[ CAS No. 4233-33-4 ] {[proInfo.proName]}

Name: 4233-33-4|4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione|95%
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SKU: A270911
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3d Animation Molecule Structure of 4233-33-4

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COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4233-33-4 ]

Product Details of [ 4233-33-4 ]

CAS No. :	4233-33-4	MDL No. :	MFCD00003148
Formula :	C₈H₅N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ISULLEUFOQSBGY-UHFFFAOYSA-N
M.W :	175.14	Pubchem ID :	77913
Synonyms :

Calculated chemistry of [ 4233-33-4 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.16
TPSA :	62.1 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.48
Log Po/w (XLOGP3) :	1.78
Log Po/w (WLOGP) :	1.06
Log Po/w (MLOGP) :	2.06
Log Po/w (SILICOS-IT) :	1.63
Consensus Log Po/w :	1.6

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.32
Solubility :	0.833 mg/ml ; 0.00476 mol/l
Class :	Soluble
Log S (Ali) :	-2.7
Solubility :	0.348 mg/ml ; 0.00198 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.15
Solubility :	1.23 mg/ml ; 0.007 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.19

Safety of [ 4233-33-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4233-33-4 ]

* 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.

Upstream synthesis route of [ 4233-33-4 ]
Downstream synthetic route of [ 4233-33-4 ]

[ 4233-33-4 ] Synthesis Path-Upstream 1~1

1
[ 857048-92-1 ]
[ 4233-33-4 ]
[ 20005-42-9 ]

Reference： [1] Advanced Synthesis and Catalysis, 2007, vol. 349, # 10, p. 1743 - 1750

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Yield	Reaction Conditions	Operation in experiment
95%	In acetone
91%	In dichloromethane for 1h; Ambient temperature;
82%	In dichloromethane for 0.5h; Reflux;	7.1; 8-9 Step 1: General procedure: Dissolve 20 g of the compound represented by formula 1-1 in 200 ml of dichloromethane, add 12 g of the compound represented by formula 2-1, and react for 30 minutes by heating and refluxing. After the reaction, distillation under reduced pressure was carried out, and then 300ml of ethyl acetate was added to continue heating to reflux. Filter when cooled to 20-25°C to obtain 28.8 g of the compound represented by formula 3-1 with a yield of 90%;

Yield	Reaction Conditions	Operation in experiment
100%	With tetrabutylammonium (meta)periodate In acetone at 20℃; for 0.5h;
99%	With SiO₂-supported HNO₃ In dichloromethane at 20℃; for 0.583333h; chemoselective reaction;
98%	With chlorine In ethyl acetate for 18h;

98%	With silicium tetrachloride; mesoporous silica; NaNO₂ In dichloromethane at 20℃; for 3h;
98%	With ICl supported on silica gel In dichloromethane at 20℃; for 0.166667h;
98%	With aluminium(III) nitrate nonahydrate In dichloromethane at 20℃; for 2h;
98%	With guanidinium nitrate In dichloromethane at 20℃; for 0.75h;
98%	With ammonium nitrate; aluminum hydrogen sulfate In dichloromethane at 20℃; for 0.666667h;
97%	With aluminium chloride anhydrous; benzyltriphenylphosphonium chlorate In dichloromethane at 20℃; for 0.25h;
97%	With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In dichloromethane at 20℃; for 2h;
96%	With sodium hydrogen sulphate; mesoporous silica; NaNO₂ In dichloromethane at 20℃; for 1h;
96%	With hydrogensulfate; mesoporous silica; NaNO₂ In dichloromethane at 20℃; for 2h;
96%	With 1,3,4,6-tetrachloro-3α,6α-diphenylglycoluril In dichloromethane at 20℃; for 1h;
96%	With Aluminum Chloride; benzyltriphenylphosphonium nitrate In dichloromethane for 0.5h;
95%	With [bis(acetoxy)iodo]benzene In dichloromethane for 0.25h; Ambient temperature;
95%	With potassium dichromate\|\|potassium bichromate\|\|K₂Cr₂O₇\|\|Cr₂O₇K₂; aluminium chloride anhydrous for 0.05h;
95%	With mesoporous silica; zirconium tetrachloride; 1,4-diazabicyclo[2,2,2]octane-N,N′-dioxide In dichloromethane at 20℃; for 1h;
95%	With 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide; water monomer In dichloromethane at 20℃; for 0.5h;
95%	With poly(ethylene glycol) impregnated with dinitrogen tetroxide In dichloromethane at 20℃; for 0.5h;
95%	With Nitroharnstoff In dichloromethane at 20℃; for 1h;
94%	With magnesium hydrogen sulfate; mesoporous silica; NaNO₂ In dichloromethane at 20℃; for 1h;
94%	With benzyltriphenylphosphonium peroxymonosulfate at 20℃; for 0.166667h; grinding;
94%	With potassium peroxomonosulfate; mesoporous silica; NaNO₂ In dichloromethane at 20℃; for 1.5h;
94%	With chromium (VI) oxide; 1-butyl-3-methyl-1H-imidazol-3-ium bromide at 20℃; for 1.5h;
92%	With calcium hypochlorite In dichloromethane at 20℃; for 0.25h;
90%	With KMnO₄/alumina at 20℃; for 0.133333h;
86%	With dinitrogen tertoxide In dichloromethane at 0℃;
86%	With mesoporous silica; iodic acid; NaNO₂ In dichloromethane at 20℃; for 1.5h;
84%	With dihydrogen peroxide at 70℃; for 3h;	5 Example 5 (1) will be 1 millimole N-phenyl urazole of added to the reactor, by adding 1 ml of water, adding catalyst (WO3-x) 0.05 millimole, 30% hydrogen peroxide of 3 millimole, 70 °C stirring 3 hours;(2) adding the above-mentioned diluted solution releases to 10 ml, ether extraction, concentrated to remove the solvent, rapid column chromatography, to obtain N-phenyl -3,5-dioxo -1, 2, 4-triazole, red solid, yield 84%
82%	With N-Bromosuccinimide In dichloromethane at 0℃; for 0.333333h;
82%	With n-propylsilica kryptofix 21-supported dinitrogen tetroxide In dichloromethane at 20℃;
81%	With melamine-(H₂SO₄)3; C₃H₆N₆*3HNO₃ In neat (no solvent) Green chemistry;	Oxidation of 4-Phenylurazole 4-Phenylurazole (3a, 0.177 g, 1 mmol) was added to the mixture of melamine-(H2SO4)3 (0.21 g, 0.5 mmol), and melamine-(HNO3)3 (0.16 g, 0.5 mmol) and the mixture was ground with a mortar and pestle for 5-10 minutes. Then, the product (4-phenyl-1,2,4-triazole- 3,5-dione) was extracted with dichloromethane (2 10 mL). Simple distillation of the CH2Cl2 gave the pure product. 1H-NMR (FT-90 MHz-CDCl3) d 7.48 (s, 5H, Ar); 13C-NMR (FT-22.5 MHz-CDCl3) d 124.2, 129.01, 129.9, 157.971.15
80%	With oxalic acid; mesoporous silica; NaNO₂ In dichloromethane at 20℃; for 1h;
74%	With trichloroisocyanuric acid In dichloromethane at 20℃; for 0.5h;
65%	With iodosylbenzene In ethyl acetate at 25℃; for 4h; Darkness; Inert atmosphere;	5 Preparation of Triazolinedione Solution (Oxidation of Triazolidinedione Compound) A suspension in which 0.30 g (1.69 mmol) of 4-phenyl-1,2,4-triazolidine-3,5-dione (DMU) was suspended in ethyl acetate (30 mL) was obtained. To the obtained suspension, 0.37 g (1.68 mmol) of iodosobenzene (PIO) was added in a light-shielded condition under a nitrogen stream, the mixture was stirred at 25° C. for 4 hours, and an ethyl acetate solution in which 4-phenyl-1,2,4-triazoline-3,5-dione was dissolved was obtained. The reaction scheme is shown below. Contacting Step After the obtained ethyl acetate solution was filtered, 100 mL of hexane was added to the filtrate in a light-shielded condition, and the filtrate was stirred at room temperature (about 20° C.) for 1 hour to crystallize 4-phenyl-1,2,4-triazoline-3,5-dione out. The ethyl acetate-hexane mixed solution in which the 4-phenyl-1,2,4-triazoline-3,5-dione was crystallized was filtered, the obtained solid was washed with hexane and dried under reduced pressure at room temperature, and a solid 4-phenyl-1,2,4-triazoline-3,5-dione was obtained. The resulting solid weighed 192 mg and the yield was 65%. Physical Property Evaluation The results of various analyses of the obtained solid 4-phenyl-1,2,4-triazoline-3,5-dione are shown below. Mp: 165 to 175° C. (dec) IR (KBr): 1745 cm-1 1H-NMR(CDCl3): δ6.70-8.00 (m, 5H)
38%	With hypochlorous acid tert-butyl ester In ethyl acetate at 20℃; for 1.66667h; Inert atmosphere;
	With hypochlorous acid tert-butyl ester
	With perchloric acid; anhydrous sodium perchlorate In acetonitrile at 0℃; electrolyse, Pt-electrode;
	With benzeneseleninic anhydride In tetrahydrofuran for 0.0666667h; Ambient temperature; Yield given;
	With hypochlorous acid tert-butyl ester In dichloromethane at 0℃;
	With hypochlorous acid tert-butyl ester In acetone at -60℃;
	With dinitrogen tertoxide; Sodium sulfate [anhydrous] In dichloromethane at 0℃;
65.6 g	With hypochlorous acid tert-butyl ester In ethyl acetate at 15 - 20℃; for 0.666667h;
	With hypochlorous acid tert-butyl ester In acetone
	With hypochlorous acid tert-butyl ester In ethyl acetate at 0℃; for 0.0833333h;
	With hypochlorous acid tert-butyl ester In acetone
	In sulfuric acid; acetonitrile Electrolysis;
	With hypochlorous acid tert-butyl ester In ethyl acetate at 0℃; for 0.166667h;
	With [NO⁽¹⁺⁾18-crown-6H(NO₃)2^(1-)]; mesoporous silica In dichloromethane at 20℃;
	With N,N,2,3,4,5,6-heptachloroaniline In dichloromethane at 20℃; for 1h;
	With iron nitrate (III)
	With hypochlorous acid tert-butyl ester In dichloromethane at 0 - 20℃; for 2h;
	With dinitrogen trioxide; dinitrogen tertoxide; Nitrogen dioxide In dichloromethane at 0 - 5℃; for 0.5h;
	With hypochlorous acid tert-butyl ester
	Electrochemical reaction; aq. phosphate buffer;
	With calcium hypochlorite; Sodium sulfate [anhydrous] In dichloromethane at 20℃; for 2h;	4 One-Pot Synthesis of Compound 1 To a flame dried round bottom flask equipped with a stir bar was added a solution of 4-phenylurazole (271 mg, 1.5 mmol) and calcium hypochlorite (429 mg, 3 mmol) in dichloromethane (15 mL). The reaction was stirred at room temperature for 1.5 h. Anhydrous sodium sulfate (426 mg, 3 mmol) was added to the flask and the mixture was stirred for an additional 0.5 h. The suspension was gravity filtered into a clean flask and the resultant mixture was concentrated under reduced pressure to afford a red residue. The residue was transferred with dry dichloromethane (3 mL) to a new flame dried round bottom flask equipped with a stir bar and anhydrous magnesium chloride (14 mg, 0.15 mmol). To this stirring solution was added dropwise a solution of methyl phenylalkynyl sulfide (74 mg, 0.5 mmol) in dry dichloromethane (2 mL). The mixture was stirred at room temperature for 24 h. The resultant mixture was concentrated under reduced pressure and purified via flash chromatography with hexane and ethyl acetate (gradient from 100% hexane to 9:1 hexane/ ethyl acetate) to afford the corresponding diazacyclobutene (158 mg, 98% yield). Compound 1: Light yellow solid; Yield: 89% (288 mg); Mp: 98.6-99.6° C.; IR (neat): 2927 (w), 1784 (m), 1732 (s), 1595 (w), 1384 (s), 1220 (s), 696 (s), 686 (s) cm-1; 1H-NMR (500 MHz, CDCl3) δ 8.00-7.78 (m, 2H), 7.67-7.31 (m, 8H), 2.59 (s, 3H); 13C NMR (125 MHz, CDCl3) δ=156.5, 155.1, 145.3, 130.8, 129.9, 129.3, 129.1, 128.8, 126.3, 125.6, 125.4, 17.4; HRMS (ESI+): Calcd for C17H14N3O2S, [M+H]+ 324.0807 Found m/z 324.0822.
	With N-Bromosuccinimide In acetonitrile for 0.25h;

Yield	Reaction Conditions	Operation in experiment
90%	In hexane; toluene at 20℃; for 72h;	17 2,4-pentadiene acid 45 (196 mg, 2.0 mmol) and 4-phenyl-l,2,4-triazolin-3,5-dion 46 (350 mg, 2.0 mmol) were dissolved in a mixture of hexane and toluene. The reaction mixture was agitated under inert atmosphere at room temperature for 3 days. After completion of the reaction, the solvent was evaporated, thus giving the Diels-Alder adduct 47 (493 mg, 1.80 mmol, 90 %).
	In ethyl acetate 1.) 0 deg C to r.t., 30 min, 2.) r.t., 18 h; Yield given;
	for 3h; Ambient temperature; Yield given;

[ CAS No. 4233-33-4 ] {[proInfo.proName]}

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