Home Cart Sign in  
HazMat Fee +

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+
Chemical Structure| 1166829-72-6 Chemical Structure| 1166829-72-6

Structure of 1166829-72-6

Chemical Structure| 1166829-72-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 1166829-72-6 ]

CAS No. :1166829-72-6
Formula : C11H15F3O5S
M.W : 316.29
SMILES Code : O=C(OCC)CC1CC=C(OS(=O)(C(F)(F)F)=O)CC1
MDL No. :MFCD22199561
InChI Key :SISNOPMWHKFMNU-UHFFFAOYSA-N
Pubchem ID :57992150

Safety of [ 1166829-72-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H312-H332-H335-H314
Precautionary Statements:P260-P264-P270-P271-P280-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P403+P233-P405-P501
Class:8
UN#:1760
Packing Group:

Application In Synthesis of [ 1166829-72-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1166829-72-6 ]

[ 1166829-72-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1166829-72-6 ]
  • [ 73183-34-3 ]
  • [ 1166829-70-4 ]
YieldReaction ConditionsOperation in experiment
73.5% Step 2. Ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex-3-en-l- yl)acetate. A vial was charged with ethyl 2-[4-(trifluoromethanesulfonyloxy)cyclohex-3-en-l- yl] acetate (1.71 g, 0.01 mol), l,l'-bis(diphenylphosphino)ferrocene (150 mg, 0.27 mmol), potassium acetate (1.59 g, 16.2 mmol) and bis(pinacolato)diboron (1.51 g, 5.94 mmol). The vial was purged with N2 (x3), then dioxane (5.4 mL) was added and the mixture degassed for 5 min. [l,r-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)complex with dichloromethane (221 mg, 0.27 mol) was then added and the resulting mixture degassed again for 5 min. The resulting orange reaction mixture was stirred at 80C overnight. After 18 h, the reaction was cooled to room temperature. A saturated aqueous solution of NaHCCb (2 mL) was added and the aqueous layer was extracted with EtOAc (3 x 2 mL). The organic layers were combined and removed solvent in vacuo. Purified by flash chromatography (silica, 0- 10% MeOH/DCM) to afford the title compound (1.17 g, 73.5%). 1H NMR (400 MHz, CDCb) d 6.52 (d, / = 1.96 Hz, 1H), 4.14 (d, / = 7.09 Hz, 2H), 1.99 - 2.36 (m, 6H), 1.69 - 1.91 (m, 2H), 1.55 (s, 1H), 1.21 - 1.34 (m, 15H).
51% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃;Inert atmosphere; ethyl 2-(4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-1-yl)acetate 1b (3.0 g, 9.3 mmol), bis(pinacolato)diboron (2.9g, 11.4mmol), Potassium acetate (1.86 g, 19.0 mmol),[1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (347 mg, 0.47 mmol) and 1,4-dioxane (40 ml) were heated to 80 C under nitrogen and stirred for overnight. Cooled to room temperature, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (0-10% ethyl acetate / petroleum ether) used, To give the desired product ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)acetate 35a (1.4 g, white solid), yield: 51%.
50.2% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 16h;Inert atmosphere; In 2 liter 4 neck flask was taken ethyl 2-(4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-1-yl)acetate (120 g, 379 mmol), BISPN (106 g, 417 mmol), and potassium acetate (112 g, 1138 mmol) in 1,4-dioxane (1200 mL) under nitrogen. Nitrogen was purged inside the reaction mixture for 10 minutes. Then 1,1 ‘-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane complex (15.49 g, 18.97 mmol) was added. The reaction mixture was heated at 80 C for 16 h. The reaction mixture wasconcentrated. The residue was partitioned between ethyl acetate and water, filtered through CELITE bed. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3X). Combined organic layer was washed with water, brine, and dried over sodium sulfate and concentrated in vacuo. The crude material was purified through flash column chromatography, eluting with 0-10% ethyl acetate in petroleumether to give Intermediate 164E (pale yellow oil, 56 g, 190 mmol, 50.2% yield). GC-MS Anal. Calc’d for C,6H27B04, 294.20 found [M] 295.3. T = 1.10 mm (Method A). ‘H NMR (400MHz, chloroform-d) ö: 6.52 (dd, J=4.i, 1.9 Hz, 1H), 4.14 (q, J=7.i Hz, 2H), 2.62- 1.97 (m, 6H), 1.94- 1.68 (m, 2H), 1.33- 1.21 (m, 16H).
50.2% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 80℃; for 16h;Inert atmosphere; In 2 liter 4 neck flask was taken Intermediate 154D (120 g, 379 mmol), bis(pinacolato)diboron (106 g, 417 mmol), and potassium acetate (112 g, 1138 mmol) in 1,4-dioxane (1200 mL) under nitrogen. Nitrogen was purged inside the reaction mixture for 10 minutes. Then 1 , 1 '-bis(diphenylphosphino)ferrocene -palladium dichloride dichloromethane complex (15.49 g, 18.97 mmol) was added. The reaction mixture was heated at 80 C for 16 h. The reaction mixture was concentrated. The residue was partitioned between ethyl acetate and water, filtered through CELITE bed. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3X). Combined organic layer was washed with water, brine, and dried over sodium sulfate and concentrated in vacuo. The crude material was purified through flash column chromatography, eluting with 0-10% ethyl acetate in petroleum ether to give Intermediate 154E (pale yellow oil, 56 g, 190 mmol, 50.2% yield). GC-MS Anal. Calc'd for Ci6H27B04, 294.20 found [M+H]+ 295.3. Tr = 1.10 min (Method A). 1H NMR (400MHz, chloroform-d) δ: 6.52 (dd, J=4.1, 1.9 Hz, 1H), 4.14 (q, J=7.1 Hz, 2H), 2.62 - 1.97 (m, 6H), 1.94 - 1.68 (m, 2H), 1.33 - 1.21 (m, 16H)
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 95℃; for 18h;Inert atmosphere; To a mixture of ethyl 2- (4- ( ( (trifluoromethyl) sulfonyl) oxy) cyclohex-3-en-1-yl) acetate (30.32 g, crude, 96 mmol, 1.00 eq) dissolved in 1, 4-dioxane (400 ml) , 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2, 2'-bi (1, 3, 2-dioxaborolane) (26.8 g, 106 mmol, 1.10 eq) , CH 3COOK (38.02 g, 192 mmol, 2.00 eq) and Pd (dppf) Cl 2 (14.04 g, 19.2 mmol, 0.20 eq) were added. The mixture was stirred at 95 under nitrogen protection for 18 hours. The solution was filtered and concentrated to dryness. The crude (12.50 g, 100 %yield) was filtered through the silica gel pad and washed with PE/EA = 6: 1. The filtrate was concentrated to dryness to give a black oil (33.2 g, 112.3 %yield) which was used in next step without further purification. 1H NMR (CDCl 3) δ H 6.51 (s, 1H) , 4.13 (q, J = 7.2 Hz, 3H) , 1.99-2.40 (m, 9H) , 1.68-1.94 (m, 3H) and 1.18-1.26 (m, 12H) .

  • 2
  • [ 1023595-17-6 ]
  • [ 1166829-72-6 ]
  • C17H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; To ethyl 2-(4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-l-yl)acetatei: (1.0 eq.), boronic acid (1.2 equiv), Na2C03 (2.5 eq.), KBr (1.1 eq.) in 1 ,4-dioxane/water (10:1 by volume, 0.25M) was added Pd(PPh3)4 (5 mol.%). The resulting reaction mixture was heated to 80-90 C for 16 h, upon which the crude reaction mixture was concentrated. The resulting solids were diluted with EtOAc and water and the layers were separated. The aqueous layer was extracted with EtOAc thrice. The combined organic extracts were dried over anhydrous MgS04, filtered, and concentrated under reduced pressure. The crude reaction mixture was purified employing silica gel chromatography to afford the desired product. * Ethyl 2-(4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-l-yl)acetate is a known compound that can be prepared from commercially available l,4-dioxaspiro[4.5]decan-8- one using the procedures outlined in 1) Stocks, P.A. et al, Angew. Chem. Int. Ed., 46:6278-6283 (2007); 2) Barlind, J.G. et al, J. Med. Chem., 55: 10610-10629 (2012). General Procedure A utilized <strong>[1023595-17-6]indazole-4-boronic acid</strong> and ethyl 2-(4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-l- yl)acetate with dimethoxyethane as solvent, Pd(dppf)Cl2 as catalyst, K2CO3 as base, and omitted KBr as an additive.
  • 3
  • [ 1166829-72-6 ]
  • [ 182482-25-3 ]
  • ethyl 2-[4-(2,4,6-trifluorophenyl)cyclohex-3-en-1-yl]acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40.5% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; at 70℃; for 20h;Sealed tube; Step 2. Ethyl 2-[4-(2,4,6-trifluorophenyl)cyclohex-3-en-l-yl]acetate. In a sealed microwave tube, a mixture of tetrakis(triphenylphosphine)palladium(0) (96.9 mg, 0.08 mmol), <strong>[182482-25-3](2,4,6-trifluorophenyl)boronic acid</strong> (227 mg, 1.29 mmol), ethyl 2-[4- (trifluoromethanesulfonyloxy)cyclohex-3-en-l-yl]acetate (340 mg, 1.07 mmol) and sodium carbonate (2.52 mL, 2.0 M, 5.03 mmol) in l,2-dimethoxyethane (8.38 mL) was heated at 70C for 20 hours. The reaction mixture was filter through celite and washed thoroughly with EtOAc. The crude product was purified by flash chromatography (silica, 0-20% EtO Ac/heptanes) to obtain the title compound as a colorless oil. (130 mg, 40.5%).
 

Historical Records

Technical Information

Categories