35356-70-8

Basic information

• Product Name: Methyl 2-acetamidoacrylate
• Synonyms: 2-ACETAMIDOACRYLIC ACID METHYL ESTER;METHYL 2-ACETAMIDOACRYLATE;Ac-DL-Dha-OMe~2-Acetamidoacrylic acid methyl ester~N-Acetyldehydroalanine methyl ester;2-ACETAMIDOACRYLIC ACID METHYL ESTER 95+%;ac-dl-dha-ome;2-Acetylaminoacrylic acid methyl ester;Methyl 2-(acetylamino)acrylate;Methyl 2-(acetylamino)propenoate
• CAS NO: 35356-70-8
• Molecular Formula: C₆H₉NO₃
• Molecular Weight: 143.14
• Product Categories: AcrylateCarbonyl Compounds;Acrylic Monomers;C6 to C7;Esters;Monomers
• Mol File: 35356-70-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 50-52 °C(lit.)
• Boiling Point: 104 °C8 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.3075 (rough estimate)
• Vapor Pressure: 0.000618mmHg at 25°C
• Refractive Index: 1.4340 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• BRN: 1812208
• CAS DataBase Reference: Methyl 2-acetamidoacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-acetamidoacrylate(35356-70-8)
• EPA Substance Registry System: Methyl 2-acetamidoacrylate(35356-70-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 35356-70-8(Hazardous Substances Data)

Usage

Uses

Methyl 2-acetamidoacrylate exhibits anti-inflammatory property and decreases induced acute kidney injury in mice.

General Description

Conjugated addition of secondary amines, imidazole and pyrazole to methyl 2 methyl 2-acetamidoacrylate in the presence of a catalyst results in the formation of β-Dialkylamino-α-alanine and β-(N-heteroaryl)-α-alanine derivatives. Methyl-2-acetamidoacrylate (M2AA) is an anti-inflammatory agent. The catalytic reaction of methyl 2-acetamidoacrylate with Grignard′s reagents affords α-amino esters. M2AA can form thermosensitive copolymers with methyl acrylate.

InChI:InChI=1/C6H9NO3/c1-4(6(9)10-3)7-5(2)8/h1H2,2-3H3,(H,7,8)

Upstream product

• 7652-46-2 Ac-Cys-OMe 
• 108036-67-5 Co(CO)3Ru(C(CH₃)(COOCH₃)NHC(O)CH₃)(CO)2W(C₅H₅)(CO)2CCH₃ 
• 108036-64-2 Co(CO)3Ru(C(CH₃)(COOCH₃)NHC(O)CH₃)(CO)2Mo(C₅H₅)(CO)2CC₆H₅ 
• 108036-67-5 (μ3-MeC)CoRuWCp(CO)7(C(Me)(COOMe)NHC(Me)O) 
• 16088-62-3 (S)-Propylene oxide 

Downstream Products

• 72431-82-4 methyl 2-endo-acetamidobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate 
• 111317-85-2 2-Benzoylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 
• 108868-37-7 4-bromo-3-(2-acetamido-2-carbomethoxyethen-1-yl)-1-tosylindole 
• 73344-28-2 2-Acetylamino-3-(3-trifluoromethyl-phenylsulfanyl)-propionic acid methyl ester 
• 170305-15-4 N-acetyl-β-(1-pyrazolyl)alanine methyl ester 
• 848555-92-0 2-acetamido-3-(1-imidazolyl)propanoic acid 
• 863487-03-0 methyl α-acetamido-β-(2-bromophenyl)-acrylate 
• 556828-99-0 (Z)-2-Acetylamino-3-(4-acetyl-phenyl)-acrylic acid methyl ester 
• 910567-25-8 methyl (Z)-2-acetamido-3-(2'-isopropyl-6'-methylphenyl)-2-propenoate 
• 910567-26-9 methyl (Z)-2-acetamido-3-(2',4',6'-trimethylphenyl)-2-propenoate 
• 126312-79-6 methyl (Z)-2-acetamido-3-(2',6'-dimethylphenyl)-2-propenoate 
• 910567-28-1 methyl (Z)-2-acetamido-3-(3',5'-dimethylphenyl)-2-propenoate 

Relevant articles and documents

Synthesis of water-soluble hypervalent iodine reagents for fluoroalkylation of biological thiols

New open-chain and water-soluble hypervalent iodine reagents were synthesized and used for the transfer of fluoroalkyl groups to sulfur atoms of cysteine and cysteine-containing peptides under biocompatible conditions. Some of the reagents displayed excellent reactivity despite their limited stability in aqueous media. In reactions with a short cysteine-containing peptide, in addition to the expected S-fluoroalkylated product, a range of side-products were obtained. The amount of side-products depended on the conditions used (type of reagent, concentration, and pH). With highly activated hypervalent iodine reagents, a new reactive mode was observed-reaction with disulfides to form fluoroalkyl thiols.

Rapid cross-metathesis for reversible protein modifications via chemical access to se-allyl-selenocysteine in proteins

Cross-metathesis (CM) has recently emerged as a viable strategy for protein modification. Here, efficient protein CM has been demonstrated through biomimetic chemical access to Se-allyl-selenocysteine (Seac), a metathesis-reactive amino acid substrate, via dehydroalanine. On-protein reaction kinetics reveal a rapid reaction with rate constants of Seac-mediated-CM comparable or superior to off-protein rates of many current bioconjugations. This use of Se-relayed Seac CM on proteins has now enabled reactions with substrates (allyl GlcNAc, N-allyl acetamide) that were previously not possible for the corresponding sulfur analogue. This CM strategy was applied to histone proteins to install a mimic of acetylated lysine (KAc, an epigenetic marker). The resulting synthetic H3 was successfully recognized by antibody that binds natural H3-K9Ac. Moreover, Cope-type selenoxide elimination allowed this putative marker (and function) to be chemically expunged, regenerating an H3 that can be rewritten to complete a chemically enabled "write (CM)-erase (ox)-rewrite (CM)" cycle.

Reversible and diastereospecific olefin insertion into a cluster Ru-H unit. Formation of metallacycles with tertiary carbon-ruthenium σ bonds

The chiral hydrido metal clusters (μ3-RC)Ru-CoMCp(CO)8H with R = Me or Ph and M = Mo or W react reversibly with the prochiral alanine precursor acetamido acrylic acid methyl ester according to a Markownikow-type insertion of the X2C=CH2 substrate into a Ru-H bond. The cluster products formed consist of only one pair of the possible diastereoisomers rendering the reaction diastereospecific. The resulting σ-alkyl cluster complexes contain a Ru-C-N-C-O metallacycle with a tertiary carbon atom bound to ruthenium.