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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.
WGK
WGK 3
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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%
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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