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Tetrahydro pyrrole
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Name

Tetrahydro pyrrole

 EINECS 204-648-7
CAS No. 123-75-1 Density 0.866 g/cm3
PSA 12.03000 LogP 0.69860
Solubility Miscible with water Melting Point -63 °C, 210 K, -81 °F
Formula C4H9N Boiling Point 89.451 °C at 760 mmHg
Molecular Weight 71.1222 Flash Point 2.778 °C
Transport Information UN 1922 3/PG 2 Appearance Colourless to pale yellow liquid
Safety 16-26-36/37/39-45-33 Risk Codes 11-22-23-34-35-20/21/22-20/22
Molecular Structure Molecular Structure of 123-75-1 (Tetrahydro pyrrole) Hazard Symbols FlammableF,ToxicT,CorrosiveC
Synonyms

Pyrrolidin;Tetramethylenimine;Pyrrolidine ring;Perhydropyrrole;Pyrrole, tetrahydro-;2,3,4,5-Tetrahydropyrrole;Azacyclopentane;Butylenimine;Pyrrolidine (Tetrahydropyrrole);Pyrrolidine 99%;Pyrrolidine;Prolamine;

Article Data 313

Tetrahydro pyrrole Synthetic route

109-97-7

pyrrole

123-75-1

pyrrolidine

Conditions
ConditionsYield
With 5% Ru/MgO; hydrogen In tetrahydrofuran at 150℃; under 38002.6 Torr; for 0.7h;100%
With dichloro(μ-chloro)(μ-hydrido)bis(η-p-cymene)diruthenium(II); hydrogen In neat (no solvent) at 90℃; under 60006 Torr; for 40h;89%
With Cp*Rh(2-(2-pyridyl)phenyl)H; hydrogen In neat (no solvent) at 100℃; under 27361.8 Torr; for 48h; Catalytic behavior; Glovebox;74%
56475-80-0

N-(methoxycarbonyl)pyrrolidine

123-75-1

pyrrolidine

Conditions
ConditionsYield
With tert-butylamine In methanol for 3h; Heating;100%
With methyllithium; lithium bromide In tetrahydrofuran at 0℃; for 1h;95%
78521-30-9

1-(pyrrolidinyl)-2,4-dinitronaphthalene

74-89-5

methylamine

A

123-75-1

pyrrolidine

B

39139-78-1

1-(Methylamino)-2,4-dinitronaphthalene

Conditions
ConditionsYield
In water at 30℃; for 1h;A n/a
B 98%
616-45-5

2-pyrrolidinon

123-75-1

pyrrolidine

Conditions
ConditionsYield
With methanesulfonic acid; ruthenium(1,1,1-tris(di(3,5-dimethylphenyl)phosphinomethyl)ethane)(η4-trimethylenemethane); hydrogen In tetrahydrofuran at 160℃; under 75007.5 Torr; for 16h; Autoclave; Schlenk technique;98%
With tris(pentafluorophenyl)borate; C21H35BrMnNO2P2; potassium tert-butylate; hydrogen In m-xylene at 150℃; under 37503.8 Torr; for 72h;81%
With borane-ammonia complex; boron trifluoride diethyl etherate; tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 60℃; for 16h;77%
110-60-1

1,4-diaminobutane

123-75-1

pyrrolidine

Conditions
ConditionsYield
HZSM-5(280) zeolite In water at 300℃; Cyclization;97%
tris(triphenylphosphine)ruthenium(II) chloride In diphenylether at 180℃; for 5h; Product distribution; other α,ω-aliphatic diamines;90%
With carbonylchloro[4,5-bis(diisopropylphosphinomethyl)acridine]hydridoruthenium(II) In 1,4-dioxane; water at 100℃; for 22h; Schlenk technique; Inert atmosphere;88%
123477-57-6

pyrrolidine-1-carboxylic acid prop-2-ynyl ester

123-75-1

pyrrolidine

Conditions
ConditionsYield
With benzyltriethylammonium tetrathiomolybdate In acetonitrile at 20℃; for 2.5h;97%
110-63-4

Butane-1,4-diol

123-75-1

pyrrolidine

Conditions
ConditionsYield
With ammonia; hydrogen; CuO/ZnO/Al2O3 at 220℃; under 26252.1 Torr;94%
With aluminum oxide; ammonia at 400℃;
With aluminum oxide; ammonia at 325℃;
5470-26-8

ethyl pyrrolidine-1-carboxylate

123-75-1

pyrrolidine

Conditions
ConditionsYield
With methyllithium; lithium bromide In tetrahydrofuran at 0℃; for 1h;94%
142653-70-1

1-(9-fluorenylmethoxycarbonyl)pyrrolidine

123-75-1

pyrrolidine

Conditions
ConditionsYield
With triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate In neat (no solvent) at 25℃; for 0.0666667h; Green chemistry;93%
29897-82-3

N-benzylpyrrolidine

123-75-1

pyrrolidine

Conditions
ConditionsYield
With 9,10-Dicyanoanthracene In water; acetonitrile Irradiation;90%

Tetrahydro pyrrole Consensus Reports

Reported in EPA TSCA Inventory.

Tetrahydro pyrrole Standards and Recommendations

DOT Classification:  3;
Label: Flammable Liquid

Tetrahydro pyrrole Specification

The Pyrrolidine with CAS registry number of 123-75-1 is also known as Tetrahydropyrrole. The IUPAC name and product name are the same. It belongs to product categories of Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines; Flavor. Its EINECS registry number is 204-648-7. In addition, the formula is C4H9N and the molecular weight is 71.12. This chemical is a colourless to pale yellow liquid and should be sealed in dark place.

Physical properties about Pyrrolidine are: (1)ACD/LogP: 0.09; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 1; (7)#H bond donors: 1; (8)Index of Refraction: 1.428; (9)Molar Refractivity: 21.795 cm3; (10)Molar Volume: 84.749 cm3; (11)Surface Tension: 26.891 dyne/cm; (12)Density: 0.839 g/cm3; (13)Flash Point: 2.778 °C; (14)Enthalpy of Vaporization: 33.01 kJ/mol; (15)Boiling Point: 89.451 °C at 760 mmHg; (16)Vapour Pressure: 58.582 mmHg at 25 °C.

Preparation of Pyrrolidine: it is prepared by reaction of maleic anhydride. Product is obtained by hydrogenation and amination.

Pyrrolidine is prepared by reaction of maleic anhydride.

Uses of Pyrrolidine: it is used to produce 1-prop-2-ynyl-pyrrolidine by reaction with 3-bromo-propyne. The reaction occurs with reagents KOH, alumina and solvent aliquat 336 at 20 °C. The yield is about 55%. Besides, it is also used as pharmaceutical raw materials, organic synthesis and special organic solvent.

Pyrrolidine is used to produce 1-prop-2-ynyl-pyrrolidine by reaction with 3-bromo-propyne.

When you are using this chemical, please be cautious about it. As a chemical, it is harmful by inhalation, in contact with skin and if swallowed. It is highly flammable and may cause severe burns. During using it, wear suitable protective clothing, gloves and eye/face protection. Take precautionary measures against static discharges and keep away from sources of ignition. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1CCNC1
2. InChI: InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
3. InChIKey: RWRDLPDLKQPQOW-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo oral 250mg/kg (250mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 104, 1982.
mammal (species unspecified) LD50 oral 250mg/kg (250mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974.
mouse LC50 inhalation 1300mg/m3/2H (1300mg/m3) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

VASCULAR: OTHER CHANGES		 Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(2), Pg. 29, 1974.
mouse LD50 intraperitoneal 420mg/kg (420mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 82, 1946.
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#06769,
mouse LD50 oral 450mg/kg (450mg/kg)   Bollettino Chimico Farmaceutico. Vol. 103, Pg. 414, 1964.
rabbit LDLo oral 250mg/kg (250mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 104, 1982.
rat LD50 oral 300mg/kg (300mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

VASCULAR: OTHER CHANGES		 Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(2), Pg. 29, 1974.

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