tert-Butyl cyanoacetate Chemical Properties

Boiling point:

40-42 °C/0.1 mmHg (lit.)

Density 

0.988 g/mL at 20 °C (lit.)

refractive index 

n20/D 1.420

Flash point:

91°C

storage temp. 

2-8°C

solubility 

Difficult to mix.

pka

3.21±0.10(Predicted)

form 

Oil

color 

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 DataBase Reference

1116-98-9(CAS DataBase Reference)

EPA Substance Registry System

Acetic acid, cyano-, 1,1-dimethylethyl ester (1116-98-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25

WGK Germany 

3

F 

10-21

TSCA 

Yes

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

tert-Butyl cyanoacetate Usage And Synthesis

Chemical Properties

Yellow liquid

Uses

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.

General Description

tert-Butyl cyanoacetate undergoes functionalization and decarboxylation to form 3-amino-4-alkyl isoquinolines.

Synthesis

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).

Purification Methods

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(1116-98-9)Related Product Information

• Ethyl cyanoacetate
• Ethyl N-cyanoethanimideate
• Isobutyl cyanoacetate
• Ethyl cyanoformate
• Sodium cyanoborohydride
• Vitamin B12
• BENZYL CYANOACETATE
• Cyanomethanesulfonyl chloride
• Diethyl cyanomethylphosphonate
• 2-Octyl cyanoacetate
• N-Carbethoxy-4-piperidone
• tert-Butyl acetoacetate
• tert-Butyl methyl ether
• tert-Butyl chloroacetate
• tert-Butyl bromoacetate
• tert-Butyl carbazate
• tert-Butyl acrylate
• Cyanoacetic acid