Select Region or Location
Americas
  • Argentina
  • Brazil
  • Canada
  • Mexico
  • United States
  • Other Americas
Europe
  • Austria
  • Belgium
  • Bulgaria
  • Croatia/Hrvatska
  • Cyprus
  • Czech Republic
  • Denmark
  • Estonia
  • Finland
  • France
  • Germany
  • Greece
  • Hungary
  • Ireland
  • Italy
  • Latvia
  • Liechtenstein
  • Lithuania
  • Luxembourg
  • Malta
  • Netherlands
  • Norway
  • Poland
  • Portugal
  • Romania
  • Slovak Republic
  • Slovenia
  • Spain
  • Sweden
  • Switzerland
  • Turkey
  • United Kingdom
  • Other Europe
Asia Pacific
  • Australia
  • China
  • India
  • Indonesia
  • Japan
  • Korea, Republic of
  • Malaysia
  • New Zealand
  • Philippines
  • Singapore
  • Thailand
  • Vietnam
  • Other Asia Pacific
Africa And Middle East
  • Egypt
  • Israel
  • Other Africa And Middle East
USD
Home Cart Sign in  
Chemical Structure| 1242770-51-9 Chemical Structure| 1242770-51-9

Structure of 1242770-51-9

Chemical Structure| 1242770-51-9

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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

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,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}
    {[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]}

In Stock

- +

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

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

Alternative Products

Product Details of [ 1242770-51-9 ]

CAS No. :1242770-51-9
Formula : C14H18BBrO2
M.W : 309.01
SMILES Code : CC1(C)C(C)(C)OB(/C=C/C2=CC=C(Br)C=C2)O1
English Name :(E)-2-(4-Bromostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
MDL No. :MFCD12546200
InChI Key :KOKMZNDSHKZFHO-MDZDMXLPSA-N
Pubchem ID :46900787

Safety of [ 1242770-51-9 ]

Application In Synthesis of [ 1242770-51-9 ]

* 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 [ 1242770-51-9 ]

[ 1242770-51-9 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 909792-33-2 ]
  • [ 1242770-51-9 ]
  • [ 1242770-60-0 ]
YieldReaction ConditionsOperation in experiment
82% With potassium fluoride; 18-crown-6 ether In 1,4-dioxane at 100℃; for 9h; Inert atmosphere;
  • 2
  • [ 909792-33-2 ]
  • [ 1242770-51-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
82% With KF; 18-crown-6 In 1,4-dioxane 1-PhOC(O)OCH2-2-(Me3SiCH2)C6H4, 2-((E)-(4-BrPh)-CH=CH)-(4,4,5,5-Me4-dihydro-1,3,2-dioxaborol), KF, 18-crown-6 (3:2:3.3:3.3 mol) heated in dioxane soln. at 100°C for 9 h;
  • 3
  • [ 766-96-1 ]
  • [ 73183-34-3 ]
  • [ 1242770-51-9 ]
  • [ 2170408-50-9 ]
YieldReaction ConditionsOperation in experiment
73% 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.; 91:9 ratio of isomers;
  • 4
  • [ 1242770-51-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
98% With potassium hydrogen bifluoride In water; acetonitrile at 0 - 20℃; for 2.08333h;
  • 5
  • [ 1279123-63-5 ]
  • [ 1242770-51-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
82% In tetrahydrofuran; water at 20℃;
  • 6
  • [ 766-96-1 ]
  • [ 25015-63-8 ]
  • [ 1242770-51-9 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: pinacolborane With C32H41CuN2O2S In toluene at 20℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: 4-bromo-1-ethynylbenzene In toluene at 20℃; for 2h; Schlenk technique; Inert atmosphere; stereoselective reaction;
94% With sodium triethylborohydride; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran; toluene at 100℃; for 24h; Microwave irradiation; Inert atmosphere; regioselective reaction;
94% With lithium triethylborohydride; C76H65Cl2CoN3 In neat (no solvent) at 80℃; for 18h; Schlenk technique; Inert atmosphere;
89% With [RuHCl(CO)(PPh3)3] at 60℃; for 3h; Schlenk technique; Inert atmosphere; stereoselective reaction;
88% at 60℃; for 16h; Inert atmosphere; Schlenk technique;
86% With [RuHCl(CO)(PPh3)3] In toluene at 50℃; for 16h; Inert atmosphere;
85% With zinc trifluoromethanesulfonate; sodium triethylborohydride In tetrahydrofuran; toluene at 80℃; for 10h; Schlenk technique; Inert atmosphere; regioselective reaction;
85% With tropylium tetrafluoroborate In neat (no solvent) at 70℃; for 12h; Inert atmosphere;
82% With dibutylmagnesium In n-heptane; toluene at 80℃; for 18h; Inert atmosphere; regioselective reaction;
82% With 8C4H8O*10Br(1-)*5Co(2+)*2C14H10N8; sodium triethylborohydride In tetrahydrofuran; tert-butyl methyl ether at 45℃; for 10h; Inert atmosphere; Schlenk technique; regioselective reaction;
78% With trimethylsilylmethyllithium In neat (no solvent) at 90℃; for 8h; Schlenk technique; Glovebox; Inert atmosphere;
76% In neat (no solvent) at 110℃; for 12h; Inert atmosphere;
75% With silver(I) acetate In toluene at 120℃; for 18h; Schlenk technique; Inert atmosphere; stereoselective reaction;
74% With C30H26Br4Fe2N6; sodium t-butanolate In toluene at 25℃; Sealed tube; Inert atmosphere; Glovebox; stereoselective reaction;
58% With LDBBA In neat (no solvent) at 50℃; for 15h; Inert atmosphere;
54% With C27H44N3Si3V In diethyl ether at 20℃; for 16h; Inert atmosphere; regioselective reaction;
46% With Lithium 1,1,1,3,3,3-hexamethyldisilazide In toluene at 100℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique;
37% With CoH{PPh(OEt)2}4 In tetrahydrofuran Schlenk technique; Inert atmosphere; Irradiation; diastereoselective reaction; 4. General procedure and characterization data of reduction products General procedure: In an oven-dried vial the cobalt catalyst (1 mol%, 2 μmol, 1.7 mg) and a stirring bar were introduced. A cap with rubber septum was used to close the vial and the system was then purged with Argon. THF (0.2 mL, 1.0M), alkyne (1.0 equiv, 0.2 mmol) and HBPin (1.1 equiv, 0.22 mmol, 32 μL) were then successively added and the mixture was stirred overnight under irradiation of blue LED light. After this time, the solution was diluted with Et2O and washed two times with distilled water, the combined aqueous layers were extracted two timeswith Et2O and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under vacuum. The crude material was purified by column chromatography to afford the titled compounds.
32% Stage #1: pinacolborane With 1,3-bis-(diphenylphosphino)propane; cobalt acetylacetonate In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #2: 4-bromo-1-ethynylbenzene In tetrahydrofuran at 50℃; for 46h; Inert atmosphere; Schlenk technique;
In neat (no solvent) at 110℃; for 14h;
With [RuHCl(CO)(PPh3)3] In toluene at 100℃; for 3h; Schlenk technique; Inert atmosphere;
302.9 mg With C20H22AlN2PSe In toluene at 30℃; for 8h; Schlenk technique; Glovebox; Inert atmosphere; chemoselective reaction;
at 215℃; for 0.3h; Schlenk technique; Inert atmosphere; Microwave irradiation;
34 %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).
68 %Spectr. With C43H65MgNOP2 In neat (no solvent) at 80℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;
With C36H72B3P7Si3 In benzene-d6 at 50℃; Schlenk technique; Inert atmosphere; Glovebox;
66% With Schwartz's reagent In dichloromethane at 20℃; Inert atmosphere;
99 %Spectr. With [bis(phosphinimino)amide AlH]+[B(C6F5)4]- In benzene at 60℃; Glovebox; Schlenk technique;
55 % With C31H50NO2Si2Y In toluene at 110℃; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;
86 % With manganese(II) bromide; sodium triethylborohydride In hexane at 70℃; Inert atmosphere; Sealed tube; chemoselective reaction;
84 % With C38H30ClNOP2Pt In tetrahydrofuran at 50℃; Inert atmosphere; Schlenk technique; stereoselective reaction;
75 % With sodium triethylborohydride; C9H13Cl2CoN6 In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;
With Triethoxysilane In 1,4-dioxane at 80℃; for 24h; regioselective reaction;

References: [1]Jang, Won Jun; Kang, Byung-Nam; Lee, Ji Hun; Choi, Yoon Mi; Kim, Chong-Hyeak; Yun, Jaesook [Organic and Biomolecular Chemistry, 2019, vol. 17, # 21, p. 5249 - 5252].
[2]Mandal, Souvik; Verma, Piyush Kumar; Geetharani [Chemical Communications, 2018, vol. 54, # 97, p. 13690 - 13693].
[3]Bołt, Małgorzata; Żak, Patrycja [RSC Advances, 2022, vol. 12, # 29, p. 18572 - 18577].
[4]Szyling, Jakub; Franczyk, Adrian; Stefanowska, Kinga; Walkowiak, Jędrzej [Advanced Synthesis and Catalysis, 2018, vol. 360, # 15, p. 2966 - 2974].
[5]Sharma, Alisha; Bansal, Surbhi; Velloth, Archana; Venkataramani, Sugumar; Singh, Sanjay [Chemistry - A European Journal, 2025, vol. 31, # 44].
[6]Yasu, Yusuke; Koike, Takashi; Akita, Munetaka [Chemical Communications, 2013, vol. 49, # 20, p. 2037 - 2039].
[7]Mandal, Souvik; Mandal, Sayantan; Geetharani [Chemistry - An Asian Journal, 2019, vol. 14, # 24, p. 4553 - 4556].
[8]Ton, Nhan N. H.; Mai, Binh Khanh; Nguyen, Thanh Vinh [Journal of Organic Chemistry, 2021, vol. 86, # 13, p. 9117 - 9133].
[9]Magre, Marc; Maity, Bholanath; Falconnet, Alban; Cavallo, Luigi; Rueping, Magnus [Angewandte Chemie - International Edition, 2019, vol. 58, # 21, p. 7025 - 7029][Angew. Chem., 2019, vol. 131, # 21, p. 7099 - 7103,5].
[10]Jia, Jun-Song; Wu, Tai-Xue; Fu, Yi-Jia; Hu, Zhi-Rong; Tang, Hai-Tao; Pan, Ying-Ming; Huang, Fu-Ping [Advanced Synthesis and Catalysis, 2022, vol. 364, # 11, p. 1873 - 1878].
[11]Kumar, Gobbilla Sai; Moorthy, Shruti; Karmakar, Himadri; Singh, Saurabh Kumar; Panda, Tarun K. [European Journal of Inorganic Chemistry, 2022, vol. 2022, # 2].
[12]Jaladi, Ashok Kumar; Choi, Hyeon Seong; An, Duk Keun [New Journal of Chemistry, 2020, vol. 44, # 32, p. 13626 - 13632].
[13]Wang, Yan; Guan, Rui; Sivaguru, Paramasivam; Cong, Xuefeng; Bi, Xihe [Organic Letters, 2019, vol. 21, # 11, p. 4035 - 4038].
[14]Pradhan, Chandini; Dubey, Shivansh; Samal, Pragnya Paramita; Krishnamurty, Sailaja; Punji, Benudhar [Catalysis Science and Technology, 2025, vol. 15, # 22, p. 6716 - 6725].
[15]Jaladi, Ashok Kumar; Kim, Hanbi; Lee, Ji Hye; Shin, Won Kyu; Hwang, Hyonseok; An, Duk Keun [New Journal of Chemistry, 2019, vol. 43, # 42, p. 16524 - 16529].
[16]Zhang, Guoqi; Zeng, Haisu; Zheng, Shengping; Neary, Michelle C.; Dub, Pavel A. [ACS Catalysis, 2022, vol. 12, # 9, p. 5425 - 5429].
[17]Liu, Jichao; Wu, Caiyan; Hu, Tinghui; Yang, Wei; Xie, Yaoyao; Shi, Yinyin; Liu, Qianrui; Shao, Yinlin; Zhang, Fangjun [Journal of Organic Chemistry, 2022, vol. 87, # 5, p. 3442 - 3452].
[18]Bergamaschi, Enrico; Teskey, Christopher J. [Tetrahedron Letters, 2022, vol. 98].
[19]González, María J.; Bauer, Felix; Breit, Bernhard [Organic Letters, 2021, vol. 23, # 21, p. 8199 - 8203].
[20]Carreras, Javier; Caballero, Ana; Pérez, Pedro J. [Angewandte Chemie - International Edition, 2018, vol. 57, # 9, p. 2334 - 2338][Angew. Chem., 2018, vol. 130, p. 2358 - 2362,5].
[21]Szyling, Jakub; Franczyk, Adrian; Stefanowska, Kinga; Klarek, Mateusz; Maciejewski, Hieronim; Walkowiak, Jędrzej [ChemCatChem, 2018, vol. 10, # 3, p. 531 - 539].
[22]Harinath, Adimulam; Banerjee, Indrani; Bhattacharjee, Jayeeta; Panda, Tarun K. [New Journal of Chemistry, 2019, vol. 43, # 26, p. 10531 - 10536].
[23]Altarejos, Julia; Sucunza, David; Vaquero, Juan J.; Carreras, Javier [Organic Letters, 2021, vol. 23, # 15, p. 6174 - 6178].
[24]Maj, Anna M.; Szarłan, Bartłomiej; Pawluć, Piotr; Zaranek, Maciej [Polyhedron, 2022, vol. 223].
[25]Kumar, Rohit; Dutta, Sayan; Sharma, Vishal; Singh, Praval P.; Gonnade, Rajesh G.; Koley, Debasis; Sen, Sakya S. [Chemistry - A European Journal, 2022, vol. 28, # 56].
[26]Réant, Benjamin L. L.; van IJzendoorn, Bono; Whitehead, George F. S.; Mehta, Meera [Dalton Transactions, 2022, vol. 51, # 47, p. 18329 - 18336].
[27]Brambilla, Elisa; Moretti, Elisa; Magni, Mirko; Abbiati, Giorgio; Pirovano, Valentina [Chemical Communications, 2023, vol. 59, # 22, p. 3281 - 3284].
[28]Bhandari, Mamta; Kaur, Mandeep; Rawat, Sandeep; Singh, Sanjay [Inorganic Chemistry, 2023, vol. 62, # 17, p. 6598 - 6607].
[29]Iqbal, Muhammad Asif; Yan, Xiangqian; Li, Ruoling; Zhijia, Fu; Zhang, Shaowen; Li, Xiaofang [New Journal of Chemistry, 2024, vol. 48, # 7, p. 3149 - 3155].
[30]Pawar, Rameshwar B.; Karmur, Mital H.; Punji, Benudhar [Chemistry - An Asian Journal, 2024, vol. 19, # 9].
[31]Dwivedi, Khilesh C.; Sabharwal, Gazal; Kote, Basvaraj S.; Balakrishna, Maravanji S. [Dalton Transactions, 2024, vol. 53, # 45, p. 18321 - 18329].
[32]Andruszak, Piotr; Pawluć, Piotr; Kubicki, Maciej; Zaranek, Maciej [Journal of Catalysis, 2025, vol. 442].
[33]Kaur, Harleen; Ahuja, Himani; Arevalo, Rebeca [ACS Catalysis, 2025, vol. 15, # 2, p. 976 - 981].
  • 7
  • [ 1242770-51-9 ]
  • [ 1795770-81-8 ]
YieldReaction ConditionsOperation in experiment
With sodium periodate; ammonium acetate In water; acetone Inert atmosphere;
  • 8
  • [ 766-96-1 ]
  • [ 73183-34-3 ]
  • [ 1242770-51-9 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: bis(pinacol)diborane With DPEPhos; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 25℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: 4-bromo-1-ethynylbenzene In tetrahydrofuran; methanol at 25℃; Schlenk technique; Inert atmosphere; Sealed tube;
91% With sodium methylate; Cu(2+)*4Cu(1+)*4I(1-)*2C5H3N2O2(1-)*C5H5N*C2H7N*3C3H7NO In ethanol at 25℃; for 1h; Inert atmosphere; 2.3. Typical procedure for the hydroborylation of alkynes General procedure: The typical experimental procedure for the hydroborylation ofalkynes is as follows: a mixture of alkyne (2 mmol), compound 1(0.006 mmol), bis(pinacolato)diboron (2.5 mmol), NaOMe(0.2 mmol) and 5 mL EtOH were successively added into a reaction flask equipped with a Ar (99.99%) balloon. Then the flask was vacuumedand charged in Ar three times to exclude air in the reactionsystem. Subsequently, the obtained reaction mixture was magneticallystirred at 25 °C for 1 h. After the reaction was completed, thecatalysts were separated by filtration and the yield was determinedby GC analysis. The pure products were obtained by columnchromatography on silica gel (petroleum ether/ethyl acetate as aneluent).
90% With potassium methanolate In acetonitrile at 20℃; for 2h; Inert atmosphere;
83% With [Cu(phen)(xantphosTEPD)]PF6; potassium carbonate In water; acetonitrile at 20℃; for 7h; Sealed tube; Inert atmosphere; Irradiation; diastereoselective reaction;
80% With 2.9 weight% Cu(II) loaded porous coordination network-222 nanoparticles In ethanol; water at 80℃; Sealed tube; regioselective reaction; 4.2. Catalytic performance test of PCN-222(Cu) with different particlesizes General procedure: Taking the synthesis of 2a for example: PCN-222(Cu, 1200 nm)(1.5 mol%) was used as catalyst, 4-methylphenylacetylene 1a(22 lL, 0.2 mmol) and B2pin2 (76 mg, 0.4 mmol) were dispersed in solvent (1 mL, VEtOH : VH2O = 3 : 7) in a sealed tube, which were kept in 80 °C for 5 h. The conversion was determined by GC-MS.After the reaction was finished, the reaction mixture was cooled to room temperature and concentrated in vacuum. Purification of the crude product with flash column chromatography (silica gel;Petroleum ether:EtOAc = 100:1-50:1) gave product 2a.
79% With potassium carbonate; 6Cu(1+)*3C20H14N6O4(2-) In water; acetonitrile at 25℃; for 0.333333h; stereoselective reaction;
79% With water; potassium carbonate; 6Cu(1+)*3C20H14N6O4(2-) In acetonitrile at 25℃; for 0.333333h; stereoselective reaction;
74.4% With methanol; potassium <i>tert</i>-butylate; [CuI(4,7-di(1H-imidazole-1-yl)benzo[c][1,2,5]thiadiazole)]n at 25℃; for 1h; Schlenk technique;
68% With tetrabutylammonium tetrafluoroborate In methanol at 20℃; Electrochemical reaction;
68% With tetrabutylammonium tetrafluoroborate In methanol
33% With sodium t-butanolate In methanol at 50℃; for 20h;
With methanol; DPEPhos; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Glovebox; Sealed tube;
85 % With ethanol at 30℃; Autoclave; Inert atmosphere;
93 % With cerium(IV) oxide; potassium methanolate In methanol; toluene at 50℃; Inert atmosphere;
85 % With methanol; N-propyl-N-(2-(pyridin-2-ylamino)phenyl)formamide In tetrahydrofuran at 60℃; Schlenk technique; stereoselective reaction;
66 % With methanol; sodium t-butanolate In tetrahydrofuran at 60℃; Inert atmosphere; Schlenk technique; Glovebox;

References: [1]Feng, Chao; Wang, Hong; Xu, Liang; Li, Pengfei [Organic and Biomolecular Chemistry, 2015, vol. 13, # 26, p. 7136 - 7139].
[2]Wu, Zhi-Lei; Lan, Xingwang; Gao, Ning; Kang, Xiaomin; Wang, Zhenguang; Hu, Tianding; Zhao, Bin [Journal of Catalysis, 2021, vol. 404, p. 250 - 257].
[3]Prakash, Aishwarya; Basappa, Suma; Urkude, Rajashri R.; Jangir, Ravindra; Dhayal, Rajendra S.; Kumar Bose, Shubhankar [Angewandte Chemie - International Edition, 2025, vol. 64, # 8][Angew. Chem., 2025, vol. 137, # 8].
[4]Zhong, Mingbing; Gagné, Yohann; Hope, Taylor O.; Pannecoucke, Xavier; Frenette, Mathieu; Jubault, Philippe; Poisson, Thomas [Angewandte Chemie - International Edition, 2021, vol. 60, # 26, p. 14498 - 14503][Angew. Chem., 2021, vol. 133, # 26, p. 14619 - 14624].
[5]Zhang; Yuan; Ma; Tang [Journal of Catalysis, 2021, vol. 401, p. 63 - 69].
[6]Wei, Rong-Jia; You, Pei-Ye; Duan, Haiyan; Xie, Mo; Xia, Ri-Qin; Chen, Xu; Zhao, Xiaoxu; Ning, Guo-Hong; Cooper, Andrew I.; Li, Dan [Journal of the American Chemical Society, 2022, vol. 144, # 38, p. 17487 - 17495].
[7]Wei, Rong-Jia; You, Pei-Ye; Duan, Haiyan; Xie, Mo; Xia, Ri-Qin; Chen, Xu; Zhao, Xiaoxu; Ning, Guo-Hong; Cooper, Andrew I.; Li, Dan [Journal of the American Chemical Society, 2022, vol. 144, # 38, p. 17487 - 17495].
[8]Xie, Wang; Qiu, Heng; Shi, Conghao; Li, Yumei; Lin, Chen; Jiang, Yu-Fei; Zhao, Yue [Inorganic Chemistry, 2025, vol. 64, # 49, p. 24289 - 24300].
[9]Aelterman, Maude; Sayes, Morgane; Jubault, Philippe; Poisson, Thomas [Chemistry - A European Journal, 2021, vol. 27, # 32, p. 8277 - 8282].
[10]Xia, Ming; Mutailipu, Miriding; Li, Fuming; Yang, Zhihua; Pan, Shilie [Chemistry - A European Journal, 2021, vol. 27, # 38, p. 9753 - 9757].
[11]Nunes, Mateus P.; Machado, Luana A.; Calado, Hállen D. R.; Jardim, Guilherme A. M.; Tchuiteng Kouatchou, Joel A.; Geertsen, Valérie; Yuan, Youzhu; Doris, Eric; da Silva Júnior, Eufrânio N.; Gravel, Edmond [Catalysis Science and Technology, 2025, vol. 15, # 11, p. 3445 - 3449].
[12]Liu, Yanyao; Ni, Dongshun; Brown, M. Kevin [Journal of the American Chemical Society, 2022, vol. 144, # 41, p. 18790 - 18796].
[13]Xu, Hang; Yamaguchi, Sho; Mitsudome, Takato; Mizugaki, Tomoo [Organic and Biomolecular Chemistry, 2022, vol. 21, # 7, p. 1404 - 1410].
[14]Bhawar, Ramesh; Saini, Suresh; Nagaraju; Bose, Shubhankar Kumar [Advanced Synthesis and Catalysis, 2023, vol. 365, # 4, p. 584 - 593].
[15]Tao, Sheng; Wang, Yang; Pan, Qianxiu; Zhao, Jixing; Bu, Qingqing; Chen, Fei; Liu, Jichang; Dai, Bin; Wei, Donghui; Liu, Ning [Green Chemistry, 2023, vol. 25, # 17, p. 6704 - 6716].
[16]Mandal, Vijay Kumar; Gaurav, Kumar; Kaulage, Sandeep H.; Khan, Shabana [Inorganic Chemistry, 2024, vol. 63, # 43, p. 20510 - 20520].
  • 9
  • [ 1242770-51-9 ]
  • [ CAS Unavailable ]
  • [ 1850379-73-5 ]
YieldReaction ConditionsOperation in experiment
77% With dimethyl zinc(II) In N,N-dimethyl-formamide at 60℃; for 3h; Inert atmosphere;
  • 10
  • [ 25294-65-9 ]
  • [ 73183-34-3 ]
  • [ 1242770-51-9 ]
YieldReaction ConditionsOperation in experiment
77% With copper(II) trifluoroacetate; sodium carbonate In 1,4-dioxane at 80℃; for 18h; Inert atmosphere; regioselective reaction; General procedure for the synthesis of (E)-4,4,5,5-tetramethyl-2-styryl-1,3,2-dioxaborolane (3a) General procedure: A Schlenk tube with a magnetic stirring bar was charged with 3-phenylpropiolic acid (1a, 68 mg, 0.5 mmol), bis(pinacolato)diboron (2a, 152 mg, 0.6 mmol), Cu(TFA)2 (29 mg, 10 mol%), Na2CO3 (127 mg, 1.2 mmol), and 1,4-dioxane (2 mL) under N2. The reaction mixture was stirred at 80 °C for 18 h (monitored by TLC and GC). Upon completion of the reaction, the reaction mixture was then cooled to ambient temperature, diluted with ethyl acetate (20 mL), filtered through a plug of silica gel, and washed with ethyl acetate (20 mL). The organic layer was washed with saturated brine (20 mL×2) and dried over anhydrous Na2SO4. The solvents were removed via rotary evaporator and the residue was purified by flash chromatography (silica gel, ethyl acetate: petroleum ether=1:30) to give 89.7 mg of desired product 3a in 78 % yield as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.48-7.50 (m, 2H), 7.41 (d, 1H, J=18.5Hz), 7.29-7.32 (m, 3H), 6.18 (d, 1H, J=18.4Hz), 1.32 (s, 12H). 13C NMR (100 MHz, CDCl3): δ 148.5, 136.4, 127.9, 127.5, 126.0, 82.3, 23.8
  • 11
  • [ 2039-82-9 ]
  • [ 75927-49-0 ]
  • [ 1242770-51-9 ]
YieldReaction ConditionsOperation in experiment
92% With carbonylchlorohydridobis(tricyclohexylphosphine)ruthenium(II) In toluene at 80℃; for 5h; Schlenk technique; Inert atmosphere;
82% With Ru(CO)(Cl)H(PCy3)2 at 110℃; for 18h; Schlenk technique; Inert atmosphere; Green chemistry; stereoselective reaction; 2.2.2. Borylative coupling under repetitive batch mode - Aliphaticsolvent extraction General procedure: A 50 mL Schlenk vessel was charged with dried PEG (1 g) and[Ru(CO)Cl(H)(PCy3)2] (0.01 mmol) under an argon atmosphere. Subsequently, vinyl boronate (0.5 mmol) and olefin (1.0 mmol)were added. The reaction was carried out for 18 h at 110 °C. Thereaction mixture was cooled to room temperature and the products were extracted with aliphatic solvent: n-hexane or n-heptane(3 5 mL) and analyzed by GC-MS analysis. The residual amount of solvent was evaporated under a vacuum and a new portion of substrates was added under an argon atmosphere, and subsequent batches and extractions were carried out under the above-described conditions.
  • 12
  • [ 1242770-51-9 ]
  • [ 115665-77-5 ]
  • [ 115665-68-4 ]
YieldReaction ConditionsOperation in experiment
77.778 % de Stage #1: (E)-1-(4’,4’,5’,5’-tetramethyl)-1’,3’,2’-dioxaboronalyl-2-(4’’-bromophenyl)ethene With bromine In diethyl ether; dichloromethane for 0.666667h; Stage #2: With sodium methylate In methanol; diethyl ether; dichloromethane at -20℃; for 2h; Overall yield = 84 %; stereoselective reaction;
80 % de Stage #1: (E)-1-(4’,4’,5’,5’-tetramethyl)-1’,3’,2’-dioxaboronalyl-2-(4’’-bromophenyl)ethene With sodium methylate In diethyl ether at -20℃; for 0.666667h; Stage #2: With bromine In diethyl ether; dichloromethane at -20℃; for 2h; Overall yield = 89 %; stereoselective reaction;
  • 13
  • [ 1242770-51-9 ]
  • [ 1085710-27-5 ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: (E)-1-(4’,4’,5’,5’-tetramethyl)-1’,3’,2’-dioxaboronalyl-2-(4’’-bromophenyl)ethene With sodium hydroxide In diethyl ether; water at 0℃; Stage #2: With iodine In diethyl ether; water at 0℃; for 0.5h; stereoselective reaction;
  • 14
  • [ 623-73-4 ]
  • [ 1242770-51-9 ]
  • [ 2171321-55-2 ]
YieldReaction ConditionsOperation in experiment
81% With tetrakis(actonitrile)copper(I) hexafluorophosphate; (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) In dichloromethane at 25℃; for 8h; Inert atmosphere; Schlenk technique; stereoselective reaction;
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 1242770-51-9 ]

Organoborons

Chemical Structure| 74213-48-2

A104177 [74213-48-2]

(Z)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 149777-84-4

A360687 [149777-84-4]

(E)-4,4,5,5-Tetramethyl-2-(4-methylstyryl)-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 1315277-67-8

A653819 [1315277-67-8]

4,4,5,5-Tetramethyl-2-(3-methylstyryl)-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 83947-56-2

A746288 [83947-56-2]

E-Phenylethenylboronic acid, pinacol ester

Similarity: 0.91

Chemical Structure| 78782-27-1

A527554 [78782-27-1]

4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane

Similarity: 0.91

Aryls

Chemical Structure| 1192488-87-1

A371038 [1192488-87-1]

(Z)-4,4,5,5-tetramethyl-2-(4-methylstyryl)-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 149777-84-4

A360687 [149777-84-4]

(E)-4,4,5,5-Tetramethyl-2-(4-methylstyryl)-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 1315277-67-8

A653819 [1315277-67-8]

4,4,5,5-Tetramethyl-2-(3-methylstyryl)-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 83947-56-2

A746288 [83947-56-2]

E-Phenylethenylboronic acid, pinacol ester

Similarity: 0.91

Chemical Structure| 78782-27-1

A527554 [78782-27-1]

4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane

Similarity: 0.91

Alkenyls

Chemical Structure| 74213-48-2

A104177 [74213-48-2]

(Z)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 149777-84-4

A360687 [149777-84-4]

(E)-4,4,5,5-Tetramethyl-2-(4-methylstyryl)-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 1315277-67-8

A653819 [1315277-67-8]

4,4,5,5-Tetramethyl-2-(3-methylstyryl)-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 83947-56-2

A746288 [83947-56-2]

E-Phenylethenylboronic acid, pinacol ester

Similarity: 0.91

Chemical Structure| 78782-27-1

A527554 [78782-27-1]

4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane

Similarity: 0.91