16737-44-3

Basic information

• Product Name: Benzene,1,1',1''-[methylidynetris(oxy)]tris-
• Synonyms: Orthoformicacid, triphenyl ester (6CI,7CI,8CI); NSC 509368; Phenyl orthocarbonate; Phenylorthoformate; Triphenoxymethane; Triphenyl orthoformate
• CAS NO: 16737-44-3
• Molecular Formula: C19H16 O3
• Molecular Weight: 292.334
• Mol File: 16737-44-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzene,1,1',1''-[methylidynetris(oxy)]tris-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene,1,1',1''-[methylidynetris(oxy)]tris-(16737-44-3)
• EPA Substance Registry System: Benzene,1,1',1''-[methylidynetris(oxy)]tris-(16737-44-3)

Safety Data

• Hazardous Substances Data: 16737-44-3(Hazardous Substances Data)

Upstream product

• 67-66-3 chloroform 
• 100-67-4 potassium phenolate 
• 4431-86-1 chlorodiphenoxymethane 
• 60-29-7 diethyl ether 
• 591-51-5 phenyllithium 
• 115262-01-6 [bromo(difluoro)methyl]-trimethyl-silane 
• 139-02-6 sodium phenoxide 
• 108-95-2 phenol 
• 351197-65-4 2-acetoxy-5,5-dimethyl-2-phenoxy-Δ³-1,3,4-oxadiazoline 
• 351197-63-2 (phenoxycarbonyl)hydrazone of acetone 
• 102-09-0 bis(phenyl) carbonate 
• 107-13-1 acrylonitrile 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 308086-26-2 5,5-dimethyl-2,2-diphenoxy-Δ³-1,3,4-oxadiazoline 

Downstream Products

• 4431-86-1 chlorodiphenoxymethane 
• 98783-19-8 Monothio-orthoameisensaeure-triphenylester 
• 6006-64-0 Dimethylformamid-diphenylacetal 
• 4442-41-5 diphenoxymethane 
• 4895-47-0 tetraphenoxyethene 
• 64-18-6 formic acid 
• 108-95-2 phenol 

Relevant articles and documents

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Efficient Difluoromethylation of Alcohols Using TMSCF2Br as a Unique and Practical Difluorocarbene Reagent under Mild Conditions

A general method for the efficient difluoromethylation of alcohols using commercially available TMSCF2Br (TMS=trimethylsilyl) as a unique and practical difluorocarbene source is developed. This method allows primary, secondary, and even tertiary alkyl difluoromethyl ethers to be synthesized under weakly basic or acidic conditions. The reaction mainly proceeds through the direct interaction between a neutral alcohol and difluorocarbene, which is different from the difluoromethylation of phenols. Moreover, alcohols containing other moieties that are also reactive toward difluorocarbene can be transformed divergently by using TMSCF2Br. This research not only solves the synthetic problem of difluorocarbene-mediated difluoromethylation of alcohols, it also provides new insights into the different reaction mechanisms of alcohol difluoromethylation and phenol difluoromethylation with difluorocarbene species.

Diaryloxycarbenes from oxadiazolines

Symmetric and unsymmetric 2,2-diaryloxy-5,5-dimethyl-Δ3-1,3,4-oxadiazolines were synthesized by oxidative cyclization of aryloxycarbonyl hydrazones of acetone with lead tetraacetate and subsequent treatment of the product mixture with a phenol in acidic solution. Thermolysis of the oxadiazolines in benzene solution at 110°C afforded carbonyl ylide intermediates that cyclize, in part, to the corresponding 2,2-diaryloxyoxirane intermediates. The oxiranes, which were not observed, are required to account for the 1,1-diaryloxy-2-methylpropenes (ketene acetals) that were isolated. Most of the carbonyl ylides fragment to acetone and diaryloxycarbenes. The latter form dimers (tetraaryloxyethenes) or they can be trapped with phenols to form orthoformates. Diphenoxycarbene was also trapped with dimethyl acetylenedicarboxylate (DMAD). The method appears to be the first for generating the parent diphenoxycarbene under relatively mild conditions in solution, and the only one to date for generating unsymmetrically substituted diaryloxycarbenes. Minor competing fragmentations of the oxadiazolines to 2-diazopropane and the appropriate diaryl carbonates, were also observed.