/75702,2016,A1 .Location in patent: Paragraph 0126-0129

3
[ 21080-80-8 ]
[ 934-22-5 ]
[ 71605-72-6 ]
[ 1024609-37-7 ]

Yield	Reaction Conditions	Operation in experiment
16%		Compound 287: 1 -(1 H-Benzoimidazol-5-yl)-5-benzo[c][1 ,2,5]thiadiazol-5-yl-4- cyclopropanecarbonyl-S-hydroxy-I .S-dihydro-pyrrol^-one; 1 H-Benzoimidazol-5-ylamine (1 mmol) and Benzo[1 ,2,5]thiadiazole-5-carbaldehyde (1 mmol) were added to ethanol (5 ml). After 30 min 4-Cyclopropyl-2,4-dioxo-butyric acid ethyl ester (1 mmol) was added. The reaction was heated to 500C and stirred for 24h. After evaporation of the solvent the residue was purified with chromatographic methods.molecular weight (g/mol): 417.45 IC50 hQC (nM): 0.7Yield: 0.05 g (16 percent); mp: 270.000C, decomposed, 1H NMR delta 1 H-NMR (500 MHz, DMSO-D6): 0.66-0.71 (m, 1 H, CH2), 0.77-0.84 (m, 2 H, CH2), 0.89-0.95 (m, 1 H, CH2), 2.91-2.95 (CH-CH2), 6.36 (s, 1 H, CH-N), 7.45-7.50 (m, 3 H, Ar), 7.85-7.87 (m, 2 H, Benzimid), 8.12 (d, 4J=0.9 Hz, 1 H, Benzimid), 9.03 (s, 1 H, Benzimid). MS m/z 418.4 (M+H)+, HPLC (254 nm): rt 2.74 min (100 percent).

Reference： [1]Patent: WO2008/55945,2008,A1 .Location in patent: Page/Page column 177

4
[ 7025-19-6 ]
[ 71605-72-6 ]
[ 1367579-48-3 ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 352 - 356

5
[ 614750-85-5 ]
[ 71605-72-6 ]
2-(benzo[c][1,2,5]thiadiazol-5-yl)-1-(6-methylpyridin-2-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With caesium carbonate; In tetrahydrofuran; isopropyl alcohol; at 20℃; for 7h;	General procedure: To a stirred solution of compound 9 or 15 (6.09 mmol) in a mixture of tetrahydrofuran (THF, 16 mL) and i-PrOH (4 mL), <strong>[614750-85-5]diphenyl (6-methylpyridin-2-yl)(phenylamino)methylphosphonate</strong> (6.09 mmol) and Cs2CO3 (7.92 mmol) were added. The mixture was stirred at room temperature for 7 h, and to it, 1 N HCl (30 mL) was added dropwise about 15 min. The reaction mixture was diluted with tert-butyl methyl ether (MTBE, 30 mL). The aqueous layer was separated, and the organic layer was extracted with 1 N HCl (3 60 mL). The combined aqueous layer was neutralized with saturated NaHCO3 solution at 0 C. The precipitates were collected by filtration using a Buchner funnel and dried in a vacuum oven to gain the compound 10 or 16 as a solid.
68%	With caesium carbonate; In tetrahydrofuran; isopropyl alcohol; at 20℃; for 8h;	General procedure: To a stirred solution of 14a or 14b (18.40mmol) in a mixture of THF (40mL) and i-PrOH (10mL), <strong>[614750-85-5]diphenyl (6-methylpyridin-2-yl)(phenylamino)methylphosphonate</strong> (20.24mmol) and Cs2CO3 (24.65mmol) were added. The mixture was stirred at room temperature for 8h, and to it, 1N HCl (74mL) was added dropwise about 20min. The reaction mixture was diluted with tert-butyl methyl ether (MTBE, 40mL). The aqueous layer was separated, and the organic layer was extracted with 1N HCl (3×100mL). The combined aqueous layer was neutralized with 2N KOH (pH 7-8) at 0C. The precipitates were collected by filtration using a Buchner funnel and dried in a vacuum oven to gain the compound 15a or 15b as a yellow solid. 4.1.5.1 1-(6-Methylpyridin-2-yl)-2-(thieno[3,2-c]pyridin-2-yl)ethanone (15a) (0028) Yield 68%; 1H NMR (300MHz, CDCl3) delta 7.96-7.93 (m, 2H), 7.87 (d, 1H, J=9.0Hz), 7.72 (t, 1H, J=9.0Hz), 7.61 (d, 1H, J=9.0Hz), 7.36 (d, 1H, J=9.0Hz), 4.74 (s, 2H), 2.67 (s, 3H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2070 - 2075
[2]European Journal of Medicinal Chemistry,2019,vol. 180,p. 15 - 27

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[ CAS No. 71605-72-6 ] {[proInfo.proName]}

Quality Control of [ 71605-72-6 ]

Related Doc. of [ 71605-72-6 ]

Product Details of [ 71605-72-6 ]

Safety of [ 71605-72-6 ]

Application In Synthesis of [ 71605-72-6 ]

[ 71605-72-6 ] Synthesis Path-Upstream 1~7

[ 71605-72-6 ] Synthesis Path-Downstream 1~5

Related Functional Groups of [ 71605-72-6 ]

Aldehydes

Related Parent Nucleus of [ 71605-72-6 ]

Other Aromatic Heterocycles

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Environmental hazards

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Related Functional Groups of
[ 71605-72-6 ]

Related Parent Nucleus of
[ 71605-72-6 ]