Cas no 1218790-34-1 (3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester)
3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester Chemical and Physical Properties
Names and Identifiers
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- 2-(3-Bromo-5-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- 3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester
- BS-21163
- 3-Bromo-5-isopropoxyphenylboronic acid pinacol ester
- AKOS015999352
- CS-0174351
- MFCD12546586
- 1,3,2-Dioxaborolane, 2-[3-bromo-5-(1-methylethoxy)phenyl]-4,4,5,5-tetramethyl-
- 1218790-34-1
- 2-(3-bromo-5-propan-2-yloxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- AT28111
- 3-Bromo-5-isopropoxyphenylboronic acid,pinacol ester
- DTXSID40675271
- 2-{3-Bromo-5-[(propan-2-yl)oxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- DB-366231
- 2-[3-bromo-5-(propan-2-yloxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
-
- MDL: MFCD12546586
- Inchi: 1S/C15H22BBrO3/c1-10(2)18-13-8-11(7-12(17)9-13)16-19-14(3,4)15(5,6)20-16/h7-10H,1-6H3
- InChI Key: SDXSFUDLZJNXFE-UHFFFAOYSA-N
- SMILES: BrC1C=C(C=C(B2OC(C)(C)C(C)(C)O2)C=1)OC(C)C
Computed Properties
- Exact Mass: 340.08500
- Monoisotopic Mass: 340.08454g/mol
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 3
- Heavy Atom Count: 20
- Rotatable Bond Count: 3
- Complexity: 330
- 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: 27.7?2
Experimental Properties
- PSA: 27.69000
- LogP: 3.53550
3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester Customs Data
- HS CODE:2934999090
- Customs Data:
China Customs Code:
2934999090Overview:
2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%
Declaration elements:
Product Name, component content, use to
Summary:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%
3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| Fluorochem | 213538-250mg |
2-(3-Bromo-5-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
1218790-34-1 | 95% | 250mg |
£125.00 | 2022-03-01 | |
| Fluorochem | 213538-1g |
2-(3-Bromo-5-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
1218790-34-1 | 95% | 1g |
£300.00 | 2022-03-01 | |
| Alichem | A019113003-25g |
2-(3-Bromo-5-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
1218790-34-1 | 95% | 25g |
$1254.24 | 2023-09-03 | |
| Alichem | A019113003-100g |
2-(3-Bromo-5-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
1218790-34-1 | 95% | 100g |
$3283.00 | 2023-09-03 | |
| Alichem | A019113003-500g |
2-(3-Bromo-5-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
1218790-34-1 | 95% | 500g |
$11013.79 | 2023-09-03 | |
| TRC | B694578-25mg |
3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester |
1218790-34-1 | 25mg |
$ 64.00 | 2023-04-18 | ||
| TRC | B694578-50mg |
3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester |
1218790-34-1 | 50mg |
$ 81.00 | 2023-04-18 | ||
| TRC | B694578-100mg |
3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester |
1218790-34-1 | 100mg |
$ 121.00 | 2023-04-18 | ||
| TRC | B694578-250mg |
3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester |
1218790-34-1 | 250mg |
$ 207.00 | 2023-04-18 | ||
| Ambeed | A479889-100mg |
2-(3-Bromo-5-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane |
1218790-34-1 | 96% | 100mg |
$20.0 | 2024-04-25 |
3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester Related Literature
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Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
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Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa Caccamo Phys. Chem. Chem. Phys., 2019,21, 11983-11991
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J. Xu,T. J. Carrocci,A. A. Hoskins Chem. Commun., 2016,52, 549-552
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Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789
Additional information on 3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester
Introduction to 3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester (CAS No: 1218790-34-1)
3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester, identified by the chemical abstracts service number 1218790-34-1, is a specialized boronic acid derivative that has garnered significant attention in the field of pharmaceutical chemistry and materials science. This compound serves as a crucial intermediate in the synthesis of various high-value molecules, particularly in the development of novel therapeutic agents and advanced functional materials. The unique structural features of this molecule, including the presence of both bromine and isopropoxy substituents on a phenyl ring, coupled with its boronic acid functionality, make it a versatile building block for organic synthesis.
The pinacol ester form of this boronic acid derivative enhances its stability and solubility, making it more amenable to handling and incorporation into complex synthetic protocols. Boronic acids are well-known for their role in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern organic synthesis that enables the formation of carbon-carbon bonds under mild conditions. The boronic acid moiety in 3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester facilitates such transformations, allowing for the construction of intricate molecular architectures with high precision.
In recent years, there has been a surge in research focused on developing new methodologies for the construction of biaryl compounds, which are prevalent in many biologically active molecules. The bromine substituent on the phenyl ring of 3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester provides a handle for further functionalization via palladium-catalyzed reactions, enabling the introduction of diverse groups at specific positions. This flexibility has made it an indispensable tool in medicinal chemistry laboratories seeking to optimize drug candidates.
One of the most compelling applications of this compound is in the synthesis of small-molecule inhibitors targeting protein-protein interactions. Protein-protein interactions play a pivotal role in numerous cellular processes, and modulating these interactions is a key strategy in drug discovery. Boronic acids have emerged as effective tools for disrupting such interactions due to their ability to form reversible covalent bonds with specific amino acid residues. The isopropoxy group in 3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester not only enhances steric bulk but also influences electronic properties, potentially fine-tuning binding affinity and selectivity.
Recent studies have highlighted the utility of this compound in the development of kinase inhibitors. Kinases are enzymes that phosphorylate other proteins and are involved in a wide range of cellular signaling pathways. Dysregulation of kinase activity is implicated in various diseases, making them attractive therapeutic targets. The ability to precisely modify aryl kinase inhibitors using 3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester has led to the discovery of several promising lead compounds with improved pharmacokinetic profiles.
The compound's stability under various reaction conditions has also been exploited in materials science applications. For instance, it has been used in the preparation of organic electronic materials such as conjugated polymers and small-molecule emitters for light-emitting diodes (LEDs). The boronic acid functionality allows for polymerization via cross-coupling reactions, leading to materials with tailored electronic properties. These advancements underscore the broad utility of 3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester beyond traditional pharmaceutical applications.
The synthesis of this compound typically involves multi-step organic transformations starting from commercially available aromatic precursors. Key steps include bromination at the desired position on the phenyl ring followed by protection of the hydroxyl group as a pinacol ester. This synthetic route has been optimized to ensure high yields and purity, making it suitable for large-scale production when needed. Advances in catalytic systems have further refined these processes, reducing reaction times and minimizing waste generation.
In conclusion,3-Bromo-5-isopropoxyphenylboronic acid, pinacol ester (CAS No: 1218790-34-1) is a multifunctional building block with significant implications across multiple domains of chemistry and biology. Its role in facilitating cross-coupling reactions and its potential applications in drug discovery and materials science highlight its importance as a research tool. As synthetic methodologies continue to evolve, compounds like this will remain at the forefront of innovation, driving progress toward new therapeutic interventions and advanced functional materials.
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