Published TCIMAIL newest issue No.197
Maximum quantity allowed is 999
CAS RN: 73183-34-3 | Produkte #: B1964
Bis(pinacolato)diboron

Reinheit: >99.0%(GC)
- 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane
Einheit | Stückpreis | Belgien | Japan* | Menge |
---|---|---|---|---|
1G |
16,00 €
|
1 | 30 |
|
5G |
37,00 €
|
24 | ≥100 |
|
25G |
120,00 €
|
12 | ≥100 |
|
100G |
352,00 €
|
Kontaktieren Sie uns | ≥100 |
|
*In Belgien verfügbare Lagerbestände werden in 1 bis 3 Tagen geliefert.
*In Japan verfügbare Lagerbestände werden in 1 bis 2 Wochen geliefert. (unter Ausschluss von regulierten Artikeln und Trockeneislieferungen).
Artikel # | B1964 |
Reinheit / Analysenmethode | >99.0%(GC) |
Summenformel / Molekülmasse | C__1__2H__2__4B__2O__4 = 253.94 |
Physikalischer Zustand (20 °C) | Solid |
Lagerungstemperatur | Refrigerated (0-10°C) |
Unter Inertgas lagern | Store under inert gas |
Zu vermeidende Bedingungen | Moisture Sensitive,Heat Sensitive |
Verpackung und Behälter | 1G-Glass Bottle with Plastic Insert (Bild ansehen) |
CAS RN | 73183-34-3 |
Reaxys Registrierungsnummer | 7703552 |
PubChem-Stoff-ID | 87564847 |
Merck-Index (14) | 1300 |
MDL-Nummer | MFCD00799570 |
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 |
Schmelzpunkt | 138 °C |
Löslichkeit (löslich in) | Ethanol, Benzene, Methanol |
Piktogramm |
![]() |
Signalwort | Achtung |
Gefahrenhinweise | H302 + H312 + H332 : Gesundheitsschädlich bei Verschlucken, Hautkontakt oder Einatmen. H315 : Verursacht Hautreizungen. H319 : Verursacht schwere Augenreizung. |
Sicherheitshinweise | P261 : Einatmen von Staub vermeiden. P264 : Nach Gebrauch Haut gründlich waschen. P280 : Schutzhandschuhe/ Schutzkleidung/ Augenschutz/ Gesichtsschutz/ Gehörschutz Tragen. P337 + P313 : Bei anhaltender Augenreizung: Ärztlichen Rat einholen/ ärztliche Hilfe hinzuziehen. P302 + P352 + P312 : BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser waschen. Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt anrufen. P304 + P340 + P312 : BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen. Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt anrufen. |
HS-Nr. (Import / Export) (TCI-E) | 2920907080 |
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
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
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
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
References
- Diastereoselective Construction of Functionalized Homoallylic Alcohols by Ni-Catalyzed Diboron-Promoted Coupling of Dienes and Aldehydes
Artikel / Broschüren
[Research Articles] Ni/Cu-Catalyzed Defluoroborylation of Fluoroarenes
Sicherheitsdatenblatt (SDB)
Das angeforderte SDB ist nicht verfügbar.
Bitte Kontaktieren Sie uns für mehr Informationen.
Spezifikationsdokumenten
AZ & andere Zertifikate
Muster-AZ
Ein Muster-AZ für dieses Produkt ist zur Zeit nicht verfügbar.
Analytische Diagramme
Das angeforderte Analysediagramm ist nicht verfügbar. Wir entschuldigen uns für die Unannehmlichkeiten.