[ CAS No. 1753-75-9 ] {[proInfo.proName]}

Name: 1753-75-9|5-Bromobenzo[c][1,2,5]thiadiazole|95%
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Quality Control of [ 1753-75-9 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1753-75-9 ]

CAS No. :	1753-75-9	MDL No. :	MFCD00460091
Formula :	C₆H₃BrN₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LLCRUZDFDGTAAN-UHFFFAOYSA-N
M.W :	215.07	Pubchem ID :	2776295
Synonyms :

Calculated chemistry of [ 1753-75-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.12
TPSA :	54.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.06
Log Po/w (XLOGP3) :	2.48
Log Po/w (WLOGP) :	2.45
Log Po/w (MLOGP) :	1.42
Log Po/w (SILICOS-IT) :	3.4
Consensus Log Po/w :	2.36

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.4
Solubility :	0.0853 mg/ml ; 0.000396 mol/l
Class :	Soluble
Log S (Ali) :	-3.26
Solubility :	0.118 mg/ml ; 0.000551 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.46
Solubility :	0.0753 mg/ml ; 0.00035 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.77

Safety of [ 1753-75-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1753-75-9 ]

* 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 [ 1753-75-9 ]
Downstream synthetic route of [ 1753-75-9 ]

[ 1753-75-9 ] Synthesis Path-Upstream 1~2

1
[ 1575-37-7 ]
[ 1753-75-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	for 1 h; Heating / reflux	Example 2 Synthesis of 5-bromo-2,1,3-benzothiadiazole A mixture was prepared by mixing 4.0 g (21 mmol) of 4-bromo-o-phenylenediamine, 14 mL of thionyl chloride and 0.62 mL of concentrated sulfuric acid and was refluxed for one hour. This mixture was cooled and then poured onto ice, and a resulting precipitate was filtered and collected. This precipitate was washed with water till the waste water became neutral and then thoroughly dried to yield 4.5 g of 5-bromo-2,1,3-benzothiadiazole as a crude product (melting point, 48 to 50° C.; yield, 96.5percent).

Reference： [1] RSC Advances, 2016, vol. 6, # 71, p. 66978 - 66989
[2] Patent: US2009/149676, 2009, A1, . Location in patent: Page/Page column 5
[3] ChemMedChem, 2018, vol. 13, # 21, p. 2332 - 2348
[4] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1967, vol. 3, p. 662 - 666[5] Khimiya Geterotsiklicheskikh Soedinenii, 1967, vol. 3, # 5, p. 839 - 844
[6] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1979, vol. 17, p. 13 - 16
[7] Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 629 - 633
[8] Patent: US2004/152738, 2004, A1,
[9] Chemistry - A European Journal, 2010, vol. 16, # 3, p. 899 - 906
[10] Chemistry--A European Journal, 2012, vol. 18, # 37, p. 11685 - 11694,10

2
[ 1753-75-9 ]
[ 72023-79-1 ]

Reference： [1] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 2599,2603; engl. Ausg. S. 2656, 2659
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1967, vol. 3, p. 662 - 666[3] Khimiya Geterotsiklicheskikh Soedinenii, 1967, vol. 3, # 5, p. 839 - 844
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1979, vol. 17, p. 13 - 16

[ 1753-75-9 ] Synthesis Path-Downstream 1~88

1
[ 1753-75-9 ]
[ 72023-79-1 ]

Reference： [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2599,2603; engl. Ausg. S. 2656, 2659
[2]Chemistry of Heterocyclic Compounds,1967,vol. 3,p. 662 - 666
Khimiya Geterotsiklicheskikh Soedinenii,1967,vol. 3,p. 839 - 844
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1979,vol. 17,p. 13 - 16

2
[ 1575-37-7 ]
[ 1753-75-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With thionyl chloride; sulfuric acid; for 1h;Heating / reflux;	Example 2 Synthesis of 5-bromo-2,1,3-benzothiadiazole A mixture was prepared by mixing 4.0 g (21 mmol) of 4-bromo-o-phenylenediamine, 14 mL of thionyl chloride and 0.62 mL of concentrated sulfuric acid and was refluxed for one hour. This mixture was cooled and then poured onto ice, and a resulting precipitate was filtered and collected. This precipitate was washed with water till the waste water became neutral and then thoroughly dried to yield 4.5 g of 5-bromo-2,1,3-benzothiadiazole as a crude product (melting point, 48 to 50 C.; yield, 96.5%).
	With thionyl chloride; In N,N-dimethyl-formamide;	Preparation 1 5-Bromo-benzo[1,2,5]thiadiazole To 4-bromo-benzene-1,2-diamine (17 g, 91 mmol) was added thionyl chloride (200 ml). One drop of DMF was added to the reaction mixture. The reaction mixture was heated at reflux under argon at 80 C. overnight. The reaction mixture was cooled to room temperature and added portionwise to ice in a large beaker and neutralised with solid sodium bicarbonate. The mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was collected and dried (MgSO4). The solvent was removed under reduced pressure. The title compound was isolated by column chromatography on silica gel eluding with 90% ethyl acetate/10% methanol. (12 g, 62%); 1H NMR (250 MHz, CDCl3) delta: 7.61 (1H, dd, J=9, 2 Hz), 7.82 (1H, d, J=9 Hz), 8.16 (1H, s).

Reference： [1]RSC Advances,2016,vol. 6,p. 66978 - 66989
[2]Patent: US2009/149676,2009,A1 .Location in patent: Page/Page column 5
[3]ChemMedChem,2018,vol. 13,p. 2332 - 2348
[4]Chemistry of Heterocyclic Compounds,1967,vol. 3,p. 662 - 666
Khimiya Geterotsiklicheskikh Soedinenii,1967,vol. 3,p. 839 - 844
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1979,vol. 17,p. 13 - 16
[6]Journal of Heterocyclic Chemistry,1970,vol. 7,p. 629 - 633
[7]Patent: US2004/152738,2004,A1
[8]Chemistry - A European Journal,2010,vol. 16,p. 899 - 906
[9]Chemistry - A European Journal,2012,vol. 18,p. 11685 - 11694,10

4
[ 1753-75-9 ]
[ 16750-63-3 ]
5-(2-methoxyphenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With lithium chloride;[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; In tetrahydrofuran; 1,2-dimethoxyethane; at 20℃; for 1h;Product distribution / selectivity;	A vial was charged with Ih (7 mg, 2 mol %) and LiCl (67.0 mg, 1.6 mmol) as necessary followed by a stirbar under an inert atmosphere. The vial was then sealed with a septum and purged under an inert atmosphere after which DME (0.8 mL) was added and the suspension was stirred until 1 h had dissolved. After this time, the organohalide (0.5 mmol) and the organomagnesium (0.8 mL, 1.0 M in THF or ether, 0.8 mmol) were added (active catalyst is indicated by the reaction solution turning orange). The septum was replaced with a Teflon-lined screw cap under an inert atmosphere and the reaction stirred at RT or warmed to 60 or 70 C. until complete. After this time, the mixture was diluted with a suitable organic solvent (15 mL) and washed successively with 1 M Na3EDTA solution (prepared from EDTA and 3 equiv of NaOH), water and brine. After drying (anhydrous MgSO4) the solution was filtered, the solvent removed in vacuo, and the residue purified by flash chromatography. A summary of the substrate scope that was explored is presented in Table 8.
60%	With lithium chloride;[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; In tetrahydrofuran; 1,3-dimethyl-2-imidazolidinone (DMI); at 20℃; for 1h;Product distribution / selectivity;	A vial was charged with Ih (7 mg, 2 mol %) and LiCl (67.0 mg, 1.6 mmol) as necessary followed by a stirbar under an inert atmosphere. The vial was then sealed with a septum and purged under an inert atmosphere after which DME (0.8 mL) was added and the suspension was stirred until 1 h had dissolved. After this time, the organohalide (0.5 mmol) and the organomagnesium (0.8 mL, 1.0 M in THF or ether, 0.8 mmol) were added (active catalyst is indicated by the reaction solution turning orange). The septum was replaced with a Teflon-lined screw cap under an inert atmosphere and the reaction stirred at RT or warmed to 60 or 70 C. until complete. After this time, the mixture was diluted with a suitable organic solvent (15 mL) and washed successively with 1 M Na3EDTA solution (prepared from EDTA and 3 equiv of NaOH), water and brine. After drying (anhydrous MgSO4) the solution was filtered, the solvent removed in vacuo, and the residue purified by flash chromatography. A summary of the substrate scope that was explored is presented in Table 8.

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 150 - 157
[2]Patent: US2007/73055,2007,A1 .Location in patent: Page/Page column 13-14; 22
[3]Patent: US2007/73055,2007,A1 .Location in patent: Page/Page column 13-14; 21

5
potassium 5-methyl-thiophen-2-yltrifluoroborate [ No CAS ]
[ 1753-75-9 ]
C₁₁H₈N₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate;[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; In methanol; at 60℃; for 6h;Product distribution / selectivity;	In air, a vial was charged with complex Ih (6.8 mg, 0.01 mmol), potassium carbonate (207 mg, 1.50 mmol), the potassium trifluoroborate (0.55 mmol) and the organohalide (0.5 mmol). The vial was sealed with a septum and purged with argon (3×). Technical grade methanol (2.0 mL) was added and the contents stirred at 60 C. for the specified period of time. The reaction was then diluted with diethyl ether (2 mL) and transferred to a round bottom flask. The reaction vial was rinsed with additional diethyl ether (2 mL) and combined with the previous dilution. Each reaction was performed in duplicate and the contents were combined, concentrated onto silica gel and purified by flash chromatography.

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 4743 - 4748
[2]Patent: US2007/73055,2007,A1 .Location in patent: Page/Page column 11; 16

6
[ 1753-75-9 ]
2,4,6-trimethylphenyl-ZnX, X = halide [ No CAS ]
5-(2,4,6-trimethylphenyl)benzo[1,2,5]thiadiazole [ No CAS ]

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 4749 - 4755

7
[ 1753-75-9 ]
[ 30669-83-1 ]

Reference： [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2599,2603; engl. Ausg. S. 2656, 2659

8
[ 1753-75-9 ]
[ 72023-80-4 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1979,vol. 17,p. 13 - 16

9
[ 1753-75-9 ]
[ 49716-23-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1979,vol. 17,p. 13 - 16

10
[ 1753-75-9 ]
[ 72023-81-5 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1979,vol. 17,p. 13 - 16

11
[ 1753-75-9 ]
[ 32863-29-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1979,vol. 17,p. 13 - 16

12
[ 1753-75-9 ]
argon [ No CAS ]
[ 428817-49-6 ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropylamine; In ethyl acetate;	Preparation 2 5-Trimethylsilanylethynylbenzo[1,2,5]thiadiazole A solution of <strong>[1753-75-9]5-bromo-benzo[1,2,5]thiadiazole</strong> (10 g, 80 mmol) was degassed with argon for 10 min, then copper iodide (1.53 g, 8 mmol) and bis-triphenylphospine-palladium-dichloride (1.12 g, 1.6 mmol) were added. TMS-acetylene (12.75 ml) was added via syringe followed by dropwise addition of diisopropylamine over 20 min. The reaction mixture was stirred at ambient temprature overnight. The THF was removed under reduced pressure. Ethyl acetate was added to the resulting brown oil and the mixture was filtered through celite. The residue was partitioned between ethyl acetate and water. The title compound was isolated by column chromatography using petroleum ether as the eluent (9 g, 49%); m/z (API+): 231.1 (MH+), m/z (API-): 233.1 (M).

Reference： [1]Patent: US2004/152738,2004,A1

13
[ 1753-75-9 ]
copper dichloride [ No CAS ]
di-μ-chlorobis{chlorobis(5-bromo-2,1,3-benzothiadiazole)copper(II)} [ No CAS ]

Reference： [1]Journal of general chemistry of the USSR,1989,vol. 59,p. 385 - 390
J.Gen.Chem.USSR (Engl.Transl.),1989,vol. 59,p. 435 - 441

14
di-μ-chlorobis{chlorobis(5-bromo-2,1,3-benzothiadiazole)copper(II)} [ No CAS ]
[ 1753-75-9 ]
copper dichloride [ No CAS ]

Reference： [1]Journal of general chemistry of the USSR,1989,vol. 59,p. 385 - 390
J.Gen.Chem.USSR (Engl.Transl.),1989,vol. 59,p. 435 - 441

15
[ 1753-75-9 ]
[ 917499-87-7 ]
Rh₂(O₂CCH₃)4*(5-Br-2,1,3-benzothiadiazole)2 [ No CAS ]

Reference： [1]Zhurnal Obshchei Khimii,1976,vol. 46,p. 885 - 888
Zhurnal Obshchei Khimii,1976,vol. 46,p. 888 - 892
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Rh: SVol.B2, 1.1.2.2.5, page 29 - 32

16
[ 1753-75-9 ]
5,5'-Bibenzo<c>thiadiazol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	copper; In N,N-dimethyl-formamide; at 150℃; for 6h;Product distribution / selectivity;	Synthesis of 5,5'-bis(2,1,3-benzothiadiazole) A reaction mixture prepared by adding 4.6 g (21.4 mmol) of <strong>[1753-75-9]5-bromo-2,1,3-benzothiadiazole</strong> and 2 g (31.5 mmol) of copper powder to 10 mL of dimethylformamide was heated with stirring at 150 C. for 6 hours. This reaction mixture was cooled and then poured into water (40 mL), and a resulting precipitate was filtered and collected. After this precipitate was dried, it was extracted with benzene (20 mL*3). After combining these benzene extracts, the combined extract was dried under vacuum to complete dryness. A resulting oily residue was triturated with petroleum ether, and a mother liquor was removed to yield 2.1 g of 5,5'-bis(2,1,3-benzothiadiazole) (melting point, 61 to 62 C.; yield, 73%).

Reference： [1]Patent: US2009/149676,2009,A1 .Location in patent: Page/Page column 5

17
[ 1753-75-9 ]
[ 110556-33-7 ]
C₁₁H₁₂N₂O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1728 - 1734

18
[ 1753-75-9 ]
[ 1314874-80-0 ]
[ 1360609-47-7 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃; for 14h;	Benzo[1 ,2,5]thiadiazol-5-yl-(8-chloro-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-yl)-amine ("BIO")100 mg (0.6 mmol) of 8-pyridin-3-yl-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-ylamine, mg (0.9 mmol) 5-bromo-2,1 ,3-benzothiadiazole, 68 mg (0.1 mmol) 9,9- dimethyl-4,5-bis(diphenylphosphino)xanthene , 578 mg (1.8 mmol) cesium carbonate and 34 mg bis(dibenzylideneacetone)palladium are dissolved in 1 ml dioxane and stirred at 90 C for 14 h. HPLC and LC-MS analysis show formation of the product (LCMS (method C): mass found (M+H+, 303), HPLC (method D) Rt (min): 3.07.

Reference： [1]Patent: WO2012/25186,2012,A1 .Location in patent: Page/Page column 116-117

19
4-bromo-1,2-phenylenediamine dihydrochloride [ No CAS ]
[ 1753-75-9 ]

Reference： [1]Journal of Physical Chemistry B,2012,vol. 116,p. 7259 - 7268

20
[ 1753-75-9 ]
[ 1380415-20-2 ]

Reference： [1]Journal of Physical Chemistry B,2012,vol. 116,p. 7259 - 7268

21
[ 1753-75-9 ]
[ 1404481-85-1 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 11685 - 11694,10

22
[ 1753-75-9 ]
[ 1168135-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate; In N,N-dimethyl-formamide;	Preparation 44 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole Dichloro[1,1'-bis(diphenylphosphino)ferrocene]-palladium(II) (100 mg, 0.14 mmol, 0.03), potassium acetate (1.4 g, 14 mmol), and diboron bis(pinocol) ester (1.2 g, 4.7 mmol) were sequentially added to a stirred solution of <strong>[1753-75-9]5-bromobenzo[c][1,2,5]thiadiazole</strong> (1.0 g, 4.7 mmol) in N,N-dimethylformamide (12 mL) at 23 C. The resulting dark brown mixture was sealed under nitrogen, heated to 80 C., and stirred for 24 h. The cooled reaction mixture was diluted with water (500 mL) and extracted with diethyl ether (4100 mL). The combined organic layers were diluted with hexane (100 mL) and washed with water (1200 mL). The organic layer was dried (magnesium sulfate), gravity filtered, and concentrated by rotary evaporation to afford the title compound as a brown powder (960 mg, 80% yield): IR (KBr thin film) 2977 (m), 2930 (w), 1607 (w), 1471 (m) cm-1; 1H NMR (400 MHz, CDCl3) delta 8.54 (s, 1H), 7.93-8.01 (m, 2H), 1.40 (s, 12H).

Reference： [1]Patent: US2014/274702,2014,A1 .Location in patent: Page/Page column

23
[ 1753-75-9 ]
[ 23112-96-1 ]
5-(2,6-dimethoxyphenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,2016,vol. 120,p. 1853 - 1866

24
[ 1753-75-9 ]
[ 28611-39-4 ]
5-(4-dimethylaminophenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,2016,vol. 120,p. 1853 - 1866

25
[ 1753-75-9 ]
[ 201802-67-7 ]
5-(4-diphenylaminophenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium hydroxide; In toluene; at 120℃; for 48h;	1. 1 mmol of 5-bromobenzothiadiazole,1 mmol of triphenylamine-4-boronic acid pinacol ester,0.05 mmol of tetrakis(triphenylphosphine)palladium, 0.1 mmol of tetrabutylammonium bromide,6mmol sodium hydroxide andMix 10 ml of toluene, react at 120 C for 48 h, extract with water and dichloromethane, and combine the organic layers.After drying, the organic solvent is removed, and purified by using a mixed solvent of dichloromethane and petroleum ether as a solvent column chromatography.Obtaining 4-(benzo[c][1,2,5]thiadiazol-5-yl)-N,N-diphenylaniline

Reference： [1]Journal of Physical Chemistry A,2016,vol. 120,p. 1853 - 1866
[2]Inorganic Chemistry,2016,vol. 55,p. 8446 - 8458
[3]Patent: CN110028506,2019,A .Location in patent: Paragraph 0107-0108; 0111-0112

26
[ 1753-75-9 ]
4-trimethylsilyl-2,6-dimethoxyphenylboronic acid [ No CAS ]
5-(4-trimethylsilyl-2,6-dimethoxyphenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,2016,vol. 120,p. 1853 - 1866

27
[ 1753-75-9 ]
[ 201733-56-4 ]
5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Organometallics,2016,vol. 35,p. 1008 - 1014

28
[ 1753-75-9 ]
[ 28320-36-7 ]
7-(benzo[c][1,2,5]thiadiazol-5-yl)-N,N,9,9-tetramethyl-9H-fluoren-2-amine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 10627 - 10637

29
[ 1753-75-9 ]
7-bromo-9,9-dimethyl-N-phenyl-9H-fluoren-2-amine [ No CAS ]
7-(benzo[c][1,2,5]thiadiazol-5-yl)-9,9-dimethyl-N-phenyl-9H-fluoren-2-amine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 7566 - 7573

30
[ 1753-75-9 ]
4-(benzo[c][1,2,5]thiadiazol-5-yl)-N,N-bis(4-bromophenyl)aniline [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 66978 - 66989

31
[ 1753-75-9 ]
4-(benzo[c][1,2,5]thiadiazol-5-yl)-N-(4-(benzo[c][1,2,5]thiadiazol-5-yl)phenyl)-N-(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)aniline [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 66978 - 66989

32
[ 1753-75-9 ]
4-(benzo[c][1,2,5]thiadiazol-5-yl)-N,N-bis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)aniline [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 66978 - 66989

33
[ 1753-75-9 ]
[ 61676-62-8 ]
[ 1168135-03-2 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 66978 - 66989

34
[ 1753-75-9 ]
5-(4-iodophenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Inorganic Chemistry,2016,vol. 55,p. 8446 - 8458

35
[ 1753-75-9 ]
5-(4-di(4-iodophenyl)aminophenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Inorganic Chemistry,2016,vol. 55,p. 8446 - 8458

36
[ 1753-75-9 ]
5-(4-di(4-methoxyphenyl)aminophenyl)benzo[c][1,2,5]-thiadiazole [ No CAS ]

Reference： [1]Inorganic Chemistry,2016,vol. 55,p. 8446 - 8458

37
[ 1753-75-9 ]
5-(4-di(4-cyanophenyl)aminophenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Inorganic Chemistry,2016,vol. 55,p. 8446 - 8458

38
[ 1753-75-9 ]
[ 1541809-17-9 ]

Reference： [1]Inorganic Chemistry,2016,vol. 55,p. 8446 - 8458
[2]Patent: CN110028506,2019,A

39
[ 1753-75-9 ]
11-(4-di(4-methoxyphenyl)aminophenyl)dipyrido[3,2-a:2′,3′-c]phenazine [ No CAS ]

Reference： [1]Inorganic Chemistry,2016,vol. 55,p. 8446 - 8458

40
[ 1753-75-9 ]
[ 17865-11-1 ]
5-(4-trimethylsilylphenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Inorganic Chemistry,2016,vol. 55,p. 8446 - 8458

41
[ 1753-75-9 ]
5-[(1R)-2-(2,8-diazaspiro[4.5]dec-8-yl)-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one dihydrochloride [ No CAS ]
(R)-5-(2-(2-(benzo[c][1,2,5]thiadiazol-5-yl)-2,8-diazaspiro[4.5]decan-8-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl acetamide; at 85℃;Inert atmosphere; Sealed tube;	In a 1 dram vial containing 1 mL of degassed (N2) Nu,Nu'-dimethylamide, were added (R)- 5-(l -hydroxy-2-(2,8-diazaspiro[4.5]decan-8-yl)ethyl)-4-methylisobenzofuran- 1 (3H)-one dihydrochloride (INTERMEDIATE 17) (52.4 mg, 0.13 mmol), (9,9-dimethyl-9H-xanthene-4,5- diyl)bis(diphenylphosphine) (12.01 mg, 0.021 mmol), tris(dibenzylideneacetone)dipalladium (0) (4.75 mg, 5.2 umol), 5-bromobenzo[c][l,2,5]thiadiazole (34 mg, 0.156 mmol) and cesium carbonate (101 mg, 0.311 mmol). The vial was purged with N2 gas, sealed and heated at 85C overnight. The reaction mixture was cooled to room temperature, filtered and the filtrates were concentrated. The residue was purified by semi-preparative HPLC (focused gradient 0-40% ACN over 12 minutes using 0.1%TFA as the acidic modifier). The pure fractions were combined and the solvents were removed in vacuo. The final product was dissolved in 1 mL of 4:1 mixture of water/acetonitrile and lyophilized to dryness to give (R)-5-(2-(2-(benzo[c][l,2,5]thiadiazol-5- yl)-2,8-diazaspiro[4.5]decan-8-yl)-l-hydroxyethyl)-4-methylisobenzofuran-l(3H)-one. LC-MS (IE, m/z): 465 (M+l)+.

Reference： [1]Patent: WO2016/60941,2016,A1 .Location in patent: Page/Page column 79

42
[ 6165-69-1 ]
[ 1753-75-9 ]
5-(3-thienyl)-2,1,3-benzothiadiazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 18484 - 18487
[2]Chemistry - A European Journal,2019,vol. 25,p. 2069 - 2081

43
[ 1753-75-9 ]
C₆₃H₅₇ClN₂O₆P₂RuS₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 18484 - 18487

44
[ 1753-75-9 ]
5-(5-bromothien-2-yl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 841 - 845
Angew. Chem.,2018,p. 850 - 855,6
[2]Journal of Physical Chemistry A,2018,vol. 122,p. 7991 - 8006

45
[ 1753-75-9 ]
5-(5-(4-dianis-4-ylaminophenyl)thien-2-yl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 841 - 845
Angew. Chem.,2018,p. 850 - 855,6

46
[ 1753-75-9 ]
[ 193978-23-3 ]
5-thien-2-ylbenzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 841 - 845
Angew. Chem.,2018,p. 850 - 855,6

47
[ 1753-75-9 ]
2-(3,5-dimethylphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine [ No CAS ]
C₁₉H₁₅N₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water;Inert atmosphere; Reflux;	<strong>[1753-75-9]5-bromobenzo[c][1,2,5]thiadiazole</strong> (5.65 g, 26 3 mmol), 2-(3,5-dimethylphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (12.2 g, 39.4 mmol), potassium carbonate (9.08 g, 65.7 mmol), DME (120 mL), and Water (30 mL) were combined in a flask. The solution was purged with nitrogen for 15 min then palladium tetrakis (1.34 g, 1.16 mmol) was added. The reaction was heated to reflux under nitrogen overnight. The reaction mixture was extracted with ethyl acetate (3 times), then washed with Brine and Water. The crude solid was purified with silica gel using 60/40 Heptanes/Ethyl Acetate as the solvent system. After concentrating down the fraction containing the target, the white solid was recystallized from Ethyl Acetate to afford 5.15 g (62% yield) of the title compound.

Reference： [1]Patent: US2018/13077,2018,A1 .Location in patent: Paragraph 0133

48
2-(2-phenylpyridin-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
[ 1753-75-9 ]
5-(2-phenylpyridin-4-yl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water;Inert atmosphere; Reflux;	<strong>[1753-75-9]5-bromobenzo[c][1,2,5]thiadiazole</strong> (5.00 g, 23.3 mmol), 2-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (9.80 g, 34.9 mmol), potassium carbonate (8.03 g, 58.1 mmol), Dimethoxyethane (DME) (100 mL), and Water (25 mL) were combined in a flask. The solution was purged with nitrogen for 15 min then palladium tetrakis (1.34 g, 1.16 mmol) was added. The reaction was heated to reflux under nitrogen overnight. The reaction mixture was extracted with ethyl acetate (3 times), then washed with Brine and Water. The crude solid was purified with silica gel using 60/40 heptanes/Ethyl Acetate as the solvent system to afford a 4.70 g (70% yield) of a white solid.

Reference： [1]Patent: US2018/13077,2018,A1 .Location in patent: Paragraph 0131

49
[ 557-21-1 ]
[ 1753-75-9 ]
[ 54512-76-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 110℃; for 16h;Inert atmosphere;	To a stirred solution of 5-bromobenzo[c][1 ,2,5]thiadiazole (200 mg, 930 imol) in N,Ndimethylformamide (2 mL) was added zinc cyanide (1 09 mg, 930 imol, 59 iL) andtetrakis(triphenylphosphine)palladium(0) (107 mg, 93 imol), the mixture was degassed with nitrogen three times. The mixture was heated at 110 00 for 16 h under nitrogen. After cooling to 20 00, water (5 mL) was added to the reaction, and the mixture extracted with ethyl acetate (20 mL x 3). The combined organic phases were washed with saturated aqueous sodium chloride solution (1 0 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give crude product. The mixture wastriturated with petroleum ether (20 mL) and dichloromethane (2 mL), then the mixture was filtered, and the filter cake dried in vacuo to give benzo[c][1 ,2,5]thiadiazole-5-carbonitrile (100 mg, 620 imol, 67 %) as a red solid. LCMS (ESI) m/z: [M÷H] 162.0.

Reference： [1]Patent: WO2018/81167,2018,A1 .Location in patent: Page/Page column 208

50
[ 1753-75-9 ]
N-(2-(4-(3-(benzo[c][1,2,5]thiadiazol-5-yl)-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-2-oxoethyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2018/81167,2018,A1

51
[ 1753-75-9 ]
(Z)-N’-hydroxybenzo[c][1,2,5]thiadiazole-5-carboximidamide [ No CAS ]

Reference： [1]Patent: WO2018/81167,2018,A1

52
[ 1753-75-9 ]
[ 2510-22-7 ]
5-(pyridin-4-ylethynyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 12113 - 12124

53
[ 1753-75-9 ]
[ 122-39-4 ]
5-diphenylaminobenzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,2018,vol. 122,p. 7991 - 8006

54
[ 1753-75-9 ]
[ 205877-26-5 ]
5-(4-diphenylaminophenyl)ethynylbenzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,2018,vol. 122,p. 7991 - 8006

55
[ 1753-75-9 ]
5-(5-(4-diphenylaminophenyl)thien-2-yl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,2018,vol. 122,p. 7991 - 8006

56
[ 6165-68-0 ]
[ 1753-75-9 ]
5-thien-2-ylbenzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,2018,vol. 122,p. 7991 - 8006

57
[ 1753-75-9 ]
5-(1H-pyrrol-2-yl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 2332 - 2348

58
[ 1753-75-9 ]
1-(5-(benzo[c][1,2,5]thiadiazol-5-yl)-1H-pyrrol-2-yl)-2,2,2-trifluoroethanone [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 2332 - 2348

59
[ 1753-75-9 ]
5-(benzo[c][1,2,5]thiadiazol-5-yl)-1H-pyrrole-2-carboxylic acid [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 2332 - 2348

60
[ 1753-75-9 ]
N-(2-amino-1-(5-(hydroxymethyl)thiazol-2-yl)ethyl)-5-(benzo[c][1,2,5]thiadiazol-5-yl)-1H-pyrrole-2-carboxamide [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 2332 - 2348

61
[ 1753-75-9 ]
C₂₄H₂₄N₆O₄S₂ [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 2332 - 2348

62
[ 1753-75-9 ]
[ 135884-31-0 ]
C₁₅H₁₅N₃O₂S [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 2332 - 2348

63
[ 1753-75-9 ]
C₅₅H₄₂ClN₂OP₂RuS₂ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 2069 - 2081

64
[ 1753-75-9 ]
[ 171364-78-6 ]
5-(4-dimethylaminophenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 12415 - 12419
Angew. Chem.,2019,vol. 131,p. 12545 - 12549,5

65
[ 1753-75-9 ]
C₂₈H₂₉CuN₅⁽¹⁺⁾ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 12415 - 12419
Angew. Chem.,2019,vol. 131,p. 12545 - 12549,5

66
[ 1753-75-9 ]
[ 471240-74-1 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 12415 - 12419
Angew. Chem.,2019,vol. 131,p. 12545 - 12549,5

67
[ 1753-75-9 ]
C₂₈H₃₁N₅ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 12415 - 12419
Angew. Chem.,2019,vol. 131,p. 12545 - 12549,5

68
[ 1753-75-9 ]
[ 768-10-5 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8158 - 8163

69
[ 1753-75-9 ]
[ 73183-34-3 ]
[ 1168135-03-2 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8158 - 8163

70
[ 1753-75-9 ]
N₄',N₄'-diphenyl-[1,1'-biphenyl]-3,4,4'-triamine [ No CAS ]

Reference： [1]Patent: CN110028506,2019,A

71
[ 1753-75-9 ]
[ 108-98-5 ]
C₁₂H₈N₂S₂ [ No CAS ]