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Chemical Structure| 27329-70-0

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Product Details of [ 27329-70-0 ]

CAS No. :27329-70-0
Formula : C5H5BO4
M.W : 139.90
SMILES Code : OB(C1=CC=C(C=O)O1)O
MDL No. :MFCD01114696
InChI Key :JUWYQISLQJRRNT-UHFFFAOYSA-N
Pubchem ID :2734355

Safety of [ 27329-70-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H318-H335-H411
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P362+P364-P403+P233-P501
Class:9
UN#:3077
Packing Group:

Computational Chemistry of [ 27329-70-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 5
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 33.92
TPSA ?

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

70.67 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

-0.28
Log Po/w (WLOGP)?

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

-1.23
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.

-2.29
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

-1.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.98

Water Solubility

Log S (ESOL):?

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

-0.77
Solubility 23.8 mg/ml ; 0.17 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.

-0.74
Solubility 25.2 mg/ml ; 0.18 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

-0.42
Solubility 52.8 mg/ml ; 0.378 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.

-7.35 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)

2.56

Application In Synthesis of [ 27329-70-0 ]

* 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 [ 27329-70-0 ]

[ 27329-70-0 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 584-12-3 ]
  • [ 27329-70-0 ]
  • [ 16303-60-9 ]
  • 2
  • [ 13195-50-1 ]
  • [ 27329-70-0 ]
  • 5-(5-nitrothiophen-2-yl)-furan-2-carbaldehyde [ No CAS ]
  • 3
  • [ 13529-27-6 ]
  • [ 27329-70-0 ]
YieldReaction ConditionsOperation in experiment
75% A dried 500 mL 3-neck flask with mechanical stirrer, internal thermometer and addition funnel under nitrogen is charged with 20,16 g (0,118 mol) furfuraldiethylacetal, 33,4 g (0,177 mol) triisopropylborate and 40 mL of anhydrous THF. The water content of the reaction mixture was measured according to the Karl-Fischer-titration method and was determined to be less than 800 mug/mL of water. The solution is cooled to an internal temperature of -10C. Keeping the temperature at -10C to 0C 84 mL (25 wt%, 1.84 M solution THF, heptane, ethylbenzene from Chemmetal, content determined by titration, 1.3 equivalents) LDA was added via addition funnel to the reaction mixture over a period of 1 hour. Using a canula the reaction mixture was subsequently transferred to precooled aqueous hydrochloric acid which was obtained by mixing 33 mL of concentrated hydrochloric acid and 55 mL water. The reaction temperature was maintained at a temperature of less than 30C. The resulting tan slurry of 5-formyl-2-furylboronic acid was cooled to 0C and filtered. The filter cake was washed twice with 20 mL of cold water to give 17.6 g of wet cake. Drying (40C, vacuum oven) gave 12.41 g of an off-white product. The overall yield of 5-formyl-2-furylboronic acid was 75%. The content of unreacted furfural in the crude product was determined to be less than 0,1%.
  • 6
  • [ 27329-70-0 ]
  • [ 2051-99-2 ]
  • [ 1001010-49-6 ]
YieldReaction ConditionsOperation in experiment
31% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 20 - 60℃;Inert atmosphere; A mixture of <strong>[2051-99-2]1-bromo-4-isobutylbenzene</strong> (1.500 g, 7.04 mmol), 5-formyl-2-furanoboronic acid (1.477, 10.56 mmol) and sodium carbonate (3.134 g, 29.57 mmol) in a mixture of 1,2-dimethoxyethane (75 mL), ethanol (30 mL) and water (15 mL) was vigorously stirred and the reaction flask was purged with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.404 g, 0.35 mmol) was added and the reaction mixture was heated at 60 C. for 3 h. The mixture was allowed to cool to room temperature and was left aside for 4 days. The reaction mixture was diluted with ether (200 mL) and washed successively with water (2×100 mL) and brine. The organic layer was separated, dried over sodium sulfate and concentrated. The residue was chromatographed on flash Silica, eluted with 5 to 10% ethyl acetate in hexanes to afford 5-(4-isobutyl-phenyl)-furan-2-carbaldehyde (490 mg, 31%). 1H NMR (400 MHz, CDCl3): 0.92 (6H, d, J=6.4 Hz), 1.90 (1H, m), 2.51 (2H, d, J=7.2 Hz), 6.80 (1H, d, J=3.6 Hz), 7.20 (2H, m), 7.31 (1H, dd, J=3.6, 1.2 Hz), 7.74 (2H, m), 9.63 (1H, s). ESI-MS: 227.1.
  • 7
  • [ 27329-70-0 ]
  • [ 132131-24-9 ]
  • 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
98.6% With palladium 10% on activated carbon; triethylamine; In methanol; 1,2-dimethoxyethane; at 20 - 45℃; for 3h; At room temperature (20 ~ 25 C) to 3.5g (14.3mmol) 2- amino-5-iodobenzonitrile (compound of formula III), 3.1g (28.1mmol) 2-formylfuran-5-boronic acid was added to the three-necked flask, was added 70mL of ethylene glycol dimethyl ether, stirred at room temperature suspension system; The 4.4g (43.5mmol) of triethylamine was added to the reaction system, and 0.18g10% Pd / C was dissolved in methanol 35mL disposable Was added to the reaction system, stirring was warmed to 40 ~ 45 C the reaction; TLC trace (eluent, ethyl acetate / dichloromethane = 2/ 1, V / V, UV254nm color) to the starting material disappeared after stopping the reaction (about 3h). Filtered to remove Pd / C, to obtain a reddish black filter Solution, and the filtrate was washed with 100mL water, once with ethyl acetate (50mL * 2) The aqueous phase was extracted twice, the combined organic phases with saturated Brine (80mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to give a white solid 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile (IV compound of the formula) 3.0g (14.1mmol, molar yield of 98.6%, HPLC purity 98.5%).
  • 8
  • [ 27329-70-0 ]
  • [ 104-15-4 ]
  • [ 132131-24-9 ]
  • 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile p-toluenesulfonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% At room temperature (20 ~ 25 C) to 9.2g (37.7mmol) 2- amino-5-iodo-benzonitrile (compound of formula III), 8.3g (75.2mmol) 2- Formyl-5-boronic acid was added to the three-necked flask, was added 200mL of ethylene glycol dimethyl ether, stirred at room temperature suspension system; The 11.6g (114.6mmol) of triethylamine was added to the reaction system, the 0.5g10% Pd / C was dissolved in 100mL of methanol disposable Was added to the reaction system, stirring was warmed to 40 ~ 45 C the reaction; TLC trace (eluent, ethyl acetate / dichloromethane = 2/ 1, V / V, UV254nm color) to the starting material disappeared after stopping the reaction (about 3h); filtered to remove Pd / C, to obtain a reddish black filter Solution, the filtrate was transferred to the reaction flask, heated with stirring to 60 C.Weigh toluenesulfonic acid monohydrate 11.5g (60.5mmol), dissolved in 5.0mL water, dubbed p-toluenesulfonic acid solution, The prepared solution of p-toluenesulfonic acid was dropped into the reaction vessel, which was within 20 ~ 30min after the dripping, dripping completed, yellow Colored powdery solid was precipitated, 60 C incubation for 1 hour, the system was slowly cooled to 5 C, 0.5 hours incubation, filtration, A yellow filter cake, the filter cake was rinsed with 20mL of ethylene glycol dimethyl ether, 40 C and dried in vacuo 8h, to give a white solid of 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile p-toluenesulfonic acid(IV compound of the formula) p-toluenesulfonate 13.9g (36.2mmol, 96.0% molar yield, HPLC purity 99.1%).
  • 9
  • [ 27329-70-0 ]
  • [ 42860-10-6 ]
  • [ 425630-53-1 ]
  • 10
  • [ 27329-70-0 ]
  • [ 156150-67-3 ]
  • [ 310459-43-9 ]
YieldReaction ConditionsOperation in experiment
80% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 65℃; for 1h; General procedure: 1.00 mmol arylhalide, 1.30 mmol furfural-boronic acid and 0.05 mmolBis(triphenylphosphine)palladium(II) dichloride were treated with 0.30 mLdimethoxyethane, 0.50 mL ethanol and 0.30 mL aqueous 2M sodium carbonate solution.The reaction was heated to 65C for 1h or until the TLC showed no remaining startingmaterial. The mixture was evaporated and extracted three times with ethyl acetate. Thecombined organic layers were washed with brine, dried over MgSO4, filtered andconcentrated. The crude product was purified by column chromatography usinghexanes/ethyl acetate (9:1).
  • 11
  • [ 27329-70-0 ]
  • [ 3032-81-3 ]
  • [ 106827-27-4 ]
YieldReaction ConditionsOperation in experiment
89% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 65℃; for 1h; General procedure: 1.00 mmol arylhalide, 1.30 mmol furfural-boronic acid and 0.05 mmolBis(triphenylphosphine)palladium(II) dichloride were treated with 0.30 mLdimethoxyethane, 0.50 mL ethanol and 0.30 mL aqueous 2M sodium carbonate solution.The reaction was heated to 65°C for 1h or until the TLC showed no remaining startingmaterial. The mixture was evaporated and extracted three times with ethyl acetate. Thecombined organic layers were washed with brine, dried over MgSO4, filtered andconcentrated. The crude product was purified by column chromatography usinghexanes/ethyl acetate (9:1).
  • 12
  • [ 27329-70-0 ]
  • [ 2401-21-0 ]
  • 5-(2',3'-dichlorophenyl)furan-2-carbaldehyde [ No CAS ]
  • 13
  • [ 27329-70-0 ]
  • [ 1123-63-3 ]
  • 5-(4-hydroxy-2,6-dimethylphenyl)furan-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; at 75℃;Inert atmosphere; General procedure: In 25 mL round bottom flask equipped with reflux condenser, 0.0004 mol of 4-chloro-3,5-dimethylphenol mixed with appropriate quantity of arylboronic acid (1-6) and 0.05 g of Pd(PPh3)4 were added into the flask containing 20 mL of absolute ethanol under inert atmospheric condition (N2) gas. The mixture was stirred and heated and 5 mL of solution (5% Na2CO3) were added into the flask.The reaction mixture was stirred and heated at 75 C for 5-6 h then followed by TLC and monitor reactions using (n-hexane and ethyl acetate) in 2:3 ratio v/v. The mixture was filtrated off to remove the inorganic salt and the residue of pallidum catalyst, washed by cooled ethanol and the solvent was removed and decanted by cooled ether (Scheme-I).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 27329-70-0 ]

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[ 27329-70-0 ]

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