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Chemical Structure| 101-55-3 Chemical Structure| 101-55-3

Structure of 101-55-3

Chemical Structure| 101-55-3

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Product Citations

Product Citations

Lim, Taeho ; Ryoo, Jeong Yup ; Han, Min Su ;

Abstract: In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.

Alternative Products

Product Details of [ 101-55-3 ]

CAS No. :101-55-3
Formula : C12H9BrO
M.W : 249.10
SMILES Code : BrC1=CC=C(OC2=CC=CC=C2)C=C1
MDL No. :MFCD00000094
InChI Key :JDUYPUMQALQRCN-UHFFFAOYSA-N
Pubchem ID :7565

Safety of [ 101-55-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H315-H318-H335-H410
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P362+P364-P403+P233-P501
Class:9
UN#:3077
Packing Group:

Computational Chemistry of [ 101-55-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 60.66
TPSA ?

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

9.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.92
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

4.3
Log Po/w (WLOGP)?

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

4.24
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.

4.01
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

3.73
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.84

Water Solubility

Log S (ESOL):?

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

-4.6
Solubility 0.00632 mg/ml ; 0.0000254 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-4.21
Solubility 0.0155 mg/ml ; 0.0000621 mol/l
Class?

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

Moderately 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

-5.51
Solubility 0.000766 mg/ml ; 0.00000308 mol/l
Class?

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

Moderately 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

Yes
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

Yes
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

Yes
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.

-4.77 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

1.0
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

0.0 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<2.0
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)

1.81

Application In Synthesis of [ 101-55-3 ]

* 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 [ 101-55-3 ]

[ 101-55-3 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 101-55-3 ]
  • [ 1190-39-2 ]
  • 2-(4-phenoxy-phenyl)-malonic acid dibutyl ester [ No CAS ]
  • 2
  • [ 101-55-3 ]
  • [ 25015-63-8 ]
  • [ 269410-26-6 ]
YieldReaction ConditionsOperation in experiment
[00432] In a reaction tube under nitrogen, a mixture of PdCl2(dppf)CH2Cl2 (22 mg; 0.027 mmol) and triethylamine (0.36 ml; 2.58 mmol) in dioxane (4 ml; dried over 4 ? sieves) was sealed and stirred at 80 C. overnight (18 h). After cooling to room temperature, HB(pin) (0.19 ml;, 1.31 mmol) and 4-bromodiphenyl ether (216 mg; 0.865 mmol) were added and the reaction mixture was stirred at 80 C. GC analysis after 18 h showed a peak at 13.84 mins which was identified by GC/MS as the desired compound.
  • 3
  • [ 101-55-3 ]
  • potassiumhexacyanoferrate(II) trihydrate [ No CAS ]
  • [ 3096-81-9 ]
  • 4
  • [ 101-55-3 ]
  • potassium ferrocyanide [ No CAS ]
  • [ 3096-81-9 ]
  • 5
  • [ 101-55-3 ]
  • [ 269410-26-6 ]
  • 7
  • [ 101-55-3 ]
  • [ 381-98-6 ]
  • [ 1404363-17-2 ]
  • 8
  • [ 101-55-3 ]
  • [ 61676-62-8 ]
  • [ 269410-26-6 ]
YieldReaction ConditionsOperation in experiment
72% With n-butyllithium; In tetrahydrofuran; at -78 - -40℃; for 18h;Inert atmosphere; 4-bromodiphenyl ether(6.2g, 25.0mmol) Isopropanol pinacol borate (10.3 mL, 50 mmol)Soluble in dry tetrahydrofuran,Cooled to -78C under nitrogen protection.n-Butyllithium (2.5M, 18 mL, 45 mmol) was added dropwise,After completion of the addition, the mixture was stirred for 6 hours and slowly warmed to -40C for 12 hours.The reaction was added to saturated ammonium chloride solution and extracted three times with ethyl acetate.The organic phases were combined and dried over anhydrous sodium sulfate.It was evaporated to dryness by rotary evaporation and purified by column to give 5.4 g of the target compound in a yield of 72%.
  • 9
  • [ 101-55-3 ]
  • [ 2979-22-8 ]
  • 1-(2-methoxy-2-phenylethoxy)-4-phenoxybenzene [ No CAS ]
  • 10
  • [ 101-55-3 ]
  • [ 630-18-2 ]
  • [ 3096-81-9 ]
YieldReaction ConditionsOperation in experiment
76% General procedure: To a solution of 4-bromobiphenyl 1a (3.0 mmol, 699.3 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol, 1.55 M in hexane, 2.87 mL) at 50 C. The obtained mixture was stirred for 30 min at 50 C under an argon atmosphere. Pivalonitrile (6.0 mmol, 498.8 mg) in THF (2.0 mL) was added to the mixture at 50 C and the obtained mixture was stirred for 30 min in the temperature range of 50 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 4-cyanobiphenyl 2a (451.6 mg, 84%).
  • 11
  • [ 101-55-3 ]
  • [ 86164-70-7 ]
  • [ 3096-81-9 ]
  • 12
  • [ 14906-59-3 ]
  • [ 101-55-3 ]
  • [ 3096-81-9 ]
  • 13
  • [ 101-55-3 ]
  • [ 60100-09-6 ]
  • [ 3096-81-9 ]
  • 14
  • [ 557-21-1 ]
  • [ 101-55-3 ]
  • [ 3096-81-9 ]
 

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Technical Information

Categories

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