100-76-5

Basic information

• Product Name: QUINUCLIDINE
• Synonyms: 1,4-ethanopiperidine;1,4-ethylidinepiperidine;1-Azabicyclo[2.2.2]octan;4-Azabicyclo[2.2.2]octane;Chinuclidin;QUINUCLIDINE;1-AZABICYCLO[2.2.2]OCTANE;1,4-ETHYLENEPIPERIDINE
• CAS NO: 100-76-5
• Molecular Formula: C₇H₁₃N
• Molecular Weight: 111.18
• EINECS: 202-887-1
• Mol File: 100-76-5.mol
• Article Data: 26

Chemical Properties

• Melting Point: 157-160 °C(lit.)
• Boiling Point: 198.35°C (rough estimate)
• Flash Point: 36.5 °C
• Appearance: White or almost white crystalline powder
• Density: 0.8928 (rough estimate)
• Vapor Pressure: 1.5 mm Hg ( 20 °C)
• Refractive Index: 1.4500 (estimate)
• Solubility: H2O: very slightly soluble
• PKA: 10.87±0.33(Predicted)
• Water Solubility: Soluble in alcohol, diethyl ether, water and organic solvents.
• Sensitive: Air Sensitive
• Merck: 14,8081
• BRN: 103111
• CAS DataBase Reference: QUINUCLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: QUINUCLIDINE(100-76-5)
• EPA Substance Registry System: QUINUCLIDINE(100-76-5)

Safety Data

• Hazard Codes: T
• Statements: 24/25-38-41
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: CL5594625
• F: 2-10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 100-76-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Quinuclidine is used as a chemical building block for the synthesis of various pharmaceutical compounds, including quinine and alkaloids. Its ability to form salts with acids makes it a valuable component in the development of new drugs.
Used in Organic Synthesis:
Quinuclidine is employed as a catalyst and a key intermediate in organic synthesis. Its unique structure allows it to participate in various chemical reactions, making it a useful tool for the synthesis of complex organic molecules.
Used in Ligand Chemistry:
Quinuclidine serves as a ligand in the studies of OsO4-catalyzed dihydroxylation of olefins. Its presence can enhance the selectivity and efficiency of these reactions, which are important in the synthesis of various organic compounds.
Used in Analytical Chemistry:
Quinuclidine plays an important role in the formation of onium salts, which are used for testing PAC-antagonist activity. Its ability to form stable complexes with other molecules makes it a valuable tool in analytical chemistry for assessing the activity of various compounds.

Hazard

A poison by ingestion and skin contact. Low toxicity by inhalation. A moderate skin and severe eye irritant.

Purification Methods

Crystallise it from diethyl ether. The hydrochloride has m 364-365o(dec) (from EtOH or n-BuOH), and the picrate has m 225o (from aqueous EtOH). [Beilstein 20 H 144, 20 II 71, 20 III/IV 1966, 20/4 V 335.]

InChI:InChI=1/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2

Upstream product

• 622-26-4 4-(2-Hydroxyethyl)piperidine 
• 53378-77-1 1,5-dibromo-3-(2-bromoethyl)pentane 
• 7664-41-7 ammonia 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 69712-10-3 4-(2-bromo-ethyl)-piperidine; hydrobromide 
• 3731-38-2 3-Quinuclidinone 
• 3230-23-7 4-ethylpiperidine 
• 56-23-5 tetrachloromethane 
• 1849-29-2 1,1,1-trideuteromethanol 
• 1193-65-3 quinuclidin-3-one hydrochloride 
• 118764-00-4 N-methylquinuclidinium hydroxide 
• 1367879-52-4 C₇H₁₃N*C₈F₁₇I 
• 1367879-51-3 C₆F₅I*C₇H₁₃N 
• 39896-06-5 quinuclidine hydrochloride 

Downstream Products

• 73997-54-3 N-[2-(p-nitrophenyl)ethyl]quinuclidinium 
• 70275-59-1 N-methylquinuclidinium chloride 
• 35942-63-3 quinuclidinyl radical 
• 75-65-0 tert-butyl alcohol 
• 39896-06-5 quinuclidine hydrochloride 
• 87323-99-7 2-(quinuclidinio)ethanesulfonate 
• 94129-01-8 C₁₀H₁₉NO₃S 
• 73997-48-5 N-(β-p-nitrophenylethyl)quinuclidinium bromide 
• 88341-11-1 quinuclidine-bromanil (1:1) complex 
• 18370-19-9 1-chloro-2,2-bis-(4-nitrophenyl)ethene 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 1490-33-1 hexafluorothioacetone 
• 124044-92-4 Bis(trifluormethyl)sulfen-Chinuclidin-Addukt 
• 88344-29-0 quinuclidine*chloranil (1:1) complex 

Relevant articles and documents

Cucurbit[7]uril host-guest complexes of cholines and phosphonium cholines in aqueous solution

The neutral host cucurbit[7]uril forms very stable complexes with a series of cationic cholines (R3NCH2CH2OR'+) and their phosphonium analogues (R3PCH2CH 2OR'+) (R3 = Me3, Et3, or Me2Bz, or R3N = quinuclidinium, and R' = H, COCH 3, CO(CH2)2CH3, or PO3H), and (±)-carnitine, in aqueous solution. The complexation behaviour has been investigated using 1H and 31P NMR spectroscopies, and ESI mass spectrometry. The complexation-induced chemical shift changes of the guests clearly indicate the effects of replacing the N(CH3) 3+ end group by P(CH3)3+, and changing the nature of R on the position of the guest with respect to the CB[7] cavity and its polar portal-lining carbonyl groups. This study demonstrates that molecular recognition of cholines in aqueous solution is achievable with a neutral host without the need for aromatic walls for cation-π interactions. The Royal Society of Chemistry 2010.

DABCO and DMAP - Why are they different in organocatalysis?

(Chemical Equation Presented) What makes a good organocatalyst? DABCO (1,4-diazabicyclo[2.2.2]octane) is a thousandfold better nucleophile (k →) and at the same time a million times better leaving group (k←) than DMAP (4-(dimethylamino)pyridine). This apparent contradiction is resolved by consideration of the intrinsic reaction barriers.

The Soft Molecular Polycrystalline Ferroelectric Realized by the Fluorination Effect

For a century ferroelectricity has attracted widespread interest from science and industry. Inorganic ferroelectric ceramics have dominated multibillion dollar industries of electronic ceramics, ranging from nonvolatile memories to piezoelectric sonar or ultrasonic transducers, whose polarization can be reoriented in multiple directions so that they can be used in the ceramic and thin-film forms. However, the realization of macroscopic ferroelectricity in the polycrystalline form is challenging for molecular ferroelectrics. In pursuit of low-cost, biocompatible, and mechanically flexible alternatives, the development of multiaxial molecular ferroelectrics is imminent. Here, from quinuclidinium perrhenate, we applied fluorine substitution to successfully design a multiaxial molecular ferroelectric, 3-fluoroquinuclidinium perrhenate ([3-F-Q]ReO4), whose macroscopic ferroelectricity can be realized in both powder compaction and thin-film forms. The fluorination effect not only increases the intrinsic polarization but also reduces the coercive field strength. More importantly, it is also, as far as we know, the softest of all known molecular ferroelectrics, whose low Vickers hardness of 10.5 HV is comparable with that in poly(vinylidene difluoride) (PVDF) but almost 2 orders of magnitude lower than that in BaTiO3. These attributes make it an ideal candidate for flexible and wearable devices and biomechanical applications.

Mehrfachbindungen zwischen Hauptgruppenelementen und Uebergangsmetallen LXIV. Methyl(trioxo)rhenium: Basenaddukte und Basenreaktionen. Kristallstruktur von -perrhenat

In contrast to trioxo(η5-pentamethylcyclopentadienyl)rhenium(VII), (η5-C5Me5)-ReO3, te organometallic oxide methyl(tripoxo)rhenium(VII), CH3ReO3 (1), reacts with bases, e.g., sodium hydroxide and organic amines, with expansion of the

Degradation of Organic Cations under Alkaline Conditions

Understanding the degradation mechanisms of organic cations under basic conditions is extremely important for the development of durable alkaline energy conversion devices. Cations are key functional groups in alkaline anion exchange membranes (AAEMs), and AAEMs are critical components to conduct hydroxide anions in alkaline fuel cells. Previously, we have established a standard protocol to evaluate cation alkaline stability within KOH/CD3OH solution at 80 °C. Herein, we are using the protocol to compare 26 model compounds, including benzylammonium, tetraalkylammonium, spirocyclicammonium, imidazolium, benzimidazolium, triazolium, pyridinium, guanidinium, and phosphonium cations. The goal is not only to evaluate their degradation rate, but also to identify their degradation pathways and lead to the advancement of cations with improved alkaline stabilities.

Synthesis of amino-diamondoid pharmacophores: Via photocatalytic C-H aminoalkylation

We report a direct C-H aminoalkylation reaction using two light-activated H-atom transfer catalyst systems that enable the introduction of protected amines to native adamantane scaffolds with C-C bond formation. The scope of adamantane and imine reaction partners is broad and deprotection provides versatile amine and amino acid building blocks. Using readily available chiral imines, the enantioselective synthesis of the saxagliptin core and rimantadine derivatives is also described.

Lewis Acidity Scale of Diaryliodonium Ions toward Oxygen, Nitrogen, and Halogen Lewis Bases

Equilibrium constants for the associations of 17 diaryliodonium salts Ar2I+X- with 11 different Lewis bases (halide ions, carboxylates, p-nitrophenolate, amines, and tris(p-anisyl)phosphine) have been investigated by titrations followed by photometric or conductometric methods as well as by isothermal titration calorimetry (ITC) in acetonitrile at 20 °C. The resulting set of equilibrium constants KI covers 6 orders of magnitude and can be expressed by the linear free-energy relationship lg KI = sI LAI + LBI, which characterizes iodonium ions by the Lewis acidity parameter LAI, as well as the iodonium-specific affinities of Lewis bases by the Lewis basicity parameter LBI and the susceptibility sI. Least squares minimization with the definition LAI = 0 for Ph2I+ and sI = 1.00 for the benzoate ion provides Lewis acidities LAI for 17 iodonium ions and Lewis basicities LBI and sI for 10 Lewis bases. The lack of a general correlation between the Lewis basicities LBI (with respect to Ar2I+) and LB (with respect to Ar2CH+) indicates that different factors control the thermodynamics of Lewis adduct formation for iodonium ions and carbenium ions. Analysis of temperature-dependent equilibrium measurements as well as ITC experiments reveal a large entropic contribution to the observed Gibbs reaction energies for the Lewis adduct formations from iodonium ions and Lewis bases originating from solvation effects. The kinetics of the benzoate transfer from the bis(4-dimethylamino)-substituted benzhydryl benzoate Ar2CH-OBz to the phenyl(perfluorophenyl)iodonium ion was found to follow a first-order rate law. The first-order rate constant kobs was not affected by the concentration of Ph(C6F5)I+ indicating that the benzoate release from Ar2CH-OBz proceeds via an unassisted SN1-type mechanism followed by interception of the released benzoate ions by Ph(C6F5)I+ ions.

Scalable, Electrochemical Oxidation of Unactivated C-H Bonds

A practical electrochemical oxidation of unactivated C-H bonds is presented. This reaction utilizes a simple redox mediator, quinuclidine, with inexpensive carbon and nickel electrodes to selectively functionalize "deep-seated" methylene and methine moieties. The process exhibits a broad scope and good functional group compatibility. The scalability, as illustrated by a 50 g scale oxidation of sclareolide, bodes well for immediate and widespread adoption.

The method of manufacturing the amine compound Bicylic

PROBLEM TO BE SOLVED: To provide a method for simply obtaining a bicyclic amine compound at high yield and for suppressing by-product tar contents that may obstruct the continuous production. SOLUTION: The compound indicated by a formula (1) is subjected to intramolecular dehydration in a gas phase under the presence of a solid catalyst to produce the bicyclic amine compound indicated by a formula (2). In the formula (1), R1-R8each independently represents a hydrogen atom, a 1-4C alkyl group, a hydroxy group, a hydroxymethyl group or a 1-4C alkoxy group; X represents a carbon atom or a nitrogen atom; and Y represents a hydrogen atom, an alkyl group, a hydroxy group or a 1-4C hydroxyalkyl group. In the formula (2), R1-R8, X and Y are defined in the same manner as above. COPYRIGHT: (C)2012,JPOandINPIT

Ketene reactions with tertiary amines

Tertiary amines react rapidly and reversibly with arylketenes in acetonitrile forming observable zwitterions, and these undergo amine catalyzed dealkylation forming N,N-disubstituted amides. Reactions of N- methyldialkylamines show a strong preference for methyl group loss by displacement, as predicted by computational studies. Loss of ethyl groups in reactions with triethylamine also occur by displacement, but preferential loss of isopropyl groups in the phenylketene reaction with diisopropylethylamine evidently involves elimination. Quinuclidine rapidly forms long-lived zwitterions with arylketenes, providing a model for catalysis by cinchona and related alkaloids in stereoselective additions to ketenes.