5724-81-2

Basic information

• Product Name: 3,4-dihydro-2H-pyrrole
• Synonyms: 3,4-dihydro-2H-pyrrole;delta(1)-pyrroline;1-PYRROLINE;2H-Pyrrole, 3,4-dihydro-;Einecs 227-230-6
• CAS NO: 5724-81-2
• Molecular Formula: C₄H₇N
• Molecular Weight: 69.10508
• EINECS: 227-230-6
• Mol File: 5724-81-2.mol
• Article Data: 58

Chemical Properties

• Melting Point: 96-102 °C
• Boiling Point: 526.4°C at 760 mmHg
• Flash Point: 272.2°C
• Appearance: /
• Density: 1.61g/cm³
• Vapor Pressure: 3.59E-11mmHg at 25°C
• Refractive Index: 1.659
• PKA: 7.81±0.20(Predicted)
• CAS DataBase Reference: 3,4-dihydro-2H-pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dihydro-2H-pyrrole(5724-81-2)
• EPA Substance Registry System: 3,4-dihydro-2H-pyrrole(5724-81-2)

Safety Data

• Hazardous Substances Data: 5724-81-2(Hazardous Substances Data)

Usage

Chemical Properties

1-Pyrroline has a spermous odor

Occurrence

Reported present in clam and squid.

Preparation

By acid hydrolysis of 4-aminobutyraldehyde diethyl acetal.

Aroma threshold values

2.3 to 22 ppb

InChI:InChI=1/C16H15BrN4O5/c1-26-14-7-13(21(24)25)6-10(16(14)23)8-19-20-15(22)9-18-12-4-2-11(17)3-5-12/h2-8,18-19H,9H2,1H3,(H,20,22)/b10-8-

Upstream product

• 147-85-3 L-proline 
• 5981-17-9 dodecahydro-3a,6a,9a-triaza-trindene 
• 6859-99-0 3-hydroxypiperazine 
• 68970-14-9 1,2-dipyrrolidinodiazene 
• 110-61-2 butanedinitrile 
• 56-23-5 tetrachloromethane 
• 7732-18-5 water 
• 333-93-7 putrescine dihydrochloride 
• 609-36-9 rac-Pro-OH 
• 7664-93-9 sulfuric acid 
• 6346-09-4 4-aminobutyrylaldehyde diethylacetal 
• 123-75-1 pyrrolidine 
• 3184-13-2 L-ornithine hydrochloride 
• 1069-31-4 DL-ornithine hydrochloride 

Downstream Products

• 341544-01-2 (E)-3-[(2S)-N-benzyloxycarbonyl-2-pyrrolidinyl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene 
• 616-45-5 2-pyrrolidinon 
• 886503-15-7 rac-2-(2,5-difluorophenyl)pyrrolidine 
• 119011-72-2 (1aR,1bS,5aR)-1-Dimethylamino-1a,5a-diphenyl-hexahydro-4a-aza-cyclopropa[a]pentalen-5-one 
• 108342-84-3 2-Chloro-1-nitroso-pyrrolidine 
• 104267-39-2 6-(4-methoxyphenyl)-7-methyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one 
• 78178-73-1 1-(3,4-Bis-benzyloxy-phenyl)-2-pyrrolidin-2-yl-ethanone 
• 77513-53-2 3-benzyloxy-4-methoxy-ω-pyrrolidin-2-ylacetophenone 
• 78178-74-2 4-benzyloxy-3-methoxy-ω-pyrrolidin-2-ylacetophenone 
• 78178-72-0 4'-benzyloxy-2-pyrrolidin-2-ylacetophenone 
• 89140-13-6 2,3-trimethylene-1,2-dihydroquinazolinium picrate 
• 92667-14-6 2-(4-Nitrobenzoyloxy)-N-nitrosopyrrolidin 
• 59435-85-7 α-acetoxy-N-nitrosopyrrolidine 
• 92667-15-7 2-Methoxy-1-nitrosopyrrolidin 

Relevant articles and documents

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Isolation and stabilization of a pheromone in crystalline molecular capsules

The active monomer form of the male-produced pheromone of the Mediterranean fruit fly can be isolated selectively from its equilibrating trimer species by encapsulation within a calixarene pocket built into a hydrogen-bonded framework from guanidinium 4-sulfocalix[4]arene. Encapsulation of the Δ1- pyrroline guest significantly perturbs the assembly of the quasihexagonal two-dimensional guanidinium-sulfonate network of the guest-free framework, to the extent that guanidinium ions are excluded from some sites to accommodate the steric requirements of the guest. Nonetheless, single crystal X-ray diffraction reveals the preservation of a layered structrure in which the calixarene capsules stack in an antiparallel configuration. These observations illustrate that the binding of the pheromone monomer by the calixarene is sufficiently strong to overcome the loss of guanidinium-sulfonate hydrogen bonds, which is corroborated by the strong binding constants measured in solution. The solid-state encapsulation stabilizes the otherwise volatile unstable monomer form, suggesting an effective strategy for the storage, application, and controlled release of an important agricultural adjuvant.

OXIDATIVE SPALTUNG VON 2-(PYRROLIDINOMETHYL)PYRIDIN-1-OXID MIT ANSCHLIESSENDER REKOMBINATION UND DIE KRISTALLSTRUKTUR VON (E)-2-(1-PYRROLIN-3-YLIDENMETHYL)PYRIDIN-1-OXID

Mercury EDTA dehydrogenation of 2-(pyrrolidinomethyl)-pyridine-1-oxide (1) yields the pyrrolidone 5, which may be accounted for by a neighbouring effect of the amine oxide group.For an additional basic product the structure of (E)-2-(1-pyrroline-3-ylidenemethyl)-pyridine-1-oxide (11) has been proved by X-ray crystallography and synthesis.This indicates a cleavage of the doubly dehydrogenated product followed by recombination.

Structural equilibrium and ring-chain tautomerism of aqueous solutions of 4-aminobutyraldehyde

NMR spectroscopy of aqueous solutions of 4-aminobutyraldehyde in the range 0 pH 13 established the occurrence of protonated and hydrated amino aldehydes in equilibrium with pyrrolines, and pyrrolinium salts.

A rapid synthesis of racemic brevioxime

Racemic brevioxime has been synthesised starting from N-propionyl-2-pyrroline by intramolecular cyclisation of a β-ketoamide using nitrosyl chloride.

Diversification of Unprotected Alicyclic Amines by C?H Bond Functionalization: Decarboxylative Alkylation of Transient Imines

Despite extensive efforts by many practitioners in the field, methods for the direct α-C?H bond functionalization of unprotected alicyclic amines remain rare. A new advance in this area utilizes N-lithiated alicyclic amines. These readily accessible intermediates are converted to transient imines through the action of a simple ketone oxidant, followed by alkylation with a β-ketoacid under mild conditions to provide valuable β-amino ketones with unprecedented ease. Regioselective α′-alkylation is achieved for substrates with existing α-substituents. The method is further applicable to the convenient one-pot synthesis of polycyclic dihydroquinolones through the incorporation of a SNAr step.

α-C-H/N-H Annulation of Alicyclic Amines via Transient Imines: Preparation of Polycyclic Lactams

Polycyclic lactams are prepared in a single operation from o-toluamides and cyclic amines in a process that involves transient cyclic imines, species that are conveniently obtained in situ from the corresponding lithium amides and simple ketone oxidants. Imines thus generated, such as 1-pyrroline and 1-piperideine, engage lithiated o-toluamides in a facile annulation process. Undesired side reactions such as imine deprotonation and o-toluamide dimerization are suppressed through the judicious choice of reaction conditions.