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Chemical Structure| 87199-17-5 Chemical Structure| 87199-17-5
Chemical Structure| 87199-17-5

4-Formylphenylboronic acid

CAS No.: 87199-17-5

4.5 *For Research Use Only !

Cat. No.: A340775 Purity: 98%

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Product Citations

Product Citations      Show More

Nyakuchena, James ; Chiromo, Humphrey ; Radpour, Shahrzad , et al.

Abstract: Emissive covalent organic frameworks (COFs) are a promising class of crystalline materials that have demonstrated applications for sensing and light-emitting diodes. However, white light emission from a single has not been achieved yet as it requires multicomponent organic chromophores that simultaneously emit blue, green, and red light. In this work, we report the successful synthesis of a single with efficient white light emission by utilizing tunable emission properties of 2,1,3- benzothiadazole after incorporating different functional groups on its core structure, which results in the formation of three ligands, i.e., 4′,4-(benzothiadiazole-4,7-diyl)-dibenzaldehyde (BTD), 4,4′-(benzoselenadiazole-4,7-diyl)-dibenzaldehyde (BSD), and 4,4′-(naphtho[2,3-c][1,2,3] selenadiazole-4,9-diyl)-dibenzaldehyde (NSD), that emit in the blue, green, and red regions of the visible light spectrum. We show that white light emission can only occur when BTD, BSD, and NSD are assembled in a single structure due to the facilitated energy transfer process from BTD to BSD/NSD. This work demonstrates a unique approach to developing new white light-emitting materials based on the structure.

Keywords: covalent ; organic ; framework ; emissive ; white ; light

Purchased from AmBeed: ; ; ;

Anita Marfavi ; Liam D. Adair ; Elizabeth J. New , et al.

Abstract: Two novel chromenylium-based probes were developed by functionalisation of the 5-position of the xanthene core with either a para-N-methyldiaminoacetic acid (MIDA) boronate ester (CRpMD) or closo‑1,7-carborane (CRmCB). CRpMD revealed near-infrared emission at 655 nm, demonstrating a bathochromic shift compared to the analogous phenyl derivative (CRPh). Both boron-containing probes were found to be sensitive to changes in acidic pH, with CRpMD also displaying a dual fluorescence response at alkaline pH (pKa1 = 2.40 and pKa2 = 9.16). CRmCB showed a ca. 3-fold increase in fluorescence intensity at 638 nm from pH 7.01 to 2.00, with a pKa = 2.08. Moreover, CRpMD and CRmCB were successfully taken up by A549 lung cancer cells to assess their intracellular biodistributions, thereby showcasing the future potential of these probes for time-resolved pH measurements using confocal microscopy.

Keywords: Near-infrared ; Fluorescence microscopy ; Fluorescent probes ; BoronpH sensor

Purchased from AmBeed: ; ;

Alternative Products

Product Details of [ 87199-17-5 ]

CAS No. :87199-17-5
Formula : C7H7BO3
M.W : 149.94
SMILES Code : OB(C1=CC=C(C=O)C=C1)O
MDL No. :MFCD00151823
InChI Key :VXWBQOJISHAKKM-UHFFFAOYSA-N
Pubchem ID :591073

Safety of [ 87199-17-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317-H401
Precautionary Statements:P261-P272-P273-P280-P302+P352-P333+P313-P362+P364-P501

Calculated chemistry of [ 87199-17-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 41.66
TPSA ?

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

57.53 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

0.29
Log Po/w (WLOGP)?

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

-0.82
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.

-0.36
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

-0.6
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.3

Water Solubility

Log S (ESOL):?

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

-1.22
Solubility 8.95 mg/ml ; 0.0597 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.06
Solubility 13.1 mg/ml ; 0.087 mol/l
Class?

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

Very 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

-1.22
Solubility 9.08 mg/ml ; 0.0605 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

No
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.

-7.01 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

2.0 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)

1.35

Application In Synthesis [ 87199-17-5 ]

* 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 [ 87199-17-5 ]
  • Downstream synthetic route of [ 87199-17-5 ]

[ 87199-17-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 392-83-6 ]
  • [ 87199-17-5 ]
  • [ 198205-95-7 ]
YieldReaction ConditionsOperation in experiment
88% With sodium carbonate In 1,4-dioxane; water at 80 - 100℃; To a stirred solution of 2-trifluromethyl-bromobenzene (0.7 g, 2.75 mmol) and 4-carbaldehyde boronic acid (0.5 g, 3.3 mmol) in dioxane (20 ml_) under nitrogen at 80 5C was added Pd(PPh3)4 (0.05 g) followed by the addition of a solution of Na2CO3 (0.7 g) in H2O (5 m). The mixture was stirred at 100 5C for 6 h. The solvent was evaporated and the residue was diluted to 50 ml with EtOAc and washed with H2O. The solvent was devaporated to dryness and the residue was purified by FCC (SiO2) to give the title compound (0.61 g; 88percent), as creamy solid. 1H-NMR (CDCI3) 7.49 (d, 1 H, J = 7.41 Hz); 7.48 (d, 2H, J = 8.13 Hz); 7.61 - 7.53 (m, 2H); 7.76 (d, 1 H, J = 7.8 Hz); 7.91 (d, 2H, J = 8.34 Hz); 10.07 (s, 1 H).
References: [1] Patent: WO2010/42998, 2010, A1, . Location in patent: Page/Page column 95.
  • 2
  • [ 87199-17-5 ]
  • [ 283173-50-2 ]
References: [1] Patent: WO2018/140377, 2018, A1, .
 

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