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310581

Sigma-Aldrich

Ethyl 2-cyano-3-methyl-2-butenoate

97%

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Linear Formula:
(CH3)2C=C(CN)CO2C2H5
CAS Number:
Molecular Weight:
153.18
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

Assay

97%

refractive index

n20/D 1.464 (lit.)

bp

98-99 °C/1 mmHg (lit.)

density

1.014 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)\C(C#N)=C(\C)C

InChI

1S/C8H11NO2/c1-4-11-8(10)7(5-9)6(2)3/h4H2,1-3H3

InChI key

PZMDAADKKAXROL-UHFFFAOYSA-N

General description

Ethyl 2-cyano-3-methyl-2-butenoate, a highly activated acceptor, undergoes the phospha-Michael reaction upon trituration of the reagents at room temperature.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

224.6 °F

Flash Point(C)

107 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Heather K Lenker et al.
The Journal of organic chemistry, 77(3), 1378-1385 (2012-01-17)
The addition of P(O)-H bonds to internal alkenes has been accomplished under solvent-free conditions without the addition of a catalyst or radical initiator. Using a prototypical secondary phosphine oxide, a range of substrates including cinnamates, crotonates, coumarins, sulfones, and chalcones

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