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[ CAS No. 351005-12-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 351005-12-4
Chemical Structure| 351005-12-4
Chemical Structure| 351005-12-4
Structure of 351005-12-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 351005-12-4 ]

CAS No. :351005-12-4 MDL No. :MFCD00666887
Formula : C8H7BrO2S Boiling Point : -
Linear Structure Formula :- InChI Key :QRJKMGQWHAQEST-UHFFFAOYSA-N
M.W : 247.11 Pubchem ID :288396
Synonyms :

Calculated chemistry of [ 351005-12-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.92
TPSA : 42.52 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) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 1.36
Log Po/w (WLOGP) : 2.65
Log Po/w (MLOGP) : 1.93
Log Po/w (SILICOS-IT) : 2.42
Consensus Log Po/w : 1.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.6
Solubility : 0.622 mg/ml ; 0.00252 mol/l
Class : Soluble
Log S (Ali) : -1.86
Solubility : 3.45 mg/ml ; 0.014 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.73
Solubility : 0.0459 mg/ml ; 0.000186 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.43

Safety of [ 351005-12-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 351005-12-4 ]

* 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 [ 351005-12-4 ]
  • Downstream synthetic route of [ 351005-12-4 ]

[ 351005-12-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 150527-38-1 ]
  • [ 351005-12-4 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With oxone In methanol at 0℃; for 2 h;
Stage #2: With sodium hydrogen sulfite In methanol; water for 0.166667 h;
Stage #3: With sodium hydrogencarbonate In methanol; water
Dissolve 4-bromo-1, 2-bis-bromomethyl-benzene (J. Org. Chef., 1418-1421, 1985; 3.42 g, 9.96 mmol) in a 2 to 1 mixture of ethanol (EtOH) and THF (1196 mL) and heat the solution to 70°C with stirring. Add a solution of Na2S. 9H2O (2.63 g, 10.96 mmol) in water (40 mL), dropwise, over 10 hours using a syringe pump. Continue to heat and stir for another 10 hours. Cool to room temperature and remove the organic solvent under reduced pressure. Add water (200 mL) to the residue and extract the aqueous layer with EtOAc (3 x 200 mL). Combine the organic layers and dry with Na2S04, filter, concentrate and purify by flash column chromatography (silica gel, hexanes) to give 1.27 g of 5-bromo-1, 3-dihydro-benzo [c] thiophene (59percent). Dissolve 5-bromo-1, 3-dihydro-benzo [c] thiophene (1. 25 g, 5.79 mmol) in methanol (25 mL) and add oxone (10.7 g, 17. 4 mmol). Stir the reaction mixture for 2 hours at 0°C and then add a 1M aqueous sodium bisulfite solution (100 mL). Stir the reaction mixture for 10 minutes and add saturated NaHCO3 solution (200 mL). Extract the aqueous layer with CH2C12 (3 x 100 mL). Combine the organic layers and dry with Na2S04, filter, concentrate and purify by flash column chromatography (silica gel, 0-5percent MeOH/CH2Cl2) to give 930 mg of 5-bromo-1, 3-dihydro-benzo [c] thiophene 2, 2-dioxide (65percent). Dissolve 5-bromo-1, 3-dihydro-benzo [c] thiophene (860 mg, 3.50 mmol) and hexamethylditin (3 eq. ) in toluene and add tetrakis (tripheuylphosphine) palladium (0) (Pd (PPh3) 4, 0.1 eq. ). Flush the flask with N2 and then heat the mixture to 120°C with stirring. Continue to heat the mixture for 5 hours and then cool to room temperature. Add water (50 mL) and extract aqueous layer with EtOAc (3 x 50 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash chromatography (silica gel, 10-30percent EtOAc/hexane) to give 1.22 g of the title compound (100percent).
Reference: [1] Patent: WO2004/9086, 2004, A1, . Location in patent: Page/Page column 28-29
[2] Patent: WO2008/24435, 2008, A2, . Location in patent: Page/Page column 99
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