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| CAS No.: | 1692-25-7 |
|---|---|
| Name: | 3-Pyridylboronic acid |
| Article Data: | 37 |
| Molecular Structure: | |
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|
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| Formula: | C5H6BNO2 |
| Molecular Weight: | 122.919 |
| Synonyms: | 3-Pyridineboronicacid (7CI,8CI);Boronic acid, 3-pyridinyl- (9CI);(3-Pyridinyl)boronic acid;Dihydroxy(3-pyridyl)borane;Pyridin-3-ylboronic acid;Pyridine-3-boronic acid; |
| EINECS: | -0 |
| Density: | 1.23 g/cm3 |
| Melting Point: | >300 ºC |
| Boiling Point: | 308.8 ºC at 760 mmHg |
| Flash Point: | 140.5 ºC |
| Appearance: | Light yellow powder |
| Hazard Symbols: |
 Xn, Xi, C, F
|
| Risk Codes: | 36/37/38-22-34-11 |
| Safety: | 36/37/39-3-26-45-16 |
| PSA: | 53.35000 |
| LogP: | -1.23860 |
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| Conditions | Yield |
|---|---|
| Stage #1: 3-Bromopyridine; n-butyllithium In toluene at -50℃; Stage #2: With Triisopropyl borate In tetrahydrofuran at -50 - -15℃; | 98% |
| Conditions | Yield |
|---|---|
| Stage #1: 3-Bromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 2h; Stage #2: With tris(trimethylsilyl)borate In tetrahydrofuran at 0 - 20℃; for 24h; Stage #3: With hydrogenchloride at 0℃; pH=6 - 7; | 75% |
| Stage #1: 3-Bromopyridine With n-butyllithium In tetrahydrofuran; hexane; toluene at -50℃; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane; toluene at -50 - -15℃; Stage #3: With sodium hydroxide In tetrahydrofuran; hexane; toluene | 73% |
| With n-butyllithium; Triisopropyl borate In tetrahydrofuran at -78℃; for 3h; | 71% |
| Conditions | Yield |
|---|---|
| Stage #1: 3-Bromopyridine With n-butyllithium In tetrahydrofuran; hexanes; toluene at -60 - -50℃; for 0.75h; Stage #2: Triisopropyl borate With hydrogenchloride In tetrahydrofuran; hexanes; water; toluene at -50 - -15℃; | 73% |
| With n-butyllithium In tetrahydrofuran; hexane; toluene at -40℃; for 1.5h; | |
| Stage #1: 3-Bromopyridine With n-butyllithium In tetrahydrofuran; hexane; toluene at -60 - -50℃; for 0.583333h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane; toluene at -15℃; |
| Conditions | Yield |
|---|---|
| Stage #1: pyridine With lithium diisopropyl amide In diethyl ether at -78℃; for 1h; Stage #2: Trimethyl borate In diethyl ether at 20℃; for 1h; | 65% |
- 865-34-9
lithium methanolate
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4'-bromo-2,2':6',2''-terpyridine
- 201733-56-4
2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane
A
- 128143-86-2
6′,6″-di(pyridin-2-yl)-2,2′:4′,4″:2″,2′′′-quaterpyridine
B
- 1692-25-7
3-pyridylboronic acid
C
- 181866-50-2
4′-methoxy-2,2′:6′,2′′-terpyridine
D
- 381218-94-6
4'-((neopentyl glycolato)boron)-2,2':6',2''-terpyridine
| Conditions | Yield |
|---|---|
| With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In methanol at 55℃; for 18h; |
- 1692-25-7
3-pyridylboronic acid
| Conditions | Yield |
|---|---|
| With hydrogenchloride In tetrahydrofuran; hexane; toluene at -20 - 20℃; | |
| With hydrogenchloride at 0℃; pH=5 - 6; | |
| With hydrogenchloride In tetrahydrofuran; hexane; water | |
| With water; sodium hydroxide at 30℃; for 3h; Time; Temperature; |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran; hexane; toluene / -40 - -20 °C 2: aq. HCl / tetrahydrofuran; toluene; hexane / -20 - 20 °C View Scheme |
| Conditions | Yield |
|---|---|
| With n-butyllithium; acetic acid In diethyl ether; hexane; water | |
| With n-butyllithium; acetic acid In diethyl ether; hexane; water |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid | |
| With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid | |
| With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid | |
| With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid |
- 626-55-1
3-Bromopyridine
- 121-43-7
Trimethyl borate
- 594-19-4
tert.-butyl lithium
- 1692-25-7
3-pyridylboronic acid
| Conditions | Yield |
|---|---|
| With hydrogenchloride; sodium hydroxide In methanol; diethyl ether; dichloromethane; pentane | |
| With hydrogenchloride; sodium hydroxide In methanol; diethyl ether; dichloromethane; pentane |
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Specification
The IUPAC name of this chemical is pyridin-3-ylboronic acid. With the CAS registry number 1692-25-7, it is also named as 3-Pyridineboronic acid. The product's categories are Blocks; Boronic Acids; Pyridines; Pyridine; Boronic Acids & Esters; Heterocyclic Compounds; Organoborons; Aromatics Compounds; B (Classes of Boron Compounds); Aromatics; Boron Derivatives; Heterocycles; Boronic Acids and Derivatives; Heteroaryl. It is light yellow powder which is stable under normal temperature and pressure. Additionally, Pyridine-3-boronic acid should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 15.751; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 3; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 3; (8)Index of Refraction: 1.534; (9)Molar Refractivity: 31.087 cm3; (10)Molar Volume: 99.944 cm3; (11)Polarizability: 12.324×10-24 cm3; (12)Surface Tension: 51.135 dyne/cm ; (13)Enthalpy of Vaporization: 58.018 kJ/mol; (14)Vapour Pressure: 0 mmHg at 25°C; (15)Rotatable Bond Count: 1; (16)Exact Mass: 123.049159; (17)MonoIsotopic Mass: 123.049159; (18)Topological Polar Surface Area: 53.4; (19)Heavy Atom Count: 9; (20)Complexity: 89.
Preparation of Pyridine-3-boronic acid: It can be obtained by 3-bromo-pyridine. This reaction needs reagent triisopropyl borate, n-butyllithium and solvent toluene, tetrahydrofuran, hexane at temperature of -40--20 °C.
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Uses of Pyridine-3-boronic acid: It can react with 5-bromo-nicotinic acid methyl ester to get [3,3']bipyridinyl-5-carboxylic acid methyl ester. This reaction needs reagent Et3N, Pd(OAc)2, 1,1'-bis(diphenylphosφno)ferrocene and solvent dimethylformamide at temperature of 95 °C. The reaction time is 5 days. The yield is 89%.
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When you are using this chemical, please be cautious about it as the following:
It is highly flammable, so people should keep it away from sources of ignition. It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. what's more, this chemical can cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
1. SMILES:B(c1cccnc1)(O)O
2. InChI:InChI=1/C5H6BNO2/c8-6(9)5-2-1-3-7-4-5/h1-4,8-9H
3. InChIKey:ABMYEXAYWZJVOV-UHFFFAOYAR