5631-95-8

Basic information

• Product Name: 2,3-Dichlorotetrahydropyran
• Synonyms: 2,3-Dichlorotetrahydropyran
• CAS NO: 5631-95-8
• Molecular Formula: C₅H₈Cl₂O
• Molecular Weight: 155.02242
• Mol File: 5631-95-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3-Dichlorotetrahydropyran(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dichlorotetrahydropyran(5631-95-8)
• EPA Substance Registry System: 2,3-Dichlorotetrahydropyran(5631-95-8)

Safety Data

• Hazardous Substances Data: 5631-95-8(Hazardous Substances Data)

Usage

Physical state

Colorless liquid 2,3-Dichlorotetrahydropyran is a liquid at room temperature and is colorless in appearance.

Primary use

Intermediate in synthesis The compound is mainly used as an intermediate in the synthesis of various other organic compounds.

Versatility

Reagent in organic chemistry 2,3-Dichlorotetrahydropyran is a versatile reagent, meaning it can be used in a wide range of organic chemistry reactions.

Applications

Pharmaceutical and agrochemical preparation The compound is commonly used in the preparation of pharmaceuticals and agrochemicals, indicating its importance in these industries.

Solvent use

Chemical reactions 2,3-Dichlorotetrahydropyran can also serve as a solvent in chemical reactions, helping to dissolve and mix reactants.

Building block

Production of complex molecules The compound is used as a building block in the creation of more complex molecules, showcasing its utility in molecular construction.

Industrial potential

Research interest 2,3-Dichlorotetrahydropyran has potential industrial applications, making it of interest to researchers in the fields of organic synthesis and chemical engineering.

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 142-68-7 TETRAHYDROPYRANE 
• 6581-54-0 3-chlorotetrahydropyran 

Downstream Products

• 857223-20-2 3-chloro-2-phenylethynyl-tetrahydro-pyran 
• 100607-52-1 3-chloro-2-phenethyl-tetrahydro-pyran 
• 31535-05-4 trans-3-chloro-2-methyltetrahydropyran 
• 31535-05-4 cis-3-chloro-2-methyltetrahydropyran 
• 31535-06-5 trans-3-chloro-2-ethyltetrahydropyran 
• 31535-06-5 cis-3-chloro-2-ethyltetrahydropyran 
• 6963-10-6 3-chloro-2-phenyl-tetrahydro-pyran 
• 92316-41-1 4-chloro-5-phenylimino-pentan-1-ol 
• 7681-84-7 tetrahydrofuran-2-carbaldehyde 
• 13159-16-5 (E)-5-phenyl-4-penten-1-ol 
• 105401-84-1 (4E)-5-(4-methoxyphenyl)pent-4-en-1-ol 
• 76978-38-6 (E)-5-(4-methylphenyl)-4-penten-1-ol 
• 105337-73-3 (E)-5-o-tolylpent-4-en-1-ol 
• 100863-10-3 trans-8-Phenyl-octen-⁽⁴⁾-ol-⁽¹⁾ 

Relevant articles and documents

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Treatment of the acyclic allyl-octa-4,7-dienyl N-chloroamine 5 by titanium trichloride induces a chain process including three consecutive regio- and stereo-selective homolytic cyclisations. As a result of these selectivities, the main product of the reaction is an original linear cis-syn-cis aza-triquinane, the structure of which was assigned by high field (400 MHz) Nuclear Magnetic Resonance study.

Stereoselective Synthesis of Alcohols containing (Z)- and (E)-Olefins, Dienes, Enynes and Styrenes: Cyclic β-Halogeno Scissions using Samarium Diiodide as the Electron-transfer Agent

In contrast to the sodium-mediated ring scission of 2-substituted 3-chloro ethers of the tetrahydrofuran series, samarium diiodide gives olefins of high (E)-stereoselectivity and provides (E)-conjugated and unconjugated dienes, styrenes and enynes in good yield without appreciable over-reduction.Whilst the SmI2 scission of 3-chloro-2-alkyltetrahydropyrans gives (Z)-rich (Z)/(E) olefin mixtures, the 2-(alk-1'-ynyl) members give (Z)-enyne alkohols with high stereoselectivity, providing a valuable complement to the (E)-enyne synthesis employing the tetrahydrofuran series.In electron-transfer scissions using sodium, the stereochemistry of the product alcohols is related to the ground-state conformation of the cis- and trans-pyrans and -furans.The slow SmI2-mediated reactions appear to involve samarium-complexed intermediates having structures independent of the original conformation, or of the cis- or trans-geometry of the furan or pyran, and it is the transition states from these intermediates that determine the stereochemical outcome.Scissions in the tetrahydrofuran series can be accelerated by addition of HMPA or DMPU with only a little deterioration in stereoselectivity, but in the tetrahydropyran series there are drastic changes in product stereochemistry when DMPU is added.Brief comment is made on the synthesis of tetrahydro-furan and pyran precursors.

β-Halogeno Ether Synthesis of Olefinic Alcohols: Stereochemistry and Conformation of 2-Substituted 3-Halogenotetrahydro-pyran and furan Precursors

Ring-scission of cis- or trans-2-alkyl- (or aryl-) 3-chlorotetrahydropyrans proceeds regioselectively and highly stereoselectively to give (E)-alk-4-en-1-ols, but in the parallel tetrahydrofuran series (Z)-/(E)-mixtures, dependent on percursor geometry, are formed.In this paper the stereochemistry and conformation of the tetrahydro-pyran and - furan precursors are considered.The cis/trans-composition of 2,3-dihalogenotetrahydro-pyrans and-furans made by various routes is reported.Reaction with Grignard reagents gives separable cis-/trans-mixtures the stereoisomeric composition of which, in the cases examined, does not depend on the stereoisomeric composition of the dihalide, but does vary with the halogen and the composition of the Grignard or dialkylmagnesium; possible reasons are discussed.The stereochemistry and conformation of the 2-alkyl- (or aryl-)3-chlorotetrahydropyrans is analysed by n.m.r. methods (J2a,3acis ca. 1.5 Hz; J2a,3atrans ca. 9.8 Hz) but assignments for the two tetrahydrofuran series with J2,3 2.6-3.6 and 4.3-5.9 are made uncertain by pseudorotation.The stereochemical identity of the two series is rigorously proved by isolation of cis- and trans-2-allyl-3-chlorotetrahydrofuran.On the one hand the former is hydrogenated to the cis-2-propyl compound, correlated with other members of the alkyl series, but on the other it is oxidised and the acid is converted into the cis-p-bromophenyl ester.The stereochemistry and conformation of the latter is rigorously demonstrated by an X-ray structure.The stereochemistries and conformations of the 2-deuterio- and 2-methoxy-3-chlorotetrahydropyrans are discussed, and consideration is then extended to the 2-alkyl-3-chloro-2-methyltetrahydro-pyran and -furan series.