- Harnessing C-H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage FunctionalizationKallepalli, Venkata A.; Gore, Kristin A.; Shi, Feng; Sanchez, Luis; Chotana, Ghayoor A.; et al, Journal of Organic Chemistry, 2015, 80(16), 8341-8353
Cas no 942070-34-0 (3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile)
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile is a boronic ester derivative featuring a thiophene backbone with a nitrile substituent. This compound is widely utilized in Suzuki-Miyaura cross-coupling reactions due to its stability and reactivity, enabling efficient C-C bond formation in synthetic organic chemistry. The tetramethyl dioxaborolane group enhances shelf stability and handling convenience, while the electron-withdrawing nitrile group modulates reactivity for selective transformations. Its well-defined structure makes it a valuable intermediate in pharmaceutical and materials science research, particularly in constructing heterocyclic frameworks. The product is typically supplied in high purity, ensuring consistent performance in demanding synthetic applications.
942070-34-0 structure
Product Name:3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile
CAS No:942070-34-0
MF:C11H14BNO2S
MW:235.11036157608
MDL:MFCD12405473
CID:1039111
PubChem ID:15979305
Update Time:2025-11-05
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile Chemical and Physical Properties
Names and Identifiers
-
- 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile
- 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbonitrile (ACI)
- DTXSID90580548
- 3-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)THIOPHENE-2-CARBONITRILE
- SCHEMBL2656259
- 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)thiophene-2-carbonitrile
- HUZWPBPPEDMPTR-UHFFFAOYSA-N
- CS-0055013
- STL555248
- SB23046
- EN300-107826
- MFCD12405473
- BS-24649
- 942070-34-0
- 2-Cyanothiophene-3-boronic acid pinacol ester
- AKOS005259300
- BBL101452
- AT16027
- DA-00506
- Z1365493299
-
- MDL： MFCD12405473
- Inchi： 1S/C11H14BNO2S/c1-10(2)11(3,4)15-12(14-10)8-5-6-16-9(8)7-13/h5-6H,1-4H3
- InChI Key： HUZWPBPPEDMPTR-UHFFFAOYSA-N
- SMILES： N#CC1=C(B2OC(C)(C)C(C)(C)O2)C=CS1
Computed Properties
- Exact Mass: 235.0838300g/mol
- Monoisotopic Mass: 235.0838300g/mol
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 3
- Heavy Atom Count: 16
- Rotatable Bond Count: 1
- Complexity: 320
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Topological Polar Surface Area: 70.5?2
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| Alichem | A169004059-1g |
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile |
942070-34-0 | 95% | 1g |
$582.08 | 2023-08-31 | |
| Matrix Scientific | 092803-250mg |
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile, 95+% |
942070-34-0 | 95+% | 250mg |
$945.00 | 2023-09-05 | |
| Chemenu | CM136000-100mg |
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile |
942070-34-0 | 95% | 100mg |
$212 | 2024-07-19 | |
| Chemenu | CM136000-250mg |
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile |
942070-34-0 | 95% | 250mg |
$353 | 2024-07-19 | |
| Chemenu | CM136000-1g |
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile |
942070-34-0 | 95% | 1g |
$621 | 2024-07-19 | |
| TRC | T890395-10mg |
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile |
942070-34-0 | 10mg |
$ 50.00 | 2022-06-02 | ||
| TRC | T890395-50mg |
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile |
942070-34-0 | 50mg |
$ 210.00 | 2022-06-02 | ||
| TRC | T890395-100mg |
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile |
942070-34-0 | 100mg |
$ 320.00 | 2022-06-02 | ||
| Apollo Scientific | OR361646-250mg |
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile |
942070-34-0 | 98+% | 250mg |
￡171.00 | 2025-02-20 | |
| eNovation Chemicals LLC | Y1015316-100mg |
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile |
942070-34-0 | 98% | 100mg |
$180 | 2024-06-07 |
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile Production Method
Production Method 1
Reaction Conditions
1.1 Reagents: 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium Solvents: Hexane ; 1 min, rt
1.2 4 h, rt
1.3 Solvents: Methanol , Dichloromethane ; 5.5 h, 55 °C
1.2 4 h, rt
1.3 Solvents: Methanol , Dichloromethane ; 5.5 h, 55 °C
Reference
Production Method 2
Reaction Conditions
1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ; 16 h, rt → 100 °C
Reference
- Preparation of pyrazolopyridine derivatives and methods of treating hepatitis B infections, United States, , ,
Production Method 3
Reaction Conditions
1.1 Reagents: Tripotassium phosphate Catalysts: Tris(dibenzylideneacetone)dipalladium , 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl Solvents: Toluene ; 12 h, 110 °C; 110 °C → rt
Reference
- Anilinopiperazine derivatives and methods of use thereof and their preparation, World Intellectual Property Organization, , ,
Production Method 4
Reaction Conditions
1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: Dimethyl sulfoxide , 1,4-Dioxane ; 1 h, rt; 4 h, 90 °C
Reference
- Preparation of 3,7-disubstituted imidazo[1,2-a]pyrimidines as ligands for GABA receptors, World Intellectual Property Organization, , ,
Production Method 5
Reaction Conditions
1.1 Reagents: Potassium fluoride , Tri-tert-butylphosphine Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: Tetrahydrofuran , 1,4-Dioxane ; 30 min, rt; 1 h, 50 °C
1.2 Reagents: Water ; 90 min, rt
1.2 Reagents: Water ; 90 min, rt
Reference
- Imidazo-pyrimidine derivatives as ligands for GABA receptors, and their preparation, pharmaceutical compositions, and use in the treatment of adverse neurological conditions., World Intellectual Property Organization, , ,
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile Raw materials
- 3-Bromothiophene-2-carbonitrile
- Bis(pinacolato)diborane
- Pinacolborane
- Thiophene-2-carbonitrile
- 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile Preparation Products
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile Related Literature
-
Guang Xu,Wei Zhang,Ying Zhang,Xiaoxia Zhao,Ping Wen,Di Ma RSC Adv., 2018,8, 19353-19361
-
Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander Orlov Catal. Sci. Technol., 2015,5, 2059-2064
-
Amandine Altmayer-Henzien,Valérie Declerck,David J. Aitken,Ewen Lescop,Denis Merlet,Jonathan Farjon Org. Biomol. Chem., 2013,11, 7611-7615
-
Ross Harder,David C. Dunand,Ian McNulty Nanoscale, 2017,9, 5686-5693
-
Chen-Yu Chien,Sheng-Sheng Yu Chem. Commun., 2020,56, 11949-11952
942070-34-0 (3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbonitrile) Related Products
- 1642844-61-8(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)thiophene-2-carbonitrile)
- 845873-35-0(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)thiophene-2-carbaldehyde)
- 916454-57-4(2-Thiophenecarbonitrile,3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-)
- 910553-12-7(4,4,5,5-tetramethyl-2-(2-methylthiophen-3-yl)-1,3,2-dioxaborolane)
- 916454-56-3(2-Thiophenecarbonitrile,5-bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-)
- 2241877-18-7(2-(2,5-bis(methyl-d3)thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
- 942070-20-4(2-(2,5-DiMethylthiophen-3-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane)
- 2121511-82-6((3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methanol)
- 1073354-61-6(3-Cyanothiophene-4-boronic acid pinacol ester)
- 874959-74-7(4,4,5,5-tetramethyl-2-(5-methylthiophen-3-yl)-1,3,2-dioxaborolane)
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