20306-75-6

Basic information

• Product Name: N-Methylacetoacetamide
• Synonyms: Acetoacet-monomethylamide;AcetoN-methylacetamide;Butanamide,N-methyl-3-oxo-;n-methyl-3-oxo-butanamid;N-Methylacetoacetamid;N-Monomethylacetoacetamide;MONOMETHYL ACETOACETAMIDE;MMAA
• CAS NO: 20306-75-6
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• EINECS: 243-723-9
• Product Categories: ACETYLGROUP
• Mol File: 20306-75-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: -3 °C
• Boiling Point: 106°C
• Flash Point: 105 °C
• Appearance: Colourless to yellowish clear liquid
• Density: 1.069
• Vapor Pressure: 0.00403mmHg at 25°C
• Refractive Index: 1.4325-1.4345
• Storage Temp.: 2-8°C
• Solubility: hydrolysis
• PKA: 12.79±0.46(Predicted)
• Water Solubility: hydrolysis
• CAS DataBase Reference: N-Methylacetoacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylacetoacetamide(20306-75-6)
• EPA Substance Registry System: N-Methylacetoacetamide(20306-75-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• Hazardous Substances Data: 20306-75-6(Hazardous Substances Data)

Usage

Description

N-Methylacetoacetamide, also known as MMAA, is an organic compound that serves as an intermediate in the production of various chemicals and pharmaceuticals. It is a colorless to yellowish clear liquid with a minimum purity of 70% in water.

Uses

Used in Insecticide Production:
N-Methylacetoacetamide is used as an intermediate in the manufacture of insecticides, specifically monocrotophos. It plays a crucial role in the production process, contributing to the effectiveness of the final product in controlling insect pests.
Used in Pharmaceutical Synthesis:
N-Methylacetoacetamide serves as a starting material in the synthesis of 1-Carbamoyl-2-oxopropyl acetate, which is achieved with the aid of (diacetoxyiodo)benzene (DIB) as the oxidant. N-Methylacetoacetamide has potential applications in the pharmaceutical industry.
Additionally, N-Methylacetoacetamide is used as a reagent in the synthesis of 10H-Phenothiazines, a class of compounds known for their biological activity against regulatory enzymes involved in inflammatory diseases. This makes it a valuable component in the development of medications targeting inflammation and related conditions.

InChI:InChI=1/C5H9NO2/c1-4(7)3-5(8)6-2/h3H2,1-2H3,(H,6,8)

Upstream product

• 67-56-1 methanol 
• 10128-60-6 3,6-dimethyl-2H-1,3-oxazine-2,4(3H)-dione 
• 76599-91-2 1,3,6-Trimethyl-5-oxo-2,6-diazabicyclo<2.2.0>hex-2-ene 
• 7732-18-5 water 
• 57091-31-3 2,5-dimethyl-isoxazolium; iodide 
• 593-51-1 methylamine hydrochloride 
• 141-97-9 ethyl acetoacetate 
• 1694-31-1 tert-butyl acetoacetate 
• 74-89-5 methylamine 
• 4116-10-3 α-chloro-N-methylacetoacetamide 
• 96-31-1 N,N'-Dimethylurea 
• 541-50-4 2-acetoacetic acid 
• 76234-89-4 N-methyl-2-aminoethylidene-3-methylimino-butanoamide 
• 90031-14-4 2,5-dimethylisoxazolinum methyl sulfate 

Downstream Products

• 132361-88-7 (Z)-3-(1,2-Diphenyl-ethylamino)-but-2-enoic acid methylamide 
• 132361-91-2 (Z)-3-[2-(4-Chloro-phenyl)-1-phenyl-ethylamino]-but-2-enoic acid methylamide 
• 132361-98-9 β-(α-ethylbenzylamino)-N-methylcrotonamide 
• 132361-84-3 (Z)-3-[1-(3,4-Dichloro-phenyl)-ethylamino]-but-2-enoic acid methylamide 
• 132361-86-5 (Z)-3-(1-Phenyl-butylamino)-but-2-enoic acid methylamide 
• 132361-85-4 (Z)-3-[1-(4-Chloro-phenyl)-propylamino]-but-2-enoic acid methylamide 
• 132361-89-8 (Z)-3-[2-(2,4-Dimethyl-phenyl)-1-phenyl-ethylamino]-but-2-enoic acid methylamide 
• 132361-90-1 (Z)-3-[2-(4-Ethyl-phenyl)-1-phenyl-ethylamino]-but-2-enoic acid methylamide 
• 118465-58-0 5-acetyl-6-methylamino-1,4-dimethyl-2-pyridone 
• 118465-57-9 3-(diethoxyphosphinothioyl)oxy-(Z)-2-butenoic acid N-methylamide 
• 141544-04-9 2-(2-chlorophenyl)-4-hydroxy-N,N',4-trimethyl-6-oxocyclohexane-1,3-dicarboxamide 
• 141354-13-4 6-Methyl-4-(3-nitro-phenyl)-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methylamide 
• 141354-00-9 6-Methyl-4-(3-nitro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methylamide 
• 132599-15-6 4-hydroxy-2-(4-nitrophenyl)-N,N',4-trimethyl-6-oxocyclohexane-1,3-dicarboxamide 

Relevant articles and documents

PHOTOCHEMISTRY OF 4(3H)-PYRIMIDIN-4-ONES. FORMATION OF MEDIUM-RING LACTAMS

Upon irradiation, 4(3H)-pyrimidin-4-one(1) afforded a di-imine derivate(2), which, when hydrolyzed in an acidic methanol solution, gave N-methyl acetoacetamide(3).On the other hand, the fused 4(3H)-pyrimidin-4-ones, (4) and (5), gave medium ring lactams (6) and (7), which were hydrolyzed in an acidic methanol solution to give (8) and (9), respectively.

Asymmetric Synthesis of α,β-Epoxy-?-lactams through Tandem Darzens/Hemiaminalization Reaction

A catalytic asymmetric tandem Darzens/hemiaminalization reaction of glyoxals with α-bromo-β-esteramides or α-bromo-β-ketoamide was accomplished in the presence of a chiral N,N′-dioxide/Yb(III) complex. Various chiral α,β-epoxy-?-lactams were obtained in moderate to good yields with excellent diastereo- and enantioselectivities. The versatility of the transformation is illustrated in the formal synthesis of berkeleyamide D.

A convenient method for reduction dehalogenation of α-halocarbonyl compounds using benzenethiol in K+/CH3CN system

Benzenethiol, as a reductive agent for the dehalogenation of various α-halocarbonyl compounds, is investigated in the K+/CH3CN system. The reaction affords the reduced compounds in high yields under mild reaction conditions, especially α-chlorocarbonyl compounds. Furthermore, the reaction performed under ultrasonic irradiation greatly shortens the reaction time.