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CAS No. : | 14568-68-4 | MDL No. : | MFCD16883101 |
Formula : | C10H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HBZNAZRMQALFLI-UHFFFAOYSA-N |
M.W : | 164.20 | Pubchem ID : | 11629652 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 49.52 |
TPSA : | 18.46 Ų |
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) : | -5.43 cm/s |
Log Po/w (iLOGP) : | 2.59 |
Log Po/w (XLOGP3) : | 2.64 |
Log Po/w (WLOGP) : | 2.24 |
Log Po/w (MLOGP) : | 2.01 |
Log Po/w (SILICOS-IT) : | 2.63 |
Consensus Log Po/w : | 2.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.69 |
Solubility : | 0.333 mg/ml ; 0.00203 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.68 |
Solubility : | 0.344 mg/ml ; 0.0021 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.09 |
Solubility : | 0.134 mg/ml ; 0.000815 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.7 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With chromium(VI) oxide; palladium dichloride In water; acetonitrile at 20 - 60℃; for 24 h; | General procedure: To a stirred solution of olefin (0.4mmol) in CH3CN (3.5mL) and H2O (0.5mL) were added PdCl2 (3.6mg, 0.02mmol, 5molpercent) and CrO3 (20mg, 0.6mmol, 0.5equiv) at room temperature. The reaction mixture was warmed to 60°C and stirred for specified time (see Tables 5–7) in a closed flask. The reaction mixture was then filtered through a small pad of silica gel and washed with EtOAc and the filtrate concentrated. The residue in some cases contained virtually pure compound and no further purification was necessary. In other cases the residue was purified by silica gel column chromatography using petroleum ether/EtOAc as an eluent to afford the methyl ketones. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With toluene-4-sulfonic acid In chloroform for 8h; | |
With potassium hydrogensulfate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 500℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With trichloroacetic acid In toluene at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 42% 2: 45% | With tetrabutyl ammonium fluoride In tetrahydrofuran at 40℃; for 24h; | |
1: 36% 2: 45% | With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 8h; other temperatures, pressures and reaction times; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 100℃; Polymerisation bei 100grad,110grad und 125grad; | ||
Polymerisation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
/BRN= 328617/, KHSO4, Hitze; | ||
RCH2Cl 3a, Ph3P, Trioxan; | ||
entspr. Zimtsaeure-Derivat, Cu; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 74 percent / pyridine / CH2Cl2 / 1.) 0 deg C, 2 h, 2.) 5 deg C, 22 h 2: 45 percent / (n-Bu)4NF / tetrahydrofuran / 8 h / 20 °C / 6000480 Torr / other temperatures, pressures and reaction times |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 74 percent / NaBH4 / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) reflux, 2 h 2: 74 percent / pyridine / CH2Cl2 / 1.) 0 deg C, 2 h, 2.) 5 deg C, 22 h 3: 45 percent / (n-Bu)4NF / tetrahydrofuran / 8 h / 20 °C / 6000480 Torr / other temperatures, pressures and reaction times |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aluminium isopropylate; isopropyl alcohol 2: KHSO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: 1,4-dimethoxy-2-vinylbenzene With sodium periodate; lithium bromide In acetic acid at 100℃; Stage #2: With potassium carbonate In methanol at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: Methyltriphenylphosphonium bromide With sodium amide In diethyl ether at 20℃; for 10h; Inert atmosphere; Stage #2: 2,5-dimethoxybenzaldehyde In diethyl ether at -10 - 20℃; Inert atmosphere; | |
93% | Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 30℃; for 0.25h; Inert atmosphere; Stage #2: 2,5-dimethoxybenzaldehyde In tetrahydrofuran at 0 - 30℃; Inert atmosphere; | |
79% | Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 3h; Inert atmosphere; Stage #2: 2,5-dimethoxybenzaldehyde In tetrahydrofuran; hexane Reflux; |
76% | With potassium carbonate In 1,4-dioxane for 16h; Reflux; | |
1.92 g | Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 4h; Stage #2: 2,5-dimethoxybenzaldehyde In tetrahydrofuran; hexane for 1h; | Synthesis of I ,4-dimethoxy-2-vinylbenzene. Synthesis of I ,4-dimethoxy-2-vinylbenzene. A suspension of 11.71 g of methyl triphenylphosphonium bromide in 100 mL of dry THE was treated at room temperature with 14.3 mL of n-BuLi (2.5 M solution in n-hexane). The resulting orange solution was stirred for 4 hours. Then, a solution of 5.00 g of 2,5- dimethoxybenzaldehyde in 25 mL of dry THE was added dropwise. Upon addition, a white precipitate formed. The suspension was stirred for 1 hour and concentrated in vacuo to give a viscous orange oilthat was purified by passing through a short column of Si02 (heptane) then vacuum distillation to yield1.92 g of 1,4-dimethoxy-2-vinylbenzene as a colorless liquid. 1H-NMR (300 MHz, CDCI3): 6 3.71 (s,3H), 3.73 (s, 3H), 5.19 (dd, J1=11.2 Hz, J2=1.6 Hz, IH), 5.64 (dd, Ji=17.7 Hz, J2=1.6 Hz, 1H), 6.68-6.75 (m, 2H), 6.90-6.99 (m, 2H). GC-MS: 98.0% MS (El): 164. |
Microwave irradiation; Alkaline conditions; | Styrene synthesis Method 1: Wittig Reaction under microwave conditions. General procedure: Potassium carbonate (0.10 mol) and (ethyl)triphenylphosphoniumiodide (0.016 mol) were mixed and crushed in amortar to a fine powder and transferred into a 250 mLErlenmeyer flask. Aldehyde (0.016 mol) was added to thepowdered mixture and thoroughly mixed. The Erlenmeyerflask was covered with a watch glass and placed into amicrowave oven along with a 1 L beaker of ice (to ensurethat the reaction mixture did not overheat). The microwavewas run at full power for 12 min, making sure to stop theheating and replace the ice when it had melted. A tinysample of the crude reaction product was removed, dilutedin a small amount of hexanes and analyzed by TLC to checkthe reaction progress. Upon completion, the crude solidswere extracted with hexanes (3 × 20 mL). The combinedhexane extracts were placed in a round-bottomed flask andconcentrated by rotary evaporation to obtain a yellow oilwhich was purified by flash chromatography on silica gelusing hexanes or a mixture of hexanes/ethyl acetate aseluent. | |
With potassium carbonate In 1,4-dioxane for 24h; Schlenk technique; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With tetrabutylammomium bromide; potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 20 - 80℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With butyl phenylphosphinate; oxygen; cobalt(II) acetate; manganese(II) acetate In ethyl acetate at 90℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: 1,4-dimethoxy-2-vinylbenzene With N-(2,6-diisopropylphenyl)-N-((1E)-1-(6-[(1E)-N-(2,6-diisopropylphenyl)ethanimidoyl]pyridin-2-yl)ethylidene)amine; ethylmagnesium bromide; iron(II) chloride In tetrahydrofuran; diethyl ether at 20℃; for 2h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; diethyl ether for 0.5h; Inert atmosphere; regioselective reaction; | |
82% | Stage #1: 1,4-dimethoxy-2-vinylbenzene With bis(cyclopentadienyl)titanium dichloride; isopropylmagnesium chloride; lithium bromide In diethyl ether at 30℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: 1,3 dithiane With N-chloro-succinimide In 1,2-dichloro-ethane at 0℃; for 0.666667h; Stage #2: 1,4-dimethoxy-2-vinylbenzene With iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80 % de | In toluene at 70℃; for 72h; Overall yield = 95 %; | General Procedure for the Preparation of Isoxazolidines 16 and 17 General procedure: A solution of nitrone 14 (1.0 mmol) and a vinyl aryl (1.0 mmol) in toluene (2 ml) was stirred at 70°C until the disappearance (TLC) of the starting nitrone. All volatiles were removed in vacuo and the crude products were subjected to chromatography on silica gel columns with a chloroform/methanol (100:1) mixture as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With palladium diacetate; Dess-Martin periodane In water; acetonitrile at 50℃; Inert atmosphere; | |
83% | With chromium(VI) oxide; palladium dichloride In water; acetonitrile at 20 - 60℃; for 24h; | 4.2 General procedure for oxidation of terminal olefins General procedure: To a stirred solution of olefin (0.4mmol) in CH3CN (3.5mL) and H2O (0.5mL) were added PdCl2 (3.6mg, 0.02mmol, 5mol%) and CrO3 (20mg, 0.6mmol, 0.5equiv) at room temperature. The reaction mixture was warmed to 60°C and stirred for specified time (see Tables 5-7) in a closed flask. The reaction mixture was then filtered through a small pad of silica gel and washed with EtOAc and the filtrate concentrated. The residue in some cases contained virtually pure compound and no further purification was necessary. In other cases the residue was purified by silica gel column chromatography using petroleum ether/EtOAc as an eluent to afford the methyl ketones. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50 % de | With hydroquinone; epichlorohydrin In toluene at 120 - 130℃; for 12h; Inert atmosphere; Sealed tube; Overall yield = 87 %; Overall yield = 712 mg; diastereoselective reaction; | General procedure for the preparation of Diels-Alder 3/4 General procedure: The mixture of 1,2,3,4,5-pentachloro-5-methylcyclopenta-1,3-diene 1 (1 g, 3.96 mmol), styrene 2a (825 mg,7.92 mmol), catalytic amount of hydroquinone (3 mg), epichlorohydrin (0.01 mL) in dry toluene (1.5 mL) was heated at 120°C - 130°C in a sealed tube. After being heated for 10 h (reaction monitored by TLC), the reaction mixture was concentrated and the resulting crude residue was purified over silica gel column chromatography using hexane as eluent to afford adducts 3a and 4a (1.15 g, 83%, in 4:1 ratio) as colourless solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | Stage #1: 1,4-dimethoxy-2-vinylbenzene; ethylmagnesium chloride With zirconocene dichloride In tetrahydrofuran at -78 - 20℃; for 25h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium(II) trifluoroacetate; 1-<bis(adamantylcarbonyloxy)iodo>benzene In toluene; acetonitrile at 60℃; for 30h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium(II) trifluoroacetate; [bis(acetoxy)iodo]benzene In toluene; acetonitrile at 60℃; for 26h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: palladium(II) trifluoroacetate; 1-<bis(adamantylcarbonyloxy)iodo>benzene / acetonitrile; toluene / 30 h / 60 °C / 760.05 Torr / Schlenk technique 2.1: 1 h / 20 °C / Schlenk technique 2.2: 3 h / 20 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: palladium(II) trifluoroacetate; [bis(acetoxy)iodo]benzene / acetonitrile; toluene / 26 h / 60 °C / 760.05 Torr / Schlenk technique 2.1: 1 h / 20 °C / Schlenk technique 2.2: 3 h / 20 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With [bis(acetoxy)iodo]benzene In methanol at 0 - 20℃; for 0.75h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With [bis(acetoxy)iodo]benzene In methanol at 0 - 20℃; for 0.416667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.4% | With [1,3-bis(cyclohexyl)imidazol-2-ylidene]copper(I) chloride; sodium t-butanolate In tetrahydrofuran at 20℃; for 36h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With bromodichloromethane; sodium iodide In acetonitrile at 90℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | Dimerization of Alkenes; General Procedure General procedure: To a 25 mL of Schlenk tube was added NaI (36 mg, 0.24 mmol, 1.2equiv) under air, then evacuated and backfilled with N 2 (3 times). Theappropriate styrene 1 (0.2 mmol, 1.0 equiv), BrCCl 2 H (65.6 mg, 0.4mmol, 2.0 equiv) and MeCN (1 mL) were added subsequently. TheSchlenk tube was then sealed with Teflon lined cap and immersedinto a preheated oil bath. After stirring for 12 h or 18 h or 24 h(Scheme 1), the reaction mixture was cooled to r.t. and the solventwas removed under vacuum. The residue was purified by flash col-umn chromatography on silica gel to afford the desired product 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine / acetonitrile / 4 h / 10 °C / Inert atmosphere; Glovebox; Sealed tube; Irradiation 2.1: 10% Pt/activated carbon; hydrogen / ethanol / 8 h / 25 °C 2.2: 1 h / 20 °C | ||
Multi-step reaction with 3 steps 1.1: 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride / acetonitrile / 4 h / 20 °C / Inert atmosphere; Sealed tube; Irradiation 2.1: 10% Pt/activated carbon; hydrogen / ethanol / 8 h / 25 °C 3.1: 1,1'-carbonyldiimidazole / ethyl acetate / 2 h / 20 °C 3.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 10℃; for 4h; Inert atmosphere; Glovebox; Sealed tube; Irradiation; | |
35% | With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 4h; Inert atmosphere; Sealed tube; Irradiation; | 54 Example 6 1-(2-azido-1-(trifluoromethoxy)ethyl)-2,4,6-trimethylbenzene (4a) General procedure: Under the protection of N2, Ru(bpy)3(PF6)2 (2.4 mg, 0.00300 mmol, 1.0 mol%), AgF (19.2 mg, 0.150 mmol, 50.0 mol%) was added to the sealed tube. 4,4',4"-tri-tert-butyl-2,2':6',2"-terpyridine (tbtpy, 36.0 mg, 0.0900 mmol, 30.0 mol%),1-azido-1,3 benzo[d][1,2]iodohydroxy-3(1H)-one (3) (173.4 mg, 0.600 mmol, 2.00 eq.), then acetonitrile solvent (2.40 mL) ,4-phenylstyrene (1a) (43.9 mg, 0.300 mmol, 1.00 equiv), trifluoromethyl 4-methylbenzenesulfonate (2) (169 μL, 0.9 mmol, 3.00 equiv) was added to the reaction. The resulting mixture was then allowed to stand at room temperature and stirred under irradiation with a 14 W blue LED for 4 hours.After that, the reaction mixture was concentrated in vacuo and purified by silica gel chromatography.Elution with petroleum ether / ethyl acetate 100:1 (v / v) gave the corresponding product (4a), 65.5mg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; silver fluoride / acetonitrile / 4 h / 20 °C / Inert atmosphere; Sealed tube; Irradiation 2: 10% Pt/activated carbon; hydrogen / ethanol / 8 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Stage #1: 1,4-dimethoxy-2-vinylbenzene With N-Bromosuccinimide; water at 80℃; for 2h; Sealed tube; Green chemistry; Stage #2: With ammonium hydroxide; water; iodine at 80℃; for 1h; Sealed tube; Green chemistry; | General experimental procedure for the synthesis of aromatic amides: General procedure: A sealed tube equipped with a magnetic stirring bar was charged with styrene 1 (1.0mmol), NBS (2.0 mmol) and water (2.0mL) at room temperature. The resulting mixture was heated to 80 °C for 2h. After disappearance of the reactant (monitored by TLC), reaction mixture was cooled to room temperature. To this reaction mixture molecular iodine (2.2 mmol) and 30% aq. ammonia solution or n-butylamine (10 mmol) were added and it was heated to 80 °C for 1h. After completion of the reaction (monitored by TLC), saturated Na2S2O3 solution (10 mL) was added to the reaction mixture, and it was extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine solution (10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue obtained was purified by column chromatography on 60-120 mesh silica gel using ethyl acetate: n-hexane (1:2) as the eluent to obtain the corresponding aromatic amide 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With triethanolamine; palladium diacetate for 0.5h; Reflux; Microwave irradiation; | General procedure for the Mizoroki-Heck reactions General procedure: Styrene (3 mmol), 3-bromo-7-alkyloxycoumarin (4) or 2-oxo-2H-chromen-7-yl trifluoromethanesulfonate (9)(3 mmol), triethanolamine (3 mL) and Pd(OAc)2 (0.03 g)were placed in a 25 mL flat-bottomed flask equipped with amagnetic stirring bar. The mixture was stirred and heated toreflux for a period of 30 min, under microwave irradiation.The mixture was allowed to cool and then passed through apad of silica using ethyl acetate as solvent. Then the filtratewas evaporated and the crude residue was purified by preparativechromatography (silica gel, hexane/methylenechloride (1:1) mixture) affording the coupling products in35-58% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ferulic acid decarboxylase from Saccharomyces cerevisae In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 18h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 20 - 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water / 20 - 60 °C 2: ethylmagnesium bromide / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Cooling with ice 3: silver(l) oxide; dipotassium peroxodisulfate / N,N-dimethyl-formamide / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water / 20 - 60 °C 2: ethylmagnesium bromide / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With 1,4-diaza-bicyclo[2.2.2]octane; tert.-butylhydroperoxide; sodium azide; cobalt acetylacetonate In tetrahydrofuran; decane; hexane at 80℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With 1,4-diaza-bicyclo[2.2.2]octane; tert.-butylhydroperoxide; sodium azide; cobalt acetylacetonate In tetrahydrofuran; decane; hexane at 80℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis(η3-allyl-μ-chloropalladium(II)); N-ethyl-N,N-diisopropylamine; XPhos In 1,4-dioxane at 90℃; for 16h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92 %Spectr. | With triethyl borane; sodium triethylborohydride In tetrahydrofuran at 100℃; for 12h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With pyrrolidine; palladium diacetate; lithium chloride In N,N-dimethyl-formamide at 170℃; for 0.0666667h; Microwave irradiation; | 4.1.4. General Procedure for the Mizoroki-Heck Reactions General procedure: Styrene (0.3 mmoL), bromochalcone (0.3 mmoL, 100 mg), pyrrolidine (0.6 mmoL,50 L), Pd(OAc)2 (6 mg, 0.027 mmoL), LiCl (12 mg, 0.28 mmoL) and DMF (1 mL) wereplaced in a 10 mL flat-bottomed flask equipped with a magnetic stirring bar. The mixturewas stirred and heated to 170 C at 200Wfor a period of 4 min, under microwave irradiation.The mixture of reaction was allowed to cool, and then 100 mL of HCl 5% were added. Then,this mixture was extracted with dichloromethane, concentrated and the crude residue waspuried by column chromatography (silica gel, hexane-ethyl acetate mixture) affording thecoupling products in 35-55% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dipotassium hydrogenphosphate; 3-benzyl-2,4,5,6-tetra(9H-carbazol-9-yl)benzonitrile In N,N-dimethyl-formamide at 28 - 32℃; for 6h; Schlenk technique; Sealed tube; Irradiation; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 3-benzyl-2,4,5,6-tetra(9H-carbazol-9-yl)benzonitrile; dipotassium hydrogenphosphate / N,N-dimethyl-formamide / 6 h / 28 - 32 °C / Schlenk technique; Sealed tube; Irradiation 2: diethyl ether; methanol / 1 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 3-mesityl-4,5,6,7-tetrahydrobenzo[d]thiazol-3-ium perchlorate; N-ethyl-N,N-diisopropylamine In acetonitrile at 65℃; for 16h; Irradiation; regioselective reaction; |
Tags: 14568-68-4 synthesis path| 14568-68-4 SDS| 14568-68-4 COA| 14568-68-4 purity| 14568-68-4 application| 14568-68-4 NMR| 14568-68-4 COA| 14568-68-4 structure
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P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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