Sodium triacetoxyborohydride

Bezeichnung:Sodium triacetoxyborohydride

CAS-Nr56553-60-7

Englisch Name:Sodium triacetoxyborohydride

CBNumberCB3321854

SummenformelC6H10BNaO6

Molgewicht211.94

MOL-Datei56553-60-7.mol

Sodium triacetoxyborohydride physikalisch-chemischer Eigenschaften

Schmelzpunkt	116-120 °C (dec.) (lit.)
Siedepunkt	111.1℃[at 101 325 Pa]
Dichte	1.36[at 20℃]
Dampfdruck	0Pa at 25℃
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride.
Aggregatzustand	Powder
Farbe	White
Wasserlöslichkeit	reacts
Sensitive	Moisture Sensitive
Merck	14,8695
BRN	4047608
InChIKey	HHYFEYBWNZJVFQ-UHFFFAOYSA-N
LogP	-2.88--1.09 at 20℃
CAS Datenbank	56553-60-7(CAS DataBase Reference)
EPA chemische Informationen	Borate(1-), tris(acetato-.kappa.O)hydro-, sodium, (T-4)- (56553-60-7)

Sicherheit

Kennzeichnung gefährlicher	F,Xi,C
R-Sätze:	15-34-14/15-37/38-11
S-Sätze:	43-7/8-45-36/37/39-26
RIDADR	UN 1409 4.3/PG 2
WGK Germany	3
F	10-21
Hazard Note	Irritant/Flammable
TSCA	Yes
HazardClass	4.3
PackingGroup	III
HS Code	29319090

Gefahreninformationscode (GHS)

Sodium triacetoxyborohydride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R15:Reagiert mit Wasser unter Bildung hochentzündlicher Gase.
R34:Verursacht Verätzungen.
R14/15:Reagiert heftig mit Wasser unter Bildung hochentzündlicher Gase.
S-Sätze Betriebsanweisung:
S43:Zum Löschen . . . (vom Hersteller anzugeben) verwenden (wenn Wasser die Gefahr erhöht, anfügen: "Kein Wasser verwenden").
S7/8:Behälter trocken und dicht geschlossen halten.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a white hygroscopic solid that emits hydrogen gas when hydrolysed in water, which is flammable. STAB is a milder reducing agent than sodium borohydride or even sodium cyanoborohydride. Even sodium cyanoborohydride is a milder reducing agent than sodium borohydride, and is particularly suitable for the reductive amination of aldehydes and ketones. It can reduce aldehydes but not most ketones. It can also be used in the reductive alkylation of secondary amines in aldehyde-bisulfite adducts.
Chemische Eigenschaften
Sodium triacetoxyborohydride (STAB-H) is commercially available as a hygroscopic white powder with a melting point of 116-120 °C. freely soluble in benzene. It is prepared by the reaction of NaBH4 with excess acetic acid in benzene or toluene.
Verwenden
Sodium Triacetoxyborohydride(STAB) is a hydride reagent used in stereoselective reductive amination. It is able to replace toxic sodium cyanoborohydride under most conditions. It is selective in reducing aldehydes to alcohols in the presence of ketones. STAB is also stable in anhydrous acids, which enables reductive amination of aldehydes and ketones. It used in reductive amination of ketones and aldehydes and reductive amination/lactamization of carbonyl compounds with amines. The advantage of STAB compared to sodium cyanoborohydride is evident. STAB, being non-toxic, is easier to handle and forms no toxic by-products, making the treatment of process waste after the reaction simple and less costly.
Application
Sodium triacetoxyborohydride is a mild reagent that exhibits remarkable selectivity as a reducing agent. It reduces aldehydes but not ketones; however, beta-hydroxyketones can be reduced selectively to give 1,3-trans diols.The steric and the electron-withdrawing effects of the three acetoxy groups stabilize the boron-hydrogen bond and are responsible for its mild reducing properties.
Sodium triacetoxyborohydride or [NaBH(OAc)3] can be used as a reagent:
In the reductive amination of ketones and aldehydes.
To prepare N-benzyl-γ-valerolactam by reacting with methyl 4-oxopentanoate and benzylamine via reductive amination/lactamization.
To reduce imines and enamines to corresponding amines.
To reduce quinolines and isoquinolines to corresponding tetrahydro derivatives.
In the hydroboration of alkenes.
To synthesize nitroxide biradicals for creating high relaxivity terminal groups linkage to dendrimers.
Reaktionen
Sodium Triacetoxyborohydride is selective reducing agent in organic synthesis. It is especially suitable for reductive aminations. Since the reaction rate for the reduction of iminium ions is much faster than for ketones or even aldehydes, the reductive amination can be carried out as a one-pot procedure by introducing the reducing agent into a mixture of the amine and carbonyl compound. The presence of a stoichiometric amount of acetic acid, which catalyzes the imine formation and provides the iminium ion, doesn't present any problem under these conditions.

Reductive amination (simplified)

Sodium triacetoxyborohydride Upstream-Materialien And Downstream Produkte

Sodium triacetoxyborohydride Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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