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Chemical Structure| 6165-68-0
Chemical Structure| 6165-68-0
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Product Details of [ 6165-68-0 ]

CAS No. :6165-68-0 MDL No. :MFCD00151850
Formula : C4H5BO2S Boiling Point : -
Linear Structure Formula :- InChI Key :ARYHTUPFQTUBBG-UHFFFAOYSA-N
M.W :127.96 Pubchem ID :2733960
Synonyms :

Calculated chemistry of [ 6165-68-0 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 34.14
TPSA : 68.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.54
Log Po/w (WLOGP) : -0.57
Log Po/w (MLOGP) : -0.88
Log Po/w (SILICOS-IT) : 0.08
Consensus Log Po/w : -0.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.37
Solubility : 5.46 mg/ml ; 0.0427 mol/l
Class : Very soluble
Log S (Ali) : -1.55
Solubility : 3.57 mg/ml ; 0.0279 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.52
Solubility : 38.8 mg/ml ; 0.303 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.56

Safety of [ 6165-68-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6165-68-0 ]

* 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 [ 6165-68-0 ]
  • Downstream synthetic route of [ 6165-68-0 ]

[ 6165-68-0 ] Synthesis Path-Upstream   1~33

  • 1
  • [ 1003-09-4 ]
  • [ 6165-68-0 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12 h; Inert atmosphere
Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere
General procedure: Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol percent), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol percent) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 °C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3.x.10 mL). The aqueous layer was then cooled to 0 °C (ice bath) and acidified to pH <=1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3.x.10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid.
Reference: [1] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583
[2] Arkiv foer Kemi, 1957, vol. 11, p. 373,379, 380
[3] New Journal of Chemistry, 2002, vol. 26, # 4, p. 373 - 375
[4] Patent: EP674635, 2001, B1,
  • 2
  • [ 3437-95-4 ]
  • [ 6165-68-0 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With diisopropopylaminoborane; triethylamine; triphenylphosphine; palladium dichloride In tetrahydrofuran at 65℃; for 12 h; Inert atmosphere
Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere
General procedure: Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol percent), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol percent) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 °C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3.x.10 mL). The aqueous layer was then cooled to 0 °C (ice bath) and acidified to pH <=1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3.x.10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid.
Reference: [1] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583
  • 3
  • [ 1158984-92-9 ]
  • [ 6165-68-0 ]
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, p. 6961 - 6963
  • 4
  • [ 1003-09-4 ]
  • [ 150-46-9 ]
  • [ 6165-68-0 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;
Stage #2: at -78 - 20℃;
Stage #3: Cooling
To a solution of 2-bromothiophene (8.05 g, 50 mmol) in 100 mL anhydrous THF at -780C, n-BuLi (34 mL, 55 mmol, 1.6 M hexane) was added. The reaction mixture was warmed to RT and stirred for 1 h. After the mixture was cooled to -780C, triethyl borate (17 mL, 100 mmol) was slowly added into the mixture and the solution was warmed to RT and stirred for 12 h. At the end of the reaction, the mixture was poured into the 100 mL of 2N HCl and ice, the aqueous layer was extracted with ether, and the organic layer was dried over anhydrous MgSO4. The solvent was removed by rotary evaporation. The residue was recrystallized with n-hexane to obtain the product (45percent). 1H-NMR (300 MHz, CDCl3) δ 7.68 (dd, IH), 7.3 (d, IH), 7.15 (dd, IH).
Reference: [1] Patent: WO2010/12710, 2010, A1, . Location in patent: Page/Page column 22
  • 5
  • [ 188290-36-0 ]
  • [ 6165-68-0 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 23, p. 8974 - 8983
[2] Journal of Organic Chemistry, 2008, vol. 73, # 17, p. 6831 - 6834
[3] Canadian Journal of Chemistry, 2010, vol. 88, # 3, p. 236 - 246
[4] Chinese Journal of Chemistry, 2012, vol. 30, # 3, p. 681 - 688
  • 6
  • [ 1003-09-4 ]
  • [ 121-43-7 ]
  • [ 6165-68-0 ]
Reference: [1] European Journal of Inorganic Chemistry, 2008, # 13, p. 2177 - 2185
  • 7
  • [ 121-43-7 ]
  • [ 89180-57-4 ]
  • [ 6165-68-0 ]
Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 113
[2] Journal of the American Chemical Society, 1938, vol. 60, p. 111 - 115
[3] , Gmelin Handbook: B: B-Verb.13, 4.7.2.2, page 189 - 196,
  • 8
  • [ 1003-09-4 ]
  • [ 688-74-4 ]
  • [ 6165-68-0 ]
Reference: [1] Patent: US6034093, 2000, A,
[2] Patent: US5731315, 1998, A,
  • 9
  • [ 1003-09-4 ]
  • [ 22092-92-8 ]
  • [ 7732-18-5 ]
  • [ 6165-68-0 ]
Reference: [1] Heterocycles, 2012, vol. 86, # 1, p. 331 - 341
  • 10
  • [ 96-43-5 ]
  • [ 6165-68-0 ]
Reference: [1] New Journal of Chemistry, 2002, vol. 26, # 4, p. 373 - 375
[2] Organic Letters, 2012, vol. 14, # 18, p. 4814 - 4817,4
  • 11
  • [ 1003-09-4 ]
  • [ 121-43-7 ]
  • [ 188290-36-0 ]
  • [ 98-03-3 ]
  • [ 6165-68-0 ]
Reference: [1] New Journal of Chemistry, 2002, vol. 26, # 4, p. 373 - 375
[2] New Journal of Chemistry, 2002, vol. 26, # 4, p. 373 - 375
  • 12
  • [ 13283-31-3 ]
  • [ 5713-61-1 ]
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Reference: [1] Journal of Organometallic Chemistry, 1983, vol. 259, # 3, p. 269 - 274
  • 13
  • [ 96-43-5 ]
  • [ 121-43-7 ]
  • [ 188290-36-0 ]
  • [ 98-03-3 ]
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Reference: [1] New Journal of Chemistry, 2002, vol. 26, # 4, p. 373 - 375
  • 14
  • [ 188290-36-0 ]
  • [ 150-46-9 ]
  • [ 6165-68-0 ]
Reference: [1] Journal of Physical Chemistry B, 2007, vol. 111, # 39, p. 11407 - 11418
  • 15
  • [ 2786-07-4 ]
  • [ 6165-68-0 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 8851 - 8863
  • 16
  • [ 1158984-92-9 ]
  • [ 7732-18-5 ]
  • [ 6165-68-0 ]
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, p. 6961 - 6963
  • 17
  • [ 188290-36-0 ]
  • [ 121-43-7 ]
  • [ 6165-68-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 20, p. 5956 - 5960[2] Angew. Chem., 2016, vol. 128, # 20, p. 6060 - 6064,5
  • 18
  • [ 1003-09-4 ]
  • [ 13283-31-3 ]
  • [ 6165-68-0 ]
Reference: [1] Journal of Organometallic Chemistry, 1983, vol. 259, # 3, p. 269 - 274
  • 19
  • [ 121-43-7 ]
  • [ 5713-61-1 ]
  • [ 6165-68-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 12, p. 3011 - 3024
  • 20
  • [ 2786-07-4 ]
  • [ 60-29-7 ]
  • [ 688-74-4 ]
  • [ 6165-68-0 ]
Reference: [1] Arkiv foer Kemi, 1957, vol. 11, p. 373,379, 380
  • 21
  • [ 6165-68-0 ]
  • [ 589-87-7 ]
  • [ 40133-22-0 ]
Reference: [1] Journal of Physical Chemistry B, 2001, vol. 105, # 37, p. 8845 - 8860
  • 22
  • [ 6165-68-0 ]
  • [ 162607-17-2 ]
Reference: [1] Arkiv foer Kemi, 1957, vol. 11, p. 373,379, 380
[2] Arkiv foer Kemi, 1957, vol. 11, p. 373,379, 380
  • 23
  • [ 6165-68-0 ]
  • [ 3302-39-4 ]
  • [ 545442-25-9 ]
  • [ 62532-99-4 ]
  • [ 615-36-1 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 41, p. 10320 - 10329
  • 24
  • [ 6165-68-0 ]
  • [ 618-51-9 ]
  • [ 29886-63-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 24, p. 10994 - 11005
  • 25
  • [ 6165-68-0 ]
  • [ 619-58-9 ]
  • [ 29886-62-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 24, p. 10994 - 11005
[2] Journal of Organic Chemistry, 1996, vol. 61, # 15, p. 5169 - 5171
  • 26
  • [ 6165-68-0 ]
  • [ 586-76-5 ]
  • [ 29886-62-2 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 29, p. 5661 - 5663
  • 27
  • [ 6165-68-0 ]
  • [ 6630-33-7 ]
  • [ 99902-07-5 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 1, p. 58 - 61
[2] Advanced Synthesis and Catalysis, 2008, vol. 350, # 14-15, p. 2391 - 2400
[3] Patent: US6150413, 2000, A,
[4] Organic Letters, 2014, vol. 16, # 16, p. 4134 - 4137
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 23, p. 5293 - 5297
[6] Patent: EP1392687, 2017, B1, . Location in patent: Paragraph 0171-0172
  • 28
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  • [ 18013-97-3 ]
Reference: [1] Patent: EP2696351, 2014, A2, . Location in patent: Page/Page column
[2] Patent: US8890134, 2014, B2, . Location in patent: Page/Page column
  • 29
  • [ 3141-27-3 ]
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  • [ 1081-34-1 ]
  • [ 492-97-7 ]
  • [ 3480-11-3 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 25, p. 8877 - 8884
  • 30
  • [ 29504-81-2 ]
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  • [ 3480-11-3 ]
Reference: [1] Dalton Transactions, 2013, vol. 42, # 3, p. 638 - 644
  • 31
  • [ 6165-68-0 ]
  • [ 1122-91-4 ]
  • [ 107834-03-7 ]
YieldReaction ConditionsOperation in experiment
87% With C7H10N2*Pd(2+)*2Cl(1-); potassium carbonate In ethanol; water for 0.166667 h; Reflux; Schlenk technique General procedure: A 20mL Schlenk tube with a magnetic stir bar was charged with aryl halide (2mmol), arylboronic acid (2.4mmol), K2CO3 (5mmol), 10mL of solvent [H2O, H2O–MeOH (1:1), H2O–EtOH (1:1), H2O–EG (1:1)] and an aliquot of 0.01M solution of palladium complexes PdCl2(L)2 or Pd[(L)4]Cl2 in MeOH (0.001–0.2molpercent) under air atmosphere. The reaction mixture was placed in a preheated oil bath: at 100°C for MeOH–H2O, at 110°C for EtOH–H2O, at 140°C for H2O and at 160°C for EG–H2O; and stirred under reflux for the given time. After this time, the mixture was cooled, acidified by 5M HCl (in the case of acids) and diluted with 10mL of H2O and 10mL of Et2O (or EtOAc). The organic phase was separated, and the aqueous layer was extracted with Et2O EtOAc) (2×10mL). The combined organic layers were washed with H2O (10mL), brine (10mL), and dried over Na2SO4. The pure products were obtained by a simple filtration of ether solution through silica gel pad and evaporation of a solvent.
40% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; water; tolueneReflux General procedure: Tetrakis(triphenylphosphine)palladium(0) (0.0168 mmol) was added to a solution of 4-bromobenzaldehyde (50, 5.6 mmol) in ethanol-toluene (40 mL, 1:1). After 15 min, the appropriate boronic acid 51b-m (6.75 mmol) was added, followed by sodium hydrogen carbonate (22.4 mmol) and water (11 mL). The resulting mixture was heated under reflux for 9-15 hours. After cooling, the reaction mixture was filtered through Celite.(R)., the organic phase was separated, washed with brine (2x20 mL), dried and the solvent evaporated in vacuo. The residue thus obtained was purified by flash-chromatography. Elution by light petroleum-ethyl acetate mixtures afforded the desired compounds.
Reference: [1] Chemistry of Heterocyclic Compounds, 2014, vol. 50, # 1, p. 19 - 25[2] Khim. Geterotsikl. Soedin., 2014, vol. 50, # 1, p. 24 - 31,7
[3] Russian Journal of General Chemistry, 2014, vol. 84, # 9, p. 1782 - 1792[4] Zh. Obshch. Khim., 2014, vol. 84, # 9, p. 1546 - 1556,11
[5] RSC Advances, 2015, vol. 5, # 85, p. 69776 - 69781
[6] Journal of Medicinal Chemistry, 2003, vol. 46, # 10, p. 1918 - 1930
[7] Catalysis Communications, 2016, vol. 79, p. 17 - 20
[8] European Journal of Organic Chemistry, 2006, # 17, p. 3938 - 3946
[9] Macromolecules, 2011, vol. 44, # 13, p. 5155 - 5167
[10] Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6379 - 6397
[11] Advanced Synthesis and Catalysis, 2008, vol. 350, # 14-15, p. 2391 - 2400
[12] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3429 - 3445
[13] Journal of Medicinal Chemistry, 2014, vol. 57, # 20, p. 8445 - 8458
[14] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 453 - 462
  • 32
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  • [ 107834-03-7 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 24, p. 4179 - 4182
  • 33
  • [ 6165-68-0 ]
  • [ 15155-41-6 ]
  • [ 165190-76-1 ]
YieldReaction ConditionsOperation in experiment
95% With O4P(3-)*3K(1+)*5H2O; tri(1-adamantyl)phosphine; {2-[((acetyl-κO)amino)phenyl-κC](tri-1-adamantylphosphine)palladium}(p-toluenesulfonate) In tetrahydrofuran at 20℃; for 1 h; To a mixture of 4,7-dibromobenzo[cJ{1,2,5]thiadiazole (147 mg, 0.50 mmol, 1 equiv),thiophen-2-ylboronic acid (192 mg, 1.50 mmol, 3 equiv), and K3P045H20 (0.90 g, 3.0 mmol, 6 equiv) was added THF (900 jiL) then a THF stock solution of 3 and PAd3 (100 iL, 0.25 jtmol ofPd/PAds). The mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate then extracted with water. The combine organic layers were evaporated andthe crude product was purified by flash chromatography. After drying, 143 mg (95percent) of 40 was obtained as an orange solid. NMR spectroscopic data agreed with literature values.
84.3% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 75℃; Inert atmosphere I) 4,7-dibromo-2,1,3-benzothiadiazole (2.01 g, 6.84 mmol), 2-thiopheneBoric acid (1.42 g, 11 mmol) was dissolved in 20 mL of toluene and 15 mL of 2M potassium carbonate solution was injected.(Tetraphenylphosphine) palladium (150 mg, 0.14 mmol) was added and heated to 75 ° C for 2-8 h. Natural cold to room temperature, dichloromethaneHexane extraction, drying, concentration and column chromatography to obtain red crystals of 4,7-dithiophene-2,1,3-benzothiadiazole 1.73 g, yield84.3percent.
80%
Stage #1: With potassium phosphate In 1,4-dioxane; water at 80℃; for 7 h;
Stage #2: With sodium cyanide In 1,3-dioxane; water
Preparation of bis-4,7-(thien-2-yl)-2,1,3-benzothiadiazole
13.5 g (11.7 mmol, 0.065 eq.) of Pd(PPh3)4 were added to a nitrogen-saturated mixture consisting of 52.92 g (180 mmol) of 1',4'-dibromo-2,1,3-benzothiadiazole, 60 g (468.9 mmol, 2.6 eq.) of thiophene-2-boronic acid, 149 g (702 mmol, 3.9 eq.) of K3PO4, 1 l of dioxane and 1 l of water and the suspension was heated at 80° C. for 7 hours. 0.8 g of NaCN was then added and the aqueous phase was separated off.
The organic phase washed twice with H2O and subsequently dried over Na2SO4.
The solvent was removed and the residue was recrystallized twice from CH2Cl2/MeOH to give dark red needles which according to HPLC had a purity of about 99percent.
The yield was 43 g (80percent).
1H NMR (CDCl3, 500 MHz): [ppm]=8.11 (dd, 3JHH=3.68 Hz, 2H), 7.89 (s, 2H), 7.46 (dd, 3JHH=5.2 Hz, 2H), 7.21 (dd, 3JHH=5.2 Hz, 2H).
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 20, p. 6392 - 6395
[2] Patent: WO2017/75581, 2017, A1, . Location in patent: Page/Page column 31
[3] Organic Letters, 2017, vol. 19, # 3, p. 654 - 657
[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 17, p. 6111 - 6119
[5] Patent: CN106432178, 2017, A, . Location in patent: Paragraph 0051; 0052; 0053; 0055
[6] Chemical Communications, 2004, # 20, p. 2342 - 2343
[7] Patent: WO2004/2970, 2004, A1, . Location in patent: Page/Page column 22
[8] Patent: US2007/265473, 2007, A1, . Location in patent: Page/Page column 16
[9] Journal of Materials Chemistry, 2006, vol. 16, # 8, p. 736 - 740
[10] Journal of the American Chemical Society, 2012, vol. 134, # 46, p. 19035 - 19042
[11] Patent: US2004/229925, 2004, A1, . Location in patent: Page 3
[12] Inorganic Chemistry Communications, 2013, vol. 36, p. 130 - 132
[13] Patent: CN103601757, 2016, B, . Location in patent: Page/Page column 13
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