tert-Butylcyanacetat

Bezeichnung:tert-Butylcyanacetat

CAS-Nr1116-98-9

Englisch Name:tert-Butyl cyanoacetate

CBNumberCB0725938

SummenformelC7H11NO2

Molgewicht141.17

MOL-Datei1116-98-9.mol

Synonyma

tert-Butylcyanacetat

tert-Butylcyanacetat physikalisch-chemischer Eigenschaften

Siedepunkt	40-42 °C/0.1 mmHg (lit.)
Dichte	0.988 g/mL at 20 °C (lit.)
Brechungsindex	n20/D 1.420
Flammpunkt	91°C
storage temp.	2-8°C
Löslichkeit	Difficult to mix.
pka	3.21±0.10(Predicted)
Aggregatzustand	Oil
Farbe	Clear Colorless
BRN	1755933
InChI	InChI=1S/C7H11NO2/c1-7(2,3)10-6(9)4-5-8/h4H2,1-3H3
InChIKey	BFNYNEMRWHFIMR-UHFFFAOYSA-N
SMILES	C(OC(C)(C)C)(=O)CC#N
CAS Datenbank	1116-98-9(CAS DataBase Reference)
EPA chemische Informationen	Acetic acid, cyano-, 1,1-dimethylethyl ester (1116-98-9)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22
S-Sätze:	24/25
WGK Germany	3
F	10-21
TSCA	Yes
HS Code	29269090

Gefahreninformationscode (GHS)

tert-Butyl cyanoacetate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
Yellow liquid
Verwenden
tert-Butyl cyanoacetate is used in the synthesis of vinylogous urea and tert-butyl phenylcyanoacrylates. It is also used as a new additive for the sugar nucleoside base coupling step en route to DAPD with improved β-selectivity.
Allgemeine Beschreibung
tert-Butyl cyanoacetate undergoes functionalization and decarboxylation to form 3-amino-4-alkyl isoquinolines.
Synthese
tert-butyl cyanoacetate synthesis: 2-Cyanoacetic acid (1.701 g, 20 mmol) was suspended in a cetonitrile (20 ml) and tert-butanol (2.391 ml, 25.00 mmol). To this, a solution of N,N′-Dicyclohexylcarbodiimide (4.54 g, 22.00 mmol) in DCM (22 ml) was added under stirring at RT. The reaction mixture was stirred for 30 minutes, then filtered through Celite, and the solvents were evaporated. Proton NMR analysis of the residue showed complete conversion to the product. The product, tert-butyl cyanoacetate was not purified, but was taken straight through to the next reaction.

1H NMR (400 MHz, CDCl 3 ) δ 3.37 (s, 2H), 1.50 (s, 9H).
läuterung methode
The IR spectrum of a film should have bands at 1742 (ester CO) and 2273 (CN), but no band at ca 3500 broad (OH) cm-1 . If it does not have the last-named band, then fractionally distil; otherwise dissolve in Et2O, wash with saturated aqueous NaHCO3, dry over K2CO3, evaporate Et2O, and distil the residue under a vacuum (see tert-butyl ethyl malonate for precautions to avoid decomposition during distillation). [Beech & Piggott J Chem Soc 423 1955, Dahn & Hauth Helv Chim Acta 42 1214 1959, Beilstein 2 I 255.]

tert-Butyl cyanoacetate Upstream-Materialien And Downstream Produkte

tert-Butylcyanacetat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

1116-98-9, tert-Butyl cyanoacetate Verwandte Suche:

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