methyl 2-acetamidoprop-2-enoate

• ChemBase ID: 150889
• Molecular Formular: C6H9NO3
• Molecular Mass: 143.14056
• Monoisotopic Mass: 143.05824315
• SMILES: CC(=O)NC(=C)C(=O)OC
• Canonical SMILES: COC(=O)C(=C)NC(=O)C
• InChI: InChI=1S/C6H9NO3/c1-4(6(9)10-3)7-5(2)8/h1H2,2-3H3,(H,7,8)
• InChIKey: SMWNFFKPVLVOQQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-acetamidoprop-2-enoate
• IUPAC Traditional name: methyl 2-acetamidoprop-2-enoate
• Synonyms: Methyl 2-acetamidoacrylate; Ac-DL-Dha-OMe; 2-Acetamidoacrylic acid methyl ester; 2-乙酰胺基丙烯酸甲酯; 2-乙酰氨基丙烯酸甲酯

Database IDs

• CAS Number: 35356-70-8
• MDL Number: MFCD00013394
• Beilstein Number: 1812208
• PubChem SID: 162245049; 24859082
• PubChem CID: 98644

CALCULATED PROPERTIES

• Acid pKa: 12.697392
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.42481732
• LogD (pH = 7.4): -0.42481926
• Log P: -0.4248173
• Molar Refractivity: 35.1292 cm^3
• Polarizability: 13.588454 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 49-51°C; 50-52 °C(lit.)
• Boiling Point: 103-104°C/8mm; 104 °C/8 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%; 99%
• Linear Formula: H2C=C(NHCOCH3)CO2CH3

DETAILS

Sigma Aldrich - 317519

Packaging
1, 5 g in glass bottle

REFERENCES

• Building block for amino acid synthesis.
• Heck coupling with 4-iodo-3,5-dimethylphenyl acetate, promoted by palladium acetate and Tri(o-tolyl)phosphine, A12093, is one of the key steps in a convenient asymmetric synthesis of the unnatural amino acid 2,6-dimethyl-L-tyrosine: Synthesis, 741 (1992).
• Asymmetric catalytic hydrogenation in supercritical carbon dioxide in the presence of a chiral rhodium catalyst gives the N-acetylalanine methyl ester in 99.5% ee: J. Am. Chem. Soc., 117, 8277 (1995).
• Undergoes rhodium-catalyzed addition with potassium organotrifluoroborates to give substituted alanine derivatives: Eur. J. Org. Chem., 69 (2004). In the presence of a Rh-BINAP catalyst, chiral amino acid derivaitives are formed with good ee: Angew. Chem. Int. Ed., 43, 719 (2004).