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Chemical Structure| 823-82-5 Chemical Structure| 823-82-5

Structure of 2,5-Diformylfuran
CAS No.: 823-82-5

Chemical Structure| 823-82-5

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Product Citations

Product Citations

Piao, Guangxia ; Yoon, Sun Hee ; Cha, Hyun Gil ; Han, Dong Suk ; Park, Hyunwoong ;

Abstract: The electrocatalytic hydrogenation of 5-hydroxymethylfurfural (HMF) to 2,5-bis(hydroxymethyl)furan (BHMF) is an alternative to conventional heterogeneous catalysis with H2 at high temperatures and pressures. Although Ag is the most representative electrocatalyst, it works only under limited conditions. This study synthesizes highly porous dendritic Bi, Sn, and BiSn electrocatalysts using an in situ generated hydrogen bubble template. Density functional theory computations on the adsorption energy and elementary hydrogenation reaction steps of HMF predict the superiority of Bi to Sn and the intermediate behavior of BiSn between Bi and Sn. The dendritic BiSn catalyst generates a current density of ∼144 mA cm−2 at a faradaic efficiency (FE) of ∼100% for BHMF production at pH ∼ 7 (corresponding to the BHMF production rate of ∼2.7 mmol h−1 cm−2) in prolonged electrolysis. Considering the material cost (

Purchased from AmBeed: ; ; ; ; ; 1883-75-6

Alternative Products

Product Details of [ 823-82-5 ]

CAS No. :823-82-5
Formula : C6H4O3
M.W : 124.09
SMILES Code : O=CC1=CC=C(C=O)O1
MDL No. :MFCD00671517
InChI Key :PXJJKVNIMAZHCB-UHFFFAOYSA-N
Pubchem ID :69980

Safety of [ 823-82-5 ]

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

Computational Chemistry of [ 823-82-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 5
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 29.48
TPSA ?

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

47.28 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.56
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

0.58
Log Po/w (WLOGP)?

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

0.9
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.

-1.15
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

1.55
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.49

Water Solubility

Log S (ESOL):?

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

-1.25
Solubility 6.92 mg/ml ; 0.0557 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.

-1.15
Solubility 8.87 mg/ml ; 0.0715 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

-1.46
Solubility 4.26 mg/ml ; 0.0344 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.

-6.65 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

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)

2.08

Application In Synthesis of [ 823-82-5 ]

* 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.

  • Downstream synthetic route of [ 823-82-5 ]

[ 823-82-5 ] Synthesis Path-Downstream   1~15

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YieldReaction ConditionsOperation in experiment
9%; 60%; 7% With iron(II) phthalocyanine; In aq. phosphate buffer; at 37 - 80℃; for 16.0833h;pH 7; HMF (100 mM) was added to KPi buffer (500 mM pH 7.0). GOase M35 (103p1 of3.3mg/mL), PaoABC (ipI of 28.9mg/mL) and a metal complex (see Table 4) were added at 37 00 and the pH was continuously adjusted with NaHCO3 for a period of 16 hours. The reaction was heated to 80 00 for 5 minutes and left to cool. The solution containing denatured protein was centrifuged and the supernatant removed and analysed by RP20 HPLC.
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  • [ 56-45-1 ]
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  • [ 109-08-0 ]
  • [ 123-32-0 ]
  • [ 271-89-6 ]
  • [ 13925-00-3 ]
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  • [ 13360-65-1 ]
  • [ 1438-94-4 ]
  • [ 96-76-4 ]
  • [ 13360-64-0 ]
  • [ 21835-01-8 ]
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YieldReaction ConditionsOperation in experiment
With oxygen; In water; at 90℃; under 6000.6 Torr; for 24h;Autoclave;Catalytic behavior; General procedure: As a general procedure, the oxidation of HMF was performed under a vigorous stirring in a stainless steel autoclave in the presence of molecular O2 (8 bars), 1 mmole of substrate (HMF), 10 mLsolvent, 0.05 g of catalyst and a temperature of 90C for 24 h. All the changes of reaction parameters: temperature, pressure, solvent, amount of the catalysts or reaction time were notified inthe text. After ending the HMF oxidation and filtering off the catalyst, the mother liquor was diluted 5 times and the products were analyzed by high performance liquid chromatography (HPLC), ona Thermo Scientific Accela 600 device equipped with a UV-vis detector and a Rezex-ROA H+column. 5-Hydroxymethyl furfural(HMF), diformyl furan (DFF), 5-hydroxymethyl-2-furancarboxylicacid (HMFCA), 5-formyl-2-furancarboxylic acid (FFCA) and 2,5-furandicarboxylic acid (FDCA) from Sigma-Aldrich were used as standards. The maximum of absorption for FDCA and HMFCA corresponded to = 260 nm while for HMF, FFCA and DFF to = 285 nm. The mobile phase consisted of 0.05 N H2SO4, at a flow rate of 0.5 mL/min, and the analysis was carried out at 40C, using a two channels detection (260 nm and 285 nm) and an injection volume of 3 L. A carbon mass balance of 98-99% was obtained for all the performed reactions.
  • 8
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  • [ 13529-17-4 ]
  • [ 6338-41-6 ]
  • [ 3238-40-2 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; In water; at 25℃; under 760.051 Torr; for 24h;Green chemistry; The catalytic activity performance of the metal Salen complexessupported on SBA-15 (Co/SBA-15, Fe/SBA-15 and Cu Salen/SBA-15) inthe oxidation of HMF were evaluated. The HMF oxidation reaction wascarried out in an aqueous system at neutral pH (the pH was not adjusted)using H2O2 as oxidant agent. The reaction was performed undermild conditions (aqueous media, neutral pH, atmospheric temperatureand pressure). The system consisted of a 125 mL round-bottom flaskwith a refrigerant column to avoid the HMF volatilization. All testswere performed with an initial substrate HMF 0.4 mM [8], 50 mL reactionvolume, H2O2 30 w/Vpercent (100 muL) as oxidant agent and using0.05 g of catalyst. Aliquots of 500 muL were taken during 24 h, fromwhich 75 muL were injected in the chromatograph for their analysis. Thesamples were taken in short periods of time at the early minutes of thereaction, and in a longer period as the reaction advanced in order tohave enough information for the kinetic study. The reaction mixturewas stirred at a constant 500 rpm. Tests were done at low temperatures25, 30 and 40 °C to know how the temperature affects the reaction.Although the catalyst can be used at higher moderate temperatures,40 °C level was selected as the maximum temperature to avoid H2O2degradation. Temperature levels were recorded with thermocouplespreviously connected to a temperature monitoring program using theLabview System Design Software.
  • 9
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  • 13
  • [ 823-82-5 ]
  • [ 13134-38-8 ]
  • N,N’-(furan-2,5-diylbis(methylene))bis(3,6-dimethylpyrazin-2-amine) [ No CAS ]
  • (5-(((3,6-dimethylpyrazin-2-yl)amino)methyl)furan-2-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
10 mg [0090] To a stuffed solution of 53 mg (0.427 mmol) of furan-2,5-dicarbaldehyde and 111 mg (0.90 1 mmol) of <strong>[13134-38-8]3,6-dimethylpyrazin-2-amine</strong> in 5 mL of DCE was added 100 tL of acetic acid and approximately 500 mg of anhydrous Na2504. After 30 mm at rt under argon, the mixture was treated with 386 mg (1.82 mmol) of sodium triacetoxyborohydride, then was stirred further for 48 h. The mixture was treated with water (-- 3 mL), excess satd. aq. NaHCO3, and EtOAc, and was stuffed an additional 1 h at rt. The mixture was extracted with EtOAc (3 x). The combined organic layers were washed with brine, dried over Na2504, and concentrated in vacuo. Purification by preparative TLC (90% EtOAc/hexanes) provided 10 mg of the title compound. MS (ESj: [M + H] 339.3; [M+Na] 361.4; MS (ES): EM-H] 337.4. ?H NMR: (500 MHz, CDC13) oe 7.62 (2H, s), 6.2 (2H, s), 4.63 (4H, d, J= 5 Hz), 4.55 (2H, br s), 2.35 (6H, s), 2.31 (6H,s). Also obtained was (5- (((3 ,6-dimethylpyrazin-2-yl)amino)methyl)furan-2-yl)methanol as a side product (See Example 8).
  • 14
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  • [ 13134-38-8 ]
  • N-((5-(((3,6-dimethylpyrazin-2-yl)oxy)methyl)furan-2-yl)methyl)-3,6-dimethylpyrazin-2-amine [ No CAS ]
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  • [ 823-82-5 ]
  • [ 13529-17-4 ]
  • [ 64-18-6 ]
  • [ 6338-41-6 ]
 

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Technical Information

Categories

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