28440

Sigma-Aldrich

tert-Butyl cyanoacetate

≥97.0% (GC)

Linear Formula:
NCCH2COOC(CH3)3
CAS Number:
Molecular Weight:
141.17
Beilstein/REAXYS Number:
1755933
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

≥97.0% (GC)

refractive index

n20/D 1.420

bp

40-42 °C/0.1 mmHg (lit.)

density

0.988 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)CC#N

InChI

1S/C7H11NO2/c1-7(2,3)10-6(9)4-5-8/h4H2,1-3H3

InChI key

BFNYNEMRWHFIMR-UHFFFAOYSA-N

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General description

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

Application

tert-Butyl cyanoacetate was used in the synthesis of vinylogous urea.

Packaging

10 mL in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xn

Risk Statement

22

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

244.4 °F - closed cup

Flash Point(C)

118 °C - closed cup

Barry B Snider et al.
Organic letters, 7(20), 4519-4522 (2005-09-24)
[reaction: see text] Addition of the enolate of tert-butyl acetate to cyanamide methyl ester 17 followed by treatment with LHMDS afforded vinylogous urea 19 in 27% yield. Vinylogous urea 19 was also obtained from 37 and tert-butyl cyanoacetate in 50%...
Ben S Pilgrim et al.
Organic letters, 15(24), 6190-6193 (2013-11-21)
A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed α-arylation reaction...

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