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Structure of 584-13-4

Chemical Structure| 584-13-4

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Product Citations

Product Citations

Kopacka, Gabriela ; Wasiluk, Kinga ; Majewski, Pawel W. ; Kopyt, Michal ; Kwiatkowski, Piotr ; Megiel, Elzbieta

Abstract: The fixation of carbon dioxide with is one of the most attractive methods for the green utilization of this greenhouse gas and leads to many valuable chems. This process is characterised by 100% atom efficiency; however, an efficient catalyst is required to achieve satisfactory yields. are recognized as being extremely promising for this purpose. Nevertheless, many of the proposed catalysts are based on ions of rare elements or elements not entirely safe for the environment; this is notable with com. unavailable ligands. In an effort to develop novel catalysts for CO2 fixation on an industrial scale, we propose novel , which consist of aluminum ions coordinated with commercially available (Al@NDC) and their nanocomposites with gold nanoparticles entrapped inside their structure (AlAu@NDC). Due to the application of and 5-amino tetrazole as crystallization mediators, the morphol. of the synthesized materials can be modified. The introduction of gold nanoparticles (AuNPs) into the structure of the synthesized Al-based causes the change in morphol. from nano cuboids to nanoflakes, simultaneously decreasing their porosity. However, the homogeneity of the nanostructures in the system is preserved. All synthesized MOF materials are highly crystalline, and the simulation of PXRD patterns suggests the same tetragonal crystallog. system for all fabricated . The fabricated materials are proven to be highly efficient catalysts for carbon dioxide oxide; and propylene oxide. Applying the synthesized catalysts enables the reactions to be performed under mild conditions (90℃; 1 MPa CO2) within a short time and with high conversion and yield (90% conversion of towards with 89% product yield within 2 h). The developed nanocatalysts can be easily separated from the reaction mixture and reused several times (both conversion and yield do not change after five cycles). The excellent performance of the fabricated catalytic materials might be explained by their high microporosity (from 421 m2 g-1 to 735 m2 g-1); many catalytic centers in the structure exhibit Lewis acids' behavior, increased capacity for CO2 adsorption, and high stability. The presence of AuNPs in the synthesized nanocatalysts (0.8% weight/weight) enables the reaction to be performed with a higher yield within a shorter time; this is especially important for less-active such as propylene oxide (two times higher yield was obtained using a nanocomposite, in comparison with Al- without nanoparticles).

Keywords: metal-organic frameworks ; cyclic carbonates ; heterogeneous catalysts ; nanoparticles ; CO2 fixation ; epoxides

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Product Details of [ 584-13-4 ]

CAS No. :584-13-4
Formula : C2H4N4
M.W : 84.08
SMILES Code : C1=NN=C[N]1N
MDL No. :MFCD00003099
InChI Key :FMCUPJKTGNBGEC-UHFFFAOYSA-N
Pubchem ID :11432

Safety of [ 584-13-4 ]

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

Computational Chemistry of [ 584-13-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 6
Num. arom. heavy atoms 5
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 20.16
TPSA ?

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

56.73 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.34
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

-0.82
Log Po/w (WLOGP)?

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

-1.0
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.

-0.87
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

-0.55
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.58

Water Solubility

Log S (ESOL):?

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

-0.46
Solubility 29.1 mg/ml ; 0.346 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.

0.11
Solubility 108.0 mg/ml ; 1.28 mol/l
Class?

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

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

0.43
Solubility 227.0 mg/ml ; 2.7 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.

-7.4 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

2.0
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<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)

1.78

Application In Synthesis of [ 584-13-4 ]

* 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 [ 584-13-4 ]

[ 584-13-4 ] Synthesis Path-Downstream   1~7

  • 2
  • [ 584-13-4 ]
  • 1.) methylating agent [ No CAS ]
  • [ 6086-21-1 ]
  • 3
  • [ 584-13-4 ]
  • [ 74205-82-6 ]
  • 4-aminomethylene(1,2,4-triazol-1-yl)-1,2,4-triazole [ No CAS ]
  • 4
  • [ 584-13-4 ]
  • [ 7732-18-5 ]
  • [ 6046-93-1 ]
  • [ 68-04-2 ]
  • [Cu4(4-amino-1,2,4-triazole)2(H2O)3(citrate)2]*3H2O}n [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% at 100℃; for 96h;High pressure; Autoclave; Atr (16.8 mg, 0.2 mmol), Cu(OAc)2H2O (40.0 mg, 0.2 mmol), and <strong>[68-04-2]sodium citrate</strong> (29.4 mg, 0.1 mmol) were dissolved in doubly deionized water (8.0 mL). The resulting mixture was then transferred into a Parr Teflon-lined stainless steel vessel (23.0 mL) and heated at 100 C for 96 h under autogenous pressure. After the mixture was cooled to room temperature at a rate of 3.3 C h1, blue block-shaped crystals suitable for X-ray analysis were generated directly, washed with water, and dried in air. Yield: 50% based on CuII salt. Anal. Calc. for C16H28Cu4N8O20: C, 21.20; H, 3.11; N,12.36. Found: C, 20.20; H, 3.10; N, 12.37%. FT-IR (KBr, cm-1):3339 (br), 1606 (s), 1561 (s), 1423 (s), 1394 (s), 1319 (s), 1262(w), 1217 (m), 1081 (m), 1064 (m), 1022 (w), 914 (m), 859 (w), 706 (m), 625 (m), 551 (w), 472 (w), 413 (w).
  • 5
  • [ 584-13-4 ]
  • copper(II) nitrate hexahydrate [ No CAS ]
  • [ 7732-18-5 ]
  • [ 68-04-2 ]
  • [Cu2(4-amino-1,2,4-triazole)2(H2O)2(citrate)]n [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With triethylamine; In methanol; at 100℃; for 96h;High pressure; Autoclave; To a methanol solution (5.0 mL) containing atr (25.2 mg,0.3 mmol), H4cit (20.9 mg, 0.1 mmol), and triethylamine (40.4 mg, 0.4 mmol) was slowly added an aqueous solution (5.0 mL) of Cu(NO3)2*6H2O (48.4 mg, 0.2 mmol) with constant stirring. The resulting mixture was filtered after further stirring for half an hour. Blue block-shaped crystals suitable for X-ray diffraction were grown by slow evaporation of the filtrate within aweek. Yield: 67% based on CuII salt. Anal. Calc. for C10H16N8O9Cu2: C, 23.13; H, 3.10; N, 21.57. Found: C, 23.11; H, 3.10; N, 21.56%. FT-IR (KBr, cm1): 3442 (br), 1636 (s), 1362 (s), 1222 (w), 1125(m), 1062 (m), 1007 (m), 936 (m), 858 (m), 761 (s), 620 (m),501 (w), 438 (w).
  • 6
  • [ 584-13-4 ]
  • copper(II) nitrate hexahydrate [ No CAS ]
  • [ 7732-18-5 ]
  • [ 68-04-2 ]
  • [Cu2(4-amino-1,2,4-triazole)(H2O)3.25(citrate)]H2O}n [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With lithium hydroxide; In methanol; at 100℃; for 96h;High pressure; Autoclave; To a methanol solution (5.0 mL) containing atr (16.8 mg,0.2 mmol), H4cit (21.0 mg, 0.1 mmol), and lithium hydroxide (8.4 mg, 0.2 mmol) was slowly added an aqueous solution(5.0 mL) of Cu(NO3)2*6H2O (72.3 mg, 0.3 mmol) with constant stirring. The resulting mixture was filtered after further stirring for half an hour. Blue block-shaped crystals suitable for X-ray diffraction were generated by slow evaporation of the filtrate within a week. Yield: 50% based on H4cit. Anal. Calc. for C8H16.50Cu2N4O11.25: C, 20.19; H, 3.50; N, 11.77. Found: C, 20.20; H, 3.48; N, 11.79%. FT-IR (KBr, cm-1): 3468 (br), 1639 (s), 1617 (s), 1421 (s), 1307(m), 1249 (m), 1086 (m), 1049(m), 1008 (m), 957 (s), 926 (w),699 (w), 619 (w), 698 (w), 514 (w).
  • 7
  • [ 584-13-4 ]
  • [ 19955-99-8 ]
  • N-(3-vinylbenzylidene)-4H-1,2,4-triazol-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With 2,6-di-t-butyl catechol; acetic acid; In ethanol; for 3h;Reflux; General procedure: A mixture of equal volumes of heterocyclic amine (0.02 mol), and vinylbenzaldehyde (1p and 1m) (0.02 mol) in the presence of some traces of 2,6-di-t-butyl catechol as the polymerization inhibitor, and 4-5 drops of glacial acetic acid used as reaction catalyst in 30 mL of absolute ethanol was refluxed for 3 h in water bath as shown in the Scheme 1. The resulting solution was concentrated in vacuum and cooled down in a freezer for 24 h. The precipitated product was filtered, washed with cold absolute ethanol and then dried.
 

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Technical Information

Categories

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