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CAS RN: 73183-34-3 | Numéro de produit: B1964
Bis(pinacolato)diboron
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Pureté: >99.0%(GC)
Synonymes
- 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane
Documents de produit:
| Taille | Prix unitaire | Belgique | Japon * | Quantité |
|---|---|---|---|---|
| 1G |
€16.00
|
2 | 30 |
|
| 5G |
€39.00
|
15 | ≥100 |
|
| 25G |
€126.00
|
14 | ≥100 |
|
| 100G |
€371.00
|
Contactez-nous | ≥100 |
|
*Le délai de livraison pour des produits disponibles en stock en Belgique est 1 à 2 jours
*Le délai de livraison pour des produits disponibles en stock en Japon est 1 à 2 semaines (sauf des produits réglementés et des envois avec de la glace carbonique)
| Numéro de produit | B1964 |
| Pureté / Méthode d'analyse | >99.0%(GC) |
| Formule moléculaire / poids moléculaire | C__1__2H__2__4B__2O__4 = 253.94 |
| Etat physique (20 ° C) | Solid |
| Condition de stockage | Refrigerated (0-10°C) |
| Stocker sous gaz inerte | Store under inert gas |
| Condition à éviter | Moisture Sensitive,Heat Sensitive |
| Emballage Et Conteneur | 1G-Glass Bottle with Plastic Insert (Voir l'image) |
| CAS RN | 73183-34-3 |
| Numéro de registre de Reaxys | 7703552 |
| Identifiant de la substance PubChem | 87564847 |
| Indice Merck (14) | 1300 |
| Numéro MDL | MFCD00799570 |
Spécifications
| Appearance | White to Almost white powder to crystal |
| Purity(GC) | min. 99.0 % |
| Melting point | 135.0 to 142.0 °C |
| Solubility in Methanol | almost transparency |
Propriétés
| Point de fusion | 138 °C |
| Solubilité (soluble dans) | Ethanol, Benzene, Methanol |
SGH
| Pictogramme |
|
| Mot de signal | Attention |
| Mentions de danger | H302 + H312 + H332 : Nocif en cas d’ingestion, de contact cutané ou d’inhalation. H315 : Provoque une irritation cutanée. H319 : Provoque une sévère irritation des yeux. |
| Conseils de prudence | P261 : Éviter de respirer les poussières. P264 : Se laver la peau soigneusement après manipulation. P280 : Porter des gants de protection/ des vêtements de protection/ un équipment de protection des yeux/ du visage/ auditive. P337 + P313 : Si l'irritation oculaire persiste: consulter un médecin. P302 + P352 + P312 : EN CAS DE CONTACT AVEC LA PEAU: Laver abondamment à l’eau. Appeler un CENTRE ANTIPOISON/un médecin en cas de malaise. P304 + P340 + P312 : EN CAS D’INHALATION: transporter la personne à l’extérieur et la maintenir dans une position où elle peut confortablement respirer. Appeler un CENTRE ANTIPOISON/un médecin en cas de malaise. |
Lois connexes:
Informations de transport:
| N ° SH (import / export) (TCI-E) | 2920907080 |
Application
TCI Practical Example: Diborylation of Alkynes with a Platinum Catalyst
Used Chemicals
Procedure
To a degassed solution of diphenylacetylene (100 mg, 0.561 mmol) and bis(pinacolato)diboron (144 mg, 0.567 mmol) in DMF (0.5 mL) and toluene (0.5 mL) was added Pt(PPh3)4 (2 mg, 0.25 mol%). The reaction mixture was heated to 80 °C for 24 hours. After this time, the reaction was diluted with toluene (10 mL) and washed with saturated aqueous NH4Cl (2 x 10 mL). The organic phase was dried over MgSO4 and concentrated under reduced pressure. Recrystallization from MeOH afforded 1 as a white solid (241 mg, 0.558 mmol, 99%).
Experimenter’s Comments
The reaction mixture was monitored by TLC (CH2Cl2:hexane = 2:1, Rf = 0.45).
Analytical Data（Compound 1）
1H NMR (400 MHz, CDCl3); δ 7.02-7.09 (m, 6H), 6.94-6.96 (m, 4H), 1.32 (s, 24H).
13C NMR (101 MHz, CDCl3); δ 141.3, 129.3, 127.4, 125.8, 84.1, 24.9.
Lead Reference
- Platinum(0)-catalyzed diboration of alkynes
Other References
- Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates
Application
TCI Practical Example: Miyaura-Ishiyama Borylation using Pd(OAc)2
Used Chemicals
Procedure
To the solution of 3-iodobenzalehyde (1.16 g, 5.00 mmol) in dry DMF (15.0 mL) were added potassium acetate (981 mg, 10.0 mmol), palladium(II) acetate (112 mg, 0.500 mmol, 10 mol%) and bis(pinacolato)diborane (1.27 g, 5.00 mmol). The reaction mixture was stirred at 80 ºC for 7 h. The reaction mixture was cooled to room temperature and quenched with H2O (15 mL) and saturated NH4Cl aq. (10 mL), then the mixture was extracted twice with hexane : EtOAc = 4 : 1. The combined organic layer was washed with H2O (50 mL) and brine (50 mL), dried over Na2SO4, and concentrated under reduced pressure to afford the crude product as a yellow oil. The crude product was purified by column chromatography on silica-gel (hexane → hexane : EtOAc = 1:1) to afford 3-formylphenylboronic acid pinacol ester as a yellow oil (500 mg, 2.15 mmol, 43%).
Experimenter's Comments
(1) DMF was dried over molecular sieves.
(2) Completion of the reaction was confirmed by TLC (hexane : EtOAc = 1 : 1, Rf = 0.30) and GC.
Analytical Data（3-Formylphenylboronic Acid Pinacol Ester）
1H NMR (400 MHz, CDCl3); δ 10.1 (s, 1H), 8.30 (s, 1H), 8.06 (d, J = 4.0 Hz, 1H), 7.99 (ddd, J = 1.6, 1.8, 7.8 Hz, 1H), 7.53 (t, J = 8.0 Hz, 1H), 1.37 (s, 12H).
Lead Reference
- The bulky side chain of antillatoxin is important for potent toxicity: rational design of photoresponsive cytotoxins based on SAR studies
Application
Ni/Cu-Catalyzed Defluoroborylation of Fluoroarenes
Typical procedure (R = 4-Ph):
To a solution of 4-fluorobiphenyl (34.0 mg, 0.2 mmol, 1 eq.), bis(pinacolato)diboron (102 mg, 0.402 mmol, 2.0 eq.), copper iodide (7.6 mg, 0.04 mmol, 0.20 eq.), and cesium fluoride (91.0 mg, 0.6 mmol, 3.0 eq.) in toluene (0.5 mL) is added a solution of bis(1,5-cyclooctadiene)nickel(0) (5.1 mg, 0.02 mmol, 0.10 eq.) and tricyclohexylphosphine (28 mg, 99.8 µmol, 0.50 eq.) in toluene (0.5 mL) at room temperature. After stirring for 1 min at the same temperature, the mixture is heated at 80 °C with stirring for 20 h. After cooling to room temperature, saturated aqueous ammonium chloride (ca. 3 mL) is added to the mixture followed by extraction with EtOAc (ca. 3 mL × 3). The combined organic extract is dried over Na2SO4, and the filtrate is concentrated under reduced pressure. The residue is purified by preparative TLC (solvent: benzene/acetic acid = 20/1) to give 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl (55.6 mg, 0.198 mmol, 99% yield) as a colorless solid.
To a solution of 4-fluorobiphenyl (34.0 mg, 0.2 mmol, 1 eq.), bis(pinacolato)diboron (102 mg, 0.402 mmol, 2.0 eq.), copper iodide (7.6 mg, 0.04 mmol, 0.20 eq.), and cesium fluoride (91.0 mg, 0.6 mmol, 3.0 eq.) in toluene (0.5 mL) is added a solution of bis(1,5-cyclooctadiene)nickel(0) (5.1 mg, 0.02 mmol, 0.10 eq.) and tricyclohexylphosphine (28 mg, 99.8 µmol, 0.50 eq.) in toluene (0.5 mL) at room temperature. After stirring for 1 min at the same temperature, the mixture is heated at 80 °C with stirring for 20 h. After cooling to room temperature, saturated aqueous ammonium chloride (ca. 3 mL) is added to the mixture followed by extraction with EtOAc (ca. 3 mL × 3). The combined organic extract is dried over Na2SO4, and the filtrate is concentrated under reduced pressure. The residue is purified by preparative TLC (solvent: benzene/acetic acid = 20/1) to give 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl (55.6 mg, 0.198 mmol, 99% yield) as a colorless solid.
References
Application
C-H Borylation of Arenes
Typical Procedure:
A 25 mL-flask assembled a magnetic stirring bar, a septum inlet, and a condenser is charged with chloro(1,5-cyclooctadiene)iridium(I) dimer (10.1 mg, 0.015 mmol), 2,2’-bipyridyl (4.7 mg, 0.03 mmol), and bis-(pinacolato)diboron (254.0 mg, 1.0 mmol) and then flushed with nitrogen. An arene (60 mmol) is added, and the mixture is stirred at 80 °C for 16 h. The reaction mixture is analyzed by GC and GC mass spectroscopy. The product is extracted with benzene, washed with brine, and dried over MgSO4. Kugelrohr distillation gives analytically pure samples.
A 25 mL-flask assembled a magnetic stirring bar, a septum inlet, and a condenser is charged with chloro(1,5-cyclooctadiene)iridium(I) dimer (10.1 mg, 0.015 mmol), 2,2’-bipyridyl (4.7 mg, 0.03 mmol), and bis-(pinacolato)diboron (254.0 mg, 1.0 mmol) and then flushed with nitrogen. An arene (60 mmol) is added, and the mixture is stirred at 80 °C for 16 h. The reaction mixture is analyzed by GC and GC mass spectroscopy. The product is extracted with benzene, washed with brine, and dried over MgSO4. Kugelrohr distillation gives analytically pure samples.
References
- Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate
Application
Diastereoselective Synthesis of Homoallyic Alcohols by Diboron-Promoted Coupling of Dienes and Aldehydes
References
- Diastereoselective Construction of Functionalized Homoallylic Alcohols by Ni-Catalyzed Diboron-Promoted Coupling of Dienes and Aldehydes
PubMed Litterature
Articles / Brochures
TCIMail
[TCIMAIL No.101] for Suzuki Cross-Coupling Reaction[Research Articles] Ni/Cu-Catalyzed Defluoroborylation of Fluoroarenes
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