32012-16-1

Basic information

• Product Name: N~2~-methylalaninamide(SALTDATA: FREE)
• Synonyms: N~2~-methylalaninamide(SALTDATA: FREE);N~2~-methylalaninamide;Propanamide, 2-(methylamino)-
• CAS NO: 32012-16-1
• Molecular Formula: C₄H₁₀N₂O
• Molecular Weight: 102.135
• Mol File: 32012-16-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 124 °C
• Boiling Point: 220.029°C at 760 mmHg
• Flash Point: 86.871°C
• Appearance: /
• Density: 0.977g/cm³
• Vapor Pressure: 0.116mmHg at 25°C
• Refractive Index: 1.443
• PKA: 16.14±0.50(Predicted)
• CAS DataBase Reference: N~2~-methylalaninamide(SALTDATA: FREE)(CAS DataBase Reference)
• NIST Chemistry Reference: N~2~-methylalaninamide(SALTDATA: FREE)(32012-16-1)
• EPA Substance Registry System: N~2~-methylalaninamide(SALTDATA: FREE)(32012-16-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 32012-16-1(Hazardous Substances Data)

Usage

General Description

N^2^-methylalaninamide, also known as N-methylalaninamide, is a chemical compound that belongs to the class of amides. It has the molecular formula C4H9NO and a molecular weight of 87.12 g/mol. N~2~-methylalaninamide(SALTDATA: FREE) has a melting point of 127-130°C and a boiling point of 244-245°C. It is soluble in water and has a pKa of 8.88 at 25°C. N^2^-methylalaninamide is commonly used in organic synthesis and pharmaceutical research. Its properties and reactivity make it a valuable building block for the synthesis of various compounds, and it has potential applications in drug development and medicinal chemistry.

InChI:InChI=1/C4H10N2O/c1-3(6-2)4(5)7/h3,6H,1-2H3,(H2,5,7)

Upstream product

• 56428-90-1 ethyl-α-methylaminopropionate 
• 16752-54-8 methylaminopropionitrile 
• 497-19-8 sodium carbonate 
• 600-21-5 N-methylalanine 
• 5875-25-2 2-bromo-propionic acid amide 
• 74-89-5 methylamine 

Downstream Products

• 600-21-5 N-methylalanine 
• 95455-39-3 trimethyl-1,2,5 imidazolidinone-4 

Relevant articles and documents

PESTICIDALLY ACTIVE AZOLE-AMIDE COMPOUNDS

Compounds of formula I wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides.

Kinetics and mechanism of the cyclization of ω-(p-nitrophenyl)-hydantoic acid amides: Steric hindrance to proton transfer causes a 104-fold change in rate

The pH-rate profiles for the cyclization of primary 2,3-dimethyl and 2,2,3-trimethyl-hydantoinamides (2-UAm and 3-UAm respectively) differ strikingly from those for the cyclizations of the corresponding N-methylated amides 2-MUAm and 3-MUAm; which are dominated by the water reaction, spanning some 6 pH units. For the cyclization of UAm the plateau extends over no more than two pH units. The difference is due to the slower base-catalyzed cyclization of the N-methylamides. The solvent kinetic isotope effect for this hydroxide-catalyzed reaction is close to 1.2, consistent with a slow protonation by water of the amino-group of the negatively charged tetrahedral intermediate. General base catalysis was observed with bases of pKBH up to 8. The Bronsted β are compatible with a hydrogen bonding mechanism for the GBC. In the gem-dimethyl compounds 3 the leaving group is flanked by substituents on both sides. The N-methyl group in 3-MUAm hinders frontal access of the proton, causing a 14000 fold decrease in rate. This is only 3800 fold in the compound with one methyl group at position 2.

Mecanisme de la reaction de Bucherer-Bergs Comparaison avec l'hydratation basique des α-aminonitriles

The Bucherer-Bergs reaction provides an important tool for the synthesis of α-aminoacids and is the basis of an industrial process for producing methionine.The key compound is the α-aminonitrile 1 which leads to partial decomposition in carbonate buffer as well as in weakly basic aqueous media and to the equilibrated formation of the basic intermediate α-carboxy-aminonitrile 2a.The parameters which control the stability of 2a are summarised.These equlibria are established through an initial fast step which is then followed by the formation of the hydantoin 5a.At a constant pH this formation is first order in α-carboxyaminonitrile 2a via a 5-imino-2-oxazolidinone 3a and an α-isocyanatamide 4a.A comparison of the reactivity of 1 with that of the N-alkylated compouds 7 shows that the rate determining step of the hydantoin formation is the cyclisation of 2a at pH9.But at higher pH, the reaction is controlled by the fast partitioning of the cyclic intermediate 3a between the α-carboxyaminonitrile 2a and the isocyanatamide 4a.This study permits the direct comparison between two mechanism for the synthesis of the racemic α-aminoacids: the Bucherer-Bergs way and the catalytic hydratation of α-aminonitriles.It is clear that carbonic anhydre can be considered as a special carbonyl compound with respect to its reactivity towards α-aminonitriles.