Pinacolborane

Bezeichnung:Pinacolborane

CAS-Nr25015-63-8

Englisch Name:Pinacolborane

CBNumberCB8745950

SummenformelC6H13BO2

Molgewicht127.98

MOL-Datei25015-63-8.mol

Pinacolborane physikalisch-chemischer Eigenschaften

Siedepunkt	42-43 °C50 mm Hg(lit.)
Dichte	0.882 g/mL at 25 °C(lit.)
Dampfdruck	29-119.9hPa at 20-50℃
Brechungsindex	n20/D 1.396(lit.)
Flammpunkt	41 °F
storage temp.	2-8°C
Löslichkeit	Miscible with ether, dichloromethane, tetrahydrofuran and organic solvents.
Aggregatzustand	Liquid
Wichte	0.882
Farbe	Clear colorless to light yellow
Sensitive	Air Sensitive
BRN	7802871
Stabilität	Air Sensitive, Hygroscopic, Moisture Sensitive
InChI	InChI=1S/C6H13BO2/c1-5(2)6(3,4)9-7-8-5/h7H,1-4H3
InChIKey	UCFSYHMCKWNKAH-UHFFFAOYSA-N
SMILES	O1C(C)(C)C(C)(C)OB1
CAS Datenbank	25015-63-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	F,Xi,Xn
R-Sätze:	11-15-36/37/38-36/37-19-40
S-Sätze:	16-43-8-37/39-26-33-29-36/37
RIDADR	UN 3398 4.3/PG 2
WGK Germany	3
Hazard Note	Highly Flammable/Keep Cold/Air Sensitive
HazardClass	4.3
PackingGroup	II
HS Code	29209090
Speicherklasse	4.3 - Hazardous materials which set free flammable gases upon contact with water
Hazard Classifications	Flam. Liq. 2 Water-react 2

Gefahreninformationscode (GHS)

Pinacolborane Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R11:Leichtentzündlich.
R15:Reagiert mit Wasser unter Bildung hochentzündlicher Gase.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R36/37:Reizt die Augen und die Atmungsorgane.
R19:Kann explosionsfähige Peroxide bilden.
S-Sätze Betriebsanweisung:
S16:Von Zündquellen fernhalten - Nicht rauchen.
S43:Zum Löschen . . . (vom Hersteller anzugeben) verwenden (wenn Wasser die Gefahr erhöht, anfügen: "Kein Wasser verwenden").
S8:Behälter trocken halten.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S33:Maßnahmen gegen elektrostatische Aufladungen treffen.
S29:Nicht in die Kanalisation gelangen lassen.
Chemische Eigenschaften
Clear colorless liquid
Verwenden
Pinacolborane is used as a precursor of boronic esters by hydroboration or coupling reactions. It acts as a monofunctional hydroborating agent. It is used in the synthesis of unsymmetrical biaryls through aromatic C-H borylation-cross-coupling sequence. It is involved in the preparation of 4,4,5,5-tetramethyl-2-thiophen-2-yl-[1,3,2]dioxaborolane by reacting with 2-iodo-thiophene. Further, it is used to prepare vinylboronates by palladium-catalyzed coupling with alkenyl triflates and iodides.
Verwenden
Pinacolborane is used for synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence.
Synthese
Pinacol (177 g, 1.5 mol) and CH2Cl2 (1.6 L) were added to a 5 L round bottom flask. Borane dimethyl sulfide (10 M, 159 mL, 0.16 mol) was added to the flask via cannula and the mixture was stirred at 0C for 4 hours. The reaction mixture was then heated to room temperature overnight with stirring.17 After 17 h, the reaction mixture gave off some gas (hydrogen); however, the reaction was heated and slowly depressurized (760 mm to 200 mm). This process allowed CH2Cl2 (1.3 L) to move away from the reaction. The remaining liquid was transferred to a 500 mL flask through a cannula and the pressure was slowly reduced from atmospheric to 50 mm over 2.5 h. Some initial foaming was observed in the viscous liquid due to continued outgassing. The method provided pinacol borane suitable for subsequent reactions. The yield was 157 g, 81.7%.

Pinacolborane Upstream-Materialien And Downstream Produkte

Pinacolborane Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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