Methyl 2-acetamidoacrylate

Methyl 2-acetamidoacrylate
Names
	Preferred IUPAC name Methyl 2-acetamidoprop-2-enoate
	Other names Methyl 2-(acetylamino)propenoate
Identifiers
CAS Number	35356-70-8;
3D model (JSmol)	Interactive image;
ChemSpider	89087;
ECHA InfoCard	100.107.415
EC Number	609-121-9;
PubChem CID	98644;
UNII	GT3ARJ50FG;
CompTox Dashboard (EPA)	DTXSID70188849 ;
	InChI InChI=1S/C6H9NO3/c1-4(6(9)10-3)7-5(2)8/h1H2,2-3H3,(H,7,8) Key: SMWNFFKPVLVOQQ-UHFFFAOYSA-N;
	SMILES CC(=O)NC(=C)C(=O)OC;
Properties
Chemical formula	C6H9NO3
Molar mass	143.142 g·mol−1
Appearance	white solid
Melting point	75–76 °C (167–169 °F; 348–349 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methyl 2-acetamidoacrylate is the organic compound with the formula CH₂=C(NHC(O)CH₃)CO₂CH₃. It is the methyl ester of an N-acetyl acrylic acid, which in turn is a derivative of the unstable compound dehydroalanine. Acetylation of the amine in the latter compound prevents tautomerization. It is a white solid.

The compound can be prepared from methyl 2-acetamidopropionate (CH₃CH(NHC(O)CH₃)CO₂CH₃), i.e. the methyl ester of N-acetylalanine.^[1] Methyl 2-acetamidoacrylate undergoes Michael reactions, e.g. by thiolates.^[2]

References

^ Kolar, A. J.; Olsen, R. K. (1977). "A Convenient, Large-Scale Preparation of 2-Acetamidoacrylic Acid and Its Methyl Ester". Synthesis. 1977 (7): 457–9. doi:10.1055/s-1977-24439. S2CID 96352441.
^ Petracca, R.; Bowen, K. A.; McSweeney, L.; O’Flaherty, S.; Genna, V.; Twamley, B.; Devocelle, M.; Scanlan, E. M. (2019). "Chemoselective Synthesis of N-Terminal Cysteinyl Thioesters via β,γ-C,S Thiol-Michael Addition". Organic Letters. 21 (9): 3281–3285. doi:10.1021/acs.orglett.9b01013. PMID 31017793. S2CID 131775844.

[1] Kolar, A. J.; Olsen, R. K. (1977). "A Convenient, Large-Scale Preparation of 2-Acetamidoacrylic Acid and Its Methyl Ester". Synthesis. 1977 (7): 457–9. doi:10.1055/s-1977-24439. S2CID 96352441.

[2] Petracca, R.; Bowen, K. A.; McSweeney, L.; O’Flaherty, S.; Genna, V.; Twamley, B.; Devocelle, M.; Scanlan, E. M. (2019). "Chemoselective Synthesis of N-Terminal Cysteinyl Thioesters via β,γ-C,S Thiol-Michael Addition". Organic Letters. 21 (9): 3281–3285. doi:10.1021/acs.orglett.9b01013. PMID 31017793. S2CID 131775844.

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