6089-04-9

Basic information

• Product Name: TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN
• Synonyms: 2-(2-Propynyloxy)tetrahydro-2H-pyran;pent-4-ynoic acid;TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN, 9 8%;(Tetrahydro-2H-pyran-2-yl)(2-propynyl) ether;1-(3,4,5,6-Tetrahydro-2H-pyran-2-yloxy)-2-propyne;Propargyl(tetrahydro-2H-pyran-2-yl) ether;2-(2-Propynyloxy)tetrahydro-2H-pyran,98%;2-(prop-2-ynyloxy)tetrahydro-2H-pyran
• CAS NO: 6089-04-9
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.18
• EINECS: 228-028-0
• Product Categories: API intermediates;Boronic ester;Organoborons;Pyran;Acetylenes;Functionalized Acetylenes;Building Blocks;Heterocyclic Building Blocks;Pyrans;Alphabetic;TA - TE
• Mol File: 6089-04-9.mol
• Article Data: 120

Chemical Properties

• Boiling Point: 63-65 °C9 mm Hg(lit.)
• Flash Point: 139 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.997 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.886mmHg at 25°C
• Refractive Index: n20/D 1.458(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN(6089-04-9)
• EPA Substance Registry System: TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN(6089-04-9)

Safety Data

• Hazard Codes: Xi,F
• Statements: 11
• Safety Statements: 26-27-28-36/37/39-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 6089-04-9(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to light yellow liquid

Uses

Tetrahydro-2-(2-propynyloxy)-2H-pyran was used in preparation of 1,3-dienyl acetal.

Synthesis Reference(s)

Chemistry Letters, 6, p. 817, 1977Organic Syntheses, Coll. Vol. 7, p. 334, 1990Synthetic Communications, 19, p. 901, 1989 DOI: 10.1080/00397918908051010

General Description

The anion formed by metalation at the acetylenic carbon reacts with a variety of electrophiles.

InChI:InChI=1/C8H12O2/c1-2-6-9-8-5-3-4-7-10-8/h1,8H,3-7H2/t8-/m0/s1

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 107-19-7 propargyl alcohol 
• 3174-74-1 dihydropyran 
• 104-15-4 toluene-4-sulfonic acid 
• 927-74-2 3-Butyn-1-ol 
• 142-68-7 TETRAHYDROPYRANE 
• 51926-85-3 <3-Chlor-propin-(2)-yl>-pyranyl-aether 
• 199998-50-0 2-bromomethoxy-tetrahydro-pyran 
• 36551-06-1 3-(tetrahydropyran-2-yloxy)-1-trimethylsilylprop-1-yne 
• 64244-47-9 4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol 
• 694-54-2 tetrahydro-2H-2-pyranol 
• 106-96-7 propargyl bromide 

Downstream Products

• 32114-34-4 hex-2-yne-1,6-diol 
• 52804-67-8 5-Hydroxy-1-phenyl-pent-3-yn-2-one 
• 4117-14-0 2-decyn-1-ol 
• 6455-33-0 3-nitro-5-tetrahydropyran-2-yloxymethyl-isoxazole 
• 20739-58-6 2-octyn-1-ol 
• 51887-25-3 tridec-2-yn-1-ol 
• 4117-08-2 dec-9-en-2-yn-1-ol 
• 5871-10-3 2,5,8,11-tetradecatetrayne-1-ol 
• 61794-47-6 1-(4-trifluoromethyl-2,3,5,6-tetrafluorophenyl)-1-propyn-3-ol 
• 61794-48-7 3-(2,3,5,6-Tetrafluoro-4-methyl-phenyl)-prop-2-yn-1-ol 
• 61794-45-4 3-(Pentafluorphenyl)-prop-2-inol 
• 61794-46-5 3-(4-Methoxy-2,3,5,6-tetrafluorophenyl)-2-propyn-1-ol 
• 61794-51-2 1-(2,3,5,6-tetrafluorophenyl)-1-propyn-3-ol 
• 61794-52-3 1,4-Bis-(3'-hydroxyprop-1'-inyl)-tetrafluorbenzol. 

Relevant articles and documents

ω-Alkenylallylboronates: Design, Synthesis, and Application to the Asymmetric Allylation/RCM Tandem Sequence

The synthesis of allylboronates bearing an alkenyl moiety appended at a remote position is described for the first time. For that aim, the palladium-catalyzed borylation of the corresponding allylic alcohols was used as the key step. The required allylic alcohols were in turn obtained in 3–4 step sequences. The presence of an extra alkenyl moiety at a strategic position allows the triggering of a tandem asymmetric allylation/RCM reaction sequence that efficiently affords different sized cycles featuring two consecutive stereocenters and an exocyclic alcohol function. Products are obtained in moderate to excellent yields and high enantioselectivities, in most of the cases.

A novel oxidative cleavage reaction of propargyl alcohol derivatives using K2FeO4-Al2O3

Recent work has shown that a new K2FeO4 based oxidation protocol can promote a highly unusual carbon-carbon bond cleaving reaction of functionalised propargyl alcohols.

Structure and solvent-induced tuning of laser property and photostability of a boradiazaindacene (BODIPY) dye

Boradiazaindacene (BODIPY) class of laser dyes are highly efficient but degrade rapidly in alcohol solution during lasing action, progressively reducing output power. Photodegradation of these dyes is mainly due to reaction with the in situ generated singlet oxygen (1O2). With the aim to increase the lasing lifetimes of these dyes, we have designed and synthesized a new congener of the widely used BODIPY dye (PM567) by substitution at its B-centre. The new dye was highly fluorescent, and showed comparable lasing efficiency, but better photostability relative to PM567 in both polar (ethanol) and non-polar (1,4-dioxane) solvents, when excited by 2nd harmonic (532 nm) of a pulsed Nd-YAG laser. More interestingly, the lasing efficiency and photostability of both the dyes were much better in 1,4-dioxane than in ethanol. The relative photostabilities of the dyes were rationalized by absorption spectroscopic analyses of their triplet state properties in the respective solvents in the presence of a 1O2 generator or quencher as an additive, pulse radiolysis studies and quantum chemical calculations.

Method for synthesizing sex pheromone of hyphantria cunea

The invention relates to the technical field of hyphantria cunea prevention and treatment, in particular to a synthetic method for synthesizing sex pheromone of hyphantria cunea. According to a traditional method for synthesizing (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene by using propargyl alcohol as a starting material in the traditional technology, various side reactions are liable to occur during a sulfonic acid esterification reaction on a key intermediate (2S,3R)-2,3-epoxy-1-tetradecanol by using trifluoromethanesulfonic anhydride. In order to solve the problems, the (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene is successfully synthesized by taking propargyl alcohol as an initial raw material and taking a Sharpless asymmetric dihydroxylation reaction as a key step without the step of the sulfonic acid esterification reaction on a key intermediate (2S,3R)-2,3-epoxy-1-tetradecanol by trifluoromethanesulfonic anhydride in the preparation process. Therefore, the whole reaction is mild and controllable and few in side reactions, and enantioselectivity is high.

Ni-catalyzed direct carboxylation of propargylic alcohols with carbon dioxide

The carboxylation of propargylic alcohols containing a silyl group at the terminal position was conducted in a CO2 atmosphere at atmospheric pressure in the presence of a nickel catalyst and diethylzinc. Here, CO2 was used as not only the C1 source but also the promoter of the COH cleavage processes for the oxidative addition of propargylic alcohols.