| Identification | More | [Name]
Pyridine-4-boronic acid | [CAS]
1692-15-5 | [Synonyms]
4-PYRIDINEBORNIC ACID
4-PYRIDINEBORONIC ACID
4-PYRIDINYLBORONIC ACID
4-PYRIDYLBORONIC ACID
AKOS BRN-0273
BUTTPARK 43\57-08
CHEMBRDG-BB 3200984
PYRIDIN-4-YL-4-BORONIC ACID
PYRIDIN-4-YLBORONIC ACID
PYRIDINE-4-BORONIC ACID
PYRIDINE-4-BORONIC ACID HYDRATE
PYRIDYL-4-BORONIC ACID
RARECHEM AH PB 0240
TIMTEC-BB SBB004280
PYRIDINE-4-BORONIC ACID HYDRATE: CA 10-15% WATER
4-Pyridylboronic Acid (contains varying amounts of Anhydride)
(Pyridin-4-yl)boronic acid (may contain varying amounts of anhydride)
B-4-Pyridinylboronic Acid
Pyridine-4-boronic acid ,98% | [EINECS(EC#)]
671-679-4 | [Molecular Formula]
C5H6BNO2 | [MDL Number]
MFCD08061353 | [Molecular Weight]
122.92 | [MOL File]
1692-15-5.mol |
| Chemical Properties | Back Directory | [Appearance]
light orange granular powder | [Melting point ]
>300 °C (lit.) | [Boiling point ]
308.8±34.0 °C(Predicted) | [density ]
1.22±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [solubility ]
Aqueous Acid (Slightly), Water (Slightly) | [form ]
Solid | [pka]
7.59±0.10(Predicted) | [color ]
White to Off-White | [Usage]
Boronic acid derivatives and their binding affinities with diols. | [Detection Methods]
NMR | [BRN ]
471944 | [InChI]
InChI=1S/C5H6BNO2/c8-6(9)5-1-3-7-4-2-5/h1-4,8-9H | [InChIKey]
QLULGIRFKAWHOJ-UHFFFAOYSA-N | [SMILES]
C1=NC=CC(B(O)O)=C1 | [CAS DataBase Reference]
1692-15-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi,C,F | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed.
R34:Causes burns.
R11:Highly Flammable. | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S16:Keep away from sources of ignition-No smoking . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT, KEEP COLD | [HS Code ]
29333990 |
| Questions And Answer | Back Directory | [Uses]
Pyridine-4-boronic acid can be used as a candidate for Suzuki-Miyaura coupling reaction. Especially, as a N-containing building blocks, pyridine-4-boronic acid was employed to construct some heterocyclic compounds with superior biological activities.
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| Questions and Answers (Q&A) | Back Directory | [Description]
Pyridine-4-boronic acid is a kind of boronic acid derivative. It is useful building blocks in crystal engineering. It can also be used as a catalyst to act as a dehydrative condensation agent to synthesize amides using carboxylic acid and amines as raw materials. Its derivative, polystyrene-bound 4-pyridineboronic acid, is a useful catalyst for amidation reaction and esterification of alpha-hydrocarboxylic acids.
| [References]
http://www.wako-chem.co.jp/english/labchem/product/Org/pyridineboronic/
José J. CamposGaxiola et al. "Pyridineboronic Acids as Useful Building Blocks in Combination with Perchloroplatinate(II) and -(IV) Salts: 1D, 2D, and 3D Hydrogen-Bonded Networks Containing X-H•••Cl2Pt− (X = C, N+), B(OH)2•••Cl2Pt−, and B(OH)2•••(HO)2B Synthons." Crystal Growth & Design 10.7(2010).
Kara, H., A. G. Orpen, and T. J. Podesta. "Pyridine boronic acids as building blocks in crystal engineering." Acta Crystallographica 61.Suppl (2001): C357.
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| Hazard Information | Back Directory | [Chemical Properties]
light orange granular powder | [Synthesis]
Under argon protection, 4-bromopyridine (1.5 g, 10 mmol) was placed in a 200 mL Schlenk flask and 40 mL of anhydrous deoxytetrahydrofuran was added. After cooling the reaction mixture to -78 °C, 5 mL (2.2 M, 11 mmol) of n-butyllithium solution was slowly added dropwise and the reaction was maintained at this temperature for 1 hour. Subsequently, 4 mL of trimethyl borate was added and the reaction continued at -78 °C for 1 hour. Upon completion of the reaction, the mixture was slowly warmed to room temperature and stirred overnight. The reaction was quenched with 2 mol/L hydrochloric acid solution and purified by recrystallization from hexane to give pyridine-4-boronic acid hydrochloride (0.8 g, 65% yield). |
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