1738-25-6

Basic information

• Product Name: Dimethylaminopropionitrile
• Synonyms: 2-DIMETHYLAMINOETHYL CYANIDE;2-Dimthylaminoethyl cyanide;3-(DIMETHYLAMINO)PROPIONITRILE;3-(DIMETHYLAMINO)PROPIONONITRILE;BETA-DIMETHYLAMINOPROPIONITRILE;β-(Dimethylamino)propionitrile;DMAPN;3-(dimethylamino)-propanenitril
• CAS NO: 1738-25-6
• Molecular Formula: C₅H₁₀N₂
• Molecular Weight: 98.15
• EINECS: 217-090-4
• Product Categories: Aromatic Nitriles
• Mol File: 1738-25-6.mol

Chemical Properties

• Melting Point: −43 °C(lit.)
• Boiling Point: 171 °C750 mm Hg(lit.)
• Flash Point: 145 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.87 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.24mmHg at 25°C
• Refractive Index: n20/D 1.426(lit.)
• Storage Temp.: 2-8°C
• PKA: 8.17±0.28(Predicted)
• Explosive Limit: 1.6-11.4%(V)
• Water Solubility: 0.5 g/L (20 ºC)
• BRN: 773779
• CAS DataBase Reference: Dimethylaminopropionitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethylaminopropionitrile(1738-25-6)
• EPA Substance Registry System: Dimethylaminopropionitrile(1738-25-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-36/38-21
• Safety Statements: 26-36/37-24/25
• RIDADR: 2927
• WGK Germany: 1
• RTECS: UG1575000
• F: 8
• TSCA: Yes
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 1738-25-6(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
Dimethylaminopropionitrile is used as a solvent, dielectric fluid, and an intermediate in the chemical synthesis process. Its versatile properties make it a valuable component in various chemical reactions.
2. Used in Polymerization:
Dimethylaminopropionitrile is employed to initiate organic polymerization during the synthesis of class I hybrid poly(N-isopropylacrylamide)/silica hydrogels. This application highlights its role in the development of advanced materials with specific properties.
3. Used in Cysteine Modifying Agents:
The compound is also used in the preparation of cysteine modifying agents based on the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide (4-DMN). This application demonstrates its importance in the field of biochemistry and molecular biology.
4. Used in the Manufacturing Industry:
Dimethylaminopropionitrile is utilized in the manufacture of polyurethane foam, a widely used material in various industries, such as furniture, bedding, automotive, and construction, due to its excellent properties like flexibility, durability, and insulation.
5. Used in the Electronics Industry:
As a dielectric fluid, Dimethylaminopropionitrile is used in the electronics industry, particularly in capacitors and transformers, to provide insulation and improve the performance of these components.

Production Methods

3-Dimethylaminopropionitrile is derived from heating barium ethyl sulfate and KCN with subsequent distillation.

Reactivity Profile

Dimethylaminopropionitrile is combustible but non-flammable (flash point > 140°F), reacts with oxidizing agents (Hazardous Chemicals Desk Reference, p. 426 (1987)). Reacts violently with LIAlH4, a strong reducing agent. Emits toxic oxides of nitrogen and cyanide fumes when heated to decomposition.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and skin contact. A skin and eye irritant. Flammable liquid when exposed to heat, flame, or oxidizers; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits highly toxic fumes of NOx and CN-. See also NITRILES.

InChI:InChI=1/C5H10N2/c1-7(2)5-3-4-6/h3,5H2,1-2H3/p+1

Upstream product

• 25368-52-9 1,1-dimethyl-2-(2-methylallylidene)hydrazine 
• 124-40-3 dimethyl amine 
• 109-78-4 3-Hydroxypropionitrile 
• 107-13-1 acrylonitrile 
• 2417-90-5 bromopropionitrile 
• 506-59-2 N,N-dimethylammonium chloride 
• 15848-59-6 Trimethyl-(2,3-dichlor-3-methyl-butyl)-ammonium 
• 51822-55-0 N-dimethylaminomethyl-phthalimide 
• 372-09-8 cyanoacetic acid 
• 110-67-8 3-Methoxypropionitrile 
• 1391906-41-4 2-(dimethylamino)ethyl ethyl carbonate 

Downstream Products

• 3088-41-3 3-(piperidin-1-yl)propionitrile 
• 3314-35-0 3-Amino-1-phenyl-2-pyrazoline 
• 6463-32-7 1-(p-tolyl)-3-amino-Δ²-pyrazoline 
• 42350-94-7 (2-cyano-ethyl)-trimethyl-ammonium; iodide 
• 98138-26-2 3-(dimethylamino)propanamidoxime 
• 109-55-7 1-amino-3-(dimethylamino)propane 
• 10123-62-3 diethyl (2-cyanoethyl)phosphonate 
• 6711-48-4 N,N-bis-(3-dimethylaminopropyl)amine 
• 81676-65-5 Methyl-<3-nitro-4-dimethylamino-phenyl>-sulfon 
• 18076-02-3 hydrochloride of 3-dimethylaminopropionitrile 
• 107-13-1 acrylonitrile 
• 17417-10-6 2-cyano-4-nitro-N,N-dimethylaniline 
• 82-38-2 1-(methylamino)anthraquinone 
• 5960-55-4 1-dimethylaminoanthraquinone 

Relevant articles and documents

Addition of secondary amines to α,β-unsaturated carbonyl compounds and nitrites by using microstructured reactors

Several additions of amines to α,β-unsaturated carbonyl compounds (Michael additions) were performed in a continuous-flow microstructured reactor rig and compared to the respective batch reaction. Dimethylamine/diethylamine/piperidine and acrylic acid ethyl ester/acrylonitrile were employed as two sets of reactants, giving six reactions. Some of these reactions are highly exothermal. Using the traditional batch procedure the olefin must be added quite slowly to the diluted amine to ensure temperature control and safe operation; especially this is necessary for the addition of dimethylamine (40 mass % aqueous solution) to acrylonitrile. Good yields (>85%) are achieved in this way; however, processing time is very long (17-25 h). To reveal the intrinsic kinetic potential and thus to accelerate these reactions, the reactants were mixed in a continuous-flow microstructured reactor rig which allows rapid mixing and efficient removal of the reaction heat. In this way, reaction time was decreased to a few seconds up to about half an hour, which is a change by 2 orders of magnitude. While the yields achieved with the continuous-flow microstructured reactor rig matched those for the batch procedure, the space-time yields for the microflow processing are much higher, in the best case by a factor of about 650.

Cesium fluoride catalyzed Aza-Michael addition reaction in aqueous media

A green approach to the Aza-Michael addition reaction between an amine and α,β-unsaturated compounds has been achieved by conventional as well as non-conventional methods. The reaction is catalyzed by cesium fluoride (CsF) in aqueous media at ambient temperature to afford the product in excellent yield. Ultrasound irradiation has been used as a non-conventional energy source, which reduces the reaction time with improved product yield.

N-donor ligand as catalyst: A simple Aza-Michael addition reaction in aqueous media

(Chemical Equation Presented) A novel approach for the Aza-Michael addition reactions between various amines and α,β-unsaturated esters, nitriles and ketones using N-donor Ligand catalyst (3 mol %) is described. The reactions are carried out in aqueous media at an ambient temperature to afford the products in excellent yields.

Insights into Thiourea-Based Bifunctional Catalysts for Efficient Conversion of CO2to Cyclic Carbonates

The bifunctional thiourea catalyst system with both electrophilic and nucleophilic centers has been certified to be effective for fixing CO2 under mild reaction conditions; however, many questions remain, especially concerning the relationship between str

PREPARATION OF DIAMINE VIA THE PREPARATION OF AMINONITRILE

A continuous method (P) for preparing diamine is described. The method includes reacting the corresponding alkene nitrile with the corresponding monoamine in order to form the corresponding aminonitrile. The monoamine can be introduced in molecular excess with respect to the alkene nitrile, wherein the unreacted monoamine is recirculated to the reaction; followed by reducing the aminonitrile produced by hydrogen in the presence of at least one alkali-metal hydroxide, water, and a hydrogenation catalyst; and purifying the diamine.

Practical preparation of trimethoprim: A classical antibacterial agent

An efficient, simple, and mild preparation of the classical antibacterial agent trimethoprim (1) was achieved in 85% overall yield from 3,4,5-trimethoxybenzaldehyde (2). First, the addition of propenenitrile (3) with dimethylamine almost quantitatively afforded 3-dimethylaminopropanenitrile (7). Then, by condensation of 7 with 2 as well as the continuous replacement of 3-dimethylamino group with aniline in situ, the key intermediate 3-anilino-2-(3,4,5-trimethoxybenzyl)propenenitrile (9) was obtained in an excellent yield of 91% with a one-pot procedure. Finally, the cyclization of 9 with guanidine nitrate furnished 1 in yields as good as 95% in the presence of the excessive sodium methoxide. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

A novel photodegradable hyperbranched polymeric photoresist

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PROCESS FOR THE PREPARATION OF AMINONITRILE AND DIAMINE, AND CORRESPONDING DEVICES

The present invention relates to a continuous process for the preparation of an aminonitrile comprising the stages of: a) formation of the aminonitrile by reaction between an alkenyl nitrile, mixed with aminonitrile, and a monoamine introduced in molar excess with respect to the alkenyl nitrile; b) separation of the unreacted monoamine and the aminonitrile; c) reaction between the monoamine separated during stage b) and all or part of the alkenyl nitriie in order to form a mixture of aminonitrile and of unreacted alkenyl nitrile, with the alkenyl nitrile being introduced in molar excess with respect to the said monoamine; d) transfer of the mixture of aminonitrile and alkenyl nitrile resulting from stage c) to the reaction of stage a), e) in the case where only a portion of the alkenyl nitrile is introduced during stage c), introduction of the remaining molar amount of alkenyl nitrile into the mixture of stage d); the total molar amount of alkenyl nitrile introduced during stages c) and e) being equal to the molar amount of monoamine introduced during stage a). The present invention also relates to a process for the preparation of diamine comprising the continuous preparation of aminonitrile. The invention also relates to the devices corresponding to these processes.

Sulfur and nitrogen mustard carbonate analogues

Sulfur and nitrogen half-mustard compounds lose their aggressive properties when the chlorine atom is replaced by a carbonate moiety. The anchimeric effect of the novel mustard carbonate analogues is investigated. The reaction follows first-order kinetics, does not need any base, and occurs with -OH, -NH and acidic -CH nucleophiles. Most of these molecules are unexplored and might provide a novel strategy for the preparation of compounds previously not easily accessible. Copyright

DMAPN Having a Low DGN Content and a Process for Preparing DMAPA from DMAPN Having a Low DGN Content

The present invention relates to a process for preparing 3-dimethylaminopropylamine (DMAPA) by reacting 3-dimethylaminopropionitrile (DMAPN) with hydrogen in the presence of a catalyst, wherein the DMAPN used has a content of 2-(dimethylaminomethyl)glutaronitrile (DGN) of 300 ppm by weight or less, based on the DMAPN used. Furthermore, the present invention relates to mixtures of DMAPN and DGN, wherein the weight ratio of DMAPN to DGN is in the range from 1 000 000:5 to 1 000 000:250.