- Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot BorylationRamachandran, P. Veeraraghavan ; Hamann, Henry J.; Mishra, Sukriti, ACS Omega, 2022, 7(16), 14377-14389
Cas no 937591-69-0 (2-(2,3-dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
2-(2,3-Dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a boronic ester derivative commonly used as an intermediate in Suzuki-Miyaura cross-coupling reactions. Its stable dioxaborolane moiety enhances shelf life and handling convenience, while the dihydrobenzofuran scaffold offers versatility in pharmaceutical and agrochemical synthesis. The tetramethyl substitution improves solubility in organic solvents, facilitating reaction conditions. This compound is particularly valuable for constructing complex heterocyclic systems due to its compatibility with diverse functional groups and mild reaction conditions. Its high purity and consistent performance make it a reliable choice for research and industrial applications in medicinal chemistry and material science.
937591-69-0 structure
Product Name:2-(2,3-dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
CAS No:937591-69-0
MF:C14H19BO3
MW:246.109864473343
MDL:MFCD09743046
CID:1024685
PubChem ID:16750469
Update Time:2025-05-21
2-(2,3-dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical and Physical Properties
Names and Identifiers
-
- 2-(2,3-Dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1-benzofuran
- 2,3-Dihydrobenzofuran-5-boronic acid pinacol ester
- 2-(2,3-dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- RWJUUXWJBMIGKA-UHFFFAOYSA-N
- ST2403800
- Z2469998057
- (2,3-DIHYDROBENZOFURAN-5
- 2,3-Dihydro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran (ACI)
-
- MDL: MFCD09743046
- Inchi: 1S/C14H19BO3/c1-13(2)14(3,4)18-15(17-13)11-5-6-12-10(9-11)7-8-16-12/h5-6,9H,7-8H2,1-4H3
- InChI Key: RWJUUXWJBMIGKA-UHFFFAOYSA-N
- SMILES: O1C(C)(C)C(C)(C)OB1C1C=C2C(OCC2)=CC=1
Computed Properties
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 3
- Heavy Atom Count: 18
- Rotatable Bond Count: 1
- Complexity: 313
- Topological Polar Surface Area: 27.7
2-(2,3-dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Security Information
- Signal Word:Warning
- Hazard Statement: H315-H319-H335
- Warning Statement: P261-P305+P351+P338
- Storage Condition:Inert atmosphere,2-8°C
2-(2,3-dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| Alichem | A019097442-1g |
2-(2,3-Dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
937591-69-0 | 97% | 1g |
$179.19 | 2023-08-31 | |
| Alichem | A019097442-5g |
2-(2,3-Dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
937591-69-0 | 97% | 5g |
$537.57 | 2023-08-31 | |
| Alichem | A019097442-10g |
2-(2,3-Dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
937591-69-0 | 97% | 10g |
$814.00 | 2023-08-31 | |
| Chemenu | CM134696-1g |
2-(2,3-Dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
937591-69-0 | 97% | 1g |
$59 | 2021-08-05 | |
| Chemenu | CM134696-5g |
2-(2,3-Dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
937591-69-0 | 97% | 5g |
$235 | 2021-08-05 | |
| Chemenu | CM134696-10g |
2-(2,3-Dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
937591-69-0 | 97% | 10g |
$412 | 2021-08-05 | |
| Ambeed | A237346-100mg |
2-(2,3-Dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
937591-69-0 | 97% | 100mg |
$17.0 | 2025-04-15 | |
| Ambeed | A237346-250mg |
2-(2,3-Dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
937591-69-0 | 97% | 250mg |
$25.0 | 2025-04-15 | |
| Ambeed | A237346-1g |
2-(2,3-Dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
937591-69-0 | 97% | 1g |
$30.0 | 2025-04-15 | |
| Ambeed | A237346-5g |
2-(2,3-Dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
937591-69-0 | 97% | 5g |
$136.0 | 2025-04-15 |
2-(2,3-dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Production Method
Production Method 1
Reaction Conditions
1.1 Reagents: Iodine , (T-4)-Trihydro[N-(1-methylethyl)-2-propanamine]boron Solvents: Dichloromethane ; rt; 5 min, rt
1.2 Reagents: Diisopropylethylamine Solvents: Dichloromethane ; 5 min, rt
1.3 Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Toluene ; rt; 12 - 16 h, reflux; reflux → rt; rt → 0 °C
1.4 Solvents: Diethyl ether ; 4 h, 0 °C → rt
1.2 Reagents: Diisopropylethylamine Solvents: Dichloromethane ; 5 min, rt
1.3 Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Toluene ; rt; 12 - 16 h, reflux; reflux → rt; rt → 0 °C
1.4 Solvents: Diethyl ether ; 4 h, 0 °C → rt
Reference
Production Method 2
Reaction Conditions
1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Toluene ; 18 h, 90 °C
Reference
- Boron insertion into alkyl ether bonds via zinc/nickel tandem catalysisLyu, Hairong ; Kevlishvili, Ilia ; Yu, Xuan ; Liu, Peng ; Dong, Guangbin, Science (Washington, 2021, 372(6538), 175-182
Production Method 3
Reaction Conditions
1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,2-Dimethoxyethane ; 15 min, 150 °C; 150 °C → rt
Reference
- New 2-amino-3,5-dihydro-4H-imidazol-4-one derivatives and their use as BACE inhibitors for treatment of cognitive impairment, Alzheimer disease, neurodegeneration and dementia, World Intellectual Property Organization, , ,
Production Method 4
Reaction Conditions
1.1 Reagents: Dimethylformamide , Sodium hydride Solvents: Acetonitrile ; 24 h, 35 °C
1.2 Reagents: Water ; 35 °C
1.2 Reagents: Water ; 35 °C
Reference
- Solvent Anions Enable Photoinduced Borylation and Phosphonation of Aryl Halides via EDA ComplexesPan, Lei; Deckert, Macy M.; Cooke, Maria Victoria; Bleeke, Annika R.; Laulhe, Sebastien, Organic Letters, 2022, 24(35), 6466-6471
Production Method 5
Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Cobalt (functionalized in to cobalt oxide core shell supported on silica) , Silica Solvents: Tetrahydrofuran ; 24 h, 50 bar, 135 °C
Reference
- Development of a General and Selective Nanostructured Cobalt Catalyst for the Hydrogenation of Benzofurans, Indoles and BenzothiophenesZhou, Bei; Chandrashekhar, Vishwas G.; Ma, Zhuang; Kreyenschulte, Carsten; Bartling, Stephan; et al, Angewandte Chemie, 2023, 62(10),
Production Method 6
Reaction Conditions
1.1 Reagents: Potassium acetate Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ; 3 h, rt → 100 °C
Reference
- Preparation of imidazole derivatives as NMDA (N-methyl-D-aspartate) receptor subtype 2B selective blockers, World Intellectual Property Organization, , ,
Production Method 7
Reaction Conditions
1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ; 16 h, 90 °C
1.2 Solvents: Water
1.2 Solvents: Water
Reference
- Preparation of 1-[2-[(6-amino-9H-purin-9-yl)methyl]phenyl]pyrrolidin-3-amine derivatives as mixed lineage leukemia 1 (MLL1) inhibitors and anti-cancer agents, World Intellectual Property Organization, , ,
Production Method 8
Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 15 psi, rt → 40 °C; 48 h, 40 °C
Reference
- Pyrimidine sulfamide derivative, preparation method and medical application thereof, World Intellectual Property Organization, , ,
Production Method 9
Reaction Conditions
1.1 Reagents: Potassium acetate Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ; rt; 16 h, 80 °C
Reference
- Preparation of 2-(thiophenyl)thiopyran-1,1-dioxides as MMP or TNF-α inhibitors, World Intellectual Property Organization, , ,
2-(2,3-dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Raw materials
- 2,3-Dimethylbutane-2,3-diol
- 5-Iodo-2,3-dihydro-1-benzofuran
- Benzofuran-5-boronic acid pinacol ester
- 5-bromo-2,3-dihydro-1-benzofuran
- Bis(pinacolato)diborane
2-(2,3-dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Preparation Products
2-(2,3-dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Related Literature
-
Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789
-
Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
-
3. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
-
Xinhuan Wang,Shuangfei Cai,Cui Qi Analyst, 2017,142, 2500-2506
-
Fereshteh Bayat Environ. Sci.: Nano, 2021,8, 367-389
937591-69-0 (2-(2,3-dihydro-1-benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) Related Products
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- 1221824-16-3(4-(2-Phenylethoxy)phenylboronic acid pinacol ester)
- 937591-99-6(2-(Chroman-8-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
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