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[ CAS No. 6165-69-1 ] {[proInfo.proName]}

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Chemical Structure| 6165-69-1
Chemical Structure| 6165-69-1
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Product Details of [ 6165-69-1 ]

CAS No. :6165-69-1 MDL No. :MFCD00151851
Formula : C4H5BO2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :127.96 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 6165-69-1 ]

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) : -6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.51
Log Po/w (WLOGP) : -0.57
Log Po/w (MLOGP) : -0.88
Log Po/w (SILICOS-IT) : 0.08
Consensus Log Po/w : -0.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.35
Solubility : 5.7 mg/ml ; 0.0446 mol/l
Class : Very soluble
Log S (Ali) : -1.52
Solubility : 3.84 mg/ml ; 0.03 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 : 2.3

Safety of [ 6165-69-1 ]

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 [ 6165-69-1 ]

* 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 [ 6165-69-1 ]
  • Downstream synthetic route of [ 6165-69-1 ]

[ 6165-69-1 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 6165-69-1 ]
  • [ 14221-01-3 ]
  • [ 95-56-7 ]
  • [ 1003-09-4 ]
Reference: [1] Patent: US2002/137746, 2002, A1,
[2] Patent: US2002/137746, 2002, A1,
  • 2
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  • [ 3012-37-1 ]
  • [ 1641-09-4 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 19, p. 4331 - 4333
  • 3
  • [ 6165-69-1 ]
  • [ 105-56-6 ]
  • [ 1468-83-3 ]
Reference: [1] New Journal of Chemistry, 2015, vol. 39, # 11, p. 8763 - 8770
  • 4
  • [ 6165-69-1 ]
  • [ 107-14-2 ]
  • [ 13781-53-8 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 1, p. 50 - 53
[2] Green Chemistry, 2017, vol. 19, # 19, p. 4515 - 4519
  • 5
  • [ 6165-69-1 ]
  • [ 124156-21-4 ]
  • [ 5751-80-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 36, p. 6013 - 6022
  • 6
  • [ 6165-69-1 ]
  • [ 1609-47-8 ]
  • [ 5751-80-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3104 - 3108
  • 7
  • [ 872-31-1 ]
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YieldReaction ConditionsOperation in experiment
72%
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.
60%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1 h;
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane; toluene at -78℃; for 0.166667 h;
Stage #3: With water In tetrahydrofuran; hexane; toluene
Preparation of Compound 1-1After 3-bormothiophene (50 g, 306 mmol) was dissolved in THF (300 mL) and toluen (1,200 mL), the mixture was cooled to -78 °C, and n-BuLi (150 mL, 2.5M in hexane, 367 mmol) was added thereto. After stirring the mixture for 1 hour, triisopropylborate (112 mL, 490 mmol) was added while maintaining temperature at -78 °C. The mixture was stirred for 10 minutes. Upon completion of the reaction, H2O was added and the mixture was extracted with EA/H2O. After removing moisture with MgSO4 and performing distillation under reduced pressure, Compound 1-1 (24 g, 60percent) was obtained by column (methylene chloride (MC)/Hexane) separation.
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 224 - 239
[2] Organic Letters, 2011, vol. 13, # 17, p. 4479 - 4481
[3] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
[4] Patent: US6342610, 2002, B2, . Location in patent: Page column 77
[5] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583
[6] Patent: WO2011/99718, 2011, A1, . Location in patent: Page/Page column 13
[7] Journal of the American Chemical Society, 2007, vol. 129, # 50, p. 15436 - 15437
[8] Arkiv foer Kemi, 1957, vol. 11, p. 373,379, 380
[9] Arkiv foer Kemi, 1957, vol. 11, p. 373,379, 380
[10] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397
  • 8
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YieldReaction ConditionsOperation in experiment
57.3%
Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1.33333 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; hexanes; water at -20℃;
A solution of 3-bromothiophene (30.67 mmol=5 g) and tri-isopropyl borate (40 mmol=8.33 g or 9 ml) in 30 ml THF was treated with n-BuLi (2.5M in hexanes, 40 mmol 16 ml) at -78° C. over a period of 20 minutes. The resulting solution was stirred at -78° C. for an hour, and was then warmed up to -20° C. slowly and quenched slowly using 2N HCl. The mixture was then warmed to room temperature, diluted with ethyl acetated and brine. The organic layer was separated, concentrated and dried in vacuo. The white crude residue was re-crystallized using hot water to give 2.25 g of pure thiophene-3-boronic acid (17.58 mmol, 57.3percent) with m.p at 126-128° C. [128-130° C. reported] (see Collis, G. E.; Burrell, A. K.; Scott, S. M.; Officer, D. L., J. Org. Chem. 2003, 68, (23), 8974-8983).
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 48, p. 4554 - 4558
[2] Patent: US2009/281290, 2009, A1, . Location in patent: Page/Page column 5
  • 9
  • [ 7732-18-5 ]
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YieldReaction ConditionsOperation in experiment
96% at 25℃; for 0.75 h; General procedure: In a flask containing the appropriate potassiumorganotrifluoroborate (0.5 mmol) in distilled water(1 mL) was added montmorillonite K10 (150percent m/m). Themixture was stirred for the time indicated in Scheme 1at room temperature. After this period, the mixture wasextracted with EtOAc (3 × 10 mL) and the organic phasewas washed with water (2 × 15 mL). The organic phasewas dried over anhydrous MgSO4, filtered and the solventwas removed in vacuo to yield the corresponding boronicacids 2a-o.
Reference: [1] Journal of the Brazilian Chemical Society, 2018, vol. 29, # 9, p. 1777 - 1785
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  • [ 109-72-8 ]
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YieldReaction ConditionsOperation in experiment
80% With hydrogenchloride In tetrahydrofuran; hexane A.
3-Thiopheneboric acid
n-Butyllithium (2.5 M solution in hexane, 20 ml, 50 mmol) was added dropwise to a solution of 3-bromothiophene (8.15 g, 50 mmol) in THF (20 ml) at -78° C. under an argon atmosphere.
The resulting solution was stirred at -78° C. for 45 min, and then added to a solution of triisopropyl borate (9.4 g, 50 mmol) in THF at -78° C. over 30 min through a steel cannula.
The resulting reaction mixture was stirred at room temperature for 12 h and was decomposed by the addition of 100 ml 1 N HCl.
The aqueous layer was extracted with ether (2*100 ml) and the combined organic layers was extracted with 1 M NaOH (3*30 ml), the aqueous extract was acidified with concentrated HCl to pH 2 and extracted with ether (3*50 ml).
The combined ether extract was washed once with water, dried over MgSO4 and filtered.
Removal of the solvent gave 3-thienylboronic acid as a solid (5.2 g, 80percent yield).
80% With hydrogenchloride In tetrahydrofuran; hexane A.
3-Thiopheneboric acid
n-Butyllithium (2.5M solution in hexane, 20 ml, 50 mmol) was added dropwise to a solution of 3-bromothiophene (8.15 g, 50 mmol) in THF (20 ml) at -78° C. under an argon atmosphere.
The resulting solution was stirred at -78° C. for 45 min, and then added to a solution of triisopropyl borate (9.4 g, 50 mmol) in THF at -78° C. over 30 min through a steel cannula.
The resulting reaction mixture was stirred at room temperature for 12 h and was decomposed by the addition of 100 ml 1N HCl.
The aqueous layer was extracted with ether (2*100 ml) and the combined organic layers was extracted with 1M NaOH (3*30 ml), the aqueous extract was acidified with concentrated HCl to pH 2 and extracted with ether (3*50 ml).
The combined ether extract was washed once with water, dried over MgSO4 and filtered.
Removal of the solvent gave 3-thienylboronic acid as a solid (5.2 g, 80percent yield).
Reference: [1] Patent: US2002/95041, 2002, A1,
[2] Patent: US5594021, 1997, A,
  • 11
  • [ 17249-80-8 ]
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Reference: [1] Organic Letters, 2012, vol. 14, # 18, p. 4814 - 4817,4
  • 12
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  • [ 121-43-7 ]
  • [ 6165-69-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 53, p. 42754 - 42761
  • 13
  • [ 872-31-1 ]
  • [ 13675-18-8 ]
  • [ 6165-69-1 ]
Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
  • 14
  • [ 5419-55-6 ]
  • [ 6165-69-1 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 19, p. 4253 - 4257
  • 15
  • [ 1192-06-9 ]
  • [ 60-29-7 ]
  • [ 688-74-4 ]
  • [ 6165-69-1 ]
Reference: [1] Arkiv foer Kemi, 1957, vol. 11, p. 373,379, 380
  • 16
  • [ 6165-69-1 ]
  • [ 19524-06-2 ]
  • [ 21308-82-7 ]
YieldReaction ConditionsOperation in experiment
73% With tetrakis(triphenylphosphine) palladium(0); cetyltrimethylammonim bromide; potassium carbonate; sodium hydroxide In water at 80℃; for 0.5 h; Inert atmosphere; Micellar solution; Microwave irradiation; Green chemistry General procedure: In a 5 mL MW vial, purged with Argon for 15 min, CTAB (219 mg, 0.6 mmol), K2CO3 (278 mg, 2 mmol), 2- or 3-thiopheneboronic acid (256 mg, 2 mmol) and Pd catalyst (0.025 mmol) were introduced. The vial was purged for further 5 min and 4 mL of degassed water was added. The proper bromopyridine isomer (158 mg, 1 mmol) was added, and in the case of a 4-bromopyridine hydrocloride, NaOH (powder, 44 mg, 1.1 mmol) was added to release the pyridine in solution as a free base. The use of only one more additional equivalent of K2CO3 was not enough to make the 4-bromopyridine hydrocloride able to react considerably. The mixture was stirred and sonicated to obtain a homogeneous solution that was introduced into a pre-heated oil bath for 24 h or reacted in a MW reactor for 30 min at the proper temperature. When the starting material was consumed, the reaction was diluted with further 5 mL of water and extracted with ethyl acetate (3 5ml). For comparison a few solvents were used: CH2Cl2 (5x5mL) or Et2O (2-3x5ml) and EtOAc (2-3x5ml), with comparable efficiencies. The organic layers were then collected, dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography of the crude residue afforded the desired products 2-7. Yields of isolated products are based on the starting pyridine.
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 40, p. 10380 - 10386
[2] Advanced Functional Materials, 2010, vol. 20, # 1, p. 105 - 110
[3] Dyes and Pigments, 2017, vol. 137, p. 468 - 479
[4] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 16, p. 3340 - 3349
  • 17
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  • [ 21308-82-7 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1266 - 1272
  • 18
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  • [ 113964-72-0 ]
  • [ 21308-82-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 33, p. 9833 - 9836[2] Angew. Chem., 2017, vol. 129, p. 9965 - 9968,4
  • 19
  • [ 6165-69-1 ]
  • [ 3132-99-8 ]
  • [ 129746-42-5 ]
YieldReaction ConditionsOperation in experiment
86% With sodium carbonate In 1,2-dimethoxyethane 3-(3-Thienyl)benzaldehyde (2a)
3.11 g of 3-thiopheneboronic acid (0.024 mol) are added to a solution of 3-bromobenzaldehyde (3 g, 0.016 mol) in 1,2-dimethoxyethane (80 ml), followed by addition of aqueous 2N sodium carbonate solution (5.15 g, 0.048 mol) and a catalytic amount of tetrakis(triphenylphosphine)palladium (0.56 g, 4.9 10-4 mol).
The reaction mixture is heated at 80° C. for 16 hours and is then cooled to room temperature and poured into water.
The resulting mixture is extracted with ethyl acetate and the organic phase is washed with saturated aqueous sodium chloride solution.
The organic phase is dried over magnesium sulfate and filtered, and the solvent is evaporated off under reduced pressure.
The title product is isolated by chromatography on a column of silica (eluent: 90/10 cyclohexane/ethyl acetate).
2.61 g of a pale yellow solid are recovered.
Yield: 86percent
m.p.: 59° C.
1H NMR (CDCl3) δ: 7.46 (s, 2H); 7.53-7.59 (m, 2H); 7.79 (d, J=7.68 Hz, 1H); 7.86 (d, J=8.88 Hz, 1H).
Reference: [1] Patent: US6417222, 2002, B1,
[2] ChemMedChem, 2016, p. 2194 - 2204
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Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 24, p. 4179 - 4182
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