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Pyrrolidine

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Pyrrolidine Basic information

Product Name:
Pyrrolidine
Synonyms:
  • TETRAMETHYLENEIMINE
  • pyrrolidine,tetrahydropyrrole
  • PYRROLIDINE,REAGENT
  • TETRAHYDROPYRROLE(PYRROLIDINE)
  • PYRROLIDINE 99+%
  • PYRROLIDINE, REDISTILLED, 99.5+%
  • 1-AZACYCLOPENTANE
  • AKOS BBS-00003603
CAS:
123-75-1
MF:
C4H9N
MW:
71.12
EINECS:
204-648-7
Product Categories:
  • Building Blocks
  • C4 to C8
  • Aliphatics
  • Chemical Synthesis
  • Heterocyclic Building Blocks
  • Pyrrolidines
  • Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines
  • Flavor
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • 123-75-1
Mol File:
123-75-1.mol
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Pyrrolidine Chemical Properties

Melting point:
-63 °C
Boiling point:
87-88 °C/760 mmHg (lit.)
Density 
0.852 g/mL at 25 °C (lit.)
vapor density 
2.45 (vs air)
vapor pressure 
128 mm Hg ( 39 °C)
refractive index 
n20/D 1.443(lit.)
FEMA 
3523 | PYRROLIDINE
Flash point:
37 °F
storage temp. 
Store below +30°C.
solubility 
water: miscible
form 
Liquid
pka
11.27(at 25℃)
color 
Colorless to Almost colorless
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
Merck 
14,8015
JECFA Number
1609
BRN 
102395
Stability:
Stable; flammable. Incompatible with strong acids, strong oxidizing agents.
InChIKey
RWRDLPDLKQPQOW-UHFFFAOYSA-N
LogP
0.22 at 25℃
CAS DataBase Reference
123-75-1(CAS DataBase Reference)
NIST Chemistry Reference
Pyrrolidine(123-75-1)
EPA Substance Registry System
Pyrrolidine (123-75-1)
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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
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

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Pyrrolidine Usage And Synthesis

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.

Preparation

Pyrrolidine is formed by reduction of pyrrole. Via overall 5-endo-trig cyclizations of homoallylic tosylamides. Pyrrolidine can be produced from butanediol and ammonia, e.g., over an aluminum thorium oxide catalyst at 300°C or over a nickel catalyst at 200°C and 20 MPa under hydrogenation conditions. It can also be produced from THF and ammonia over aluminum oxide at 275-375°C.

Definition

ChEBI: 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.

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

Pyrrolidine is a saturated heterocycliccompound having one nitrogenatom in a five-membered ring. It is a colorless to pale yellow liquid with an ammonia-like odor. It is found in certain plants andthe ring structure is present in manyalkaloids. 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

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.

Flammability and Explosibility

Highlyflammable

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.]

PyrrolidineSupplier

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