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[ CAS No. 22913-25-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 22913-25-3
Chemical Structure| 22913-25-3
Chemical Structure| 22913-25-3
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Product Details of [ 22913-25-3 ]

CAS No. :22913-25-3 MDL No. :MFCD06203855
Formula : C10H8O2S Boiling Point : -
Linear Structure Formula :- InChI Key :FSJAXBXCHWMNAB-UHFFFAOYSA-N
M.W :192.23 Pubchem ID :12514024
Synonyms :

Calculated chemistry of [ 22913-25-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.1
TPSA : 54.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.38
Log Po/w (XLOGP3) : 2.79
Log Po/w (WLOGP) : 2.69
Log Po/w (MLOGP) : 2.26
Log Po/w (SILICOS-IT) : 3.48
Consensus Log Po/w : 2.72

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.13 mg/ml ; 0.000676 mol/l
Class : Soluble
Log S (Ali) : -3.59
Solubility : 0.0492 mg/ml ; 0.000256 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.42
Solubility : 0.0729 mg/ml ; 0.000379 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 22913-25-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 22913-25-3 ]

* 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 [ 22913-25-3 ]

[ 22913-25-3 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 67-56-1 ]
  • [ 5381-25-9 ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
380 mg With oxalyl dichloride; at 80℃; for 2h;Cooling with ice; Production example 10370 mg of oxalyl chloride was added to a mixture of 400 mg of <strong>[5381-25-9]benzo[b]thiophene-3-carboxylic acid</strong> and 20 ml of methanol under ice cooling. This mixture was stirred for 2 hours at 80C. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Tert-butyl methyl ether was added to the residues, and the residue was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure, thereby obtaining 380 mg of methyl benzo[b]thiophene-3-carboxylate (hereinafter, described as a "compound 12 of the present invention").1H-NMR (CDCl3) delta: 8.60 (m, 1H), 8.39 (s, 1H), 7.88 (m, 1H), 7.49 (m, 1H), 7.43 (m, 1H), 3.97 (s, 3H)
  • 2
  • [ 22913-25-3 ]
  • [ 78676-34-3 ]
YieldReaction ConditionsOperation in experiment
With ethanol; hydrazine hydrate
  • 3
  • [ 22913-25-3 ]
  • [ 64-17-5 ]
  • [ 19156-48-0 ]
YieldReaction ConditionsOperation in experiment
15.7 g With sodium ethanolate for 1h; Ambient temperature;
  • 4
  • [ 22913-25-3 ]
  • [ 5381-25-9 ]
  • 5
  • [ 22913-25-3 ]
  • [ 39891-63-9 ]
YieldReaction ConditionsOperation in experiment
24.6 g With methanol; magnesium Ambient temperature;
  • 6
  • [ 87807-50-9 ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
83% With silver(I) carbonate; acetic acid In dimethyl sulfoxide at 120℃; for 4h;
With copper at 165 - 166℃;
  • 7
  • [ 82787-77-7 ]
  • [ 71-43-2 ]
  • [ 22913-25-3 ]
  • [ 101-81-5 ]
YieldReaction ConditionsOperation in experiment
1: 7.62 g 2: 8.30 g In carbon disulfide for 2h; Ambient temperature;
  • 8
  • [ 67-56-1 ]
  • [ 7342-82-7 ]
  • [ 201230-82-2 ]
  • [ 5381-25-9 ]
  • [ 22913-25-3 ]
  • 9
  • [ 7342-82-7 ]
  • [ 201230-82-2 ]
  • [ 5381-25-9 ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
90% Preparation of methyl benzothiophene-3-carboxylate (D17) STR43 Preparation of methyl benzothiophene-3-carboxylate (D17) STR43 A stirred mixture of the acid (27.7 g, 0.156 mole, (D16)) and thionyl chloride (22.7 ml, 0.31 mole) in dry toluene (300 ml) was heated under reflux for 1 hour. The solution was then evaporated to dryness to leave a red oil. This was dissolved in dry ether (300 ml), the solution cooled in an ice bath, and treated with dry triethylamine (43 ml, 0.31 mole) followed by methanol (12.6 ml, 0.31 mole). The mixture was stirred at room temperature for 20 minutes, before acidifying with dilute hydrochloric acid. The organic layer was separated and the aqueous solution extracted with ether (1*150 ml). The organic solutions were combined and washed with 10% sodium carbonate solution, dilute hydrochloric acid and water; then dried (MgSO4) and evaporated to dryness to give the title compound as a red oil (90%). NMR: δ (CDCl3) 3.88 (s, 3H), 7.2-7.6 (m, 2H), 7.7-8.0 (m, 1H), 8.37 (s, 1H), 8.5-8.8 (m, 1H).
Benzthiophen-3-carbonbsaeure, CH2N2;
  • 11
  • [ 22913-25-3 ]
  • [ 1079-66-9 ]
  • [ 730991-24-9 ]
YieldReaction ConditionsOperation in experiment
76% With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran
  • 12
  • [ 22913-25-3 ]
  • 2-diphenylphosphanyl-benzo[<i>b</i>]thiophene-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / LTMP / tetrahydrofuran 2: aq. LiOH / methanol; tetrahydrofuran
  • 13
  • [ 22913-25-3 ]
  • C48H40N2O2P2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 76 percent / LTMP / tetrahydrofuran 2: aq. LiOH / methanol; tetrahydrofuran 3: EDC*HCl; HOBt / dimethylformamide
  • 14
  • [ 5732-24-1 ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 3.5 h / Heating 2: copper bronze / 165 - 166 °C / 17 Torr
  • 15
  • [ 493-57-2 ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) 4N sodium carbonate, 2.) H(1+) / H2O / 3 h / 60 - 70 °C 2: sulfuric acid / 24 h 3: 1.) 10percent KOH, 2.) H(1+) / methanol / 0.42 h / Heating 4: copper bronze / 165 - 166 °C / 17 Torr
  • 16
  • [ 41892-84-6 ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) 10percent KOH, 2.) H(1+) / methanol / 0.42 h / Heating 2: copper bronze / 165 - 166 °C / 17 Torr
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol; water; tetrahydrofuran / 0.42 h / 20 °C 2: silver(I) carbonate; acetic acid / dimethyl sulfoxide / 4 h / 120 °C
  • 17
  • [ 37412-26-3 ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sulfuric acid / 24 h 2: 1.) 10percent KOH, 2.) H(1+) / methanol / 0.42 h / Heating 3: copper bronze / 165 - 166 °C / 17 Torr
  • 18
  • [ 22913-25-3 ]
  • [ 93670-21-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 15.7 g / NaOEt / 1 h / Ambient temperature 2: Br2 / acetic acid / 2.5 h / Ambient temperature
  • 19
  • [ 22913-25-3 ]
  • [ 91503-28-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 15.7 g / NaOEt / 1 h / Ambient temperature 2: Br2 / acetic acid / 2.5 h / Ambient temperature 3: AlCl3 / CS2 / 72 h / Ambient temperature
  • 20
  • [ 22913-25-3 ]
  • [ 93669-93-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 15.7 g / NaOEt / 1 h / Ambient temperature 2: Br2 / acetic acid / 2.5 h / Ambient temperature 3: AlCl3 / CS2 / 72 h / Ambient temperature 4: H2, KOAc / 10percent Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature 5: Na2CO3 / ethanol / 1.5 h / Ambient temperature
  • 21
  • [ 22913-25-3 ]
  • [ 93669-94-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 15.7 g / NaOEt / 1 h / Ambient temperature 2: Br2 / acetic acid / 2.5 h / Ambient temperature 3: AlCl3 / CS2 / 72 h / Ambient temperature 4: Na2CO3 / ethanol / 1.5 h / Ambient temperature
  • 22
  • [ 22913-25-3 ]
  • [ 93669-92-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 15.7 g / NaOEt / 1 h / Ambient temperature 2: Br2 / acetic acid / 2.5 h / Ambient temperature 3: AlCl3 / CS2 / 72 h / Ambient temperature 4: H2, KOAc / 10percent Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature
  • 23
  • [ 22913-25-3 ]
  • [ 93669-91-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 15.7 g / NaOEt / 1 h / Ambient temperature 2: Br2 / acetic acid / 2.5 h / Ambient temperature 3: AlCl3 / CS2 / 72 h / Ambient temperature
  • 24
  • [ 22913-25-3 ]
  • <i>N</i>-(benzo[<i>b</i>]thiophene-3-carbonyl)-<i>N'</i>-(toluene-4-sulfonyl)-hydrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol; hydrazine hydrate 2: pyridine
  • 25
  • [ 22913-25-3 ]
  • [ 5381-24-8 ]
YieldReaction ConditionsOperation in experiment
35 1'-[2-(Benzo[b]thiophen-3-ylmethyloxy)-1-ethyl]spiro[isobenzofuran-1(3H),4'-piperidine], fumarate, 35a. EXAMPLE 35 1'-[2-(Benzo[b]thiophen-3-ylmethyloxy)-1-ethyl]spiro[isobenzofuran-1(3H),4'-piperidine], fumarate, 35a. An ether solution (50 ml) of methyl benzo[b]thiophene-3-carboxylate (15 g) was added dropwise to a suspension of lithium aluminium hydride (3.5 g) in ether (100 ml) followed by reflux for 2 h. Usual work-up gave benzo[b]thiophen-3-yl methanol (13.5 g) as an oil.
  • 26
  • [ 22913-25-3 ]
  • C10H8F2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Et4NF-nHF (n=4,5) In MeCN or DME at 20℃; Electrochemical reaction;
  • 27
  • [ 88770-22-3 ]
  • [ 6651-43-0 ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
In benzene at 160℃; Cooling with liquid nitrogen; General procedure for the thermal DA reactions: General procedure: All reactions were carried out in oven-dried glassware. An ampoule containing a solution of 1.0 mmol of the dienophile and the required amount of the diene in 0.5 mL of dry benzene was cooled in liquid nitrogen, sealed and heated in an oil bath. After completion of the reaction, it was cooled once more in liquid nitrogen and opened. The solvent was evaporated in vacuo to give the crude product, which was subjected to TLC and GC-MS spectrometry. For the case in which the reaction yield was moderate (i.e. DA reaction between 10 and 1), column chromatography and NMR analysis were also performed.
  • 28
  • [ 108-98-5 ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: oxygen; benzoic acid; manganese(II) acetate / 1,2-dichloro-ethane / 2 h / 50 °C / Schlenk technique 2: sodium hydroxide / methanol; water; tetrahydrofuran / 0.42 h / 20 °C 3: silver(I) carbonate; acetic acid / dimethyl sulfoxide / 4 h / 120 °C
Multi-step reaction with 3 steps 1: oxygen; copper(l) chloride / 2 h / 50 °C / Schlenk technique 2: sodium hydroxide / methanol; water; tetrahydrofuran / 0.42 h / 20 °C 3: silver(I) carbonate; acetic acid / dimethyl sulfoxide / 4 h / 120 °C
  • 29
  • [ 67-56-1 ]
  • 3-(2,2,2-trichloroacetyl)benzo[b]thiophene [ No CAS ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
319 mg With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
  • 30
  • [ 7342-82-7 ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium chloride; magnesium / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 1.2: 0.5 h / 0 °C / Inert atmosphere 1.3: 2 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
  • 31
  • [ 22913-25-3 ]
  • 5,6-dibromobenzo[b]thiophene-3-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid In dichloromethane at 20℃; for 24h;
  • 32
  • [ 22913-25-3 ]
  • C11H10O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; trifluoroacetic acid; sulfuric acid / dichloromethane / 24 h / 20 °C 2: copper(I) bromide; copper / methanol; N,N-dimethyl-formamide / 216 h / 120 °C / Sealed tube
  • 33
  • [ 22913-25-3 ]
  • 5,6-dimethoxybenzo[b]thiophene-3-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; trifluoroacetic acid; sulfuric acid / dichloromethane / 24 h / 20 °C 2: copper(I) bromide; copper / methanol; N,N-dimethyl-formamide / 216 h / 120 °C / Sealed tube 3: sulfuric acid / 70 °C
  • 34
  • [ 22913-25-3 ]
  • 5,6-dimethoxy-2-phenylbenzo[b]thiophene-3-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; trifluoroacetic acid; sulfuric acid / dichloromethane / 24 h / 20 °C 2: copper(I) bromide; copper / methanol; N,N-dimethyl-formamide / 216 h / 120 °C / Sealed tube 3: sulfuric acid / 70 °C 4: potassium carbonate; triphenylphosphine; palladium diacetate / N,N-dimethyl-formamide / 480 h / 120 °C / Inert atmosphere; Sealed tube
  • 35
  • [ 22913-25-3 ]
  • [ 30407-18-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; trifluoroacetic acid; sulfuric acid / dichloromethane / 24 h / 20 °C 2: copper(I) bromide; copper / methanol; N,N-dimethyl-formamide / 216 h / 120 °C / Sealed tube 3: sulfuric acid / 70 °C 4: potassium carbonate; triphenylphosphine; palladium diacetate / N,N-dimethyl-formamide / 480 h / 120 °C / Inert atmosphere; Sealed tube 5: lithium hydroxide / water; tetrahydrofuran / 96 h / 65 °C
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