Home Cart Sign in  
Chemical Structure| 146631-00-7 Chemical Structure| 146631-00-7

Structure of 4-Benzyloxyphenylboronic acid
CAS No.: 146631-00-7

Chemical Structure| 146631-00-7

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 146631-00-7 ]

CAS No. :146631-00-7
Formula : C13H13BO3
M.W : 228.05
SMILES Code : OB(O)C1=CC=C(OCC2=CC=CC=C2)C=C1
MDL No. :MFCD01075705
InChI Key :DMJHEIDWSIAXCS-UHFFFAOYSA-N
Pubchem ID :2734314

Safety of [ 146631-00-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 146631-00-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 12
Fraction Csp3 0.08
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 67.25
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

49.69 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.29
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.79
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.54
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.77
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.08

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.95
Solubility 0.253 mg/ml ; 0.00111 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.97
Solubility 0.244 mg/ml ; 0.00107 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.96
Solubility 0.0251 mg/ml ; 0.00011 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.07 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.98

Application In Synthesis of [ 146631-00-7 ]

* 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.

  • Downstream synthetic route of [ 146631-00-7 ]

[ 146631-00-7 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 38411-20-0 ]
  • [ 146631-00-7 ]
  • 4'-benzyloxy-2,3,6-trichloro-biphenyl [ No CAS ]
  • 2
  • [ 19745-07-4 ]
  • [ 146631-00-7 ]
  • 2-chloro-5-(4-benzyloxyphenyl)pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
2-(4-Benzyloxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrazine STR50 Step 1 In accordance with scheme C-I, 30 g (201 mmol) of <strong>[19745-07-4]2,5-dichloropyrazine</strong> and 45.92 g (201 mmol) of 4-benzyloxyphenylboronic acid are coupled analogously to Example 4a to give 2-chloro-5-(4-benzyloxyphenyl)pyrazine.
  • 3
  • [ 885520-70-7 ]
  • [ 146631-00-7 ]
  • [ 1181566-98-2 ]
YieldReaction ConditionsOperation in experiment
With oxygen; triethylamine;copper diacetate; In dichloromethane; at 20℃; for 16h; Description 19. 4-bromo-6-fluoro-1-{4-[(phenylmethyl)oxy]phenyl}-1H-indole A mixture of 4-bromo-6-fluoro-1 H-indole (D16),(200 mg, 0.935 mmol), 4- benzyloxyphenylboronic acid (426 mg, 1.87 mmol), copper (II) acetate (332 mg, 1.87 mmol) and triethylamine (0.26 ml_, 188 mg, 1.87 mmol) in dichloromethane (5 ml.) was stirred in air at room temperature for 16 hours. The mixture was filtered through celite, concentrated and purified by chromatography on silica gel (elution with 0-20percent ethyl acetate in hexanes) to give the tite compound as a pink solid (D19), (205 mg). LC-MS: MH+ = 396/398 (C21H15BrFNO = 395/397)
  • 4
  • [ 23351-91-9 ]
  • [ 146631-00-7 ]
  • 4′-benzyloxybiphenyl-3,5-dicarboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
17.4 g With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; triethylamine; triphenylphosphine; In 1,4-dioxane; water; for 2h;Inert atmosphere; Reflux; 4?-benzyloxy-biphenyl-3,5-dicarboxylic acid is prepared from commercially available [4-(benzyloxy)phenyl]-boronic acid and <strong>[23351-91-9]5-bromo-isophthalic acid</strong>. To a solution of sodium carbonate (31.26 g, 295.0 mol) in dist. water (135 ml) is added 1,4-dioxane (210 ml), <strong>[23351-91-9]5-bromo-isophthalic acid</strong> (14.46 g, 59.0 mmol) and [4-(benzyloxy)phenyl]-boronic acid (14.82 g, 65.0 mol) followed by bis(triphenylphosphine)palladium(II) dichloride (0.83 g, 1.2 mmol), triphenylphosphine (0.31 g, 1.2 mmol) and triethylamine (0.12 g, 1.2 mmol) under nitrogen atmosphere. The reaction mixture is heated at reflux for 2 hs. After cooling to room temperature 400 ml dist. water is added, and the reaction mixture is neutralized with conc. HCl acid under cooling to pH1. The precipitated crude product is filtrated, washed with dist. water, and further purified by recrystallization from acetonitrile to provide gray crystals of 4?-benzyloxy-biphenyl-3,5-dicarboxylic acid (17.4 g).
  • 5
  • [ 16870-28-3 ]
  • [ 146631-00-7 ]
  • 4-(4-benzyloxyphenyl)-2-hydroxybenzoic acid potassium salt [ No CAS ]
  • 6
  • [ 16870-28-3 ]
  • [ 146631-00-7 ]
  • 4-[4'-(benzyloxy)phenyl]-2-hydroxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With palladium diacetate; potassium carbonate; triphenylphosphine; In water; N,N-dimethyl-formamide; at 100℃; for 3h;Microwave irradiation; Inert atmosphere; Sealed tube; <strong>[16870-28-3]2-hydroxy-4-iodobenzoic acid</strong> (50 mg, 0.189 mmol), acid 4-(benzyloxy)phenylboronic (51.8 mg, 0.227 mmol), PPh3 (7.4 mg, 0.028 mmol), K2CO3 (91.4 mg, 0.662 mmol), Pd(AcO)2 (2.12 mg, 0.0095 mmol), 1:1 DMF: H2O (2 ml) were used. In this case, prior to chromatographic purification, the residue from evaporating the filtrate was resuspended in acetonitrile. The precipitate was separated from the liquid phase and the latter was discarded. The solid was then purified by flash chromatography (elution with AcOEt: CH3CN:H2O:CH3OH 60:10:10:10 mixture). 95 was obtained in the form of a white solid. Yield after purification: 100 % (62 mg). 1H NMR (400 MHz, acetone-d6) delta 7.93 (d, J = 8.3 Hz, 1H), 7.70 (m, 2H), 7.51 (m, 2H), 7.41 (m, 2H), 7.34 (m, 1H), 7.23 (dd, J = 8.28, 1.82 Hz, 1H), 7.19 (d, J = 1.8 Hz, 1H), 7.14 (m, 2H), 5.21 (s, 2H). 13C NMR (101 MHz, acetone-d6) delta 172.5 (CO), 163.3 (C), 160.4 (C), 149.0 (C), 138.2 (C), 132.7 (C), 131.8(CH), 129.3 (CH), 129.2 (CH), 128.7 (CH), 128.5 (CH), 118.3 (CH), 116.2 (CH), 115.2 (CH), 111.4 (C), 70.6 (CH2). HRMS (TOF, ES-): Calculated for C20H15O4: (M-H)-: m/z 319.0970. 319.0964 found (deviation 1.9 ppm).
  • 7
  • [ 126937-43-7 ]
  • [ 146631-00-7 ]
  • 1-benzyl 2-methyl 4-(4-(benzyloxy)phenyl)piperazine-1,2-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With pyridine; oxygen; In dichloromethane; at 20℃; for 48.0h;Molecular sieve; A mixture of <strong>[126937-43-7]1-benzyl 2-methyl piperazine-1,2-dicarboxylate</strong> (2 g, 7.19 mmol), (4-(benzyloxy)phenyl)boronic acid (3.3 g, 14.37 mmol) and copper (II) acetate (1.30 g, 7.19 mmol) in dichloromethane (60 mL) was added pyridine (1.2 mL, 14.37 mmol) and 2 g of 4A molecular sieves. The reaction mixture was stirred at room temperature for 48 h under oxygen atmosphere. The resulting suspension was filtered through Celite pad, washed with 50 mL of dichloromethane and filtrate was evaporated under reduced pressure to give the crude residue. The crude residue was purified by flash chromatography (0 - 10% EtOAc in pet ether) to afford 1-benzyl 2-methyl 4-(4- (benzyloxy)phenyl)piperazine-1,2-dicarboxylate (2.2 g, 8.90 mmol, 40% yield) as off- white solid. LC-MS, [M+H]+= 461.1, (Method F, tR= 3.37 min).1H NMR (300MHz, CDCl3): δ ppm 7.48 - 7.29 (m, 10H), 6.97 - 6.84 (m, 4H), 5.27 - 5.16 (m, 2H), 5.07 - 5.00 (m, 2H), 4.96 - 4.77 (m, 1H), 4.16 - 3.93 (m, 2H), 3.77 (s, 3H), 3.51 - 3.23 (m, 2H), 2.93 - 2.65 (m, 2H). (Mixture of rotamers).
40% With pyridine; oxygen; In dichloromethane; at 20℃; for 48.0h;Molecular sieve; A mixture of <strong>[126937-43-7]1-benzyl 2-methyl piperazine-1,2-dicarboxylate</strong> (2 g, 7.19 mmol), (4-(benzyloxy)phenyl)boronic acid (3.3 g, 14.37 mmol) and copper (II) acetate (1.30 g, 7.19 mmol) in dichloromethane (60 mL) was added pyridine (1.2 mL, 14.37 mmol) and 2 g of 4A molecular sieves. The reaction mixture was stirred at room temperature for 48 h under oxygen atmosphere. The resulting suspension was filtered through Celite pad, washed with 50 mL of dichloromethane and filtrate was evaporated under reduced pressure to give the crude residue. The crude residue was purified by flash chromatography (0 - 10% EtOAc in pet ether) to afford 1-benzyl 2-methyl 4-(4- (benzyloxy)phenyl)piperazine-1,2-dicarboxylate (2.2 g, 8.90 mmol, 40% yield) as off- white solid. LC-MS, [M+H]+= 461.1, (Method F, tR= 3.37 min).1H NMR (300MHz, CDCl3): δ ppm 7.48 - 7.29 (m, 10H), 6.97 - 6.84 (m, 4H), 5.27 - 5.16 (m, 2H), 5.07 - 5.00 (m, 2H), 4.96 - 4.77 (m, 1H), 4.16 - 3.93 (m, 2H), 3.77 (s, 3H), 3.51 - 3.23 (m, 2H), 2.93 - 2.65 (m, 2H). (Mixture of rotamers).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 146631-00-7 ]

Organoborons

Chemical Structure| 156682-54-1

A154175 [156682-54-1]

(3-(Benzyloxy)phenyl)boronic acid

Similarity: 0.98

Chemical Structure| 338454-30-1

A151719 [338454-30-1]

(4-(Benzyloxy)-3-methylphenyl)boronic acid

Similarity: 0.96

Chemical Structure| 847560-49-0

A230167 [847560-49-0]

4-Benzyloxy-2-methylphenylboronic acid

Similarity: 0.96

Chemical Structure| 227305-69-3

A137520 [227305-69-3]

2,3-Dihydrobenzofuran-5-boronic acid

Similarity: 0.95

Chemical Structure| 908142-03-0

A106928 [908142-03-0]

(3-(Hydroxymethyl)-4-methoxyphenyl)boronic acid

Similarity: 0.95

Aryls

Chemical Structure| 156682-54-1

A154175 [156682-54-1]

(3-(Benzyloxy)phenyl)boronic acid

Similarity: 0.98

Chemical Structure| 338454-30-1

A151719 [338454-30-1]

(4-(Benzyloxy)-3-methylphenyl)boronic acid

Similarity: 0.96

Chemical Structure| 847560-49-0

A230167 [847560-49-0]

4-Benzyloxy-2-methylphenylboronic acid

Similarity: 0.96

Chemical Structure| 908142-03-0

A106928 [908142-03-0]

(3-(Hydroxymethyl)-4-methoxyphenyl)boronic acid

Similarity: 0.95

Chemical Structure| 190661-29-1

A326788 [190661-29-1]

(2-(Benzyloxy)phenyl)boronic acid

Similarity: 0.93

Ethers

Chemical Structure| 156682-54-1

A154175 [156682-54-1]

(3-(Benzyloxy)phenyl)boronic acid

Similarity: 0.98

Chemical Structure| 338454-30-1

A151719 [338454-30-1]

(4-(Benzyloxy)-3-methylphenyl)boronic acid

Similarity: 0.96

Chemical Structure| 847560-49-0

A230167 [847560-49-0]

4-Benzyloxy-2-methylphenylboronic acid

Similarity: 0.96

Chemical Structure| 908142-03-0

A106928 [908142-03-0]

(3-(Hydroxymethyl)-4-methoxyphenyl)boronic acid

Similarity: 0.95

Chemical Structure| 190661-29-1

A326788 [190661-29-1]

(2-(Benzyloxy)phenyl)boronic acid

Similarity: 0.93