Triallylamine

Chemical Properties

dark brown liquid

Chemical Properties

Triallylamine is a flammble liquid. Triallylamine can be detected at 0.5 ppm and is severely irritating at 75 ppm.

Uses

Triallylamine is used in organic synthesis.Triallylamine has been proposed as a catalyst for the production of polyesters and as an initiator for the polymerization of butadiene.

Uses

• Triallylamine (TAA) reacts with primary aromatic amines in the presence of a ruthenium catalyst to form 2-ethyl-3-methylquinolines.
• TAA undergoes hydrozirconation followed by transmetalation with germanium tetrachloride to form 1-aza-5-germa-5-chlorobicyclo[3.3.3]undecane. This compound can react with Grignard or lithium reagents to form the corresponding 5-organo compounds.
• The cycloaddition of TAA to fluorinated 1,3,4-oxadiazoles affords octahydro-2,7-methanofuro[3,2-c]pyridines.

Application

Triallylamine (TAA) reacts with primary aromatic amines in the presence of a ruthenium catalyst to form 2-ethyl-3-methylquinolines.
TAA undergoes hydrozirconation followed by transmetalation with germanium tetrachloride to form 1-aza-5-germa-5-chlorobicyclo[3.3.3]undecane. This compound can react with Grignard or lithium reagents to form the corresponding 5-organo compounds.
The cycloaddition of TAA to fluorinated 1,3,4-oxadiazoles affords octahydro-2,7-methanofuro[3,2-c]pyridines.

Production Methods

Triallylamine is manufactured using allyl chloride and ammonia under heat and pressure. It is used as a solvent and in organic syntheses.

Definition

ChEBI: Triallylamine is a tertiary amino compound.

General Description

A colorless liquid with a fishlike odor. Density 0.800 g / cm3 and insoluble in water. Hence floats on water. Flash point 103°F. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

Triallylamine is a strong reducing agent that reacts violently with oxidizing agents. Corrosive towards Al and Zn [Handling Chemicals Safely 1980 p. 912] . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

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.

Safety Profile

Poison by skin contact and intraperitoneal routes. Moderately toxic by ingestion and inhalation. An eye and severe skin irritant. Human systemic effects by inhalation: structural or functional changes in trachea or bronchi. Flammable liquid when exposed to heat, flame or oxidlzers. To fight fire, use foam, alcohol foam, fog. When heated to decomposition it emits toxic fumes of NOx. See also AMINES and ALLYL COMPOUNDS.