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[ CAS No. 1993-03-9 ] {[proInfo.proName]}

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Chemical Structure| 1993-03-9
Chemical Structure| 1993-03-9
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Product Details of [ 1993-03-9 ]

CAS No. :1993-03-9 MDL No. :MFCD00674013
Formula : C6H6BFO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QCSLIRFWJPOENV-UHFFFAOYSA-N
M.W :139.92 Pubchem ID :2734354
Synonyms :

Calculated chemistry of [ 1993-03-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 36.23
TPSA : 40.46 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 : Yes
Log Kp (skin permeation) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.93
Log Po/w (WLOGP) : -0.07
Log Po/w (MLOGP) : 0.7
Log Po/w (SILICOS-IT) : -0.3
Consensus Log Po/w : 0.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.67
Solubility : 2.98 mg/ml ; 0.0213 mol/l
Class : Very soluble
Log S (Ali) : -1.37
Solubility : 6.03 mg/ml ; 0.0431 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.54
Solubility : 4.04 mg/ml ; 0.0288 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 1993-03-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1993-03-9 ]

* 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 [ 1993-03-9 ]
  • Downstream synthetic route of [ 1993-03-9 ]

[ 1993-03-9 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 1993-03-9 ]
  • [ 6639-36-7 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 1, p. 53 - 57
  • 2
  • [ 5922-60-1 ]
  • [ 1993-03-9 ]
  • [ 784-38-3 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 41, p. 8204 - 8211
  • 3
  • [ 1993-03-9 ]
  • [ 1609-47-8 ]
  • [ 443-26-5 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3104 - 3108
  • 4
  • [ 1993-03-9 ]
  • [ 615-36-1 ]
  • [ 316-61-0 ]
YieldReaction ConditionsOperation in experiment
92% 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.
Reference: [1] Catalysis Communications, 2016, vol. 79, p. 17 - 20
[2] Organic Letters, 2015, vol. 17, # 6, p. 1597 - 1600
  • 5
  • [ 615-43-0 ]
  • [ 1993-03-9 ]
  • [ 316-61-0 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 12, p. 2958 - 2961
[2] Organic Letters, 2016, vol. 18, # 20, p. 5192 - 5195
[3] European Journal of Medicinal Chemistry, 2018, vol. 148, p. 507 - 518
[4] Journal of Organic Chemistry, 2018, vol. 83, # 10, p. 5698 - 5706
  • 6
  • [ 1993-03-9 ]
  • [ 316-61-0 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 2, p. 346 - 349
  • 7
  • [ 1072-85-1 ]
  • [ 1993-03-9 ]
YieldReaction ConditionsOperation in experiment
61%
Stage #1: With n-butyllithium In tetrahydrofuran at -70℃; for 1.5 h;
Stage #2: With Triisopropyl borate In tetrahydrofuran at 20℃; for 4 h;
Stage #3: With hydrogenchloride In tetrahydrofuran
10.0 g (57.1 mmol) of 1-bromo-2-fluorobenzene and dehydrated tetrahydrofuran were placed, followed by cooling to -70° C. To the resulting mixture, 44.2 ml (68.5 mmol) of 1.55M-normalbutyllithium was added dropwise. The resulting mixture was stirred at -70° C. for 1.5 hours, and 21.5 g (114.2 mmol) of triisopropyl borate was added dropwise, and the temperature was elevated to room temperature, followed by stirring for 4 hours. An aqueous hydrochloric acid solution was added to the reaction mixture, and extracted with dichloromethane. The solvent in the organic phase was removed under reduced pressure, thereby to obtain a crude product of the compound (f). This crude product was purified by column chromatography (hexane: acetone), whereby 4.8 g (yield: 61percent) of compound (f) was obtained.
48%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2 h;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #3: With hydrogenchloride; water; ammonium chloride In tetrahydrofuran; n-heptane; water at 0℃; Acidic aqueous solution
EXAMPLE IV
2-Fluorophenylboronic Acid
Under argon, 155 g (0.86 mol) of 2-fluorobromobenzene are initially charged in 732 ml of absolute tetrahydrofuran and, at -78° C., mixed slowly with 600 ml of 1.6 M n-butyllithium in hexane.The mixture is then stirred at -78° C. for 2 h.At -78° C., 298 ml (1.28 mol) of trimethyl borate are then added dropwise.After 1 h, cooling is removed, and the reaction mixture is stirred overnight and warmed to room temperature.For work-up, the mixture is, at 0° C., mixed with 346 ml of saturated ammonium chloride solution, the PH is adjusted to PH 6 using 1N HCl and the aqueous phase is extracted 3 times with in each case 250 ml of methylene chloride.The combined organic phases are washed with saturated sodium chloride solution and dried with magnesium sulphate.This gives Example IV in the form of a beige solid.
Yield: 60.0 g (48percent)
MS (EI, m/z): 140 (80percent, [M]+), 96 (100percent, [C6H5F]+)
Reference: [1] Patent: US2012/273770, 2012, A1, . Location in patent: Page/Page column 24
[2] Patent: US2004/6076, 2004, A1, . Location in patent: Page 15
[3] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
  • 8
  • [ 1072-85-1 ]
  • [ 5419-55-6 ]
  • [ 1993-03-9 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With n-butyllithium In tetrahydrofuran at -70℃; for 0.5 h; Inert atmosphere; Autoclave; Large scale
Stage #2: at -70℃; Large scale
Under nitrogen atmosphere, 14 kg (22.9 mol) of the compound and 20 L of THF were sequentially added to the 50 L autoclave, and the temperature was lowered to -70 ° C.Temperature control -70 the following dropping n-BuLi6.8kg, after dropping at -70 below stirring 0.5 hours. Temperature -70 below the dropBoric acid isopropyl ester 4.75kg, drop back after the natural warm night. Poured into 20L (1N) dilute hydrochloric acid, liquid, water phase and thenEA10L. The combined organic phases were washed once with saturated brine 10 L, dried over anhydrous sodium sulfate, filtered and concentratedTo give 22.4 kg of the compound in 85percent yield.
Reference: [1] Patent: CN105801553, 2016, A, . Location in patent: Paragraph 0093; 0094; 0095
[2] Organic Letters, 2015, vol. 17, # 2, p. 346 - 349
  • 9
  • [ 1072-85-1 ]
  • [ 121-43-7 ]
  • [ 1993-03-9 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 15, p. 3630 - 3633
  • 10
  • [ 1072-85-1 ]
  • [ 109-72-8 ]
  • [ 5419-55-6 ]
  • [ 1993-03-9 ]
YieldReaction ConditionsOperation in experiment
63% With hydrogenchloride In tetrahydrofuran Preparation 3
2-Fluorobenzeneboronic Acid
A solution of 50 g (285.6 mmol) of 2-fluorobromobenzene in 400 mL of tetrahydrofuran was cooled to -78° C. and 200 mL (320.0 mmol) of 1.6M n-Butyllithium was added via a cannula.
The mixture was stirred at -78° C. for 60 minutes, then 98.9 mL (428.4 mmol) of triisopropyl borate was added via a cannula and stirring was continued for 60 minutes.
The cooling bath was removed and the mixture was stirred at ambient temperature for 1.5 hours, then 150 mL of 6N hydrochloric acid was added and stirring was continued for 1.5 hours.
To the mixture was added 100 mL of brine, and then the organic layer was separated and the aqueous layer was extracted three times with 30 mL each of ether.
The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo.
The residue was recrystallized from water to afford 25.2 g (63percent) of the title compound.
63% With hydrogenchloride In tetrahydrofuran PREPARATION 3
2-Fluorobenzeneboronic Acid
A solution of 50 g (285.6 mmol) of 2-fluorobromobenzene in 400 mL of 15 tetrahydrofuran was cooled to -78° C. and 200 mL (320.0 mmol) of 1.6M n-Butyllithium was added via a cannula.
The mixture was stirred at -78° C. for 60 minutes, then 98.9 mL (428.4 mmol) of triisopropyl borate was added via a cannula and stirring was continued for 60 minutes.
The cooling bath was removed and the mixture was stirred at ambient temperature for 1.5 hours, then 150 mL of 6N hydrochloric acid was added and stirring was continued for 1.5 hours.
To the mixture was added 100 mL of brine, and then the organic layer was separated and the aqueous layer was extracted three times with 30 mL each of ether.
The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo.
The residue was recrystallized from water to afford 25.2 g (63percent) of the title compound.
Reference: [1] Patent: US6303816, 2001, B1,
[2] Patent: US6500865, 2002, B1,
  • 11
  • [ 13675-18-8 ]
  • [ 348-54-9 ]
  • [ 1993-03-9 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
  • 12
  • [ 462-06-6 ]
  • [ 5419-55-6 ]
  • [ 1993-03-9 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 4, p. 487 - 491
  • 13
  • [ 348-52-7 ]
  • [ 1993-03-9 ]
Reference: [1] Journal of Organometallic Chemistry, 2000, vol. 598, # 1, p. 127 - 135
  • 14
  • [ 1072-85-1 ]
  • [ 13675-18-8 ]
  • [ 1993-03-9 ]
Reference: [1] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
  • 15
  • [ 13675-18-8 ]
  • [ 446-46-8 ]
  • [ 1993-03-9 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
  • 16
  • [ 348-54-9 ]
  • [ 1993-03-9 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
  • 17
  • [ 1993-03-9 ]
  • [ 1122-91-4 ]
  • [ 57592-42-4 ]
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 453 - 462
[2] Patent: EP3202759, 2017, A1, . Location in patent: Paragraph 0050
[3] Patent: WO2009/129625, 2009, A1, . Location in patent: Page/Page column 31
  • 18
  • [ 76-09-5 ]
  • [ 1993-03-9 ]
  • [ 18107-18-1 ]
  • [ 517920-60-4 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: at 60℃; for 4 h;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; 1,4-dioxane; water at 60℃; for 4 h;
To a 10 mL reaction tube equipped with a magnet was added 56 mg (0.4 mmol) of 2-fluorobenzeneboronic acid, 0.6 mL (1.2 mmol) of trimethylsilyl diazomethane (2 M n-hexane solution), 1 mL of toluene was added to the system, The rubber stopper was stoppered and reacted on an electromagnetic heating stirrer at 60 ° C for 4 hours.(0.4 mmol) of tetramethylammonium fluoride (1 M tetrahydrofuran solution) and 200 uL of water were added to an electromagnetic heating stirrer at 60 ° C On the reaction for 4 hours.After completion of the reaction, the organic solvent was removed by a rotary evaporator and purified by column chromatography2-fluorobenzyl boronic acid pinacol ester, its structure is as follows:The compound was a colorless liquid in a yield of 81percent and its NMR data was as follows:
Reference: [1] Patent: CN105884808, 2016, A, . Location in patent: Paragraph 0148; 0149; 0150; 0151; 0152; 0153
  • 19
  • [ 14221-01-3 ]
  • [ 1993-03-9 ]
  • [ 886444-12-8 ]
Reference: [1] Patent: US2007/37974, 2007, A1, . Location in patent: Page/Page column 23
  • 20
  • [ 881676-32-0 ]
  • [ 1993-03-9 ]
  • [ 881674-56-2 ]
YieldReaction ConditionsOperation in experiment
82.8% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 105℃; for 20 h; Inert atmosphere Weigh 15.0 g (0.086 mol) of 5-bromopyrrole-3-carbaldehyde, 19.0 g (0.136 mol) of 2-fluorophenylboronic acid, 15.0 g of potassium carbonate in a four-necked flask, and add 100 g of DMF and 40 g of water in a nitrogen atmosphere. A catalytic amount of tetrakis(triphenylphosphine)palladium was added thereto, and the temperature was raised to 105 ° C, and the reaction was carried out for 20 hours. After the reaction was completed, the temperature was lowered to room temperature, diluted with water, and extracted with ethyl acetate. The extract was dried, suction filtered, concentrated and weighed. Crystallization gave 13.5 g of gray solid 1, yield 82.8percent, purity 99.94percent
Reference: [1] Patent: CN109006823, 2018, A, . Location in patent: Paragraph 0060; 0062; 0070; 0071
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  • [ 1378388-20-5 ]
Reference: [1] Patent: CN105801553, 2016, A,
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