67106-71-2

Basic information

• Product Name: Benzonitrile, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-
• CAS NO: 67106-71-2
• Molecular Formula: C12H13NO2
• Molecular Weight: 203.241
• Mol File: 67106-71-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-(67106-71-2)
• EPA Substance Registry System: Benzonitrile, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-(67106-71-2)

Safety Data

• Hazardous Substances Data: 67106-71-2(Hazardous Substances Data)

Upstream product

• 694-54-2 tetrahydro-2H-2-pyranol 
• 767-00-0 4-cyanophenol 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 188922-39-6 N,N'-bis(benzyloxycarbonyl)-N''-4-hydroxybenzylguanidine 
• 1026945-77-6 C₂₉H₃₁N₃O₆ 
• 188922-40-9 C₃₃H₃₈N₄O₈ 
• 1027047-37-5 C₃₂H₃₆N₄O₈ 
• 1026750-87-7 C₃₂H₃₆N₄O₈ 
• 104575-22-6 (E)-2-phenyl-3-<4-<2-(diethylamino)ethoxy>phenyl>-3-(4-hydroxyphenyl)acrylonitrile 
• 104575-13-5 (Z)-2-phenyl-3-(4-hydroxyphenyl)-3-<4-<2-(diethylamino)ethoxy>phenyl>acrylonitrile 
• 104575-21-5 (E)-1-<4-<2-(diethylamino)ethoxy>phenyl>-1-(4-hydroxyphenyl)-2-phenylethene 
• 104575-12-4 (Z)-1-{4-[2-(diethylamino)ethoxy]phenyl}-1-(4-hydroxyphenyl)-2-phenylethene 
• 104575-16-8 4-<2-(diethylamino)ethoxy>-4'-<(tetrahydropyran-2-yl)oxy>benzophenone 
• 875708-42-2 4-tetrahydropyranyloxybenzylamine 

Relevant articles and documents

Croconamides: A new dual hydrogen bond donating motif for anion recognition and organocatalysis

We introduce bis-aryl croconamides as a new member in the family of dual hydrogen bonding anion receptors. In this study a series of croconamides are synthesised, and the selectivity for anion binding is investigated (Cl- > Br- > I- in CH2Cl2). The croconamides exhibit different structures in the crystal phase depending on the substituents on the aromatic rings, and furthermore, the crystal structure revealed the presence of tautomers. DFT calculations elucidated the complex structures formed upon addition of anion to the croconamides, confirming the order of association constants towards the halogen anions. The use of croconamides as organocatalysts in a proof-of-concept study is demonstrated in the formation of THP ethers. In addition to this, construction of a Hammet plot further elucidates the mechanism in action on formation of THP ethers.

Generally applicable organocatalytic tetrahydropyranylation of hydroxy functionalities with very low catalyst loading

This paper presents the first acid-free, organocatalytic tetrahydropyran and 2-methoxypropene protection of alcohols, phenols, and other ROH derivatives utilizing privileged N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea and a polystyrene-bound analogue. The reactions are broadly applicably (also on preparative scale), in particular, to acid-sensitive substrates such as aldol products, hydroxy esters, acetals, silyl-protected alcohols, and cyanohydrins. The catalytic efficiency is truly remarkably with turnover numbers of 100,000 and turnover frequencies of up to 5700 h-1 at catalyst loadings down to 0.001 mol%. The computationally supported mechanistic interpretation emphasizes the hydrogen bond assisted heterolysis of the alcohol and concomitant preferential stabilization of the oxyanion hole in the transition state. Georg Thieme Verlag Stuttgart.

Selective tetrahydropyranylation under non-acidic conditions

We report that the tetrahydropyranylation of hydroxyl groups, exhibiting especially very low nucleophilicities, can be achieved by means of Mitsunobu reaction with 2-hydroxytetrahydropyran. This reaction led to the protection of phenols and pyridinols without the use of an acidic catalyst. For instance hydroxypyridines could not be protected by dihydropyran under acidic conditions, whereas they underwent a smooth tetrahydropyranylation under Mitsunobu conditions. The method is selective for a phenol over an alcohol. Georg Thieme Verlag Stuttgart.