There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 4312-99-6 | MDL No. : | MFCD00036558 |
Formula : | C8H14O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KLTVSWGXIAYTHO-UHFFFAOYSA-N |
M.W : | 126.20 | Pubchem ID : | 61346 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.62 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.3 |
TPSA : | 17.07 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.33 cm/s |
Log Po/w (iLOGP) : | 2.25 |
Log Po/w (XLOGP3) : | 2.45 |
Log Po/w (WLOGP) : | 2.32 |
Log Po/w (MLOGP) : | 1.97 |
Log Po/w (SILICOS-IT) : | 2.29 |
Consensus Log Po/w : | 2.26 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.84 |
Solubility : | 1.84 mg/ml ; 0.0146 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.45 |
Solubility : | 0.446 mg/ml ; 0.00353 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.24 |
Solubility : | 0.728 mg/ml ; 0.00577 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.74 |
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P270-P280-P210-P233-P240-P242-P243-P264-P301+P312-P303+P361+P353-P305+P351+P338-P330-P332+P313-P337+P313-P370+P378-P363-P403+P235-P501 | UN#: | 1224 |
Hazard Statements: | H225-H302-H315-H319 | Packing Group: | Ⅲ |
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 |
---|---|---|
100% | With cis-dichlorotetrakis(diemethylsulfoxide) ruthenium(II); sodium formate In water; toluene at 80℃; for 1h; Inert atmosphere; | 4.5 General procedure for catalytic isomerization of allylic alcohols General procedure: Under an inert atmosphere, the catalyst precursor (0.01 mmol) and Na-formate (0.5 mmol) were dissolved in 3 mL of deoxygenated water. The solution was then heated to the indicated temperature and then allylic alcohol (0.5 mmol, in 1 mL of toluene) was introduced. The system was rapidly stirred for 1 h and then was cooled to room temperature. The separated organic phase was filtered through a short silica gel column and was subjected to gas chromatography. |
98% | With 2,2,6,6-tetramethyl-piperidine-N-oxyl; periodic acid In dichloromethane at 20℃; for 0.583333h; | |
98% | With chromium (VI) oxide In toluene for 0.333333h; microwave irradiation; |
97% | With dipyridinium dichromate In dichloromethane at 20℃; for 1h; Inert atmosphere; Molecular sieve; | |
95% | With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene In dichloromethane for 2.5h; | |
95% | With oxygen; triethylamine In tetrahydrofuran; toluene at 45℃; for 20h; | |
91% | With benzophenone; (π-C5H5)2Zr{OC(CH3)2H}2 In toluene for 8h; Heating; | |
91% | With chlorine-triphenylphosphine; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃; for 3.25h; | |
90% | In neat (no solvent) at 20℃; for 0.0666667h; Microwave irradiation; | General procedure General procedure: In a small-scale experiment 4-hydroxypyridinium chlorochromate functionalized silica gel (3.95 g, contain 10 mmol of 4-hydroxypyridinium chlorochromate) an alcohol (10 mmol) was rapidly added at room temperature and the resulting mixture stirred vigorously for the appropriate time. The mixture was irradiated for the time indicated in the table by microwave radiation (Table 2). The progresses of the reactions were monitored by TLC. After cooling to room temperature the product was extracted with diethyl ether (2 × 10 mL) and filtered. Evaporation of solvent gave a crude product which was passed through a short silica gel column by ethyl acetate: pet.ether (1:7) as eluent to afford the pure product. The structures of the products were confirmed by their melting point, IR and /or NMR spectral data and comparison with commercially available authentic samples.36-38 |
89% | With potassium permanganate on Y-Zeolite In 1,2-dichloro-ethane for 6h; Ambient temperature; | |
88% | With 2,6-dicarboxypyridinium fluorochromate at 20℃; for 0.166667h; | |
87% | With tert.-butylhydroperoxide; tetrabutyl-ammonium chloride; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 20℃; for 24h; | |
84% | With pyridinium chlorochromate at 20℃; for 1.83333h; | |
76% | With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; sodium chloride In 1,2-dichloro-ethane at 20℃; for 13h; | |
72% | With bromine; oxygen In acetic acid at 60℃; for 6h; | |
71% | With 2-chloro-1,3-dimethylimidazolinium chloride; dimethyl sulfoxide; triethylamine In dichloromethane at 20℃; for 72h; | |
70% | With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene In dichloromethane at 19.85℃; for 2h; | |
70% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 2h; | |
70% | With titanium(IV) oxide; oxygen at 29.84℃; for 24h; Sealed tube; Irradiation; | |
66% | With octadecafluorodecahydronaphthalene (cis+trans); dihydrogen peroxide at 22℃; for 8h; | |
64% | With chromic acid In acetone at 0℃; | |
61% | With potassium permanganate; copper(II) sulfate In dichloromethane for 24h; Heating; | |
48% | With oxygen In dimethyl sulfoxide at 135℃; for 3h; | |
35% | With manganese(IV) oxide In tetrahydrofuran for 8h; Reflux; | |
30% | With allyl diethyl phosphate; potassium carbonate In N,N-dimethyl-formamide for 3.25h; | |
11% | With sodium permanganate In hexane at 69℃; for 24h; | |
With manganese(IV) oxide In Petroleum ether | ||
With Py*HClCrO3 | ||
With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride | ||
With dipyridinium dichromate In dichloromethane | ||
92 % Chromat. | With potassium permanganate; bentonite In dichloromethane for 60h; Heating; | |
43.6 % Chromat. | With potassium permanganate In benzene at 50℃; for 24h; Irradiation; | |
With jones reagent In acetone at 5 - 10℃; | ||
54 % Turnov. | With N-hydroxyphthalimide; cobalt(III) acetylacetonate; oxygen In acetonitrile at 75℃; for 5h; | |
53 % Chromat. | With palladium diacetate; oxygen In dimethyl sulfoxide at 80℃; for 24h; | |
47 % Chromat. | With manganese(IV) oxide; molecular sieve In hexane for 12h; Heating; | |
With pyridinium chlorochromate | ||
80 % Chromat. | With silica-supported 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide In tetrahydrofuran at 20℃; | |
With [{nBu4N}5{PV2Mo10O40}]; dinitrogen monoxide In benzonitrile at 150℃; for 15h; | ||
With whole lyophilised cells of Rhodococcus ruber DSM 44541; acetone In phosphate buffer at 30℃; for 20h; | ||
With SiW11Zn; dihydrogen peroxide In water at 89.85℃; for 9h; | ||
Stage #1: 1-octen-3-ol With cis-[Ru(2,9-Me2phen)2(OH2)2](PF6)2 In acetonitrile at 55℃; for 0.5h; Stage #2: With dihydrogen peroxide In acetonitrile for 12h; | ||
With oxygen at 79.85℃; for 3.5h; | ||
With oxygen at 120℃; for 3h; | ||
93 % Chromat. | With oxygen; potassium carbonate In toluene at 80℃; for 6h; | |
4.5 % Turnov. | With oxygen In benzene-d6 at 60℃; for 24h; | |
76 % Chromat. | With oxygen; chloranil; decalin In water at 90℃; for 18h; | |
67 % Chromat. | With N-hydroxyphthalimide; oxygen; cobalt(II) acetate; 3-chlorobenzoate In ethyl acetate at 25℃; for 20h; | |
2.6 % Chromat. | With 1,4-dihydronicotinamide adenine dinucleotide; NAD In phosphate buffer at 30℃; for 72h; | |
With air In toluene at 90℃; for 6h; | ||
With oxygen at 119.84℃; | ||
With oxygen In N,N-dimethyl-formamide at 139.84℃; for 1.3h; | ||
With oxygen; palladium diacetate; triethylamine In N,N-dimethyl acetamide at 70℃; for 4h; | ||
100 %Chromat. | With oxygen; potassium carbonate In α,α,α-trifluorotoluene at 80℃; for 7h; | |
Stage #1: 1-octen-3-ol With gold on titanium oxide In water at 90℃; for 0.166667h; Inert atmosphere; Stage #2: With dihydrogen peroxide In water at 90℃; for 1.08333h; Inert atmosphere; chemoselective reaction; | ||
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate Reflux; | ||
90 %Chromat. | With oxygen; potassium carbonate In α,α,α-trifluorotoluene at 95℃; for 5h; | |
93 %Chromat. | With Pd(0) nanoparticle supported on aminopropyl grafted silica-based mesocellular foam; air In para-xylene at 130℃; for 8h; | |
With oxygen; palladium diacetate In N,N-dimethyl-formamide at 90℃; for 4h; Green chemistry; | ||
With Tween 20; crude enzyme extract from Marchantia polymorpha thalli In aq. phosphate buffer at 27℃; for 0.0833333h; Enzymatic reaction; | 4.6 Oxidoreductase assay To estimate the oxidoreductase activity toward 5, crude enzyme soln. (100 μL) prepared as described in Section 4.4. was mixed with 10 mgmL-1 5 (10 μL) suspended in 0.2% Tween 20, and incubated at 27 °C for 5 min in 50 mM sodium phosphate (pH 7.0) with or without 5 mM NADH or NADPH. After the reaction, the C8 compounds were extracted with 1 mL of MTBE containing nonanyl acetate (1 μgmL-1), and quantitatively analyzed using GC-MS essentially as described in Section 4.4 but with the modified column condition [40 °C (5 min) to 200 °C (2 min) at 8 °Cmin-1 with He as a carrier gas at 26.7 cms-1]. | |
34 %Chromat. | With phosphomolybdic acid; oxygen; tetrabutylammonium acetate; palladium diacetate In ethyl acetate at 100℃; for 1h; | |
With 6C16H36N(1+)*2Zn(2+)*4Na(1+)*[Bi2Zn2(ZnW9O34)2](14-); urea hydrogen peroxide adduct In acetonitrile at 70℃; for 3h; | ||
34 %Chromat. | With manganese(II) triflate; 1-Adamantanecarboxylic acid; C32H38N4O2; dihydrogen peroxide In water; acetonitrile at 0℃; for 2h; chemoselective reaction; | |
56 %Chromat. | With oxygen In water at 80℃; for 8h; | |
With gold; dihydrogen peroxide In methanol; water at 55℃; for 8h; Inert atmosphere; chemoselective reaction; | Catalytic reaction General procedure: The liquid-phase oxidation reactions were performed usinground bottom flask equipped with water condenser and a mag-netic stirrer. In a typical alcohol oxidation reaction, 0.67 g (5 mmol)of cinnamyl alcohol was mixed with 5 mL of methanol and 0.56 g(5 mmol) of dilute H2O2(30 wt% aqueous solution) in a 25 mL two-necked round bottom flask followed by addition of 5 wt% catalystwith respect to substrate. Cycloheptanone was used as an inter-nal standard to quantify the reaction product. The reaction wasperformed at 328 K while effectively circulation ice-cold waterthrough the condenser and the mixture was maintained under N2atmosphere using a N2balloon. The progress of the reaction wasmade by analyzing the products with a capillary gas chromato-graph (Agilent 13G, OV-1 column with flame ionization detector,FID). The quantification of products has been performed with spe-cial care using internal standard and response factor of reactantand products. For catalyst reusability study, the catalyst was recov-ered through centrifugation followed by activation under 5% H2(remaining N2) atmosphere at 180C. It is pertinent to mention thatlow-temperature activation was carried out to remove the physi-cally adsorbed organic reactant, product or solvent molecules fromthe metal surface of the used catalyst | |
98 %Chromat. | With dihydrogen peroxide In acetonitrile at 80℃; for 7.5h; | |
With oxygen; palladium diacetate In toluene at 90℃; for 6h; Green chemistry; | ||
With [fac-N-(2-(diphenylphosphino)ethyl)-5,6,7,8-tetrahydroquinolin-8-amine]RuCl2(triphenylphosphine); potassium <i>tert</i>-butylate In para-xylene for 10h; Reflux; Inert atmosphere; | ||
With Dess-Martin periodane In dichloromethane at 20℃; | ||
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 2h; | ||
With Dess-Martin periodane In dichloromethane at 20℃; | ||
> 99 %Chromat. | With oxygen at 120℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With triethylamine In ethanol at 80℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With triethylamine In ethanol at 80℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With N-benzyl-trimethylammonium hydroxide In 1,4-dioxane for 24h; Heating; | |
In 1,4-dioxane Heating; | ||
With hydrogenchloride In <i>N</i>-methyl-acetamide; ethyl acetate; mineral oil | 4 4-Methyl-2-(3'-oxo-octyl)-1,2,4-triazolidine-3,5-dione (Compound 7) EXAMPLE 4 4-Methyl-2-(3'-oxo-octyl)-1,2,4-triazolidine-3,5-dione (Compound 7) To a solution of 4-methyl-1,2,4-triazolidine-3,5-dione (5.75 g, 0.05 mol) in dry dimethylformamide (40 ml) stirred at 75° under a nitrogen atmosphere was added portionwise sodium hydride (1.575 g, 0.055 mol, as an 80% dispersion in mineral oil) and the resultant solution stirred at 75° for 0.5 hr. To this solution was added oct-1-en-3-one (6.57 g, 0.055 mol) dropwise in dimethylformamide (20 ml) and the solution heated with stirring for 48 hr at 75°. The reaction mixture was then cooled, taken up in ethyl acetate (100 ml) and poured into ice-cold 5 N aqueous hydrochloric acid (200 ml). The aqueous layer was separated and extracted with ethyl acetate (4*100 ml). The combined extracts were washed with 5 N aqueous hydrochloric acid, water and then brine, then dried (Na2 SO4), filtered and the solvent removed by evaporation in vacuo, to leave a gum (6.55 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With tin(IV) chloride In dichloromethane at -78℃; for 3h; | |
With tin(IV) chloride; triethylamine 1) CH2Cl2, -78 deg C, 3 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium tetrahydroborate In methanol at 20℃; for 4h; | |
With isoindoline; lithium aluminium tetrahydride In diethyl ether at -15℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Isopropylbenzene; oxygen In acetonitrile at 80℃; for 24h; var. of catalyst; | ||
With oxygen In dichloromethane; acetonitrile at 82.85℃; for 385h; | ||
With 3-methylpentane; oxygen at 90℃; for 1 - 17h; | 3 Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a magnetic stirrer, were placed 3000 mg of 1-octene and 1000 mg of 3-methyl-pentane, followed by the addition of 85 mg of a catalyst as described in Example 1 a [Au/CeO2- CAT A] . The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector (flame ionisation detector), to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products * 100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonec Glycold Dimerse 1 0.10 58.9 10.7 30.4 0 0 2 0.15 62.5 19.7 17.8 0 0 3.5 0.24 73.4 13.0 13.6 0 0 5 0.33 78.7 8.7 12.6 0 0 a- Epoxide = 1,2-epoxy-octane. b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of the olefinic compound. |
With 3-methylpentane; oxygen at 90℃; for 2 - 17h; | 5 Into a 12 ml stainless steel autoclave reactor, with an inner lining of Teflon and containing a magnetic stirrer, were placed 3000 mg of 1-octene and 1000 mg of 3-methyl-pentane, followed by the addition of a mechanical mixture of 50 mg of a catalyst as described in Examples 1 a [Au/CeO2 - CAT A] + 100 mg of a catalyst as described in Example 2b [Ti-MCM-41-Sil. - CAT T] . The autoclave is hermetically sealed, the lid having a connection to a pressure gauge (manometer), with another connection to load the source of gaseous oxygen and a third outlet allowing samples to be taken at different time intervals. The reactor is pressurised with oxygen at 10 bars, and the reaction temperature raised to 90 °C, and the autoclave immersed in a silicone bath with temperature control. The reaction mixture is shaken and samples taken at various time intervals up to a reaction time of 17 hours. The samples are analysed using GC with an FID detector, to calculate the composition of the mixture obtained, the conversion of olefinic compounds (initial moles of reactant - final moles of reactant / initial moles of reactant * 100), and the selectivities of the products obtained (moles of product i / moles of total products * 100) in each case. The following results were obtained in this manner: Time (hours) Conversion (% Mol.) Selectivity (% Mol.)Epoxidea Enolb Enonec Glycold Dimerse 1 - - - - - - 2 0.15 62.5 19.7 17.8 0 0 3.5 0.17 54.8 22.0 23.2 0 0 5 - - - - - - a- Epoxide = 1,2-epoxy-octane. b- Enol = 1-octen-3-ol. c- Enone = 1-octen-3-one. d- 1,2-octanediol. Dimers = Products of dimerisation of olefinic compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With dimethylaluminum chloride In hexane; dichloromethane at 20℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium tetrahydroborate; C11H18Cl2CoN2S; hydrogen In isopropyl alcohol at 100℃; for 16h; Glovebox; Autoclave; | |
77% | With bis(cyclopentadienyl)titanium (III) chloride; deuteromethanol In tetrahydrofuran at -25 - 20℃; | |
37 % Chromat. | With pulegone reductase from Nicotiana tabacum; NADPH; Triton X-100 In water at 35℃; for 8h; |
With pulegone reductase from Nicotiana tabacum; NADPH; Triton X-100 In water at 35℃; | ||
With recombinant barley alkenal hydrogenase 1; NADPH In phosphate buffer; ethanol at 30℃; | ||
87 %Chromat. | With D-glucose; glucose dehydrogenase (GDH; 10U); holo-(flavin free double bond reductase from Nicotiana tabacum); nicotinamide adenine dinucleotide phosphate In aq. phosphate buffer at 30℃; for 4h; Enzymatic reaction; | |
With Ph2P(CH2CH2O)22CH3-stabilized iridium nanoparticles; hydrogen In pentan-1-ol; water at 70℃; for 1h; chemoselective reaction; | ||
With hydrogen In pentan-1-ol; water at 90℃; for 0.166667h; | ||
With recombinant Cyclocybe aegerita ene/yne-reductase CaEnR1; NADPH In aq. phosphate buffer at 24℃; for 3h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 75% 2: 15% 3: 5% | With sodium acetate In water at 100℃; for 12h; | |
With oxygen; sodium acetate In water; dimethyl sulfoxide at 100℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With 4-methyl-morpholine; 2.9-dimethyl-1,10-phenanthroline; oxygen In acetonitrile at 50℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With 4-methyl-morpholine; 2.9-dimethyl-1,10-phenanthroline; oxygen In acetonitrile at 50℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With RhCl(PPh3)3; diethylzinc In tetrahydrofuran; hexane at 20℃; for 0.5h; | |
59% | Stage #1: oct-1-en-3-one; iodotrifluoromethane With Wilkinson's catalyst In tetrahydrofuran at -30℃; Inert atmosphere; Schlenk technique; Stage #2: With diethylzinc In tetrahydrofuran; hexane at 5 - 20℃; for 1h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With oxygen; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide at 110℃; for 0.25h; Flow reactor; Green chemistry; regioselective reaction; | |
68% | With copper diacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 70℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate In acetonitrile at 80℃; for 24h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With caesium carbonate In acetonitrile at 80℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With lithium aluminium deuteride In diethyl ether at -0.15 - 19.85℃; | |
63% | With lithium aluminium deuteride In diethyl ether at 20℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In dichloromethane at 45℃; for 96h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In dichloromethane at 45℃; for 96h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With titanium tetrachloride; tetra-(n-butyl)ammonium iodide In dichloromethane at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With titanium tetrachloride; tetra-(n-butyl)ammonium iodide In dichloromethane at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethyl borane In tetrahydrofuran; methanol at 20℃; for 2h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triethyl borane In tetrahydrofuran; methanol at 50℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With triethyl borane In tetrahydrofuran; methanol at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With triethyl borane In tetrahydrofuran; methanol at 50℃; for 2h; | |
74% | With methanol; bis(1,5-cyclooctadiene)nickel (0); triethyl borane; tributylphosphine In tetrahydrofuran at 20 - 50℃; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In toluene at 20℃; for 20h; | |
94% | In toluene at 20℃; for 20h; Inert atmosphere; | 1.14 EXAMPLES; Previous studies on asymmetric cyclopropanation of styrene derivatives revealed that a [Co(1)]-based system seemed insensitive to substrate electronics. (Huang et al, J. Org. Chem. 2003, 68, 8179; Chen et al., J. Am. Chem. Soc. 2004, 126, 14718; and Chen Y., Zhang, X. P., J. Org. Chem. 2007, 72, 5931.) Even the extremely electron-deficient pentafluorostyrene could be cyclopropanated. (Chen Y., Zhang, X. P., J. Org. Chem. 2007, 72, 5931.) This result prompted us to evaluate the catalytic reactivity of [Co(1)] toward more challenging substrates such as electron-deficient non-styrene olefins (Table 1). Under the one-pot protocol where olefins are the limiting reagent, using 1 mol % [Co(1)] in the presence of 0.5 equivalents of DMAP could effectively cyclopropanate both acrylates and methacrylates with EDA or tert-butyl diazoacetate (t-BDA) at room temperature in toluene, forming the corresponding 1,2-cyclopropanediesters in good yields and high diastereo- as well as enantio-selectivities (Table 1, entries 1-5). Under the same conditions, acrylamide as well as its mono- and di-substituted derivatives were also suitable substrates, providing the corresponding 1,2-cyclopropaneamidoesters with good to high yields and excellent selectivities (Table 1, entries 6-10). The amido functional groups were well tolerated; no N-H insertion products were observed. Alkenes bearing carbonyl and cyano groups such as acrylketones and acrylonitriles were fully compatible with the catalytic system as well. In most of the cases, the resulting 1,2-cyclopropaneketoesters (Table 1, entries 11-15) and 1,2-cyclopropane cyanoesters (Table 1, entries 16-19) could be synthesized in high yields and high selectivities. As the best example, cyclopropanation of 1-octen-3-one with t-BDA resulted in the formation of the desired trans-1,2-cyclopropaneketoester in 94% yield, 98% de, and 96% ee (Table 1, entry 14). Diethyl maleate could also be successfully cyclopropanated to produce the 1,2,3-cyclopropanetriester solely as the α,α,β-isomer, albeit in a lower yield (Table 1, entry 20).While most of the substrates gave high yields and selectivities, the yields of several reactions were still moderate (Table 1). To further improve the catalytic process without sacrificing its attractive practicality, several common solvents in addition to toluene were evaluated for the cyclopropanation of ethyl acrylate with t-BDA under the same conditions. Among the solvents tested (Table 2), chlorobenzene was found to be the best solvent, giving the desired cyclopropane in the highest yield and with the best enantioselectivity as well as diastereoselectivity. As a result, several lower-yielding reactions were repeated in chlorobenzene. Dramatic improvements in yield were obtained while maintaining high diastereo- and enantio-selectivities (Table 1, entries 1A-3A, 5A-7A, 10A, 15A, 18A, and 20A).As demonstrated by the results reported in Table 1, [Co(1)] is an effective catalyst for asymmetric cyclopropanation of various electron-deficient olefins under mild conditions, forming synthetically valuable electrophilic cyclopropane derivatives in high yields and high stereoselectivities. Together with its high reactivity and selectivity toward styrene derivatives shown previously, [Co(1)] may be considered one of the most selective catalysts for asymmetric cyclopropanation of both electron-sufficient and electron-deficient olefins with diazoacetates.(Lebel et al., Chem. Rev. 2003, 103, 977; Davies H. M. L., Antoulinakis E., Org. React. 2001, 57, 1; Doyle M. P., Forbes D. C., Chem. Rev. 1998, 98, 911; Padwa A., Krumpe K. E., Tetrahedron 1992, 48, 5385-5453; Pietruszka J., Chem. Rev. 2003, 103, 1051; Wessjohann et al, Chem. Rev. 2003, 103, 1625; Donaldson W. A., Tetrahedron 2001, 57, 8589; Salaun J., Chem. Rev. 1989, 89, 1247; Fritschi et al, Agnew. Chem., Int. Ed. Engl. 1986, 25, 1005; Evans et al, J. Am. Chem. Soc. 1991, 113, 726; Lo et al, J. Am. Chem. Soc. 1998, 120, 10270; Maxwell et al, Organometallics 1992, 11, 645; Doyle et al, J. Am. Chem. Soc. 1993, 115, 9968; Davies et al., J. Am. Chem. Soc. 1996, 118, 6897; Nishiyama et al, J. Am. Chem. Soc. 1994, 116, 2223; Che et al, J. Am. Chem. Soc. 2001, 123, 4119.)These results suggest that the catalytic intermediate of the current Co(II)-based system may have different reactivity characteristics from the previously reported either Cu(I)- or Rh(II)2-based systems.; aPerformed in toluene at RT for 20 h using 1 mol % [Co(1)] under N2 with 1.0 equiv of alkene and 1.2 equiv of EDA or t-BDA in the presence of 0.5 equiv of DMAP. [alkene] = 0.25 M. bPerformed in chlorobenzene. cIsolated yields. dDetermined by GC. eDetermined by GC or HPLC on chiral stationary phases. fOnly the α,α,β-isomer was observed. g(-)-[1R,2R] absolute configuration determined by optical rotation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Cs2CO3 / chiral tertiary amine / acetonitrile / 24 h / 80 °C 2: NBuLi / tetrahydrofuran 3: diethyl ether 4: 66 percent / Cs2CO3 / chiral tertiary amine / acetonitrile / 24 h / 80 °C | ||
Multi-step reaction with 4 steps 1: Cs2CO3 / chiral tertiary amine / acetonitrile / 24 h / 80 °C 2: NBuLi / tetrahydrofuran 3: diethyl ether 4: Cs2CO3 / chiral tertiary amine / acetonitrile / 24 h / 80 °C | ||
Multi-step reaction with 4 steps 1: 65 percent / Cs2CO3 / O-methylquinine / acetonitrile / 24 h / 80 °C 2: NBuLi / tetrahydrofuran 3: diethyl ether 4: 66 percent / Cs2CO3 / chiral tertiary amine / acetonitrile / 24 h / 80 °C |
Multi-step reaction with 4 steps 1: 65 percent / Cs2CO3 / O-methylquinine / acetonitrile / 24 h / 80 °C 2: NBuLi / tetrahydrofuran 3: diethyl ether 4: Cs2CO3 / chiral tertiary amine / acetonitrile / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | In ethanol at 20℃; for 15h; | 1.2 0.4 g of 1 -octene-3-one is dissolved in 5 ml of absolute ethanol. 0.49 g of the product resulting from step 1, in solution in 5 ml of absolute ethanol, is then added. The mixture is allowed to react for 15 hours at ambient temperature. The product is treated and purified on a silica column. 300 mg of product are obtained (yield: 30%). The NMR and mass spectrometry results are in accordance with the expected structure |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; triphenylphosphine In hexane; ethyl acetate; acetonitrile | 4 15-dehydroprostaglandin B1 7-(2-Bromo-5-oxo-1-cyclopentenyl) heptanoic acid methyl acid (80 mg, 0.26 mmole) and 1-octene-3-one (60.6 mg, 0.48 mmole) were dissolved in acetonitrile (10 ml), and then triethyl amine (56.2 mg, 0.56 mmole) and a catalyst (a mixture of palladium diacetate and triphenylphosphine in a ratio of 1:2, 2.4 mg) were added thereto. The mixture was refluxed by heating under an argon atmosphere for 46 hours and 30 minutes. The reaction mixture was cooled and then subjected to filtration. The solvent was distilled off and the residue thus obtained was purified by silica gel column chromatography using as a solvent a mixture of hexane and ethyl acetate to recover 7-(2-bromo-5-oxo-1-cyclopentenyl)heptanoic acid methyl ester (yield 72 mg, 90%) and obtain 15-dehydro PGB1 methyl ester (yield 4.5 mg, 5%). The NMR spectrum, the IR spectrum, and the TLC of the product agreed with those of a sample produced by the previously known method of synthesis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In ethanol at 20℃; for 15h; | 3 Example 3 Synthesis of 1-[4-(3-phenylpropyl)piperazin-1-yl]octan-3-one 1 g (4.9 mmol) of 1-(3-phenylpropyl)piperazine is dissolved in 10 ml of ethanol in a round-bottomed flask. 0.620 g of 1-octen-3-one (4.9 mmol) is added and the mixture is reacted for 15 hours at room temperature. The reaction medium is diluted with ethyl acetate and water. The aqueous phase is extracted with ethyl acetate. The organic phases are then combined, washed with saturated NaCl solution, dried and concentrated under vacuum. The crude residue is purified on a column of silica (EtOAc/heptane) to give 1.3 g (yield=81%) of 1-[4-(3-phenylpropyl)piperazin-1-yl]octan-3-one in the form of a colourless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium <i>tert</i>-butylate In toluene at 90℃; for 1h; Title compound not separated from byproducts.; | ||
With potassium <i>tert</i>-butylate In toluene at 90℃; for 1h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium <i>tert</i>-butylate In toluene at 90℃; for 1h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium <i>tert</i>-butylate In toluene at 90℃; for 2h; Title compound not separated from byproducts.; | ||
With potassium <i>tert</i>-butylate In toluene at 90℃; for 1h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With sodium acetate; hydroquinone In N,N-dimethyl-formamide at 80℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With N-ethyl-N,N-diisopropylamine at 40℃; for 18.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With [Rh(DPEphos)(nbd)]ClO4; hydrogen In 1,2-dichloro-ethane at 70℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With (bicyclo[2.2.1]hepta-2,5-diene)(1,2-bis(diphenylphosphanyl)ethane)rhodium(I) perchlorate; hydrogen In 1,2-dichloro-ethane at 70℃; for 18h; Inert atmosphere; optical yield given as %de; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With palladium diacetate; triethylamine; XPhos In tetrahydrofuran at 120℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With chromium dichloride; copper(l) cyanide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With chromium dichloride; copper(l) cyanide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With chromium dichloride; copper(l) cyanide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With methanol; bis(1,5-cyclooctadiene)nickel (0); triethyl borane; tributylphosphine In tetrahydrofuran at 20℃; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 4448A mixture of 2-chloro-4 nitroimidazole (4.11 mmol) and triethyl amine (1.58 mmol) in 1,4- dioxane is stirred for 30 min. Then 1-octene-3-one (3.16 mmol) is added to the above mixture and stirred at 60 0C for 12 h in a sealed tube. The reaction is diluted with water and extracted into EtOAc (3 x 30 mL) and is washed with water, brine and dried over Na.sum.SClambda) and concentrated. The crude sample is used for the next step with out any further purification. MS: M+ 274.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9 %Chromat. | With lithium (S,S)-1,1'-(pyridine-2,6-diylbis(methylene))bis(pyrrolidine-2,1-diyl)diformate; dihydrogen peroxide; iron(II) acetate In methanol; water at 20℃; for 16.5h; Inert atmosphere; | 3.12. Oxidative turnover reactions General procedure: Iron(II) acetate (12.0 mg, 0.070 mmol) was dissolved in degassed, dry methanol (1.20 mL) and an aliquot of this solution (0.200 mL) was added to a solution of ligand (4.00 mg, 0.010 mmol) in methanol (0.200 mL) under argon to give a yellow solution. The reaction was stirred for 1 h at room temperature under an atmosphere of argon, after which time it was diluted with methanol (10 mL) and the alkene substrate (10.00 mmol) was added. Hydrogen peroxide (30% solution in water, 13.0 μL, 0.100 mmol) in methanol (1.00 mL) was added over 30 min via syringe pump. The reaction was stirred at room temperature under argon for 16 h before the solution was concentrated in vacuo and diluted with ethyl acetate, then passed through a short silica column. The internal standard decane was added, and reaction mixtures were analysed by gas chromatography (GC). Products were identified unambiguously by comparison and spiking with authentic samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With sodium thiosulfate In dichloromethane; water at 20℃; for 1h; UV-irradiation; | 4.2. Typical procedure for photoinduced perfluoroalkylation General procedure: In a Pyrex glass tube were placed olefin (0.2 mmol), perfluoroalkyl iodide (1.0 mmol), and CH2Cl2 (5 mL). Then Na2S2O3 (0.5 mmol, 79 mg) and water (1 mL) were added to the mixture. After sealing the tube, the mixture was shaked and then irradiated with a Hg lamp at room temperature. After the reaction was completed, the mixture was extracted with CH2Cl2. The extract was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With methanol; copper nanoparticles on black carbon In toluene at 20℃; for 4h; | 4.4.9. Experimental procedures for examples described in Table 2 CuNPs/CB (2 mg, 1.25 mol %), B2(pin)2 (0.22 mmol), 1 (0.2 mmol) were added to a 25 mL oven-dried Schlenk tube in air. Then toluene (1 mL) was added with a syringe. The resulting reaction mixture was stirred at room temperature for 4 h. The reaction mixture was then diluted with Et2O, filtered through silica gel with copious washings (Et2O or EtOAc), concentrated, and purified by column chromatography. |
64% | Stage #1: bis(pinacol)diborane With copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: oct-1-en-3-one In tetrahydrofuran; water at 20℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With indium(III) triflate; water In acetonitrile at 80℃; for 24h; | |
50% | With chromium(III) chloride hexahydrate In acetonitrile at 80℃; for 24h; | |
42% | With water; bismuth(III) chloride In acetonitrile at 80℃; for 24h; | General procedure for the hydration of α,β-unsaturated ketones General procedure: α,β-Unsaturated ketones 1 (1.0 mmol, 1.0 equiv.) and BiCl3 (0.0631 g, 0.20 mmol, 20 mol%) were stirred in CH3CN/H2O (1 mL/2 mL) at 80 °C for 24 h. Upon completion of the reaction (asindicated by TLC), the reaction mixture was extracted with ethyl acetate (3 x 20 mL). The combined organic phases were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The obtained crude residue was purified by silica gel column chromatography using ethyl acetate and petroleum ether as eluant to afford pure β-hydroxyl ketones 2. |
Multi-step reaction with 2 steps 1.1: copper(l) chloride; sodium t-butanolate / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: sodium perborate monohydrate / tetrahydrofuran; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; isobutyraldehyde In dichloromethane at 9.84℃; for 9.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium carbonate In water at 20℃; for 2h; Green chemistry; | General procedure for the hydroalkoxylation reactions General procedure: To a solution of activated alkene(0.5 mmol) in alcohol (2.0 mmol) was added Na2CO3 (0.2 mL, 0.05 M aq.), and the solution wasstirred until alkene was completely consumed (monitored by TLC) or an appropriate time andextracted with ethyl acetate (3 ×5 mL). The combined organic layers washed with brine (10 mL),dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silicagel column chromatography to give the β-alkoxycarbonyl compound. |
With palladium(II) trifluoroacetate; carbon monoxide; N,N'-bis(2,6-dimethylphenyl)butane-2,3-diimine; toluene-4-sulfonic acid; p-benzoquinone In tetrahydrofuran at 20℃; for 67h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium carbonate In water at 20℃; for 2h; Green chemistry; | General procedure for the hydroalkoxylation reactions General procedure: To a solution of activated alkene(0.5 mmol) in alcohol (2.0 mmol) was added Na2CO3 (0.2 mL, 0.05 M aq.), and the solution wasstirred until alkene was completely consumed (monitored by TLC) or an appropriate time andextracted with ethyl acetate (3 ×5 mL). The combined organic layers washed with brine (10 mL),dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silicagel column chromatography to give the β-alkoxycarbonyl compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With dipotassium hydrogenphosphate; Ir[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine]2(1,10-phenantroline)PF6 In dichloromethane; water at 20℃; for 9h; Schlenk technique; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: diiodomethane With diethylzinc In hexane; dichloromethane at 0 - 25℃; for 0.5h; Inert atmosphere; Stage #2: 1-phenyl-2-(phenylsulfonyl)ethan-1-one In hexane; dichloromethane at 0 - 25℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With copper diacetate In N,N-dimethyl-formamide at 70℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With copper diacetate In N,N-dimethyl-formamide at 70℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With copper diacetate In N,N-dimethyl-formamide at 70℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In methanol Reflux; | 2 4.2.2 General procedure for the Michael addition and Robinson annulation General procedure: The vinyl ketone (2equiv) was added to a solution of β-ketoester (1equiv) in methanol (2mL/mmol of β-ketoester). Triethylamine (0.3equiv) was then added and the mixture was refluxed until the starting β-ketoester was totally consumed (1-3 h). The mixture was concentrated under reduced pressure and the resulting oil was purified by flash column chromatography on silica gel to yield the desired diketone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 32 %Chromat. 2: 24.2 %Chromat. 3: 23.9 %Chromat. | With Ce0.3Co0.7Fe2O4; dihydrogen peroxide In 1,4-dioxane at 90℃; for 9h; | 2.3. Oxidation of styrene The selective oxidation of styrene was carried out in a 25 mLSchlenk tube. In a typical procedure, 0.06 mmol (ca. 15.0 mg, basedon the given formula CexCo1xFe2O4) of catalyst, 2.0 mL(17.4 mmol) of styrene, 10 mL of solvent, and 2.7 mL of hydrogenperoxide (30%), styrene:H2O2 molar ratio of 2:3, were added successivelyinto the flask. The flask was then immersed in an oil bathat a desired temperature for a desired reaction time under stirringwith an optimum stirrer speed of 1200 rpm, at which the highestconversion rate could be obtained (Fig. S1; see the SupportingInformation). It is clear from Fig. S1 that the reaction is effectedby diffusion limitation. Under the above conditions, the atmospherein the tube included mainly air, vapor of substrate, water,and solvent, and oxygen from decomposition of H2O2. The pressurein the tube ranged from 1.1 to 1.2 atm. After the reaction, the tubewas cooled to room temperature. The gas-phase mixture was collectedand analyzed by gas chromatography (GC) equipped witha 5A molecular sieve column and a thermal conductivity detector(TCD). Liquid-phase aliquots were identified by GC-MS andquantified by GC equipped with an SE-54 capillary column and ahydrogen flame ionization detector (FID) using toluene as internalstandard. The detected products in the liquid phase included themain product benzaldehyde and byproducts phenylacetaldehyde,styrene oxide, benzoic acid, phenylacetic acid, and formaldehyde.Trace of CO was detected in the gas phase. The amount of residualH2O2 was determined by iodometric titration [63,64] and theH2O2 utilization efficiency was defined as follows: H2O2 utilizationefficiency = [(mol (benzaldehyde + phenylacetaldehyde +styrene oxide) + 2 mol (benzoic acid + phenylacetic acid))/mol(H2O2)consumed] 100%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; water at 20℃; | (2R,3S)-1,2,3-trihydroxy-1,2-O-isopropylidene-4-C-methylenedecan-5-one (24) A solution of the a,b-unsaturated ketone 23 (1.01 g, 8.00 mmol)in 1,4-dioxane/H2O (3:1 v/v; 4 mL) was treated with DABCO(880 mg, 7.80 mmol) under ambient conditions. After 15 min, a 50%solution (w/v) of aldehyde 22 (410 mg, 3.15 mmol) in 1,4-dioxanewas added. When completed conversion was observed (ca. 15 h),solvents were removed under reduced pressure and the crudeproduct was dissolved in CH2Cl2. The organic layer was extractedwith HCl (2 M) and sat. aqueous NaHCO3, dried (Na2SO4), filtered,and concentrated under reduced pressure. Chromatographic purification(cyclohexane/ethyl acetate 15:1 /5:1 v/v) of the residuegave compound 24 as colorless syrup (396 mg, 1.54 mmol, 49%).a20D : 3.5 (c 1.09, CHCl3); 1H NMR (300 MHz, CDCl3) d 6.12,6.05 (2s, 2H, H-11), 4.46 (d, 1H, J2,3 5.5 Hz, H-3), 4.17 (dd, 1H,J1,2 6.2 Hz, H-2), 3.79 (d, 2H, H-1), 3.22 (bs, 1H, 3-OH), 2.61 (dd,2H, J6,7 7.4 Hz, H-6), 1.52 (m, 2H, H-7), 1.33, 1.24 (2s, 6H, isopropylidene),1.22 (m, 4H, H-8, H-9), 0.81 (t, 3H, H-10); 13C-APTNMR (75.5 MHz, CDCl3) d 202.6 (C-5), 146.2 (C-4), 126.3 (C-11),109.5 (isopropylidene-C(CH3)2), 76.7 (C-2), 70.8 (C-3), 65.2 (C-1),38.1 (C-6), 31.4 (C-8), 26.5, 25.1 (isopropylidene-C(CH3)2), 24.0 (C-7), 22.4 (C-9), 13.9 (C-10). MALDI-TOF did not provide conclusiveMS spectra of compound 24, thus low resolution MS was employedfor characterization in this particular case.MS: Calcd for [C14H24O4Na]: m/z 279.2 [MNa]; Found[MNa] 279.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With tris(pentafluorophenyl)borate In chloroform at 80℃; for 24h; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In 1,2-dichloro-ethane at 60℃; for 20h; Sealed tube; | 4.2 general procedure for the C7-alkylation of indolines with enones and enals General procedure: To an oven-dried sealed tube charged with N-pivaloyl indoline (1a) (40.7mg, 0.2mmol, 100mol %), [RhCp Cl2]2 (3.1mg, 0.005mmol, 2.5mol %), AgSbF6 (6.9mg, 0.02mmol, 10mol %) and Cu(OAc)2 (3.6mg, 0.02mmol, 10mol %) was added 3-buten-2-one (2a) (70.1mg, 1.0mmol, 500mol %) and DCE (1mL) at room temperature under air. The reaction mixture was allowed to stir at 60°C for 20h. The reaction mixture was diluted with EtOAc (3mL) and concentrated in vacuo. The residue was purified by flash column chromatography (n-hexanes/EtOAc=5:1) to afford 49.8mg of 3a in 91% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium carbonate In acetone at 20℃; | Preparation of starting alkynones 1b-1x General procedure: Alkyne (5 mmol), ketone (6 mmol) and K2CO3 (1.04 g, 7.5 mmol) were added successively to acetone (10 mL), then the mixture was stirred at room temperature until completion of the reaction as monitored by TLC. The mixture was filtered over celite and the filtrate was concentrated in vacuum. The residue was purified by flash column chromatography (ethyl acetate: petroleum ether = 1:5) to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With copper(II) oxide In water; acetone at 95℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With dipotassium hydrogenphosphate; C29H30F6NOP at -20℃; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With dipotassium hydrogenphosphate; C29H30F6NOP at -20℃; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: 2-amino-benzeneboronic acid hydrochloride; oct-1-en-3-one With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide In toluene at 90℃; for 16h; Stage #2: With sodium tris(acetoxy)borohydride at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere; | 7 General procedure for Heck reaction A mixture of triflate derivative 4 (1.0 eq.), corresponding alkene (1.2 eq.), Pd(PPh3)2Cl2 (10 mol%), Et3N (3 equivalent) in DMF was heated under N2 at 120 °C for 12 h. The reaction mixture was cooled and extracted with ethyl acetate, washed with water and brine. The organic layer was dried with anhydrous Na2S04 and concentrated in vacuo. The resulting residue was purified by flash chromatography (10-80% Ethyl acetate/Hexane gradient) on silica gel to give the desired products 6-16. [00258] (E)-l-(4-(((lr,3r,5R,7S)-Adamantan-2-ylidene)(4-hydroxyphenyl)methyl)phenyl)oct- l-en-3-one (6) . Following the general procedure for Heck reaction using corresponding triflate and l-Octen-3-one, compound 6 was obtained as yellow solid (Yield 47%, mp 158°C). 1H NMR (500 MHz, CDC13) δ 7.51 (d, J= 16.2 Hz), 7.44 - 7.39 (m, 2H), 7.15 - 7.10 (m, 2H), 6.98 - 6.90 (m, 2H), 6.83 - 6.75 (m, 2H), 6.68 (d, J= 16.2 Hz, 1H), 2.77 (m, 1H), 2.66 - 2.60 (m, 2H), 1.98 (m, 2H), 1.83 (m, 10H), 1.66 (m, 2H), 1.31 (m, 4H), 0.93 - 0.83 (m, 3H). 13C NMR (125 MHz, CDC13) 5 201.6, 154.7, 147.6, 146.2, 142.9, 134.7, 132.2, 131.0, 130.9, 130.4, 129.8, 128.2, 128.0, 125.6, 115.2, 115.1, 41.0, 39.8, 39.8, 37.3, 36.7, 34.8, 34.7, 34.7, 31.7, 31.2, 28.4, 28.3, 24.5, 24.2, 22.7, 19.9, 14.2, 13.8. HRMS-ESI: m/z [M+H]+ for C31H37O2, calculated 441.2794; observed 441.2801. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (R)-dihydrocarvone With (<i>S</i>)-1-phenyl-ethylamine; p-toluenesulfonic acid monohydrate In cyclohexane Reflux; Stage #2: oct-1-en-3-one In cyclohexane at 60 - 80℃; | 1 Example 1: Preparation of Intermediate II-2 Add 80 g of L-dihydrocarvone to the reaction flask.(S)-phenylethylamine 50g, catalytic amount of p-toluenesulfonic acid hydrate,500mL of cyclohexane, heated to reflux for 12 to 24h, to room temperature,50 g of 1-octene-3-one was added, and the reaction was carried out at 60 to 80 ° C for 12 to 24 hours.Adding aqueous acetic acid solution and stirring at room temperature;Add 500 mL of methyl tert-butyl ether, stir, and separate the organic phase, which was washed with water, sodium carbonate aqueous solution and saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, concentrated, and evaporated under reduced pressure.91 g of the middle distillate was obtained and the next reaction was carried out directly (the yield of this step was about 62%).Optionally, (S)-phenethylamine may not be added in this step.When (S)-phenethylamine is not added, water is added directly to the aqueous acetic acid solution after the addition reaction.Whether or not (S)-phenethylamine is used has little effect on the reaction yield.However, the optical purity of the product obtained by the method of (S)-phenethylamine is better.A small amount of sample was purified by column chromatography to identify the structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With 2,2,2-trifluoroethanol; (S)-2-acetylamino-3-phenylpropanoic acid; palladium diacetate; caesium carbonate; silver carbonate In 1,4-dioxane at 70℃; for 16h; Inert atmosphere; | 6 Example 6: Take a clean reaction bottle, add small magnets, and dry it.Add palladium acetate (6.7mg, 0.03mmol, 10mol%),N-acetyl-L-phenylalanine (31.0 mg, 0.15 mmol, 50 mol%),Silver carbonate (124.1 mg, 0.45 mmol, 1.5 equivalents),Cesium carbonate (29.3mg, 0.09mmol, 30mol%),Trifluoroethanol (217 μL, 3.0 mmol, 10.0 eq), 1,4-dioxane (0.6 mL), and the corresponding alkenyl alcohol (0.3 mmol, 1.0 eq) and electron-deficient olefin (0.6 mmol, 2.0 eq) were added. .Then, after heating for 16 hours at 70 ° C under argon,The reaction solution was separated by direct column chromatography to obtain a yellow oily product (36.3 mg, yield 54%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4 g | With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; isopropyl alcohol at 75℃; for 8h; | 1 A mixture of 4-(tert-butyldimethylsiloxy)-1-(dimethyl(phenyl)silyl)butan-1-one (6.4 g), 1-octen-3-one (2.41 g), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (1.42 g), 1,8-diazabicyclo[5.4.0]-7-undecene (0.86 g), isopropanol (3.17 g), and tetrahydrofuran (11.5 mL) was stirred at 75° C. for eight hours. The solvent in the reaction solution was evaporated under reduced pressure, and the residue was then purified by silica gel column chromatography. Thereby, 1-tert-butyldimethylsiloxydodecane-4,7-dione (4.0 g) was obtained. 1H-NMR (CDCl3) δ ppm: 0.02 (s, 6H), 0.88 (s, 12H), 1.22-1.31 (m, 4H), 1.51-1.59 (m, 2H), 1.72-1.83 (m, 2H), 2.43 (J=7.6, t, 2H), 2.55 (J=7.6, t, 2H), 2.67 (s, 4H), 3.59 (J=5.9, t, 2H) |
4 g | With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; isopropyl alcohol at 75℃; for 8h; | 1 A mixture of 4-(tert-butyldimethylsiloxy)-1-(dimethyl(phenyl)silyl)butan-1-one (6.4 g), 1-octen-3-one (2.41 g), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (1.42 g), 1,8-diazabicyclo[5.4.0]-7-undecene (0.86 g), isopropanol (3.17 g), and tetrahydrofuran (11.5 mL) was stirred at 75° C. for eight hours. The solvent in the reaction solution was evaporated under reduced pressure, and the residue was then purified by silica gel column chromatography. Thereby, 1-tert-butyldimethylsiloxydodecane-4,7-dione (4.0 g) was obtained. 1H-NMR (CDCl3) δppm: 0.02 (s, 6H), 0.88 (s, 12H), 1.22-1.31 (m, 4H), 1.51-1.59 (m, 2H), 1.72-1.83 (m, 2H), 2.43 (J=7.6, t, 2H), 2.55 (J=7.6, t, 2H), 2.67 (s, 4H), 3.59 (J=5.9, t, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With acetic acid; sodium nitrite In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With palladium dichloride In N,N-dimethyl acetamide at 80℃; for 5h; | 4.3. General procedure for the Heck reaction with azastibocines General procedure: A mixture of azastibocine (1.0 mmol), alkene (3.0 mmol, 3 eq.) and PdCl 2 (18 mg, 0.1 mmol, 10 mol%) in DMA (3.0 mL) was stirred at 80 °C under air. The completion of the reaction was moni- tored using TLC. After being completed, the reaction mixture was cooled to room temperature and purified by chromatography ( 17 : n -Hexane, 3, 14 : n -Hexane:CH 2 Cl 2 = 5:1, 10 -13, 15, 18-22, 25 : n - Hexane:EtOAc = 5:1, 24 : n -Hexane:EtOAc = 2:3) to give the Heak reaction product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | Stage #1: 4-bromo-benzaldehyde With toluene-4-sulfonic acid hydrazide Stage #2: oct-1-en-3-one With tert.-butylnitrite; N,N,N,N,-tetramethylethylenediamine; copper dichloride In tetrahydrofuran at 65℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With sodium hydroxide In methanol at 45℃; | 1-3 Example one Take 10g (1.0eq) of dihydrocarvone and 7.5g (0.9eq) of 1-octene-3-one into the reaction solution, add 50ml of methanol, and add 2.4g (1.0eq) of sodium hydroxide, Stir and raise the temperature to 45°C, react for 4-5h, add 2.4g (1.0eq) of sodium hydroxide, heat up to 85°C, reflux and react for 6h, TLC spot plate detection, produce product 1-2. Post-treatment, spin-dry the solvent, add 30ml ice water, 25ml ethyl acetate extraction twice, combine the organic phases, wash with saturated sodium chloride water once, dry with anhydrous sodium sulfate, spin-dry the solvent to obtain 14.3g crude oil (crude product) 92.3%), column chromatography purification, PE:EA=50:1, a total of 13 g of colorless oil (yield 84%) was obtained in the purification, and the structure of intermediate 1-2 was determined. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; silver(l) oxide In acetonitrile at 50℃; |
Tags: 4312-99-6 synthesis path| 4312-99-6 SDS| 4312-99-6 COA| 4312-99-6 purity| 4312-99-6 application| 4312-99-6 NMR| 4312-99-6 COA| 4312-99-6 structure
[ 1117-52-8 ]
(5E,9E)-6,10,14-Trimethylpentadeca-5,9,13-trien-2-one
Similarity: 0.68
[ 1073-13-8 ]
4,4-Dimethyl-2-cyclohexen-1-one
Similarity: 0.68
[ 488-10-8 ]
(Z)-3-Methyl-2-(pent-2-en-1-yl)cyclopent-2-enone
Similarity: 0.65
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
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.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :