Home Cart 0 Sign in  

[ CAS No. 302348-51-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 302348-51-2
Chemical Structure| 302348-51-2
Structure of 302348-51-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 302348-51-2 ]

Related Doc. of [ 302348-51-2 ]

Alternatived Products of [ 302348-51-2 ]
Product Citations

Product Details of [ 302348-51-2 ]

CAS No. :302348-51-2 MDL No. :MFCD09837617
Formula : C13H19BO3 Boiling Point : -
Linear Structure Formula :HOCH2C6H4B(OC(CH3)2C(CH3)2O) InChI Key :GZZBZWITJNATOD-UHFFFAOYSA-N
M.W : 234.10 Pubchem ID :11402050
Synonyms :

Calculated chemistry of [ 302348-51-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.54
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 69.05
TPSA : 38.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.02
Log Po/w (WLOGP) : 1.33
Log Po/w (MLOGP) : 1.14
Log Po/w (SILICOS-IT) : 1.71
Consensus Log Po/w : 1.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.69
Solubility : 0.474 mg/ml ; 0.00203 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.812 mg/ml ; 0.00347 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.83
Solubility : 0.0344 mg/ml ; 0.000147 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.86

Safety of [ 302348-51-2 ]

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 [ 302348-51-2 ]

* 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 [ 302348-51-2 ]
  • Downstream synthetic route of [ 302348-51-2 ]

[ 302348-51-2 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 302348-51-2 ]
  • [ 138500-85-3 ]
YieldReaction ConditionsOperation in experiment
92% With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 20℃; for 4 h; Cooling with ice 4-hydroxymethylphenylboronic acid, pinacol ester (1.08 g, 4.61 mmol) was dissolved in THF (20 ml) together with triphenylphosphine (2.42 g, 9.23mmol). The reaction mixture was cooled in an ice-water bath, and carbon tetrabromide (3.06 g, 9.23 mmol) was added portion wise. After stirring for 4 hours at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was combined and dried by sodium sulfate. After filtration, the solvent was evaporated, and the residue was purified by flash chromatography to give the product as a white solid (1.72 g, 92percent). 1H NMR (300 MHz, CD2C12, δ): 7.62 (d, J = 6.0 Hz, 2H), 7.32 (d, J = 6.0 Hz, 2H), 4.58 (d, 2H), 1.34 (s, 9H); MS (ESI) m/z 297.0.
Reference: [1] Patent: WO2013/25885, 2013, A1, . Location in patent: Paragraph 0086
[2] Synthetic Communications, 2002, vol. 32, # 17, p. 2669 - 2676
[3] Patent: EP2450354, 2012, A1,
  • 2
  • [ 873-75-6 ]
  • [ 73183-34-3 ]
  • [ 302348-51-2 ]
YieldReaction ConditionsOperation in experiment
90% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 85℃; Inert atmosphere p-Bromobenzyl alcohol (Compound 1, 1.0 g, 5.35 mmol) was dissolved in 10 mL of dry 1,4-dioxane solution, and boranoic acid pinacol ester (247 mg, 5.88 mmol), potassium acetate and pdCl 2 ( Dppf), under N2 protection, heat to 85 ° C to stir the reaction. After the reaction was completed by thin layer chromatography, the solvent was evaporated under reduced pressure, and ethyl acetate (200 ml) was added and thenThe organic phase was dried over anhydrous sodium sulfate and concentrated under reduced vacuo.The crude product was purified by column chromatography (mobile phase ethyl acetate: petroleum ether = 1:8-1:4)Obtained 181 mg of a pale yellow oily liquid with a yield of 90percent.
1500 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 90℃; for 16 h; A mixture of (4-bromophenyl)methanol (1 g, 5.35 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (4.07 g, 16.04 mmol), KOAc (1.05 g, 10.69 mmol) and Pd(dppf)Cl2.CH2Cl2 (873.27 mg, 1.07 mmol) in 1,4-Dioxane (20 mL) was stirred at 90 C for 16 hours. After cooling to r.t., the mixture was concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0 to 50percent) to give the product (1500 mg) as oil. H NMR (400MHz DMSO-d6) __ = 7.63 (d, 2H), 7.32 (d, 2H), 5.23 (t, 1H), 4.51 (d, 2H), 1.29 (s, 12H).
Reference: [1] Patent: CN108148098, 2018, A, . Location in patent: Paragraph 0058; 0059; 0060
[2] Journal of the American Chemical Society, 2018, vol. 140, # 19, p. 6109 - 6121
[3] Patent: US2012/184520, 2012, A1, . Location in patent: Page/Page column 17
[4] Patent: CN107445885, 2017, A, . Location in patent: Paragraph 0177; 0180
[5] Patent: WO2018/98499, 2018, A1, . Location in patent: Page/Page column 215
  • 3
  • [ 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
  • 4
  • [ 128376-64-7 ]
  • [ 302348-51-2 ]
YieldReaction ConditionsOperation in experiment
513 mg at 20℃; for 5 h; To a mixture of a4-formylbenzenboronic acid (1a, 375 mg, 2.50 mmol), pinacol (355 mg, 3.00 mmol) and anhydrous magnesium sulfate (625 mg, 5.00 mmol), methanol was added (12.50 mL). The mixture was stirred at room temperature for 6 h. After the reaction was completed, the crude solution was filtered, and then sodium borohydride (47 mg, 1.25 mmol) was added to the filtrate. Afterwards, the reaction mixture was stirred for an additional 5 h. Once the reaction was completed, the reaction mixture was filtered and the filtrate was concentrated in vacuo to give the desired product 2a as a white solid (m.p. 75–77 °C) in88percent yield (513 mg). 1H-NMR (CD3OD-d4) δ ppm 7.71 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 7.8 Hz, 2H),4.62 (s, 2H), 1.34 (s, 12H); 13C-NMR (CD3OD-d4) δ ppm 146.23, 135.93, 127.26, 85.19, 65.24, 25.34;11B-NMR (CDCl3) δ ppm 34.82.
Reference: [1] Synthetic Communications, 2002, vol. 32, # 17, p. 2669 - 2676
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 9, p. 2487 - 2491
[3] Israel Journal of Chemistry, 2009, vol. 49, # 1, p. 1 - 8
[4] Molecules, 2013, vol. 18, # 10, p. 12346 - 12367
  • 5
  • [ 18282-51-4 ]
  • [ 73183-34-3 ]
  • [ 302348-51-2 ]
Reference: [1] Patent: EP2450354, 2012, A1, . Location in patent: Page/Page column 19-20
  • 6
  • [ 873-76-7 ]
  • [ 73183-34-3 ]
  • [ 302348-51-2 ]
Reference: [1] RSC Advances, 2018, vol. 8, # 25, p. 13643 - 13648
  • 7
  • [ 1225050-00-9 ]
  • [ 302348-51-2 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 13, p. 2384 - 2389
  • 8
  • [ 87199-17-5 ]
  • [ 302348-51-2 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 17, p. 2669 - 2676
[2] Molecules, 2013, vol. 18, # 10, p. 12346 - 12367
  • 9
  • [ 76-09-5 ]
  • [ 302348-51-2 ]
Reference: [1] Molecules, 2013, vol. 18, # 10, p. 12346 - 12367
  • 10
  • [ 110-91-8 ]
  • [ 302348-51-2 ]
  • [ 364794-79-6 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
  • 11
  • [ 109-01-3 ]
  • [ 302348-51-2 ]
  • [ 938043-30-2 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
  • 12
  • [ 110-89-4 ]
  • [ 302348-51-2 ]
  • [ 859833-22-0 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
  • 13
  • [ 123-75-1 ]
  • [ 302348-51-2 ]
  • [ 884507-39-5 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 302348-51-2 ]

Organoboron

Chemical Structure| 253342-48-2

[ 253342-48-2 ]

4,4,5,5-Tetramethyl-2-(m-tolyl)-1,3,2-dioxaborolane

Similarity: 0.95

Chemical Structure| 195062-57-8

[ 195062-57-8 ]

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane

Similarity: 0.95

Chemical Structure| 401797-00-0

[ 401797-00-0 ]

2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.93

Chemical Structure| 195062-59-0

[ 195062-59-0 ]

4,4,5,5-Tetramethyl-2-(o-tolyl)-1,3,2-dioxaborolane

Similarity: 0.93

Chemical Structure| 1400755-04-5

[ 1400755-04-5 ]

(4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Similarity: 0.92

Aryls

Chemical Structure| 253342-48-2

[ 253342-48-2 ]

4,4,5,5-Tetramethyl-2-(m-tolyl)-1,3,2-dioxaborolane

Similarity: 0.95

Chemical Structure| 195062-57-8

[ 195062-57-8 ]

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane

Similarity: 0.95

Chemical Structure| 401797-00-0

[ 401797-00-0 ]

2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.93

Chemical Structure| 195062-59-0

[ 195062-59-0 ]

4,4,5,5-Tetramethyl-2-(o-tolyl)-1,3,2-dioxaborolane

Similarity: 0.93

Chemical Structure| 1400755-04-5

[ 1400755-04-5 ]

(4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Similarity: 0.92

Alcohols

Chemical Structure| 1400755-04-5

[ 1400755-04-5 ]

(4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Similarity: 0.92

Chemical Structure| 651030-56-7

[ 651030-56-7 ]

2-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanol

Similarity: 0.90

Chemical Structure| 651030-55-6

[ 651030-55-6 ]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneethanol

Similarity: 0.90

Chemical Structure| 1220219-36-2

[ 1220219-36-2 ]

(1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methanol

Similarity: 0.89

Chemical Structure| 1009303-77-8

[ 1009303-77-8 ]

2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenemethanol

Similarity: 0.83