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| Chemical Structure | 1-Naphthylboronic acid is classified as an organoboronic acid, and its chemical structure is derived from naphthalene and boronic acid. |
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Uses |
1-Naphthylboronic acid, like other boronic acids, is commonly employed in organic synthesis. It plays a crucial role in Suzuki-Miyaura cross-coupling reactions, facilitating the formation of carbon-carbon bonds. |
| Chemical Reactions | The chemical reactivity of 1-naphthylboronic acid, especially in cross-coupling reactions and other transformations, is an essential aspect of its utility. |
| Storage | Proper storage conditions, such as avoiding moisture and exposure to air, are crucial for maintaining the stability of boronic acids. |
| Isomeric SMILES | B(C1=CC=CC2=CC=CC=C12)(O)O |
| Exact Mass | 172.0695597 g/mol |
| Monoisotopic Mass | 172.0695597 g/mol |
| Complexity | 172 |
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Precautions |
Incompatible with oxidizing agents. Store in a cool, dry condition in a well sealed container. Store at room temperature. |
InChI:InChI=1/C10H9BO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7,12-13H
Addition of fluoride at the 10−6 mol dm−3 level drastically reduced the fluorescence intensity of 1-naphthylboronic acid in dimethylsulfoxide. A PVC membrane electrode containing 1-naphthylboronic acid as an ionophore and tridodecylmethylammonium chloride as an additive showed a response to fluoride at concentrations of higher than 10−3 mol dm−3.
A novel highly efficient monodentate imine palladium catalyst has been tested for Suzuki cross-coupling reaction. Under the standard conditions, a series of aryl halides coupled with phenylboronic or 1-naphthylboronic acid efficiently.
Naphthylboronic acids were also reactive (9j–9n, 56–89% yields), whereas 1-naphthylboronic acids gave lower yields than those of 2-naphthylboronic acids, presumably because there …
(1-C10H7)2BNH-i-C4H9
1-Naphthylboronic acid
isobutylamine
| Conditions | Yield |
|---|---|
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With water; heating;
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With water; heating;
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(1-C10H7)2BNHCH3
naphthalene
1-Naphthylboronic acid
| Conditions | Yield |
|---|---|
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With water; In water; heating;
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With water; In water; heating;
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(1-naphthyl)dichloroborane
triisobutyl borate
1-naphthylmagnesiumbromide
Trimethyl borate
2,3-dihydro-2-(naphthalen-1-yl)benzo[d][1,3,2]diazaborinin-4(1H)-one
3-benzyl-2-naphthalen-1-yl-2,3-dihydro-1H-benzo[1,3,2]diazaborinin-4-one
1-(4-methoxyphenyl)naphthalene
1-Fluoronaphthalene
CAS:1001911-63-2
Molecular Formula:C<sub>18</sub> H<sub>14</sub> BNO<sub>2</sub>
Molecular Weight:287.1
CAS:164461-18-1
