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HomeProduct name listtert-Butyl cyanoacetate

tert-Butyl cyanoacetate

  • CAS NO.:1116-98-9
  • Empirical Formula: C7H11NO2
  • Molecular Weight: 141.17
  • MDL number: MFCD00001938
  • EINECS: 214-243-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-04-24 17:21:45
tert-Butyl cyanoacetate Structural

What is tert-Butyl cyanoacetate?

Chemical properties

Yellow liquid

The Uses of tert-Butyl cyanoacetate

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.

What are the applications of Application

tert-Butyl cyanoacetate is used in the synthesis of vinylogous urea

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.
synthesis of tert-butyl cyanoacetate
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.]

Properties of tert-Butyl cyanoacetate

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.
form  Oil
pka 3.21±0.10(Predicted)
color  Clear Colorless
BRN  1755933
InChI InChI=1S/C7H11NO2/c1-7(2,3)10-6(9)4-5-8/h4H2,1-3H3
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 for tert-Butyl cyanoacetate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H227:Flammable liquids
H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P370+P378:In case of fire: Use … for extinction.
P403+P235:Store in a well-ventilated place. Keep cool.
P501:Dispose of contents/container to..…

Computed Descriptors for tert-Butyl cyanoacetate

InChIKey BFNYNEMRWHFIMR-UHFFFAOYSA-N
SMILES C(OC(C)(C)C)(=O)CC#N

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