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Cas Database

123-75-1

123-75-1

Identification

  • Product Name:Tetrahydro pyrrole

  • CAS Number: 123-75-1

  • EINECS:204-648-7

  • Molecular Weight:71.1222

  • Molecular Formula: C4H9N

  • HS Code:2933.90 Oral rat LD50: 300 mg/kg

  • Mol File:123-75-1.mol

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

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Safety information and MSDS view more

  • Pictogram(s):FlammableF,ToxicT,CorrosiveC

  • Hazard Codes:F,T,C

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH302 Harmful if swallowed H314 Causes severe skin burns and eye damage H332 Harmful if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Refer for medical attention . Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: 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. (ERG, 2016) Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mg/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Alcohol foam, carbon dioxide, dry chemical Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: 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. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: chemical protection suit including self-contained breathing apparatus. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Personal protection: chemical protection suit including self-contained breathing apparatus.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from strong oxidants and acids. Well closed.Bundling and sills should be provided to prevent spread of liquid accidentally escaping from storage and process vessels.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
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  • Product Description:PRD
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  • Manufacture/Brand:TRC
  • Product Description:Pyrrolidine
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  • Price:$ 135
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  • Product Description:Pyrrolidine >98.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Pyrrolidine >98.0%(GC)
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  • Product Description:Pyrrolidine 99%
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Relevant articles and documentsAll total 219 Articles be found

Photo-oxidation of L-Tyrosine, an Efficient 1,4-Chirality Transfer Reaction

Endo, Katsuya,Seya, Kazuhiko,Hikino, Hiroshi

, p. 934 - 935 (1988)

Dye-sensitized oxidation of L-tyrosine with Rose Bengal yielded the optically pure ketolactam (2) stereoselectively in one step.

-

Craig,Hixon

, p. 804,806 (1930)

-

-

Sakurai

, p. 374 (1936)

-

SALT EFFECTS ON THE KINETICS OF SUBSTITUTION OF THE PENTACYANO(PYRROLIDINE)FERRATE(II) ION

Pedrosa, Graciela C.,Hernandez, Norma L.,Katz, Nestor E.,Katz, Miguel

, p. 2297 - 2299 (1980)

Rate constants at 298.2 K for the release of pyrrolidine from pentacyano(pyrrolidine)ferrate(II) have been measured under pseudo-first-order conditions and the effect of inert inorganic and alkylammonium salts on the kinetics were investigated.The observe

Mechanistic Investigations of the Catalytic Formation of Lactams from Amines and Water with Liberation of H2

Gellrich, Urs,Khusnutdinova, Julia R.,Leitus, Gregory M.,Milstein, David

, p. 4851 - 4859 (2015)

The mechanism of the unique lactam formation from amines and water with concomitant H2 liberation with no added oxidant, catalyzed by a well-defined acridine-based ruthenium pincer complex was investigated in detail by both experiment and DFT calculations. The results show that a dearomatized form of the initial complex is the active catalyst. Furthermore, reversible imine formation was shown to be part of the catalytic cycle. Water is not only the oxygen atom source but also acts as a cocatalyst for the H2 liberation, enabled by conformational flexibility of the acridine-based pincer ligand. (Figure Presented).

Ion Confinement in the Collision Cell of a Multiquadrupole Mass Spectrometer: Access to Chemical Equilibrium and Determination of Kinetic and Thermodynamic Parameters of an Ion-Molecule Reaction

Beaugrand, Claude,Jaouen, Daniel,Mestdagh, Helene,Rolando, Christian

, p. 1447 - 1453 (1989)

Ions can be confined in an rf-only collision cell of a tandem quadrupole mass spectrometer so that ion-molecule reactions can be studied for variable interaction times (0.05-250 ms).The chemical system studied (ammonium ion, pyrrolidine, piperidine) involved the following reactions: proton exchange, formation of proton-bound dimers, and amine exchange between dimers.Chemical equilibrium could be reached for the exchange reactions.The equilibrium constants of these reactions, as well as the rate constants of the different reactions involved, were thus easily determined from the variation of relative abundance of reactant and product ions versus confinement time.

PHOTOSENSITIZED SINGLE ELECTRON TRANSFER INITIATED N-DEBENZYLATION. A CONVENIENT AND MILD APPROACH

Pandey, G.,Rani, K. Sudha

, p. 4157 - 4158 (1988)

A mild method of N-debenzylation via photosensitized single electron transfer (SET) using 9,10-dicyano anthracene (DCA) as electron acceptor in neutral medium is reported.

Novel β-galactosidase-specific O2-glycosylated diazeniumdiolate probes

Bedell, Barry,Bohle,Chua, Zhijie,Czerniewski, Alexander,Evans, Alan,Mzengeza, Shadreck

, p. 969 - 980 (2010)

Three β-galactosidase-specific nitric-oxide-releasing diazeniumdiolate conjugated probes were prepared as a prelude to studies of new potential molecular MRI imaging agents. A glycosylated derivative, 2e, designed to be trafficked across cell membranes, was also prepared. We report, in detail, the synthesis and characterization of these probes. In addition, the release of diazeniumdiolate from the probes by β-galactosidase-catalyzed hydrolysis was used to estimate their efficacy as serum-stable, specific NO donors.

N-trifluoroacetylamino alcohols as phosphodiester protecting groups in the synthesis of oligodeoxyribonucleotides

Wilk, Andrzej,Srinivasachar, Kasturi,Beaucage, Serge L.

, p. 6712 - 6713 (1997)

-

-

Takayama

, p. 138,139 (1936)

-

-

Brown,van Gulick

, p. 1046 (1956)

-

Surface ligands enhance the catalytic activity of supported Au nanoparticles for the aerobic α-oxidation of amines to amides

Chatterjee, Puranjan,Kanbur, Uddhav,Manzano, J. Sebastián,Sadow, Aaron D.,Slowing, Igor I.,Wang, Hsin

, p. 1922 - 1933 (2022/04/07)

The catalytic aerobic α-oxidation of amines in water is an atom economic and green alternative to current methods of amide synthesis. The reaction uses O2 as terminal oxidant, avoids hazardous reactants and gives water as the only byproduct. Here we report that the catalytic activity of silica-supported Au nanoparticles for the aerobic α-oxidation of amines can be improved by tethering pyridyl ligands to the support. In contrast, immobilization of thiol groups on the material gives activities comparable to Au supported on bare silica. Our studies indicate that the ligands affect the electronic properties of the Au nanoparticles and thereby determine their ability to activate O2 and mediate C-H cleavage in the amine substrate. The reaction likely proceeds via an Au catalyzed β-hydride elimination enabled by backdonation from electron-rich metal to the orbital. O2, which is also activated on electron-rich Au, acts as a scavenger to remove H from the metal surface and regenerate the active sites. The mechanistic understanding of the catalytic conversion led to a new approach for forming C-C bonds α to the N atoms of amines.

Ceria supported Ru0-Ruδ+ clusters as efficient catalyst for arenes hydrogenation

Cao, Yanwei,Zheng, Huan,Zhu, Gangli,Wu, Haihong,He, Lin

supporting information, p. 770 - 774 (2020/08/24)

Selective hydrogenation of aromatic amines, especially chemicals such as aniline and bis(4-aminocyclohexyl)methane for non-yellowing polyurethane, is of particular interests due to the extensive applications. To conquer the existing difficulties in selective hydrogenation, the Ru0-Ruδ+/CeO2 catalyst with solid frustrated Lewis pairs was developed for aromatic amines hydrogenation with excellent activity and selectivity under relative milder conditions. The morphology, electronic and chemical properties, especially the Ru0-Ruδ+ clusters and reducible ceria were characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), X-ray photoelectron spectroscopy (XPS), CO2 temperature programmed desorption (CO2-TPD), H2 temperature programmed reduction (H2-TPR), H2 diffuse reflectance Fourier transform infrared spectroscopy (H2-DRIFT), Raman, etc. The 2% Ru/CeO2 catalyst exhibited good conversion of 95% and selectivity greater than 99% toward cyclohexylamine. The volcano curve describing the activity and Ru state was found. Owning to the “acidic site isolation” by surrounding alkaline sites, condensation between the neighboring amine molecules could be effectively suppressed. The catalyst also showed good stability and applicability for other aromatic amines and heteroarenes containing different functional groups.

PRODUCTION METHOD OF CYCLIC COMPOUND

-

Paragraph 0057-0058; 0061-0063, (2021/05/05)

PROBLEM TO BE SOLVED: To provide an industrially simple production method of a cyclic compound. SOLUTION: A production method of a cyclic compound includes a step to obtain a reduced form (B) by reducing an unsaturated bond in a ring structure of an aromatic compound (A) by means of catalytic hydrogenation of the aromatic compound (A) or its salt using palladium carbon as a catalyst under a normal pressure, in which the aromatic compound (A) has one or more ring structures selected from a group consisting of a five membered-ring, a six membered-ring, and a condensed ring of the five membered-ring or the six membered-ring with another six membered-ring, a hetero atom can be included in the ring structure, and the aromatic compound (A) can have one or two side chains bonded to the ring structure and does not have any carbon-carbon triple bond in the side chain. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Han, Bo,Jiao, Haijun,Wu, Lipeng,Zhang, Jiong

, p. 2059 - 2067 (2021/09/02)

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

García-Domínguez, Andrés,Gonzalez, Jorge A.,Leach, Andrew G.,Lloyd-Jones, Guy C.,Nichol, Gary S.,Taylor, Nicholas P.

supporting information, (2022/01/04)

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Process route upstream and downstream products

Process route

Butane-1,4-diol
110-63-4

Butane-1,4-diol

pyrrolidine
123-75-1

pyrrolidine

4-Aminobutanol
13325-10-5

4-Aminobutanol

Conditions
Conditions Yield
With ammonia; CrZMS-5; at 300 ℃; for 4h;
48.0 % Chromat.
3,6-dihydro-2<i>H</i>-[1,2]oxazine
3686-43-9

3,6-dihydro-2H-[1,2]oxazine

methanol
67-56-1

methanol

pyrrolidine
123-75-1

pyrrolidine

1,2-oxazinane
36652-42-3

1,2-oxazinane

4-Aminobutanol
13325-10-5

4-Aminobutanol

Conditions
Conditions Yield
Hydrogenation;
methanol
67-56-1

methanol

4-Aminobutanol
13325-10-5

4-Aminobutanol

pyrrolidine
123-75-1

pyrrolidine

4-(N-methylamino)butan-1-ol
42042-68-2

4-(N-methylamino)butan-1-ol

4-dimethylamino-1-butanol
13330-96-6

4-dimethylamino-1-butanol

Conditions
Conditions Yield
With Cs-P-Si mixed-oxide; at 300 ℃; under 61504.9 Torr; Title compound not separated from byproducts;
C<sub>4</sub>H<sub>9</sub>N*C<sub>6</sub>H<sub>5</sub>NO<sub>3</sub>
83004-32-4

C4H9N*C6H5NO3

pyrrolidine
123-75-1

pyrrolidine

Conditions
Conditions Yield
In 1,4-dioxane; at 24.84 ℃; Equilibrium constant; Ionic liquid;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

pyrrolidine
123-75-1

pyrrolidine

1-pyrroline
5724-81-2

1-pyrroline

4-Aminobutanol
13325-10-5

4-Aminobutanol

1,4-diaminobutane
110-60-1

1,4-diaminobutane

Conditions
Conditions Yield
With ammonia; chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); In para-xylene; at 180 ℃; for 12h; under 38253.8 Torr; Product distribution / selectivity; Autoclave; Inert atmosphere;
With ammonia; chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); In toluene; at 155 ℃; for 24h; under 38253.8 Torr; Product distribution / selectivity; Autoclave; Inert atmosphere;
With chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); ammonia; at 180 ℃; for 12h; Temperature; Inert atmosphere; Autoclave;
With chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); ammonia; In toluene; at 155 ℃; for 24h; under 30153 Torr; Pressure; Reagent/catalyst; Temperature; Catalytic behavior; Autoclave; Inert atmosphere;
With chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); ammonia; In toluene; at 155 ℃; for 12h; under 31503.2 Torr; Inert atmosphere; Autoclave;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

pyrrolidine
123-75-1

pyrrolidine

1-pyrroline
5724-81-2

1-pyrroline

4-Aminobutanol
13325-10-5

4-Aminobutanol

Conditions
Conditions Yield
With ammonia; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); bis(2-diphenylphosphinoethyl)phenylphosphine; In toluene; at 155 ℃; for 12h; under 28502.9 Torr; Product distribution / selectivity; Inert atmosphere;
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine]; at 155 ℃; for 12h; Temperature; Inert atmosphere; Autoclave;
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 155 ℃; for 12h; under 33753.4 Torr; Inert atmosphere; Autoclave;
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine]; In toluene; at 155 ℃; for 12h; under 36753.7 Torr; Pressure; Reagent/catalyst; Autoclave; Inert atmosphere;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

pyrrolidine
123-75-1

pyrrolidine

4-(pyrrolidin-1-yl)butan-1-ol
93264-47-2

4-(pyrrolidin-1-yl)butan-1-ol

4-Pyrrolidino-butylamin
24715-90-0

4-Pyrrolidino-butylamin

1,4-di-(1-pyrrolidinyl)butane
41726-75-4

1,4-di-(1-pyrrolidinyl)butane

4-Aminobutanol
13325-10-5

4-Aminobutanol

Conditions
Conditions Yield
With ammonia; hydrogen; at 130 ℃; under 150015 Torr; Overall yield = 38.1 %;
With ammonia; hydrogen; at 140 ℃; under 150015 Torr; Overall yield = 56.7 %;
With ammonia; hydrogen; at 150 ℃; under 150015 Torr; Temperature; Overall yield = 78.4 %;
n-benzoylpyrrolidine
3389-54-6

n-benzoylpyrrolidine

pyrrolidine
123-75-1

pyrrolidine

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
n-benzoylpyrrolidine; With potassium tert-butylate; C16H26BrN3Ru; In isopropyl alcohol; Autoclave; Inert atmosphere; Green chemistry;
With hydrogen; In isopropyl alcohol; at 90 ℃; for 24h; under 19001.3 Torr; Autoclave; Green chemistry;
33 %Spectr.
1,2-diphenyl-2-pyrrolidin-1-yl-ethanol
123074-81-7

1,2-diphenyl-2-pyrrolidin-1-yl-ethanol

pyrrolidine
123-75-1

pyrrolidine

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With thioindigo; In water; benzene; Product distribution; Mechanism; Irradiation; in the presence of air;
pyrrolidine
123-75-1

pyrrolidine

1-pyrroline
5724-81-2

1-pyrroline

2-pyrrolidinon
616-45-5

2-pyrrolidinon

4-butanolide
96-48-0

4-butanolide

4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

propionic acid
802294-64-0,79-09-4

propionic acid

butyric acid
107-92-6

butyric acid

Conditions
Conditions Yield
In water; at 225 ℃; for 6h; under 4500.45 Torr; Inert atmosphere;

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