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[ CAS No. 1160823-78-8 ] {[proInfo.proName]}

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Chemical Structure| 1160823-78-8
Chemical Structure| 1160823-78-8
Structure of 1160823-78-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1160823-78-8 ]

CAS No. :1160823-78-8 MDL No. :MFCD20275089
Formula : C32H54O2S2Sn2 Boiling Point : -
Linear Structure Formula :- InChI Key :XXMOZDBOAIICDA-UHFFFAOYSA-N
M.W : 772.32 Pubchem ID :58261083
Synonyms :

Calculated chemistry of [ 1160823-78-8 ]

Physicochemical Properties

Num. heavy atoms : 38
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.69
Num. rotatable bonds : 16
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 183.45
TPSA : 74.94 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -1.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 13.83
Log Po/w (WLOGP) : 10.4
Log Po/w (MLOGP) : 6.9
Log Po/w (SILICOS-IT) : 11.48
Consensus Log Po/w : 8.52

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 3.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -12.52
Solubility : 0.0000000002 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (Ali) : -15.48
Solubility : 0.0 mg/ml ; 3.34e-16 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -12.06
Solubility : 0.0000000007 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 6.4

Safety of [ 1160823-78-8 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P312-P304+P340+P312-P362-P405-P501 UN#:3146
Hazard Statements:H301+H311-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1160823-78-8 ]

* 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 [ 1160823-78-8 ]
  • Downstream synthetic route of [ 1160823-78-8 ]

[ 1160823-78-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 1160823-77-7 ]
  • [ 1066-45-1 ]
  • [ 1160823-78-8 ]
YieldReaction ConditionsOperation in experiment
80.2%
Stage #1: With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 0.5 h;
Stage #2: at -78 - 20℃; for 12 h;
Was added 4,8-bis (2-ethyl-hexyloxy) benzo [1,2-b: 4,5-b '] in 50ml flask bithiophene (628 mg, 1.4mmol) and the solution was cooled to 20mlTHF -78 deg.] C, 3.5ml of n-butyllithium was slowly added dropwise a THF solution, wherein the molar amount of n-butyllithium was 3.5mmol, -78 reaction was stirred for 0.5h the reaction was raised to room temperature, and then cooled to -78 after rapid addition of trimethyltin chloride 4.2ml hexane solution, wherein the molar amount of trimethyltin chloride was 4.2 mmol, the reaction warmed to room temperature 12h. After completion of the reaction, a large amount of water and extracted with n-hexane extract was dried over anhydrous Na2SO4, the solvent was removed in recrystallized from isopropanol to give 867 mg of a colorless needle crystals, yield 80.2percent. The colorless crystals of 2,6-bis (trimethyltin) -4,8-bis (2-ethyl-hexyloxy) benzo [1,2-b: 4,5-b '] dithiophene.
76%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: at -78 - 20℃;
To the solution of compound 3 (2.68 g, 6 mmol) in dry THF(80 mL), n-BuLi (2.5 M in hexane, 5.28 mL, 13.2 mmol) was addedslowly at 78 C and the mixture was stirred for 1 h at the sametemperature. Trimethyltin chloride solution (1M in hexane, 14.0mL, 14.0 mmol) was added to the mixture and the mixture waswarmed to room temperature and stirred overnight. The reactionwas quenched by addingwater (100 mL) and extracted with diethylether (3 25 mL). The combined organic extract was dried overanhydrous Na2SO4. Solvent was removed under reduced pressureand residue was purified by re-crystallization in isopropanol toafford the desired compound as white solid (yield 76percent).1H NMR (500 MHz, CDCl3, d ppm): 0.44 (s, 18H), 0.94 (t,J 7.0 Hz, 6H), 1.03 (t, J 7.5 Hz, 6H), 1.35e1.44 (m, 8H), 1.47e1.53(m, 2H), 1.55e1.74 (m, 6H), 1.76e1.85 (m, 2H), 4.19 (d, J 5.5 Hz,4H), 7.51 (s, 2H).
73%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78℃; for 3.5 h;
In 1011 ^ three bottles to join4,8-diisoctyloxybenzo [1,2-b: 4,5-b '] dithiophene(1.248, 2.8 mmo 1)And 40 mL of THF,N2 under the protection of magnetic stirring,The low temperature reaction bath is cooled to -78 ° C,A n-hexane solution of n-butyllithium (2.2 M, 3. OmL) was slowly added dropwise to the three-At this temperature for 0.5 h,Then rose to room temperature reaction 0.5h,Once again cool to _78 ° C,Trimethyltin chloride (2M, 4.2 mL) was added,After reaction at this temperature for 0.5 h, the reaction was continued at room temperature for 3 h,The aqueous phase was extracted several times with n-hexane, the organic phases were combined, washed several times with saturated NaCl solution,Washed several times, the organic phase was dried, filtered, the solvent was dried and recrystallized from isopropanol,To give colorless needles l, 1.58 g, yield 73percent
71.4%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1.5 h;
Stage #2: at -78 - 20℃; for 12 h;
Put 4 (10.3 g, 23.1 mmol) in tetrahydrofuran (THF) in 4'.50 ml lowered the temperature to 78° C after dissolving. Slowly intohexane (hexane) 1.6M nBuLi(1.6M nButyllithiumin hexane, 31.7ml, 50.8mmol) dissolved in at this temperature, stirred for30 minutes. Thereafter, 0 ° C to a temperature increase from this state, stirred for 1 hour, then again lowering thetemperature to 78° C in THF in the melt 1M trimethyl tin chloride (1M in Trimethyltinchloride THF, 53.1 ml, 53.1 mmol) to aand then placed in a once raised to room temperature and stirred for 12 hours. The solution was poured into ice, diethyl ether(Diethyl ether) back extracted 2 times, washed with water two times, and the residue was removed with magnesium sulfate(MgSO4) (Magnesium sulfate). The solvent was removed under reduced pressure and the remaining solution wasrecrystallized with ethanol (ethanol) to give a solid of colorless crystals.
71.4%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1.5 h;
Stage #2: at 20℃; for 12 h;
The compound 4-b (10.3 g, 23.1 mmol) was dissolved in 50 ml of tetrahydrofuran (THF) and the temperature was lowered to -78 ° C. At this temperature 1.6 M n-BuLi (1.6 M in hexane, 31.7 ml, 50.8 mmol) dissolved in hexane was slowly added and stirred for 30 minutes. Thereafter, the temperature was raised to 0 ° C., and the mixture was stirred for 1 hour. Then, the temperature was further lowered to -78 ° C. and 1M trimethyltinchloride in THF (53.1 ml, 53.1 mmol) dissolved in THF The mixture was stirred at room temperature for 12 hours. The solution was poured into ice, extracted twice with diethyl ether, washed twice with water, and the residue was removed with magnesium sulfate (MgSO4). The solvent was removed under reduced pressure, and the solvent was recrystallized from ethanol to obtain a colorless crystalline solid (yield: 71.4percent).
61%
Stage #1: With tert.-butyl lithium In diethyl ether; hexane at -78 - 0℃; Inert atmosphere
Stage #2: at -78 - 20℃;
A dry 500-mL three-neck flask was flushed with N2 and was charged with 4,8- diethylhexyloxybenzo[l,2-b;3,4-b]dithiophene (6.9 g, 0.015 mol) and diethyl ether (Et20) (150 mL, 0.1 M) via deoxygenated syringe. The reaction flask was cooled to -78°C and a 1.7 M solution of tert-butyllithium in hexanes (23 mL, 0.038 mol) was added dropwise via deoxygenated syringe. After 30 minutes of stirring at -78°C, the solution was chilled to 0°C and stirring was continued for 5 minutes, at which point the reaction mixture was chilled back to -78°C. A I M solution of thrimethyltin chloride in THF (39 mL, 0.038 mol) was added to the reaction flask dropwise and stirring continued for 1 hour at -76°C. The cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature. As the reaction was completed, cool DI water (20 mL) was slowly added to the reaction flask. Then, the reaction mixture was poured into 100 mL of cool water and extracted with hexanes (150 mL) three times. The combined organic layer was washed with water two times and dried over anhydrous magnesium sulfate (MgS04). After the product was filtered, the solvent was removed by rotary evaporation. The crude product was purified by recrystallization three times from THF/methanol to yield white crystalline solid (7.3 g, 61percent).Spectral data: 1H NMR (300 MHz, CDC13): δH7.15 (s, 2H), 4.18 (d, 4H), 1.81 (m, 4H), 1.60 (m, 14H), 1.08 (t, 6H), 0.95 (t, 6H), 0.45 (s, 18H).
61%
Stage #1: With tert.-butyl lithium In diethyl ether; hexane at -78 - 0℃; for 0.583333 h; Inert atmosphere
Stage #2: at -76℃; for 1 h; Inert atmosphere
A dry 500-mL three-neck flask was flushed with N2 and was charged with 4,8-diethylhexyloxybenzo[1,2-b;3,4-b]dithiophene (6.9 g, 0.015 mol) and diethyl ether (Et2O) (150 mL, 0.1 M) via deoxygenated syringe. The reaction flask was cooled to −78° C. and a 1.7 M solution of tert-butyllithium in hexanes (23 mL, 0.038 mol) was added dropwise via deoxygenated syringe. After 30 minutes of stirring at −78° C., the solution was chilled to 0° C. and stirring was continued for 5 minutes, at which point the reaction mixture was chilled back to −78° C. A 1 M solution of thrimethyltin chloride in THF (39 mL, 0.038 mol) was added to the reaction flask dropwise and stirring continued for 1 hour at −76° C. The cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature. As the reaction was completed, cool DI water (20 mL) was slowly added to the reaction flask. Then, the reaction mixture was poured into 100 mL of cool water and extracted with hexanes (150 mL) three times. The combined organic layer was washed with water two times and dried over anhydrous magnesium sulfate (MgSO4). After the product was filtered, the solvent was removed by rotary evaporation. The crude product was purified by recrystallization three times from THF/methanol to yield white crystalline solid (7.3 g, 61percent). (0226) Spectral data: 1H NMR (300 MHz, CDCl3): δH 7.15 (s, 2H), 4.18 (d, 4H), 1.81 (m, 4H), 1.60 (m, 14H), 1.08 (t, 6H), 0.95 (t, 6H), 0.45 (s, 18H).
58.3%
Stage #1: With n-butyllithium In tetrahydrofuran at -80 - 20℃; Inert atmosphere
Stage #2: With tetrabutylammomium bromide In tetrahydrofuran at -80 - 20℃; Inert atmosphere
In a flask, 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophen-4,8-dione (6) (6.6 g, 30 mmol) and zinc powder (4.29 g, 66 mmol) were added to 90 ml of water, then 18 g of NaOH was added into the mixture. After the solution was refluxed for 1 h, 1-bromo-2-ethylhexane (17.4 g, 90 mmol) and a catalytic amount of tetrabutylammonium bromide were added and heated to reflux for another 6 h. Then, cold water (300 ml) was added and the mixture was extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, the residue was purified by column chromatography on silica gel to obtain 4,8-bis(2-ethylhexyloxy)benzo[1,2-b:3,4-b]dithiophene (7) in a 65percent yield. Compound 7 (6.1 g, 13.6 mmol) was added into THF (200 ml) under nitrogen, n-butyllithium (36.3 mmol, 2.2 M) was added dropwise to the mixture at −80 °C and stirred for 1 h, the cooling bath was removed, and the reactant was stirred at ambient temperature for another 1 h. Trimethyltin chloride (8 g, 40.4 mmol) was added in one portion at −80 °C and the reactant was stirred at ambient temperature overnight. After 200 ml cold water was added and the mixture was extracted with hexane, the organic layer was dried over anhydrous magnesium sulfate, after the evaporation of solvent, the residue was recrystallized by ethyl alcohol and obtained 2,6-bis(trimethyltin)-4,8-bis(2-ethylhexyl)benzo[1,2-b:3,4-b′]dithiophene 8 (6.15 g, 7.96 mmol) in a 58.3percent yield. 1H NMR (CDCl3, 500 MHz) δ (ppm): 7.52 (s,2H), 4.23 (d,4H, J = 10 Hz), 1.79(m,2H), 1.54–1.36 (m,16H), 1.06 (t,6H, J = 7.5 Hz), 0.96 (t,6H, J = 7.5 Hz), 0.40(s,18H). 13C NMR (CDCl3, 500 MHz) δ (ppm): 143.41, 140.41, 133.91, 132.89, 128.03, 40.73, 30.60, 29.30, 23.97, 23.23, 14.24, 11.41, −6.97, −8.32, −9.95.

Reference: [1] Macromolecules, 2013, vol. 46, # 19, p. 7920 - 7931
[2] Journal of the American Chemical Society, 2014, vol. 136, # 27, p. 9608 - 9618
[3] Journal of the American Chemical Society, 2009, vol. 131, p. 7792 - 7799
[4] Journal of the American Chemical Society, 2009, vol. 131, p. 7792 - 7799
[5] New Journal of Chemistry, 2013, vol. 37, # 6, p. 1728 - 1735
[6] Patent: CN103601741, 2016, B, . Location in patent: Paragraph 0056; 0057
[7] Organic Electronics: physics, materials, applications, 2016, vol. 37, p. 312 - 325
[8] Patent: CN104530105, 2016, B, . Location in patent: Paragraph 0051-0052
[9] Patent: KR2015/48636, 2015, A, . Location in patent: Paragraph 0476; 0477
[10] Patent: KR2015/114418, 2015, A, . Location in patent: Paragraph 0476; 0479-0480
[11] Australian Journal of Chemistry, 2014, vol. 67, # 5, p. 711 - 721
[12] Patent: WO2011/28827, 2011, A2, . Location in patent: Page/Page column 50
[13] Patent: US9376529, 2016, B2, . Location in patent: Page/Page column 42-43-44
[14] Reactive and Functional Polymers, 2012, vol. 72, # 11, p. 897 - 903
[15] Journal of the American Chemical Society, 2009, vol. 131, # 43, p. 15586 - 15587
[16] Chemical Communications, 2011, vol. 47, # 31, p. 8877 - 8879
[17] Journal of Materials Chemistry, 2012, vol. 22, # 40, p. 21549 - 21559
[18] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 7, p. 1028 - 1036
[19] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 5, p. 1051 - 1057
[20] Journal of Nanoscience and Nanotechnology, 2014, vol. 14, # 8, p. 6038 - 6042
[21] Polymer, 2015, vol. 56, p. 171 - 177
[22] Polymer, 2015, vol. 71, p. 113 - 121
[23] Chemical Physics Letters, 2017, vol. 667, p. 254 - 259
[24] Physical Chemistry Chemical Physics, 2017, vol. 19, # 31, p. 20513 - 20522
  • 2
  • [ 1226782-13-3 ]
  • [ 1066-45-1 ]
  • [ 1160823-78-8 ]
YieldReaction ConditionsOperation in experiment
40%
Stage #1: With n-butyllithium In tetrahydrofuran at -70℃; for 1 h; Inert atmosphere
Stage #2: at -70 - 25℃; for 2 h; Inert atmosphere
The compound (3) (4.3 g, 6 mmol) is dissolved in 100 mL of tetrahydrofuran (THF) under a nitrogen atmosphere and cooled to −70° C. n-butyllithium (13.2 mmol) is slowly added thereto and reacted at −70° C. for about 1 hour. Trimethyltin chloride (14 mmol) is added thereto, and then the temperature is slowly increased. It is reacted at room temperature of 25° C. for about 2 hours and put in cold water to complete the reaction and extracted with ether two times to provide an organic layer. The obtained organic layer is washed with water. After removing ether under vacuum, it is recrystallized in ethanol to provide a compound (4) as a colorless needle-shaped crystal (yield of 40percent). (0202) The compound (4) shows the following 1H NMR result. (0203) 1H NMR (CDCl3, 300 MHz), δ/ppm: 7.50 (2H, s), 4.19 (4H, m), 1.54 (4H, m), 1.53 (18H, m), 1.10 (12H, m).
40%
Stage #1: With n-butyllithium In tetrahydrofuran at -70 - 25℃; for 1 h; Inert atmosphere
Stage #2: at -70 - 20℃; for 2 h;
Compound (3) (4.3 g, 6 mmol) was dissolved in 100 mL of tetrahydrofuran (THF) under a nitrogen atmosphere,Lower to -70 ° C.n-Butyllithium (13.2 mmol) was slowly added thereto,Allow to react at -70 for about one hour.After adding trimethyltin chloride (14 mmol) thereto,Slowly increase the temperature.After reacting at room temperature (25 ° C) for about 2 hours,The reaction was stopped by putting it in cold water, The organic layer obtained by extraction twice with ether is washed with water.After removal of the ether in vacuo,Recrystallization from ethanol afforded compound (4) as colorless needle-like crystals (yield: 40percent).
Reference: [1] Patent: US8933441, 2015, B2, . Location in patent: Page/Page column 45
[2] Patent: KR2018/38433, 2018, A, . Location in patent: Paragraph 0215-0216; 0226-0227
  • 3
  • [ 1160823-77-7 ]
  • [ 1160823-78-8 ]
YieldReaction ConditionsOperation in experiment
61% With tert.-butyl lithium In tetrahydrofuran; water Example 5
2,6-bis(trimethyltin)-4,8-diethylhexyloxybenzo[1,2-b;3,4-b]dithiophene
A dry 500-mL three-neck flask was flushed with N2 and was charged with 4,8-diethylhexyloxybenzo[1,2-b;3,4-b]dithiophene (6.9 g, 0.015 mol) and diethyl ether (Et2O) (150 mL, 0.1 M) via deoxygenated syringe.
The reaction flask was cooled to -78° C. and a 1.7 M solution of tert-butyllithium in hexanes (23 mL, 0.038 mol) was added dropwise via deoxygenated syringe.
After 30 minutes of stirring at -78° C., the solution was chilled to 0° C. and stirring was continued for 5 minutes, at which point the reaction mixture was chilled back to -78° C.
A 1 M solution of thrimethyltin chloride in THF (39 mL, 0.038 mol) was added to the reaction flask dropwise and stirring continued for 1 hour at -76° C.
The cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature.
As the reaction was completed, cool DI water (20 mL) was slowly added to the reaction flask.
Then, the reaction mixture was poured into 100 mL of cool water and extracted with hexanes (150 mL) three times.
The combined organic layer was washed with water two times and dried over anhydrous magnesium sulfate (MgSO4).
After the product was filtered, the solvent was removed by rotary evaporation.
The crude product was purified by recrystallization three times from THF/methanol to yield white crystalline solid (7.3 g, 61percent).
Spectral data: 1H NMR (300 MHz, CDCl3): δH 7.15 (s, 2H), 4.18 (d, 4H), 1.81 (m, 4H), 1.60 (m, 14H), 1.08 (t, 6H), 0.95 (t, 6H), 0.45 (s, 18H).
Reference: [1] Patent: US2012/152357, 2012, A1,
  • 4
  • [ 18908-66-2 ]
  • [ 32281-36-0 ]
  • [ 1160823-78-8 ]
Reference: [1] Macromolecules, 2013, vol. 46, # 19, p. 7920 - 7931
[2] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 7, p. 1028 - 1036
[3] Journal of the American Chemical Society, 2014, vol. 136, # 27, p. 9608 - 9618
[4] Patent: KR2015/48636, 2015, A,
[5] Physical Chemistry Chemical Physics, 2017, vol. 19, # 31, p. 20513 - 20522
  • 5
  • [ 32281-36-0 ]
  • [ 1160823-78-8 ]
Reference: [1] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 5, p. 1051 - 1057
[2] Patent: US8933441, 2015, B2,
[3] Organic Electronics: physics, materials, applications, 2016, vol. 37, p. 312 - 325
[4] Patent: KR2015/114418, 2015, A,
[5] Patent: KR2018/38433, 2018, A,
  • 6
  • [ 18908-66-2 ]
  • [ 1160823-78-8 ]
Reference: [1] Patent: US8933441, 2015, B2,
[2] Organic Electronics: physics, materials, applications, 2016, vol. 37, p. 312 - 325
[3] Patent: KR2015/114418, 2015, A,
[4] Patent: KR2018/38433, 2018, A,
  • 7
  • [ 32281-36-0 ]
  • [ 78016-72-5 ]
  • [ 1160823-78-8 ]
Reference: [1] New Journal of Chemistry, 2013, vol. 37, # 6, p. 1728 - 1735
  • 8
  • [ 104-76-7 ]
  • [ 1160823-78-8 ]
Reference: [1] Polymer, 2015, vol. 56, p. 171 - 177
  • 9
  • [ 1160823-77-7 ]
  • [ 1160823-78-8 ]
Reference: [1] Patent: US8933441, 2015, B2,
[2] Patent: KR2018/38433, 2018, A,
  • 10
  • [ 32281-36-0 ]
  • [ 1653-16-3 ]
  • [ 1160823-78-8 ]
Reference: [1] Polymer, 2015, vol. 71, p. 113 - 121
  • 11
  • [ 1357156-35-4 ]
  • [ 1160823-78-8 ]
Reference: [1] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 5, p. 1051 - 1057
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