593-67-9

Basic information

• Product Name: vinylamine
• Synonyms: Ethylenamine;Ethenamine;ethylene amine
• CAS NO: 593-67-9
• Molecular Formula: C₂H₅N
• Molecular Weight: 43.0678
• EINECS: 209-802-7
• Mol File: 593-67-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 16°Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 0.714g/cm³
• Vapor Pressure: 1060mmHg at 25°C
• Refractive Index: 1.398
• PKA: 8.00±0.50(Predicted)
• CAS DataBase Reference: vinylamine(CAS DataBase Reference)
• NIST Chemistry Reference: vinylamine(593-67-9)
• EPA Substance Registry System: vinylamine(593-67-9)

Safety Data

• Hazardous Substances Data: 593-67-9(Hazardous Substances Data)

Usage

General Description

Usually colorless to light colored liquids with an ammonia-like odor. Flammable. May be very corrosive to skin, eyes, mucus membranes and metals. They are often used as fungicides and to manufacture other chemicals.

Air & Water Reactions

Highly flammable. Generally soluble in water and denser than water. When dissolved in water, vinylamine is a strong base

Reactivity Profile

React violently with acids, strong oxidants and halogens; attack copper, aluminum, zinc and their alloys; react with mercury and silver oxides to form shock sensitive compounds. [Handling Chemicals Safely 1980.. p. 139]; reacts with hypochlorites to give N-chloroamines, some of which, are explosives when isolated [Bretherick 1979. p. 108].

Health Hazard

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

InChI:InChI=1/C2H5N/c1-2-3/h2H,1,3H2

Upstream product

• 124-40-3 dimethyl amine 
• 75-50-3 trimethylamine 
• 2516-34-9 cyclobutylamine 
• 6372-65-2 7-Amino-dibenzobicyclo<2.2.2>octadien 
• 6372-65-2 amino-11 ethano-9,10 dihydro-9,10 anthracene 

Downstream Products

• 638-14-2 2,4,6-trimethyl-[1,3,5]triazinane 
• 497-25-6 dimethylenecyclourethane 
• 1721-13-7 ethyl 2,6-dimethylnicotinate 
• 37669-78-6 ethyl 2,4-dimethylnicotinate 

Relevant articles and documents

Gas-phase basicity and acidity trends in α,β-unsaturated amines, phosphines, and arsines

The acidity and basicity trends in the series of α,β-unsaturated amines, phosphines, and arsines were analyzed through the use of G2 ab initio calculations and the examination of experimental data obtained by means of FT-ICR techniques. The α,β-unsaturated amines, phosphines, and arsines are less basic but significantly more acidic than the corresponding saturated analogues. However, while both vinyl- and ethynylamine protonate preferentially at the β-carbon atom, vinyl- and ethynylphosphine are phosphorus bases in the gas-phase. Arsines resemble closely the corresponding phosphines, although protonation at the Ca atom competes with protonation at the heteroatom. The enhanced acidity of unsaturated compounds can be attributed essentially to a stabilization of the anions because of a favorable interaction of the XH- group with the C-C multiple bonds. This stabilizing effect is maximum for amines and minimum for arsines. The low relative basicity of these unsaturated compounds results from a destabilization of the protonated species due to unfavorable interactions of the XH3+ group with the C-C π-system. Protonation at the β-carbon is strongly favored for amines but unfavorable for phosphines and arsines, because the carbocation formed is much less stabilized when the heteroatom of the XH2 group belongs to the second or the third-row than when it is a first-row atom.

Reversal of electronic Substituent Effects in the Retro-Diels-Alder Reaction. A Charge Neutral Analogue of Oxyanion-Accelerated Cycloreversion

The retro-Diels-Alder reaction of anthracene cycloadducts is influenced by the dienophile substituents in the following ways: (1) electron-withdrawing groups increase the rate of the reaction; (2) strongly conjugating substituents make the reaction much faster than predicted by classical electron-withdrawing or -donating ability, in the best case by a factor of 3 x 106, and (3) there is no observable steric effect, in contrast to literature statements to the contrary.

REACTIONS RETRODIENIQUES-IX. SYNTHESE PAR THERMOLYSE ECLAIR ET ETUDE D'ENAMINES PRIMAIRES INSTABLES

Etheneamine 1 and its methyl derivatives 2-7 have been synthesized from the adducts 8-14 by a retro-Diels-Alder reaction under flash thermolytic conditions.The primary enamines 1-4 have been identified (IR, (1)H and (13)C NMR in a pure state at -80 deg C; at the same temperature, the enamines 5-7, less stable, are already accompanied by their tautomeric imines 33 or 34.When warmed up to room temperature, the enamines 1-7 lead, following to their substitution, either to nitrogen heterocycles (30, 42) or to acyclic azadienes (35-37, 39, 40).