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[ CAS No. 81822-77-7 ] {[proInfo.proName]}

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Chemical Structure| 81822-77-7
Chemical Structure| 81822-77-7
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Product Details of [ 81822-77-7 ]

CAS No. :81822-77-7 MDL No. :MFCD02664330
Formula : C7H4BrClN2S Boiling Point : -
Linear Structure Formula :- InChI Key :PBCPJYFTOWXQOF-UHFFFAOYSA-N
M.W : 263.54 Pubchem ID :3735926
Synonyms :

Calculated chemistry of [ 81822-77-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.73
TPSA : 67.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 3.42
Log Po/w (WLOGP) : 3.3
Log Po/w (MLOGP) : 2.59
Log Po/w (SILICOS-IT) : 3.72
Consensus Log Po/w : 3.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.18
Solubility : 0.0173 mg/ml ; 0.0000655 mol/l
Class : Moderately soluble
Log S (Ali) : -4.51
Solubility : 0.00814 mg/ml ; 0.0000309 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.08
Solubility : 0.0219 mg/ml ; 0.000083 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.34

Safety of [ 81822-77-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 81822-77-7 ]

* 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 [ 81822-77-7 ]

[ 81822-77-7 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 38762-41-3 ]
  • [ 333-20-0 ]
  • [ 81822-77-7 ]
YieldReaction ConditionsOperation in experiment
62.6% With bromine; acetic acid; at 20℃; for 4.25h; To a solution of 4-bromo-2-chloroaniline (2.5 g, 12.11 mmol, 1 eq.) in acetic acid (25 ml) was added at RT potassium thiocyanate (4.7 g, 48.4 mmol, 4.0 eq). To this mixture was added a solution of bromine (1.25 ml, 24.22 mmol, 2 eq.) in acetic acid (5 ml) drop-wise for 15 min and allowed to stir at RT for 4 h. The reaction mixture was neutralized with aqueous sodium hydroxide solution and product was precipitated out as solid and filtered to get residue. Residue was further purified using pentane and diethyl ether wash to get desired compound as pale yellow solid (2 g, 62.6%).
43.3% To a solution of 4-bromo-2-chloroaniline 60 (2.50 g, 12.11 mmol) in acetic acid (25 ml) was added at room temperature potassium thiocyanate (4.71 g, 48.4 mmol). To the mixture was dropped for 15 minutes a solutions of bromine (1.25 ml, 24.22 mmol) in acetic acid (5 ml). After the end of dropping, it was stirred at room temperature for 15 minutes and further stirred at 30 C for 1 hour. After the end of the reaction, the mixture was neutralized with aqueous sodium hydroxide under ice-cooling and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution and brine, respectively and dried over sodium sulfate. The solvent was evaporated under reduced pressure. To the residue was added ethyl acetate and di-isopropyl ether. The mixture was filtered to give Compound 61 (2.02 g, yield 43.3%) as a yellow solid. 1H-NMR (DMSO-d6) delta: 7.48 (dd, J= 2.1, 0.9 Hz, 1H), 7.89 (dd, J= 2.7, 1.8 Hz, 1H), 7.97 (brs, 2H).
  • 2
  • [ 81822-77-7 ]
  • [ 1188053-85-1 ]
YieldReaction ConditionsOperation in experiment
51.4% With copper dichloride; isopentyl nitrite In acetonitrile at 20 - 60℃; for 2.16667h; 22 To a suspension of copper chloride (II) (1.78 g, 13.20 mmol) in acetonitrile (29 ml) was added under ice-cooling and nitrogen atmosphere isopentyl nitrate (2.22 ml, 16.51 mmol). To the mixture was added for 10 minutes 2-amino-6-bromo-4-chlorobenzo[d]thiazole 61 (2.90 g, 11.00 mmol). It was stirred at room temperature for 10 minutes. The mixture was heated at 60 °C for 2 hours. After the end of the reaction, 2N HCl was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, respectively and dried over sodium sulfates. The solvent was evaporated under reduced pressure. The residue was purified with column chromatography (n-hexane : ethyl acetate = 4 : 1) to give Compound 62 (1.60 g, yield 51.4%). 1H-NMR(DMSO-d6) δ: 7.93 (d, J=1.8 Hz, 1H), 8.40 (d, J=1.8 Hz, 1H).
  • 3
  • [ 764-33-0 ]
  • [ 81822-77-7 ]
  • 8-bromo-6-chloro-4-propyl-2H-pyrimido[2,1-b]benzothiazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% In butan-1-ol for 48h; Reflux; General Procedure for the Synthesis of Substituted 2Hpyrimido[2,1-b]benzothiazol-2-ones 6-9 General procedure: The alkynoic acid 2 (20 mmol) and the appropriate2-aminobenzothiazole 1 (10 mmol) were heated to reflux in1-butanol (50 mL) for 48h. Evaporation of solvent underreduced pressure gave the crude product which was crystallizedfrom hexane / ethyl acetate to give the correspondingsubstituted 2H-pyrimido[2,1-b]benzothiazol-2-ones 6-9.
  • 4
  • [ 590-93-2 ]
  • [ 81822-77-7 ]
  • 8-bromo-6-chloro-4-methyl-2H-pyrimido[2,1-b]benzothiazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% In butan-1-ol for 48h; Reflux; General Procedure for the Synthesis of Substituted 2Hpyrimido[2,1-b]benzothiazol-2-ones 6-9 General procedure: The alkynoic acid 2 (20 mmol) and the appropriate2-aminobenzothiazole 1 (10 mmol) were heated to reflux in1-butanol (50 mL) for 48h. Evaporation of solvent underreduced pressure gave the crude product which was crystallizedfrom hexane / ethyl acetate to give the correspondingsubstituted 2H-pyrimido[2,1-b]benzothiazol-2-ones 6-9.
  • 5
  • [ 81822-77-7 ]
  • 2-amino-5-bromo-3-chlorobenzenethiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.4% With potassium hydroxide In ethylene glycol at 180℃; for 1h; Microwave irradiation; S68.2 Step 2:
synthesis of 2-amino-5-bromo-3-chlorobenzenethiol: To the stirred solution of 6-bromo-4-chlorobenzo[d]thiazol-2-amine (0.5 g, 1.89 mmol, 1 eq.) in ethylene glycol (3 ml) was added 10 N KOH solution (3.77 ml, 37.9 mmol, 20.0 eq.) and the reaction mixture was microwave irradiated at 180° C. for 1 h. Reaction mixture was neutralized using 1N HCl solution and product was precipitated out as solid which was filtered to get residue. The obtained residue was further dissolved in methanol, filtered & concentrated under reduced pressure to get desired product as yellow viscous compound (350 mg, 77.4%).
  • 6
  • [ 81822-77-7 ]
  • 6-bromo-4-chloro-1,3-benzothiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethylene glycol / 1 h / 180 °C / Microwave irradiation 2: formic acid / 16 h / 100 °C
  • 7
  • [ 81822-77-7 ]
  • 4-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hydroxide / ethylene glycol / 1 h / 180 °C / Microwave irradiation 2: formic acid / 16 h / 100 °C 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
  • 8
  • [ 81822-77-7 ]
  • 5-(4-chlorobenzo[d]thiazol-6-yl)-6-(1-methyl-1H-pyrazol-3-yl)pyrazin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium hydroxide / ethylene glycol / 1 h / 180 °C / Microwave irradiation 2: formic acid / 16 h / 100 °C 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 4: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 16 h / 100 °C
  • 9
  • [ 81822-77-7 ]
  • [ 110-46-3 ]
  • 6-bromo-4-chloro-1,3-benzothiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% In N,N-dimethyl-formamide at 80℃; for 1h; 165.A In a flask 6-bromo-4-chloro-1 ,3-benzothiazol-2-amine (298 mg, 1 .2 mmol) was dissolvedin DMF (5 mL) and then isoamyl nitrite (0.49 mL, 3.6 mmol) was added dropwise. Reaction washeated at 80°C for 1 h. After cooling to room temperature, the crude reaction mixture was concentrated under reduced pressure. The resulting residue was purified by column chromatography, eluting with hexane/ethyl acetate mixture to afford the 6-bromo-4-chloro-1 ,3-benzothia- zole as an off-white solid (111mg, 62%). ESI-MS: 249.9 [M+H]+.
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