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

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Chemical Structure| 1753-75-9
Chemical Structure| 1753-75-9
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Product Details of [ 1753-75-9 ]

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

Calculated chemistry of [ 1753-75-9 ]      Expand+

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 Ų

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:
Precautionary Statements:P305+P351+P338 UN#:
Hazard Statements:H302-H319 Packing Group:
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.

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

[ 1753-75-9 ] Synthesis Path-Downstream   1~14

  • 5
  • [ 1575-37-7 ]
  • [ 1753-75-9 ]
YieldReaction ConditionsOperation 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).
  • 8
  • [ 1753-75-9 ]
  • [ 16750-63-3 ]
  • 5-(2-methoxyphenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 9
  • potassium 5-methyl-thiophen-2-yltrifluoroborate [ No CAS ]
  • [ 1753-75-9 ]
  • C11H8N2S2 [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 10
  • [ 1753-75-9 ]
  • 2,4,6-trimethylphenyl-ZnX, X = halide [ No CAS ]
  • 5-(2,4,6-trimethylphenyl)benzo[1,2,5]thiadiazole [ No CAS ]
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