General Description
A colorless to pale yellow liquid with an ammonia-like odor. Flash point 37°F. Density 0.85 g/cm3. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.
Reactivity Profile
PYRROLIDINE(123-75-1) 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. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. An explosion occurred when a mixture of PYRROLIDINE(123-75-1), benzaldehyde, and propionic acid was heated in an attempt to form porphyrins.
Air & Water Reactions
Highly flammable. Very soluble in water.
Hazard
Flammable, dangerous fire risk. Toxic by
ingestion and inhalation.
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.
Chemical Properties
Pyrrolidine is acolourless to pale yellow liquid with a penetrating, It is infinitely miscible with water and conventional organic solvents such as methanol, acetone, ether, and chloroform. It acts as a lachrymator.
Chemically, pyrrolidine behaves like a secondary amine in every respect. For example, it undergoes Leuckart – Wallach and Mannich reactions and is readily converted into an enamine. In the presence of a catalyst, such as platinum at 360°C or rhodium at 650°C, pyrrole is formed. In the presence of a copper catalyst, N-methylpyrrolidone is converted into Nmethylpyrrolidine.
Physical properties
Pyrrolidine has a penetrating amine-type odor, reminiscent of ammonia and piperidine. It is easy to turn yellow when exposed to light or humid air, easily soluble in water and ethanol. It is nauseating and diffusive.
Occurrence
Reported found in beer, bread, wheat bread, salmon caviar, fish, milk, leaves and stalks of celery, Camembert cheese, Limburger cheese, Russian cheeses, tilsit cheese, other cheeses, caviar, raw fatty fish, beer, Finnish whiskey, white wine, red wine, coffee, radish, malt, roasted peanut, sweet corn and roasted barley.
Uses
Pyrrolidine is a flammable alkaline liquid that undergoes
reactions typical of secondary amines. It is used to prepare
pesticides and rubber accelerators and as a chemical intermediate
(usually the hydrochloride form) in the pharmaceutical
industry. There is relatively limited industrial exposure
to this material.
Application
Pyrrolidine is a heterocyclic compound used as a building block in the synthesis of wide range of pharmaceutical compounds, namely matrix metalloprotein inhibitors (MMPIs) and aminopeptidase N inhibitors (APNIs). It has been used for the synthesis of N-benzoyl pyrrolidine from benzaldehyde via oxidative amination. It may be used as a catalyst for the synthesis of N-sulfinyl aldimines from carbonyl compounds and sulfonamides.
Pyrrolidine can also be used to synthesize:
Taddol-pyrrolidine phosphoramidite, a ligand for rhodium-catalyzed [2+2+2] cycloaddition of pentenyl isocyanate and 4- ethynylanisole.
H,4 PyrrolidineQuin-BAM (′PBAM′), a selective catalyst for the aza-Henry addition of nitroalkanes to aryl aldimines.
1,2,3,3a,4,9-Hexahydropyrrolo[2,1-b]quinazoline by reacting with o-aminobenzaldehyde.
Definition
ChEBI: A cyclic amine whose five-membered ring contains four carbon atoms and one nitrogen atom; the parent compound of the pyrrolidine family.
Definition
pyrrolidine: A saturated heterocycliccompound having one nitrogenatom in a five-membered ring,C4H9N; r.d. 0.87; m.p. –63°C b.p.87°C. It is found in certain plants andthe ring structure is present in manyalkaloids.
Preparation
Via overall 5-endo-trig cyclizations of homoallylic tosylamides.
Aroma threshold values
Detection: 20.2 ppm
Taste threshold values
Taste characteristics at 50 ppm: ammonia and fishy, amine-like with seaweed and shellfish nuances.
Flammability and Explosibility
Highlyflammable
Purification Methods
Dry pyrrolidine with BaO or sodium, then fractionally distil it, under N2, through a Todd column (p 11) packed with glass helices. [Beilstein 20 H 159, 20 I 36, 20 II 79, 20 III/IV 2072, 20/1 V 162.]
