Structure of 1294009-26-9
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only! Not for Human Use. We Do Not Sell to Patients.
Change View
| Size | Price | VIP Price |
DE Stock US Stock |
Asia Stock Global Stock |
In Stock |
| {[ item.pr_size ]}{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | {[ item.p_spot_brand_remark ]} 1-2 weeks {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.p_spot_brand_remark ]} 1-2 weeks {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock Inquiry - | Login - + |
Please Login or Create an Account to: See VIP prices and availability
Asia Stock: Ship in 3-5 business days
EU Stock: ship in 0-1 business day
Global Stock: ship in 7-10 days
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
{[ item.p_spot_brand_remark ]}
1-2weeks
Inquiry
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ item.p_spot_brand_remark ]}
1-2weeks
Inquiry
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
Asia Stock: Ship in 3-5 business days
EU Stock: ship in 0-1 business day
Global Stock: ship in 7-10 days
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Gruszczyński, Marcin ; Lewandowski, Dariusz ; Kuciński, Krzysztof ; Kubicki, Maciej ; Hreczycho, Grzegorz ;
Abstract: Nickel catalysis provides opportunities to modulate reaction pathways through changes in the coordination environment, yet strategies to deliberately redirect nickel reactivity remain limited. Here we show that ligand exchange at nickel allows a single catalytic system to produce different products from the same alkyne substrates. Aminophosphine-supported nickel catalysts promote selective hydroboration in the presence of pinacolborane, which functions both as a boron source and a reaction activator. The addition of TEMPO forms a distinct ligand-coordinated nickel species that suppresses hydroboration and directs the reaction toward enyne formation. Our further studies identify TEMPO coordination as a key step that directs the catalytic cycle, illustrating how simple additives can influence reaction outcomes. These results offer a straightforward strategy to access divergent reactivity in nickel catalysis and provide insight into the factors controlling catalytic pathway selection.
Show More >
Keywords: Alkynes ; Nickel catalysis ; Ligand effects ; Hydroboration ; Enynes
Show More >
| CAS No. : | 1294009-26-9 |
| Formula : | C15H21BO2 |
| M.W : | 244.14 |
| SMILES Code : | CC1=CC=CC=C1/C=C/B2OC(C)(C)C(C)(C)O2 |
| English Name : | (E)-4,4,5,5-Tetramethyl-2-(2-methylstyryl)-1,3,2-dioxaborolane |
| MDL No. : | MFCD19703869 |
* 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 |
|---|---|---|
| 89% | With [Cu(phen)(xantphosTEPD)]PF6; potassium carbonate In water; acetonitrile at 20℃; for 7h; Sealed tube; Inert atmosphere; Irradiation; diastereoselective reaction; | |
| 85% | With copper(I) oxide supported on ceria nanoparticle In ethanol at 90℃; for 1h; Inert atmosphere; Schlenk technique; | Substrate scope investigations with the Cu1-O(I)/CeO2 catalyst General procedure: In a typical procedure, B2Pin2 (0.7 mmol, 177.4 mg) and Cu1-O(I)/CeO2 (Cu = 0.5 mol %, 7.6 mg) were placed in adried Schlenk tube equipped with a stir bar. After evacuation under vacuum and flushing with N2 for three times,alkyne substrate (0.5 mmol) and ethanol (2.0 mL) were injected under the atmosphere of N2. The mixture wasultrasonically vibrated to form a uniform suspension and then stirred at 90oC for 1.0 h. Upon completion, the reactionmixture was analyzed by GC-MS to determine the selectivity of vinylboronate products. To determine the isolatedyield of the target product, the reaction mixture was centrifuged to remove the catalyst, and the supernate wasconcentrated in vacuum. The residue was purified by flash column chromatography on silica gel with petroleumether/ethyl acetate as eluent. |
| 85% | With tetrabutylammonium phosphomolybdate; sodium methylate In ethanol at 25℃; for 18h; |
| 84% | With potassium carbonate; 6Cu(1+)*3C20H14N6O4(2-) In water; acetonitrile at 25℃; for 0.333333h; stereoselective reaction; | |
| 84% | With water; potassium carbonate; 6Cu(1+)*3C20H14N6O4(2-) In acetonitrile at 25℃; for 0.333333h; stereoselective reaction; | |
| 75% | Stage #1: bis(pinacol)diborane With [1,3-bis(1-adamantyl)imidazolidin-2-yl]chloro-copper; sodium t-butanolate In tetrahydrofuran at 22℃; for 0.5h; Inert atmosphere; Stage #2: 1-ethynyl-2-methylbenzene With methanol In tetrahydrofuran at 22℃; for 12h; Inert atmosphere; regioselective reaction; | |
| 73% | With tetrabutylammonium tetrafluoroborate In methanol at 20℃; Electrochemical reaction; | |
| 73% | With tetrabutylammonium tetrafluoroborate In methanol | |
| 70% | With [bis(acetoxy)iodo]benzene; sodium t-butanolate In ethanol at 20℃; for 12h; regioselective reaction; | |
| Stage #1: bis(pinacol)diborane With copper; sodium methylate In 1,4-dioxane; ethanol for 0.5h; Inert atmosphere; Sealed tube; Stage #2: 1-ethynyl-2-methylbenzene In 1,4-dioxane; ethanol at 60℃; Inert atmosphere; | ||
| With methanol; DPEPhos; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Glovebox; Sealed tube; | ||
| 95 % | With ethanol at 30℃; Autoclave; Inert atmosphere; | |
| 88 % | With methanol; N-propyl-N-(2-(pyridin-2-ylamino)phenyl)formamide In tetrahydrofuran at 60℃; Schlenk technique; stereoselective reaction; | |
| With sodium methylate; copper In ethanol at 20℃; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 51% | With NaOC(CH3)3; CH3OH In tetrahydrofuran 1.0 mol% Cu-complex, alkyne, diborane, NaOC(CH3)3, CH3OH, THF, -15°C, 24 h, N2 atm.; 70:30 ratio of isomers; | |
| Stage #1: bis(pinacol)diborane With C178H184ClCuN2O33; potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-ethynyl-2-methylbenzene In tetrahydrofuran; methanol at -20℃; for 16h; regioselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triethylamine; tricyclohexylphosphine In tetrahydrofuran at 25℃; for 4h; Inert atmosphere; regioselective reaction; | ||
| 1: 71 %Spectr. 2: 7 %Spectr. | With 2Fe(1+)*9CO In toluene at 100℃; for 24h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 79% | In tetrahydrofuran; water at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 96% | With lithium triethylborohydride; C76H65Cl2CoN3 In neat (no solvent) at 80℃; for 18h; Schlenk technique; Inert atmosphere; | |
| 90% | With LDBBA In neat (no solvent) at 50℃; for 12h; Inert atmosphere; | |
| 86% | With [RuHCl(CO)(PPh3)3] In toluene at 50℃; for 16h; Inert atmosphere; |
| 85% | In neat (no solvent) at 110℃; for 12h; Inert atmosphere; | |
| 80% | With dibutylmagnesium In n-heptane; toluene at 80℃; for 18h; Inert atmosphere; regioselective reaction; | |
| 76% | With Lithium 1,1,1,3,3,3-hexamethyldisilazide In toluene at 100℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique; | |
| In neat (no solvent) at 110℃; for 14h; Inert atmosphere; | ||
| 64 %Spectr. | With MIL-53(Al) metal-organic framework-CoH In neat (no solvent) at 90℃; for 22h; | |
| at 215℃; for 0.3h; Schlenk technique; Inert atmosphere; Microwave irradiation; | ||
| 59 %Chromat. | With sodium triethylborohydride for 1h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction; | 2.2. General procedure of NaHBEt3-catalysed hydroboration General procedure: 1.0 mmol of alkyne, 0.1 mL of decane and 1.1 mmol of pinacolborane,were placed in previously evacuated Schlenk bomb flask fitted witha plug valve. A reference sample was taken. Next, 0.1 mL of 1 M solutionof NaHBEt3 (0.1 mmol) in toluene was added, reaction vessel was closedand heated at 60 C with stirring. After specified time, reaction mixturewas cooled down to the room temperature and analysed using GC andGC-MS. Products of hydroboration were isolated by extraction with 1mL of DCM followed by column chromatography of concentrated extract(SiO2, hexane/Et2O, 98:2). |
| 86 % | With C31H50NO2Si2Y In toluene at 110℃; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction; | |
| 74 % | With [Mn(2,6-bis(diisopropylphosphinomethyl)pyridine)Cl2]10 In tetrahydrofuran at 30℃; | |
| 80 % | With manganese(II) bromide; sodium triethylborohydride In hexane at 70℃; Inert atmosphere; Sealed tube; chemoselective reaction; | |
| 58 % | With 3,3'-bis[(diphenylphosphino)methyl]-2,2'-bipyridine; cobalt(II) aceylacetonate In ethyl acetate at 25℃; Schlenk technique; | |
| With Triethoxysilane In 1,4-dioxane at 80℃; for 24h; regioselective reaction; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: tetrahydrofuran; water / 20 °C 2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate / methanol / 5 h / 20 °C / Inert atmosphere; Irradiation; Schlenk technique |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane at 95℃; Inert atmosphere; Schlenk technique; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane at 95℃; Inert atmosphere; Schlenk technique; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 74% | With copper(l) iodide; lithium methanolate; bis[2-(diphenylphosphino)phenyl] ether In dimethyl sulfoxide at 50℃; for 16h; | General Procedure. General procedure: Phenylpropiolic acid (439 mg, 3.0 mmol), B2pin2 (763 mg, 3.0 mmol), lithium methoxide (23 mg, 0.6 mmol), copper iodide (57 mg, 0.3 mmol), and Dpe-Phos (324 mg, 0.6 mmol) were added to a vial containing DMSO (5 mL). The suspension was stirred for 16 h at 50 °C. The reaction was monitored by TLC, and after the completion of the reaction, the reaction mass was cooled to 25-28 °C and quenched into a mixture of 50 mL of water and 50 mL of ethyl acetate. The ethyl acetate layer was washed with water (2 × 25 mL), brine (2 × 25 mL), and then dried over Na2SO4. Evaporation of the solvent under reduced pressure provided the crude product, which was purified by column chromatography (hexane:EtOAc = 9.5:0.5). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 76% | With Walphos SL-W001-1; copper(l) chloride; lithium tert-butoxide In diethyl ether at 40℃; for 12h; Schlenk technique; enantioselective reaction; |