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[ CAS No. 59016-93-2 ] {[proInfo.proName]}

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Chemical Structure| 59016-93-2
Chemical Structure| 59016-93-2
Structure of 59016-93-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 59016-93-2 ]

CAS No. :59016-93-2 MDL No. :MFCD00792672
Formula : C7H9BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :PZRPBPMLSSNFOM-UHFFFAOYSA-N
M.W : 151.96 Pubchem ID :2734706
Synonyms :
4-(Hydroxymethyl)benzeneboronic acid

Calculated chemistry of [ 59016-93-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 42.4
TPSA : 60.69 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) : -7.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.06
Log Po/w (WLOGP) : -1.29
Log Po/w (MLOGP) : -0.27
Log Po/w (SILICOS-IT) : -0.91
Consensus Log Po/w : -0.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.02
Solubility : 14.6 mg/ml ; 0.0964 mol/l
Class : Very soluble
Log S (Ali) : -0.76
Solubility : 26.2 mg/ml ; 0.172 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.1
Solubility : 12.0 mg/ml ; 0.0793 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 59016-93-2 ]

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 [ 59016-93-2 ]

* 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 [ 59016-93-2 ]
  • Downstream synthetic route of [ 59016-93-2 ]

[ 59016-93-2 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 109-09-1 ]
  • [ 59016-93-2 ]
  • [ 127406-56-8 ]
YieldReaction ConditionsOperation in experiment
88% With C46H49BrClFeN3Pd; copper diacetate; caesium carbonate In 1,4-dioxane at 110℃; for 24 h; General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a–k, and4m are known compounds [6,9] except for 4l and 4n.
88% With C46H49BrClFeN3Pd; copper diacetate; caesium carbonate In 1,4-dioxane at 110℃; for 24 h; General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a–k, and4m are known compounds [6,9] except for 4l and 4n.
88% With C46H49BrClFeN3Pd; copper diacetate; caesium carbonate In 1,4-dioxane at 110℃; for 24 h; General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a–k, and4m are known compounds [6,9] except for 4l and 4n.
Reference: [1] Inorganica Chimica Acta, 2014, vol. 423, # PART A, p. 11 - 15
[2] Inorganica Chimica Acta, 2014, vol. 423, # 1, p. 11 - 15
[3] Inorganica Chimica Acta, 2014, # PA, p. 11 - 15
  • 2
  • [ 87199-17-5 ]
  • [ 59016-93-2 ]
YieldReaction ConditionsOperation in experiment
80% With sodium tetrahydroborate In methanol at 0℃; for 1 h; j00699j A solution of (4-formylphenyl)boronic acid (1.5 g, 11 mmol.) in methanol (40mL), was charged with sodiumborohydride (0.38 g, 11 mmol) at 0°C and the reaction mixturewas stirred for 1 h. The reaction mixture was concentrated in vacuo resulting in a crude product was dissolved in water and cooled to 0-5°C and 5percent aqueous acetic acid solution was added up to pH=5. Precipitated solid was collected by filtration and dried to afford 1.2 (80 percent yield) the titled compound. ‘H NMR (400 MHz, CD3OD) 5 7.72 (d, J= 7.2 Hz, 1H), 7.59 (d, J= 7.6 Hz, 2H), 7.35 —7.30 (m, 2H), 4.60 (s, 2H); MS (ES+): m/z 542.15 , 544.35 [M+H] LCMS: tR =2.42 mm.
Reference: [1] Patent: WO2015/81280, 2015, A1, . Location in patent: Paragraph 00689; 00698; 00699
[2] Patent: US5827887, 1998, A,
[3] Dyes and Pigments, 2012, vol. 92, # 3, p. 982 - 987
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5781 - 5788
[5] Patent: US6576789, 2003, B1,
  • 3
  • [ 1072960-82-7 ]
  • [ 59016-93-2 ]
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 43, p. 14084 - 14085
  • 4
  • [ 164460-51-9 ]
  • [ 59016-93-2 ]
Reference: [1] European Journal of Organic Chemistry, 2000, # 23, p. 3825 - 3834
  • 5
  • [ 873-75-6 ]
  • [ 59016-93-2 ]
Reference: [1] Tetrahedron Asymmetry, 2003, vol. 14, # 22, p. 3435 - 3446
[2] European Journal of Organic Chemistry, 2000, # 23, p. 3825 - 3834
  • 6
  • [ 104-88-1 ]
  • [ 59016-93-2 ]
  • [ 87199-17-5 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
  • 7
  • [ 1122-91-4 ]
  • [ 59016-93-2 ]
  • [ 87199-17-5 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
  • 8
  • [ 17100-68-4 ]
  • [ 59016-93-2 ]
Reference: [1] European Journal of Organic Chemistry, 2000, # 23, p. 3825 - 3834
  • 9
  • [ 59016-93-2 ]
  • [ 108-98-5 ]
  • [ 6317-56-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 6, p. 2878 - 2884
  • 10
  • [ 76-09-5 ]
  • [ 59016-93-2 ]
  • [ 302348-51-2 ]
YieldReaction ConditionsOperation in experiment
92% for 22 h; Reflux A suspension of 4-(hydroxymethyl)phenylboronic acid (1.00 g, 6.6. mmol) and pinacol (0.79 g, 6.7 mmol) in tetrahydrofurane (40 mL) was refluxed over 22 h.
During this time the starting materials were completely dissolved.
The solvent was removed in vacuum (10 mbar), the residue redissolved in CH2Cl2 / EtOAc and purified by column chromatography on silica gel using the mixture of CH2Cl2 / EtOAc (9/1, v/v) as eluent.
Yield 1.4 g (92percent). Rf= 0.3 (silica, eluent - CH2Cl2 / EtOAc, 9/1, v/v).
1H NMR (200 MHz, CDCl3), δ in ppm: 1.35 (s, 12H), 4.71 (s, 2H), 7.37 (d, 2H, 3J = 8.2 Hz), 7.81 (d, 2H, 3J = 8.2 Hz).
92% for 22 h; Reflux Synthesis4-(Hvdroxymethyl)phenylboronic acid pinacol ester:A suspension of 4-(hydroxymethyl)phenylboronic acid (1.00 g, 6.6 mmol) and pinacol (0.79 g, 6.7 mmol) in tetrahydrofurane (40 ml_) was refluxed over 22 h. During this time the starting materials were completely dissolved. The solvent was removed in vacuum (10 mbar), the residue redissolved in CH2CI2 / EtOAc and purified by column chromatography on silica gel using the mixture of CH2CI2 / EtOAc (9/1 , v/v) as eluent. Yield 1.4 g (92percent). Rf= 0.3 (silica, eluent - CH2CI2 / EtOAc, 9/1 , v/v). H NMR (200 MHz, CDCI3), δ in ppm: 1.35 (s, 12H), 4.71 (s, 2H), 7.37 (d, 2H, 3J = 8.2 Hz), 7.81 (d, 2H, 3J = 8.2 Hz).
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 4, p. 756 - 758
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 924 - 934
[3] Patent: EP2497775, 2012, A1, . Location in patent: Page/Page column 11
[4] Patent: WO2012/123076, 2012, A1, . Location in patent: Page/Page column 21-22
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 45, p. 14025 - 14030[6] Angew. Chem., 2017, vol. 129, p. 14213 - 14218,6
[7] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
[8] Angewandte Chemie - International Edition, 2017, vol. 56, # 12, p. 3206 - 3210[9] Angew. Chem., 2017, vol. 129, # 12, p. 3254 - 3258,5
[10] Angewandte Chemie - International Edition, 2017, vol. 56, # 31, p. 9155 - 9159[11] Angew. Chem., 2017, vol. 129, # 31, p. 9283 - 9287,5
[12] Organic and Biomolecular Chemistry, 2017, vol. 15, # 11, p. 2459 - 2466
[13] Analytical Chemistry, 2016, vol. 88, # 21, p. 10728 - 10735
[14] Patent: WO2017/33163, 2017, A1, . Location in patent: Page/Page column 33; 34
  • 11
  • [ 59016-93-2 ]
  • [ 364794-79-6 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
  • 12
  • [ 14508-49-7 ]
  • [ 59016-93-2 ]
  • [ 127406-08-0 ]
YieldReaction ConditionsOperation in experiment
90% With C46H49BrClFeN3Pd; copper diacetate; caesium carbonate In 1,4-dioxane at 110℃; for 24 h; General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a–k, and4m are known compounds [6,9] except for 4l and 4n.
90% With C46H49BrClFeN3Pd; copper diacetate; caesium carbonate In 1,4-dioxane at 110℃; for 24 h; General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a–k, and4m are known compounds [6,9] except for 4l and 4n.
90% With C46H49BrClFeN3Pd; copper diacetate; caesium carbonate In 1,4-dioxane at 110℃; for 24 h; General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a–k, and4m are known compounds [6,9] except for 4l and 4n.
Reference: [1] Inorganica Chimica Acta, 2014, vol. 423, # PART A, p. 11 - 15
[2] Inorganica Chimica Acta, 2014, vol. 423, # 1, p. 11 - 15
[3] Inorganica Chimica Acta, 2014, # PA, p. 11 - 15
  • 13
  • [ 402-43-7 ]
  • [ 59016-93-2 ]
  • [ 457889-46-2 ]
Reference: [1] Patent: US2004/209936, 2004, A1,
[2] Patent: US2003/225158, 2003, A1, . Location in patent: Page 24
  • 14
  • [ 59016-93-2 ]
  • [ 938043-30-2 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
  • 15
  • [ 59016-93-2 ]
  • [ 859833-22-0 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
  • 16
  • [ 59016-93-2 ]
  • [ 884507-39-5 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
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