Pyrrolidine Chemical Properties

Melting point:

-63 °C

Boiling point:

87-88 °C(lit.)

Density 

0.866

vapor density 

2.45 (vs air)

vapor pressure 

128 mm Hg ( 39 °C)

FEMA 

3523 | PYRROLIDINE

refractive index 

n20/D 1.443(lit.)

Flash point:

37 °F

storage temp. 

Flammables area

solubility 

water: miscible

form 

Liquid

pka

11.27(at 25℃)

PH

12.9 (100g/l, H2O, 20℃)

explosive limit

1.6-10.6%(V)

Water Solubility 

Miscible with alcohol, ether, chloroform and water.

Sensitive 

Air Sensitive

JECFA Number

1609

Merck 

14,8015

BRN 

102395

Stability:

Stable; flammable. Incompatible with strong acids, strong oxidizing agents.

InChIKey

RWRDLPDLKQPQOW-UHFFFAOYSA-N

CAS DataBase Reference

123-75-1(CAS DataBase Reference)

NIST Chemistry Reference

Pyrrolidine(123-75-1)

EPA Substance Registry System

Pyrrolidine (123-75-1)

Safety Information

Hazard Codes 

F,T,C

Risk Statements 

11-22-23-34-35-20/21/22-20/22-R35-R20/21/22-R11

Safety Statements 

16-26-36/37/39-45-33-S45-S36/37/39-S26-S16

RIDADR 

UN 1922 3/PG 2

WGK Germany 

2

RTECS 

UX9650000

F 

34

Autoignition Temperature

653 °F

TSCA 

Yes

HS Code 

2933 99 80

HazardClass 

3

PackingGroup 

II

Hazardous Substances Data

123-75-1(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 433 mg/kg

MSDS

• Language:EnglishProvider:SigmaAldrich
• Language:EnglishProvider:ACROS
• Language:EnglishProvider:ALFA

Pyrrolidine Usage And Synthesis

Chemical Properties

Pyrrolidine appears as a colorless to pale yellow liquid with an ammonia-like odor. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.
Pyrrolidine is a cyclic amine whose five-membered ring contains four carbon atoms and one nitrogen atom; the parent compound of the pyrrolidine family. It is a saturated organic heteromonocyclic parent, a member of pyrrolidines and an azacycloalkane. It is a conjugate base of a pyrrolidinium ion.

Production

Pyrrolidine can be produced from butanediol and ammonia, e.g., over an aluminum thorium oxide catalyst at 300℃ or over a nickel catalyst at 200℃ and 20 MPa under hydrogenation conditions. It can also be produced from tetrahydrofuran and ammonia over aluminum oxide at 275-375℃.Production can be obtained by reaction of 1,4-dihydroxyalkanes with amines in the presence of dehydrating agents at elevated temperatures or by reaction of primary amines with 1,4-dihaloalkanes. The dry distillation of 1,4-butanediamine dihydrochloride also generates pyrrolidine.

Pyrrolidine

Pyrrolidine is also known as tetrahydro pyrrole, and it is colorless to pale yellow liquid with a pungent ammonia odor, smoke in air, and toxic. The relative density is 0.8618, the boiling point is 88~89℃, refractive index is 1.4402 (28℃). It is strong alkaline, miscible with water, soluble in alcohol, ether and chloroform.
Pyrrole can synthesize pyrrolidine by catalytic hydrogenation, pyrrolidine present in tobacco and carrot leaves, and it is natural substances, the molecular structure of pyrrolidine is cyclic secondary amine, which is generally the same with the reaction of amine. Pyrrolidine is an important organic chemical raw material, it can be used for drug preparation, fungicides and insecticides.
Preparation:
1. 1,4-butanediol as the raw material, dehydrate to tetrahydrofuran, and then reacte with ammonia, then pyrrolidine can be obtained.
2. Furan as raw material, react with ammonia in the catalyst at 400℃ can obtain tetrahydro pyrrole.
3. The 1,4-dichloro-butane as raw material, react with ammonia, pyrrolidine can be obtained.
4. Pyrrole as raw material, with the catalyst of rhodium or ruthenium, with the reaction of reduction can obtain .
The above information is edited by the chemicalbook of Wang Xiaodong.

Chemical Properties

It is colorless, transparent liquid with special smell. When exposed to light or moist air, it can turn yellow. It can be soluble in water, ethanol. It is corrosive and flammable. Boiling point is 87.0~89.0℃.

Uses

Pharmaceutical raw materials, organic synthesis, special organic solvents.
It can be used for the preparation of drugs, fungicides, insecticides, etc.

Category

Flammable liquid.

Toxicity grading

Highly toxic.

Acute toxicity

Oral-rat LD50: 300 mg/kg; Oral-Mouse LD50: 450 mg/kg.

Flammability hazard characteristics

When exposed to fire, high temperature, oxidant, it is flammable; when heat, toxic nitric oxide gas can produce.

Storage Characteristics

Treasury ventilation low-temperature drying; oxidants, acids stored separately.

Extinguishing agent

Dry, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent.

Occupational standards

STEL 0.1 mg /m.

Chemical Properties

colourless to pale yellow liquid with a penetrating

Chemical Properties

Pyrrolidine has a penetrating amine-type odor, reminiscent of ammonia and piperidine. 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.

Uses

Uses of this compound in any major scalehave not been made. It occurs in tobacco andcarrot leaves. It is formed by reduction ofpyrrole.

Uses

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).

Definition

ChEBI: A cyclic amine whose five-membered ring contains four carbon atoms and one nitrogen atom; the parent compound of the pyrrolidine family.

Preparation

Via overall 5-endo-trig cyclizations of homoallylic tosylamides.

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.

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.

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.

Air & Water Reactions

Highly flammable. Very soluble in water.

Reactivity Profile

Tetrahydro pyrrole 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 Tetrahydro pyrrole, benzaldehyde, and propionic acid was heated in an attempt to form porphyrins.

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.

Health Hazard

The acute toxicity of pyrrolidine is moderateon test animals. It is somewhat less toxicthan pyrrole. The vapors are an irritant tothe eyes and respiratory tract. The liquid iscorrosive to the skin. Contact with the eyescan cause damage. The oral LD50 value inrats is 300 mg/kg, while the inhalation LC50value in mice is 1300 mg/m³/2 h (NIOSH1986).

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 ingestion and intravenous routes. Moderately toxic by inhalation. Dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits hghly toxic fumes of NOx.

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.]

Pyrrolidine(123-75-1)Related Product Information

• 1-(TRIMETHYLSILYL)PYRROLIDINE
• 1-Methyl-2-pyrrolidineethanol
• N-NITROSOPYRROLIDINE
• 2-(2-Aminoethyl)-1-methylpyrrolidine
• 1-Pyrrolidino-1-cyclopentene
• N-[2-(4-Bromophenoxy)ethyl]pyrrolidine
• 3-PYRROLIDINO-1,2-PROPANEDIOL
• 1-AMINOPYRROLIDINE
• 1-Methyl-3-pyrrolidinol
• 3-CARBAMOYL-PROXYL
• 1-Cyanopyrrolidine
• 1-FORMYLPYRROLIDINE
• 1-Pyrrolidino-1-cyclohexene
• 3-Carboxy-2,2,5,5-tetraMethylpyrrolidine 1-Oxyl Free Radical
• 1-(3,4-DIHYDRO-2-NAPHTHYL)PYRROLIDINE
• 1-ETHYL-3-PYRROLIDINOL
• Pyrrolidine
• 1-Methylpyrrolidine