41302-05-0

Basic information

• Product Name: 2-(4-CHLOROBUTOXY)TETRAHYDROPYRAN
• Synonyms: 2-(4-chlorobutoxy)tetrahydro-2h-pyra;2-(4-CHLOROBUTOXY)TETRAHYDRO-2H-PYRAN;2-(4-CHLOROBUTOXY)TETRAHYDROPYRAN;(4-Chlorobutyl)(tetrahydro-2H-pyran-2-yl) ether;1-Chloro-4-(tetrahydro-2H-pyran-2-yloxy)butane
• CAS NO: 41302-05-0
• Molecular Formula: C₉H₁₇ClO₂
• Molecular Weight: 192.68
• EINECS: 255-305-3
• Mol File: 41302-05-0.mol

Chemical Properties

• Boiling Point: 131 °C / 18mmHg
• Flash Point: 109 °C
• Appearance: /
• Density: 1,07 g/cm3
• Vapor Pressure: 0.0129mmHg at 25°C
• Refractive Index: n20/D 1.4605(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Hexane (Slightly)
• CAS DataBase Reference: 2-(4-CHLOROBUTOXY)TETRAHYDROPYRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-CHLOROBUTOXY)TETRAHYDROPYRAN(41302-05-0)
• EPA Substance Registry System: 2-(4-CHLOROBUTOXY)TETRAHYDROPYRAN(41302-05-0)

Safety Data

• Hazardous Substances Data: 41302-05-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(4-Chlorobutoxy)tetrahydropyran is used as a synthetic intermediate for the tetrahydropyranylation of alcohols under solvent-free conditions. This application is particularly important in the field of organic chemistry, as it allows for the selective protection of alcohol functional groups, which is crucial for various chemical transformations and the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(4-Chlorobutoxy)tetrahydropyran is utilized as a key building block in the development of novel drug candidates. Its unique structural features and reactivity make it a valuable component in the design and synthesis of new pharmaceutical compounds, potentially leading to the discovery of innovative treatments for various diseases and medical conditions.
Used in Chemical Research:
2-(4-Chlorobutoxy)tetrahydropyran also plays a significant role in chemical research, where it is employed as a model compound to study various reaction mechanisms and explore new synthetic methodologies. This contributes to the advancement of chemical knowledge and the development of more efficient and environmentally friendly synthetic processes.

InChI:InChI=1/C9H17ClO2/c10-6-2-4-8-12-9-5-1-3-7-11-9/h9H,1-8H2

Upstream product

• 928-51-8 4-Chloro-1-butanol 
• 96754-03-9 2-(phenylsulfonyl)tetrahydro-2H-pyran 
• 51326-51-3 4-(tetrahydropyran-2-yloxy)butan-1-ol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 142-68-7 TETRAHYDROPYRANE 

Downstream Products

• 2683-56-9 4-(N,N-diethylamino)-1-butanol 
• 103187-59-3 5-(2,3,4,5-tetramethoxy-6-methylphenyl)-5-phenylpentane-1-ol 
• 138100-26-2 (S)-2-((S)-1-Methyl-cyclohex-2-enyl)-5-(tetrahydro-pyran-2-yloxy)-pentanoic acid 
• 138100-26-2 (R)-2-((S)-1-Methyl-cyclohex-2-enyl)-5-(tetrahydro-pyran-2-yloxy)-pentanoic acid 
• 138100-27-3 (S)-3-((S)-1-Methyl-cyclohex-2-enyl)-6-(tetrahydro-pyran-2-yloxy)-hexan-2-one 
• 138100-27-3 (R)-3-((S)-1-Methyl-cyclohex-2-enyl)-6-(tetrahydro-pyran-2-yloxy)-hexan-2-one 
• 107112-67-4 iodure d'N,N,N-trimethylhydrazonium de methyl-2 phenyl-1 (tetrahydropyrannyle ether)-6 hexanone 
• 107112-77-6 (2S,5S)-2-Methyl-3,5-diphenyl-2-[4-(tetrahydro-pyran-2-yloxy)-butyl]-2,5-dihydro-1H-pyrrole 
• 107112-69-6 methyl-2 (tetrahydropyrannyloxy-4' butyl)-2 diphenyl-3,5 2H-pyrrole 
• 107112-68-5 (tetrahydropyrannyloxy-4'butyl)-2 methyl-2 phenyl-3 2H-azirine 
• 258523-66-9 2-phenyl 2[4(2-tetrahydropyranoxy)butyl] diethyl malonate 
• 302914-54-1 benzyl-bis-[4-(tetrahydro-pyran-2-yloxy)-butyl]-amine 
• 928-90-5 5-hexyl-1-ol 
• 88338-92-5 NSC 142288 

Relevant articles and documents

Total Synthesis of Phenanthropiperidine Alkaloids by Sequential Alkylation of N,N-Dibenzylaminoacetonitrile

Two representative members of the phenanthropiperidine alkaloid family, tylophorine (1) and cryptopleurine (2), were synthesized by a bidirectional alkylation strategy employing dibenzylaminoacetonitrile as a substrate. This approach relies on the unprecedented condensation of metallated α-aminonitriles with bromomethylphenanthrenes to provide fully substituted α-aminonitriles, which are subjected to a NaBH4-mediated reductive decyanation process to form homobenzylic amines. From these intermediates, a terminal leaving group was introduced by simple chemical manipulation, and its displacement by a free primary amine under two favorable cyclization processes led to the formation of the future E-ring of both alkaloids in high yields. Finally, a late Pictet-Spengler cyclization ensured the formation of a D-ring for the alkaloids 1 and 2.

Donepezil–melatonin hybrids as butyrylcholinesterase inhibitors: Improving binding affinity through varying mode of linking fragments

Hybrid inhibitors of acetyl- and butyrylcholinesterase are compounds that combine structural motifs of two different classical inhibitors, leading to a dual binding ligand. A rapidly growing collection of those compounds involves a wide diversity of structural motifs, but the way of linking two active fragments and its impact on the affinity toward cholinesterases usually remains beyond the extent of investigation. We present hereby a detailed analysis of this aspect using melatonin–donepezil hybrids. A new series of compounds, in which two fragments are connected using a carbamate linker, exhibits excellent activity and selectivity toward butyrylcholinesterase.

Selexipag intermediates and method for preparing selexipag

The invention belongs to the field of chemical preparation, and relates to selexipag intermediates and a method for preparing selexipag. The selexipag intermediates are a compound SLP-4, a compound SLP-7, a compound SLP-8 and a compound SLP-10. The selexipag intermediates and the method have the advantages that the method for preparing the selexipag includes reasonable routes and is low in cost and operative difficulty and little in environmental pollution, raw materials are easily available, accordingly, requirements of large-scale industrial production can be met by the method, and the like.

POLYMERIZABLE COMPOUND AND OPTICAL ANISOTROPIC BODY

PROBLEM TO BE SOLVED: To provide a polymerizable compound having high storage stability without causing precipitation of crystals or the like when added to a polymerizable composition and large refractive index anisotropy and to provide a polymerizable composition which hardly causes haze when polymerized by attaching a resin mold to a polymerizable composition containing the polymerizable compound. SOLUTION: There are provided: a compound represented by the formula (I), for example, a compound represented by the formula (I-106); a composition containing the compound; a polymer obtained by polymerizing the compound; and an optical anisotropic body using the polymer. COPYRIGHT: (C)2016,JPOandINPIT

Studies towards the synthesis of crotogoudin

An effective synthesis of the tricyclic core structure of the new diterpene crotogoudin was achieved. The synthesis features an intermolecular domino Michael reaction to construct a bicyclo[2.2.2]octane motif and an aldol condensation to close ring B. Stork reductive alkylation with allyl bromide proceeded from the β side, resulting in the wrong stereochemistry at C-10. Georg Thieme Verlag Stuttgart - New York.

Mild and efficient chemoselective tetrahydropyranylation of alcohols using bronsted acidic ionic liquid as catalyst under solvent-free conditions

A straightforward and efficient method for preparation of morpholinium bisulfate ([mroH]HSO4) as a novel acidic ionic liquid is reported. The application of this efficient and inexpensive acidic ionic liquid catalyst for tetrahydropyranylation of alcohols under mild and solvent-free conditions at room was investigated.

Tetrahydropyranylation of alcohols under solvent-free conditions

A green, efficient, and large-scale method for tetrahydropyranylation of alcohols in the presence of a catalytic amount of pyridinium chloride at room temperature under solvent-free conditions is reported. Copyright Taylor & Francis Group, LLC.

Synthesis of new analogs of benzotriazole, benzimidazole and phthalimide-potential inhibitors of human protein kinase CK2

New derivatives of 4,5,6,7-tetrabromo-1H-1,2,3-benzotriazole (TBBt), 4,5,6,7-tetrabromo-1H-benzimidazole (TBBi), and N-substituted tetrabromophthalimides were synthesized and their effect on the activity of human protein kinase CK2 was examined. The most active were derivatives with N-hydroxypropyl substituents (IC50 in 0.32-0.54 μM range) whereas derivatives of phthalimide were almost ineffective.

Design, synthesis, and evaluation of new chemosensitizers in multi-drug-resistant Plasmodium falciparum

A series of new chemosensitizers (modulators) against chloroquine-resistant Plasmodium falciparum were designed and synthesized in an attempt to fabricate modulators with enhancing drug-resistant reversing efficacy and minimal side effects. Four aromatic amine ring systems phenothiazine, iminodibenzyl, iminostilbene, and diphenylamine-were examined. Various tertiary amino groups including either noncyclic or cyclic aliphatic amines were introduced to explore the steric tolerance at the end of the side chain. The new compounds showed better drug-resistant reversing activity in chloroquine-resistant than in mefloquine-resistant cell lines and were generally more effective against chloroquine-resistant P. falciparum isolates from Southeast Asian (W2 and TM91C235) than those from South America (PC49 and RCS). Structure-activity relationship studies revealed that elongation of the alkyl side chain of the molecule retained the chemosensitizing activity, and analogues with four-carbon side chains showed superior activity. Furthermore, new modulators with phenothiazine ring exhibited the best chemosensitizing activity among the four different ring systems examined. Terminal amino function has limited steric tolerance as evidenced by the dramatic lose of the modulating activity, when the size of substituent at the amino group increases. The best new modulator synthesized in this study possesses all three optimized structural features, which consist of a phenothiazine ring and a pyrrolidinyl group joined by a four-carbon alkyl bridge. The fractional inhibitory concentration (FIC) index of the best compound is 0.21, which is superior to that of verapamil (0.51), one of the best-known multi-drug-resistant reversing agents. Some of the analogues displayed moderate intrinsic in vitro antimalarial activity against a W-2 clone of P. falciparum.

Progress toward the development of a safe and effective agent for treating reentrant cardiac arrhythmias: Synthesis and evaluation of ibutilide analogues with enhanced metabolic stability and diminished proarrhythmic potential

A series of ibutilide analogues with fluorine substituents on the heptyl side chain was prepared and evaluated for class III antiarrhythmic activity, metabolic stability, and proarrhythmic potential. It was found that fluorine substituents stabilized the side chain to metabolic oxidation. Many of the compounds also retained the ability to increase the refractoriness of cardiac tissue at both slow and fast pacing rates. The potential for producing polymorphic ventricular tachycardia in the rabbit model was dependent on the chirality of the benzylic carbon. The S-enantiomers generally had less proarrhythmic activity than the corresponding racemates. One compound from this series (45E, trecetilide fumarate) had excellent antiarrhythmic activity and metabolic stability and was devoid of proarrhythmic activity in the rabbit model. It was chosen for further development.