17811-54-0

Basic information

• Product Name: Phenol, 2,3,5,6-tetrachloro-4-(phenylmethoxy)-
• CAS NO: 17811-54-0
• Molecular Formula: C13H8Cl4O2
• Molecular Weight: 338.017
• Mol File: 17811-54-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Phenol, 2,3,5,6-tetrachloro-4-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2,3,5,6-tetrachloro-4-(phenylmethoxy)-(17811-54-0)
• EPA Substance Registry System: Phenol, 2,3,5,6-tetrachloro-4-(phenylmethoxy)-(17811-54-0)

Safety Data

• Hazardous Substances Data: 17811-54-0(Hazardous Substances Data)

Upstream product

• 109-99-9 tetrahydrofuran 
• 87-87-6 2,3,5,6-tetrachlorobenzene-1,4-diol 
• 908094-04-2 phenyldiazomethane 
• 118-75-2 chloranil 
• 2768-31-2 benzyl diethyl phosphite 
• 108-88-3 toluene 
• 770-09-2 benzyltrimethylsilane 
• 18637-20-2 2,2'-azobis(α-ethylbutyronitrile) 

Relevant articles and documents

Photocycloadditions of chloranil to homobenzvalene, norbornadiene, and quadricyclane

Solutions of chloranil (CA) in toluene or benzene have been irradiated in the presence of the C7H8 valence isomers homobenzvalene (HB), norbornadiene (N), and quadricyclane (Q). In the case of HB, the adducts 3-6 were obtained, all of them having a rearranged structure. By a separate irradiation it was shown that 4 is a consecutive product of 3. The structure of 4 was established by X-ray diffraction analysis. These reactions are most probably initiated by an electron transfer (ET) from HB to 3CA, continue by bond formation between the radical ions to give the zwitterion 14, which undergoes Wagner-Meerwein rearrangements, and are completed by ring-closure between the charged centres of the resulting zwitterions. The oxidation potential of N is not larger than that of HB and the products 8-10 may well be formed through an ET to 3CA. However, the pathway leading to product 3 most probably involves diradical intermediates. This should also be the case for the adducts 11 and 12, which were produced upon irradiation of methyl phenylglyoxylate (PG) in the presence of N. In the case of Q, an ET to 3CA is again highly likely, followed by a combination of the radical ions to generate the zwitterion 29, which eventually collapses to produce the oxetane 8 as the sole identifiable product. The photoreactions of CA with N and Q proceeded much less efficiently in acetonitrile solution.

Reactions of Aryldiazomethanes with Chloranil

The reactions of several aryldiazomethanes (1a: p-tolyl; 2b: phenyl; 1c: p-chlorophenyl) with chloranil gave stilbenes (3) and spiro-oxetanes (4) at 20 deg C in tetrahydrofuran or 1,2-dichloroethane.The isomer ratios of 3 were ca. 2 to 3:1 in favor of cis, depending on the solvents and on the substituents 1.In the case of 4, however, stable trans-isomers were selectively formed.On the other hand, the presence of added CH3OH supressed the formation of 3 and 4 and, instead induced redox reactions giving α,α-dimethoxyarylmethanes and tetrachlorohydroquinone (6).In these redox reactions, the acid decompositions of 1 with 6 were also found.However, the presence of CF3CH2OH allowed the formation of considerable amount of 3 and 4, along with the redox products.The mechanism of these reactions will be discussed.