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28440

Sigma-Aldrich

tert-Butyl cyanoacetate

≥97.0% (GC)

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About This Item

Linear Formula:
NCCH2COOC(CH3)3
CAS Number:
1116-98-9
Molecular Weight:
141.17
Beilstein:
1755933
EC Number:
214-243-7
MDL number:
MFCD00001938
UNSPSC Code:
12352100
PubChem Substance ID:
57648301
NACRES:
NA.22

Quality Level

100

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.)

functional group

ester
nitrile

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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

244.4 °F - closed cup

Flash Point(C)

118 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL5659
BCCD8842
1344389V
1334472V
1344389

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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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