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Chemical Structure| 123324-71-0
Chemical Structure| 123324-71-0
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Product Details of [ 123324-71-0 ]

CAS No. :123324-71-0 MDL No. :MFCD01009697
Formula : C10H15BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MNJYZNVROSZZQC-UHFFFAOYSA-N
M.W : 178.04 Pubchem ID :2734320
Synonyms :
Chemical Name :(4-(tert-Butyl)phenyl)boronic acid

Calculated chemistry of [ 123324-71-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 55.54
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.5
Log Po/w (WLOGP) : 0.66
Log Po/w (MLOGP) : 1.56
Log Po/w (SILICOS-IT) : 0.4
Consensus Log Po/w : 1.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.73
Solubility : 0.333 mg/ml ; 0.00187 mol/l
Class : Soluble
Log S (Ali) : -3.0
Solubility : 0.18 mg/ml ; 0.00101 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.5
Solubility : 0.568 mg/ml ; 0.00319 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 123324-71-0 ]

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

Application In Synthesis of [ 123324-71-0 ]

* 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 [ 123324-71-0 ]
  • Downstream synthetic route of [ 123324-71-0 ]

[ 123324-71-0 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 4857-06-1 ]
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  • [ 49671-76-3 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 34, p. 12877 - 12885
[2] ACS Catalysis, 2015, vol. 5, # 6, p. 3680 - 3688
  • 2
  • [ 123324-71-0 ]
  • [ 35779-04-5 ]
YieldReaction ConditionsOperation in experiment
86% With perfluoroisopropyl iodide; copper; hydroquinone In N,N-dimethyl-formamide at 20℃; for 24 h; General procedure: (4-Nitrophenyl)boronic acid (0.067 g, 0.4 mmol), copper powder (0.0052 g, 0.08 mmol,), (CF3)2CFI (0.178 g, 0.6 mmol), and DMF (2 mL) were placed in a closed tube with a rubber stopper. The mixture was reacted at room temperature equipped with an air balloon for 24 h. The resulting suspension was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness. The crude product was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate = 20: 1 (v/v) as eluent to give 0.086 g of 2j as a light yellow solid (0.35 mmol, 87percent).
85% With copper(II) nitrate trihydrate; iodine In acetonitrile at 20℃; for 6 h; Sealed tube General procedure: 0.05 mmol Cu(NO3)2·3H2O, 1 mmol I2, 1 mmol arylboronic acids and 0.8 mL acetonitrile were added into an about 15 mL tube. Subsequently, the reaction tube was sealed to perform the reaction for 6 h without inert gas protection. Once the reaction time was reached, 10 mL water was added. The mixture was then extracted with dichloromethane (3 x 15 mL). The combined organic layers were washed with aqueous sodium hyposulfite, distilled water, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography and identified by 1H NMR, 13C NMR or GC-MS data.
82% With potassium fluoride; iodine In 1,4-dioxane at 80℃; for 1 h; General procedure: A mixture of the arylboronic acid (0.55mmol), KF (96mg, 1.65mmol) and I2 (127mg, 0.50mmol) in 1,4-dioxane (5mL) was stirred at 80°C for 1h. Then it was filtered through silica gel, eluting with Et2O (10mL) and the solvent was removed by rotary evaporation. When necessary, the product was purified by chromatography on silica gel (petroleum ether/Et2O 98:2).
Reference: [1] Journal of Fluorine Chemistry, 2016, vol. 189, p. 59 - 67
[2] Catalysis Communications, 2013, vol. 32, p. 15 - 17
[3] Tetrahedron Letters, 2015, vol. 56, # 9, p. 1122 - 1123
  • 3
  • [ 123324-71-0 ]
  • [ 3282-56-2 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 7, p. 3645 - 3650
[2] Letters in Organic Chemistry, 2012, vol. 9, # 2, p. 133 - 137
[3] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 643 - 646
[4] Organic Letters, 2012, vol. 14, # 7, p. 1736 - 1739
[5] Synthetic Communications, 2016, vol. 46, # 11, p. 963 - 970
  • 4
  • [ 123324-71-0 ]
  • [ 98-54-4 ]
  • [ 3279-07-0 ]
  • [ 3282-56-2 ]
Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 643 - 646
  • 5
  • [ 123324-71-0 ]
  • [ 3282-56-2 ]
  • [ 6637-03-2 ]
Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 643 - 646
[2] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 643 - 646
  • 6
  • [ 6637-03-2 ]
  • [ 123324-71-0 ]
  • [ 4627-22-9 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 51, p. 12575 - 12584
  • 7
  • [ 769-92-6 ]
  • [ 123324-71-0 ]
  • [ 4627-22-9 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 51, p. 12575 - 12584
  • 8
  • [ 3972-65-4 ]
  • [ 123324-71-0 ]
YieldReaction ConditionsOperation in experiment
72.8%
Stage #1: With magnesium In tetrahydrofuran
Stage #2: With Trimethyl borate In tetrahydrofuran at -70℃;
Compound   4b was synthesized according to the method described for compound   4a Yield was 72.8percent as white solid; m.p. 158–160 °C (lit. [22]: 160 °C). 1H NMR (CD3Cl, 300 MHz): δ (ppm): 8.17 (d, 2H, J = 6.6 Hz), 7.42–7.54 (m, 2H), 1.38 (s, 9H).
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 30, p. 5747 - 5750
[2] Macromolecules, 2003, vol. 36, # 7, p. 2327 - 2332
[3] Organic and Biomolecular Chemistry, 2012, vol. 10, # 33, p. 6693 - 6704
[4] Dyes and Pigments, 2012, vol. 95, # 3, p. 679 - 688
[5] Journal of the Chemical Society. Perkin Transactions 2, 2001, # 11, p. 2166 - 2173
[6] Organic and Biomolecular Chemistry, 2012, vol. 10, # 24, p. 4704 - 4711
[7] Chemistry - A European Journal, 2013, vol. 19, # 46, p. 15565 - 15571
  • 9
  • [ 7732-18-5 ]
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YieldReaction ConditionsOperation in experiment
85% at 20℃; for 0.25 h; Inert atmosphere General procedure: To a solution of potassium aryltrifluoroborate (1 mmol) in distilled H2O (4 mL) was added,sequentially, a solution of FeCl3 (8 mg, 0.05 mmol, 5 molpercent) in H2O (1 mL) and imidazole(204 mg, 3 mmol). The resulting colourless solution was stirred at room temperature for 15min. The reaction was then diluted with H2O (5 mL) and extracted with Et2O (3 x 8 mL). Thecombined organic extracts were dried (Na2SO4) and concentrated in vacuo, affording pureproduct without the requirement for further purification
Reference: [1] Synlett, 2014, vol. 25, # 4, p. 551 - 555
  • 10
  • [ 121-43-7 ]
  • [ 3972-65-4 ]
  • [ 123324-71-0 ]
Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2002, vol. 57, # 10, p. 1141 - 1146
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2002, vol. 57, # 10, p. 1141 - 1146
[3] Organometallics, 2001, vol. 20, # 11, p. 2321 - 2330
[4] Patent: US5514696, 1996, A,
[5] Organic and Biomolecular Chemistry, 2012, vol. 10, # 33, p. 6693 - 6704
[6] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 6, p. 514 - 516
  • 11
  • [ 688-74-4 ]
  • [ 3972-65-4 ]
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YieldReaction ConditionsOperation in experiment
10% With sulfuric acid; magnesium In diethyl ether; water 4-tert-Butylphenyl Boronic Acid
A solution of para-tert-butylphenyl magnesium bromide prepared from 52 ml of para-tert-butylphenyl bromide and 8.0 g of the magnesium turnings in 250 ml of diethyl ether was added to 81 ml of tri-n-butyl borate in 250 ml of diethyl ether at -80° C. with stirring under argon.
The reaction mixture was allowed to warm to ambient temperature, and was poured into 150 ml of 10percent sulfuric acid in water.
The organic phase was extracted twice by 100 ml of diethyl ether.
The solvent and n-butanol were removed under vacuum.
The viscous residue was recrystallized from boiling water.
Yield of 4-tert-butylphenyl boronic acid was 10percent as white crystals with mp. 202-203° C.
Reference: [1] Patent: US2006/9597, 2006, A1,
  • 12
  • [ 1092730-06-7 ]
  • [ 123324-71-0 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 46, p. 15565 - 15571
  • 13
  • [ 253185-03-4 ]
  • [ 123324-71-0 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 30, p. 5747 - 5750
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