123-75-1 Usage
Description
Tetrahydro pyrrole, also known as pyrrolidine, is a saturated heterocyclic compound with one nitrogen atom in a five-membered ring. It is a colorless to pale yellow liquid with an ammonia-like odor and is found in certain plants. The ring structure is present in many alkaloids, and it has a flash point of 37°F and a density of 0.85 g/cm3. Tetrahydro pyrrole is a conjugate base of a pyrrolidinium ion and is a member of the pyrrolidine family.
Uses
Tetrahydro pyrrole is used in various applications across different industries due to its unique properties and reactivity.
Used in Pharmaceutical Industry:
Tetrahydro pyrrole is used as a chemical intermediate, particularly in the synthesis of a wide range of pharmaceutical compounds. It serves as a building block for the synthesis of matrix metalloprotein inhibitors (MMPIs) and aminopeptidase N inhibitors (APNIs). It is also used in the synthesis of N-benzoyl pyrrolidine from benzaldehyde via oxidative amination and as a catalyst for the synthesis of N-sulfinyl aldimines from carbonyl compounds and sulfonamides.
Used in Pesticide Industry:
Tetrahydro pyrrole is used to prepare pesticides, where its reactivity and alkaline nature contribute to the development of effective pest control agents.
Used in Rubber Industry:
Tetrahydro pyrrole is used as a rubber accelerator, enhancing the curing process and improving the overall properties of the rubber products.
Used in Flavor and Fragrance Industry:
Tetrahydro pyrrole is found in various food items and beverages, such as 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, Finnish whiskey, white wine, red wine, coffee, radish, malt, roasted peanut, and roasted barley. Its taste characteristics at 50 ppm include ammonia and fishy, amine-like with seaweed and shellfish nuances, making it a valuable component in the flavor and fragrance industry.
Used in Chemical Synthesis:
Tetrahydro pyrrole can be used to synthesize various compounds, such as Taddol-pyrrolidine phosphoramidite, a ligand for rhodium-catalyzed [2+2+2] cycloaddition of pentenyl isocyanate and 4-ethynylanisole, and H,4 PyrrolidineQuin-BAM (′PBAM′), a selective catalyst for the aza-Henry addition of nitroalkanes to aryl aldimines. Additionally, it can be used to synthesize 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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 123-75-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 3 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 123-75:
(5*1)+(4*2)+(3*3)+(2*7)+(1*5)=41
41 % 10 = 1
So 123-75-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H9N/c1-2-4-5-3-1/h5H,1-4H2/p+1
123-75-1Relevant articles and documents
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.
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Sakurai
, p. 374 (1936)
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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).
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.
N-trifluoroacetylamino alcohols as phosphodiester protecting groups in the synthesis of oligodeoxyribonucleotides
Wilk, Andrzej,Srinivasachar, Kasturi,Beaucage, Serge L.
, p. 6712 - 6713 (1997)
-
-
Brown,van Gulick
, p. 1046 (1956)
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Method for protecting sulfonyl of deamination amine
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Paragraph 0054-0056, (2021/11/03)
The invention discloses a method for removing sulfenyl protection of amine. The method comprises the following steps: dissolving N - sulfonyl-protected amine and a base in a reaction solvent, then adding diphenylphosphine to uniformly mix and maintain 90 °C. When TCL detection reaction is complete, a recrystallization method or an extraction separation method is adopted to obtain the target product. The method disclosed by the invention adopts diphenylphosphine as an extraction reagent, is good in reaction activity, high in selectivity and wide in application range, and can replace the use of a hazardous reagent under the basic heating condition. Prodrug research and development and industrial production are of great significance.
Highly economical and direct amination of sp3carbon using low-cost nickel pincer catalyst
Brandt, Andrew,Rangumagar, Ambar B.,Szwedo, Peter,Wayland, Hunter A.,Parnell, Charlette M.,Munshi, Pradip,Ghosh, Anindya
, p. 1862 - 1874 (2021/01/20)
Developing more efficient routes to achieve C-N bond coupling is of great importance to industries ranging from products in pharmaceuticals and fertilizers to biomedical technologies and next-generation electroactive materials. Over the past decade, improvements in catalyst design have moved synthesis away from expensive metals to newer inexpensive C-N cross-coupling approaches via direct amine alkylation. For the first time, we report the use of an amide-based nickel pincer catalyst (1) for direct alkylation of amines via activation of sp3 C-H bonds. The reaction was accomplished using a 0.2 mol% catalyst and no additional activating agents other than the base. Upon optimization, it was determined that the ideal reaction conditions involved solvent dimethyl sulfoxide at 110 °C for 3 h. The catalyst demonstrated excellent reactivity in the formation of various imines, intramolecularly cyclized amines, and substituted amines with a turnover number (TON) as high as 183. Depending on the base used for the reaction and the starting amines, the catalyst demonstrated high selectivity towards the product formation. The exploration into the mechanism and kinetics of the reaction pathway suggested the C-H activation as the rate-limiting step, with the reaction second-order overall, holding first-order behavior towards the catalyst and toluene substrate.