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Usage

Uses

Used in Chemical Synthesis:
Dimethylaminoacetonitrile is used as a chemical intermediate for the production of various chemicals. Its unique structure allows it to be a versatile building block in the synthesis of a wide range of compounds, making it valuable in the chemical industry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Dimethylaminoacetonitrile is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form a variety of chemical bonds makes it an essential component in the development of new drugs and medications.
Used in Agrochemical Industry:
Dimethylaminoacetonitrile is also utilized in the agrochemical industry as a precursor for the synthesis of various agrochemicals. Its role in creating essential compounds for crop protection and pest control highlights its importance in this sector.
Used in Flavor and Fragrance Industry:
In the flavor and fragrance industry, Dimethylaminoacetonitrile is used as a starting material for the creation of unique scents and flavors. Its ability to form complex molecules with distinct olfactory properties makes it a valuable component in the development of new fragrances and flavorings.

Reactivity Profile

Dimethylaminoacetonitrile has an amine and nitrile group. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Safety Profile

Poison by ingestion, skin contact, and ocular routes. Moderately toxic by inhalation. A skin and eye irritant. A dangerous fire hazard when exposed to heat or flame. When heated to decomposition it emits toxic fumes of NOx and CN-. See also NITRILES.

InChI:InChI=1/C4H8N2/c1-6(2)4-3-5/h4H2,1-2H3/p+1

Upstream product

• 51-82-1 dimethyl-dithiocarbamic acid dimethylaminomethyl ester 
• 151-50-8 potassium cyanide 
• 19555-13-6 2-(dimethylamino)malononitrile 
• 632-22-4 tetramethylurea 
• 2074-87-5 carbon nitride 
• 75-50-3 trimethylamine 
• 143-33-9 sodium cyanide 
• 50-00-0 formaldehyd 
• 74-90-8 hydrogen cyanide 
• 124-40-3 dimethyl amine 
• 14002-21-2 dimethylaminomethanol 
• 7732-18-5 water 
• 7677-24-9 trimethylsilyl cyanide 
• 1209493-93-5 Me₂NCH₂OCH₂OCH₂Ph 

Downstream Products

• 771-51-7 indole-3-acetonitrile 
• 598-56-1 N,N-dimethyl-ethanamine 
• 15364-56-4 dimethylaminoacetone 
• 104-19-8 N-methyl-N'-(2-dimethylaminoethyl)piperazine 
• 3319-03-7 2-dimethylamino-1-phenyl-ethanone 
• 1118-68-9 dimethylaminoacetic acid 
• 6318-44-1 2-dimethylamino-acetamide 
• 67015-08-1 2-dimethylamino-acetamide oxime 
• 108-00-9 N,N-dimethylethylenediamine 
• 87192-49-2 (2-amino-2-hydroxyimino-ethyl)-benzyl-dimethyl-ammonium; chloride 
• 114049-98-8 1-dimethylamino-3-phenyl-acetone 
• 82272-28-4 cyanomethylenetrimethylammonium iodide 
• 6968-81-6 2-(dimethylamino)-3-hydroxy-3,3-diphenylpropionitrile 
• 432-23-5 2,2-dimethyl-6-methylenecyclohexane-1-carbaldehyde 

Relevant academic research and scientific papers

Degradation of gaseous unsymmetrical dimethylhydrazine by vacuum ultraviolet coupled with MnO2

In this study, α-, β-, and δ-MnO2 were prepared by a uniform hydrothermal method and then coupled with vacuum ultraviolet (VUV) for the degradation of gaseous unsymmetrical dimethylhydrazine (UDMH). The performance in the removal of UDMH, by-product distribution and mechanism were systematically investigated. The catalysts were characterized by X-ray diffraction (XRD), N2 adsorption/desorption, Field Emission Scanning Electron Microscopy (FE-SEM), Raman, thermogravimetry (TG), Fourier-transform infrared (FT-IR), X-ray photoelectron spectroscopy (XPS) and electron paramagnetic resonance (EPR) to investigate the factors affecting the catalytic activity. The results showed that O2 and H2O were essential for the removal of UDMH. Photooxidation and ozone catalytic oxidation contribute to the removal and mineralization of UDMH. The integrated process considerably improved the removal and mineralization of UDMH by ozone catalytic oxidation. More reactive oxygen species were generated in the integrated process. The catalytic activity of the prepared catalysts follows the order: δ-MnO2 > α-MnO2 > β-MnO2. δ-MnO2 displayed the highest removal rate of 100% and a CO2 concentration of 42 ppmv. The good performance of δ-MnO2 was mainly attributed to the large number of surface oxygen vacancies.

TiO2-reduced graphene oxide for the removal of gas-phase unsymmetrical dimethylhydrazine

Unsymmetrical dimethylhydrazine (UDMH) contaminated waste gas and related intermediates pose a great threat to human health. TiO2-reduced graphene oxide aerogel (rGA) samples with different graphene content levels were synthetized and characterized for the degradation of UDMH. The effects of GO content, humidity, and temperature were investigated under UV and VUV light, with highest UDMH conversion values of 68% and 95%, respectively. Compared with pure TiO2, the enhanced degradation activity of TiO2-rGA under UV light can be attributed to a synergetic effect between absorption and photocatalysis, while the high UDMH conversion under VUV light relies on photolysis and ozonation. The high oxygen-containing group content, rather than a high SSA, and electron trapping by graphene are key factors determining the outstanding performance of TiO2-rGA with 80 mg of GO. The prepared TiO2-graphene aerogels are promising for the degradation of gas-phase UDMH. This journal is

Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations

Simple and efficient methods have been developed to obtain cyanomethylamines and azidomethylamines using reactions of methoxymethylamines with TMSCN and TMSN3, respectively. In the case of dimethylformamide dimethylacetal, only one MeO group wa

Heterocyclic compounds

The present invention relates to heterocyclic compounds which have been found to have anti-tumour activity. More specifically, the invention concerns Pyrrolo ?3,2-b! carbazoles, 1H-Benzofuro ?3,2-f! indoles and 1H-?1! Benzothieno ?2,3-f! indoles, methods for their preparation, pharmaceutical formulations containing them and their use as anti-tumour agents.

Substituent effects on the C-C bond strength, 20 geminal substituent effects, 14: Stabilization of the cyano(dimethylamino)methyl radical - Synergistic effect due to interaction between α-amino and α-cyano groups on the radical stabilization energy

The thermolysis reactions of 3a and 2a, b were studied over a temperature range of 40°C and the activation parameters were determined. They were compared with the activation parameters of structurally comparable hydrocarbons of similar strain in order to obtain the radical stabilization enthalpies RSEs of the cyano(dimethylamino)methyl radical 1a. For this comparison the geminal interaction enthalpies of the cyano and the dimethylamino groups in the ground state had to be determined for the series of amino nitrites 4a-4c and 4j-4n by thermochemical methods. The geminal interaction in the ground state varies between -0.6 kcal/mol stabilization in 4a and a destabilization of +10.7 and +7.0 kJ mol-1 for secondary and tertiary α-dialkylaminonitriles, respectively. A synergistic (i.e. more than additive) stabilization enthalpy of 26 kJ mol-1 of la was found in contrast to predictions in the literature. This stabilization is interpreted by conjugation between the substituents, which are separated by the radical center. (Chemical Equation Presented) VCH Verlagsgesellschaft mbH, 1997.

FORMATION OF DIALKYLAMINOACETONITRILE FROM N,N-DIALKYLAMIDES IN AN RF PLASMA

An unprecedented transformation of N,N-dimethylamides into dimethylaminoacetonitrile (1) by passing through a 13.56 MHz gaseous discharge was found.Diethylaminoacetonitrile (2) was similarly given from N,N-dimethylformamide.

Direct Spectrophotometric Observation of an O-Acylisourea Intermediate: Concerted General Acid Catalysis in the Reaction of Acetate Ion with a Water-soluble Carbodi-imide

The rate constants for formation and decay of O-acylureas from carbodi-imide and acids have been measured using aqueous media.The O-acetylisourea from acetate and N-ethyl-N'-(3-trimethylammoniopropyl)carbodi-imide (ETC) possesses an acidic group of pK 6.8 and decomposes (k2) in its acid form as the dication by reaction with acetate ion or water.The reaction of the carboxylate anion with ETC is general acid catalysed (k1 = ΣkHA-> and the deuterium oxide solvent isotope effect indicates a rate-limiting proton transfer except for the oxonium ion acting as acid.The Broensted α value for variation of the structure of HA (0.67) is consistent with a proton transfer concerted with nucleophilic attack by the acetate anion.A concerted mechanism is consistent with the weak basicity of the carbodi-imide and the weak acidity of the isourea adduct.The third-order term involving acetic acid, acetate ion, and carbodi-imide carries ca. 60 percent of the total reaction flux at pH 6.80 and 1 M total acetic acid buffer concentration.At this pH ca. 40 percent of the reaction flux goes through the stepwise 'Khorana' mechanism with specific acid catalysis.Intramolecular general acid catalysis is demonstrated to occur in the reaction of 2,2-diethylmalonic acid monoanion with ETC and the effective molarity compared with intermolecular catalysis is 15 M.Attack of carboxylate anions on ETC with N-chloroethylmorpholinium ion as the general acid has a Broensted type βN of 0.46.

Direct vs. Indirect Mechanisms in Organic Electrochemistry. Estimates of Activation Energies for Hydrogen Atom Transfer Processes of Relevance in Indirect Mechanisms Using the Bond Energy-Bond Order (BEBO) and Equibonding Methods

Activation energies for a number of hydrogen abstraction reactions of interest in mechanistic organic electrochemistry have been calculated using the bond energy-bond-order (BEBO) and equibonding method.The main emphasis has been put on processes with bearing on the problem of deciding between direct and indirect mechanisms in anodic oxidation, viz. acyloxylation, hydroxylation, methoxylation, nitrooxylation, cyanation, carbomethoxylation and azidation.The results indicate that indirect mechanisms might play a more important role than presently assumed.

Process for the preparation of unsaturated aldehydes

Process for the preparation of unsaturated aldehydes, in particular γ,δ-unsaturated aldehydes, which comprises reacting an amino-nitrile with a basic or a neutral agent. The products obtained in accordance with the process of the invention are useful intermediates for the preparation of flavoring ingredients.