10075-90-8

Usage

Appearance

Colorless to light yellow solid

Uses

a. Optical brighteners in laundry detergents
b. Building block in the synthesis of various organic compounds and materials

Stability

Relatively stable

Toxicity

Low toxicity, but precautions should be taken

Hazards

a. Harmful if ingested or inhaled
b. Causes irritation upon contact with skin and eyes

Precautions

Avoid contact with skin and eyes, and handle with care to prevent ingestion or inhalation

Industrial applications

Versatile compound with various uses in the chemical and manufacturing industries

Upstream product

• 88847-60-3 bis(4-methylthiophenyl) methylphosphonate 
• 104-95-0 (4-bromophenyl)thioanisole 
• 98-56-6 4-chlorobenzotrifluoride 
• 149418-41-7 3,4-dibromo-2(5H)-furanone 
• 17113-79-0 trimethyl(4-(methylthio)phenyl)stannane 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 
• 62674-12-8 3,4-dichloro-5H-furan-2-one 
• 624-92-0 Dimethyldisulphide 
• 92-86-4 4-(4-bromophenyl)bromobenzene 
• 593-60-2 Vinyl bromide 
• 35371-03-0 4-iodothioanisole 
• 694-53-1 phenylsilane 
• 123-09-1 4-chlorophenyl methyl sulfide 
• 1068-55-9 isopropylmagnesium chloride 

Downstream Products

• 92-52-4 biphenyl 

Relevant academic research and scientific papers

Magnesiation of Aryl Fluorides Catalyzed by a Rhodium-Aluminum Complex

We report the magnesiation of aryl fluorides catalyzed by an Al-Rh heterobimetallic complex. We show that the complex is highly reactive to cleave the C-F bonds across the polarized Al-Rh bond under mild conditions. The reaction allows the use of an easy-to-handle magnesium powder to generate a range of arylmagnesium reagents from aryl fluorides, which are conventionally inert to such metalation compared with other aryl halides.

Iron-Catalyzed Isopropylation of Electron-Deficient Aryl and Heteroaryl Chlorides

Traditional methods for the preparation of secondary alkyl-substituted aryl and heteroaryl chlorides challenge both selectivity and functional group tolerance. This contribution describes the use of statistical design of experiments to develop an effective procedure for the preparation of isopropyl-substituted (hetero)arenes with minimal isopropyl to n-propyl isomerization. The reaction tolerates electronically diverse aryl chloride coupling partners, with excellent conversion observed for strongly electron-deficient aromatic rings, such as esters and amides. Electron-rich systems, including methyl- and methoxy-substituted aryl chlorides, were found to be less reactive. Furthermore, the reaction was found to be most successful when heteroaryl chlorides were submitted to the cross-coupling protocol. By mapping substituent effects on reaction selectivity, we were able to show that electron-deficient aryl chlorides are essential for efficient coupling, and use electronic structure calculations to predict the likelihood of successful coupling through the estimation of the electron affinity of each aryl chloride. Moderate isolated yields were achieved with selected aryl chlorides, and moderate to good isolated yields were obtained for all the heteroaryl chlorides coupled. Excellent selectivity was observed when a 2,6-dichloroquinoline was used, allowing mono-substitution on a challenging substrate. (Figure presented.).

Integrated palladium-catalyzed arylation of heavier groupa 14 hydrides

A convenient procedure has been developed for the preparation of Groupa 14 compounds by integrated palladium-catalyzed cross-coupling of aromatic iodides with the corresponding Groupa 14 hydrides in the presence of a base. The reaction conditions can be applied to the cross-coupling of tertiary, secondary, and primary Groupa 14 compounds. In most cases, the desired arylated products were obtained in synthetically useful yields. Even in the case of aryl iodides containing OH, NH2, CN, or CO2R groups, the reactions proceeded with good to high yields with tolerance of these reactive functional groups. A possible application of this method is the unique synthesis of a fungicidal diarylmethyl(1H-1,2,4-triazol-1-ylmethyl)silane derivative. A convenient procedure has been developed for the preparation of Groupa 14 compounds by integrated palladium-catalyzed cross-coupling of aromatic iodides with the corresponding Groupa 14 hydrides in the presence of a base (see picture). Application of this method in the synthesis of a fungicidal diarylmethyl(1H-1,2,4-triazol-1-yl-methyl)silane derivative is demonstrated. Copyright

Synthesis of sulfur-containing aryl and heteroaryl vinyls via Suzuki-Miyaura cross-coupling for the preparation of SERS-active polymers

The preparation of sulfur-containing aryl and heteroaryl vinyl co-monomers via Suzuki-Miyaura cross-coupling between the corresponding mercaptomethyl arylboronates and in situ-generated vinyl bromides is described. Surface-enhanced Raman scattering (SERS) studies of the target compounds on gold nanoparticles confirmed their potential as spectroscopic tags in the fabrication of SERS-encoded polymers for combinatorial screening and biomedical diagnostics.

Selective metal-halogen exchange of 4,4′-dibromobiphenyl mediated by lithium tributylmagnesiate

A selective metal-halogen exchange/electrophilic quench protocol on 4,4′-dibromobiphenyl 4 that proceeds under non-cryogenic conditions is reported. This method provides an economic alternative to traditional transition-metal catalyzed cross-coupling chemistry to prepare various biaryls 7a-g. This novel route to functionalized biaryls was used as the basis for the kg-scale preparation of a biphenyl ketone 1, a key intermediate in the synthesis of a potent cathepsin K inhibitor.

Mucochloric acid: A useful synthon for the selective synthesis of 4-aryl-3-chloro-2(5H)-furanones, (Z)-4-aryl-5-[1-(aryl)methylidenel-3-chloro-2(5H)-furanones and 3,4-diaryl-2(5H)-furanones

3,4-Dichloro-2(5H)-furanone, which has been prepared efficiently from mucochloric acid, has been transformed selectively into 4-aryl-3-chloro-2(5H)-furanones either by Suzukior Stille-type reactions. These monochloro derivatives have been used as precursors either to (Z)-4-aryl-5-[1-(aryl)methylidene]-3-chloro-2(5H)-furanones, including naturally occurring rubrolide M, or to unsymmetrical 3,4-diaryl-2(5H)-furanones. Some 2(5H)-furanone derivatives so prepared have been found to exhibit significant cytotoxic activity in vitro against the NCI three-cell-line panel, but limited cytotoxicity against the NCI human tumor 60 cell-line panel. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Selective synthesis of (Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5H)-furanones

4-Aryl-3-bromo-2(5H)-furanones have been selectively synthesized in satisfactory yields by treatment of easily available 3,4-dibromo-2(5H)-furanone either with arylboronic acids in the presence of Ag2O and a catalytic amount of PdCl2(MeCN)2 or with aryl(trialkyl)stannanes in the presence of a catalyst precursor consisting of AsPh3 and a Pd(II) or a Pd(0) compound. These monobromo derivatives have been then used as precursors to a variety of (Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5H)-furanones including the compound with the structure corresponding to that reported for naturally occurring rubrolide N. The structure and stereochemistry of these synthetic compounds have been unambiguously established by NMR techniques.

Selective synthesis of unsymmetrical 3,4-disubstituted and 4-substituted 2(5H)-furanones

Easily available 3,4-dibromo-2(5H)-furanone undergoes regioselective palladium-catalyzed reaction with aryl(trialkyl)stannanes to give the corresponding 4-aryl-3-bromo-2(5H)-furanones in satisfactory yields. These monobromo derivatives have proven to be useful precursors to unsymmetrical 3,4-diaryl-2(5H)-furanones, 4-aryl-3-methyl-2(5H)-furanones and 4-aryl-2(5H)-furanones.

PHOTOLYSIS OF ARYL ESTERS OF TRI- AND TETRACOORDINATED PHOSPHORUS COMPOUNDS

Upon UV excitation in methanol, some diaryl esters of alkly- or alkenyl phosphonates underwent an elimination of two aryl groups to give biaryls and the corresponding alkyl- or alkenylphosphonic acids.Tris(4-methoxyphenyl) phosphite also underwent a similar elimination to give 4,4'-dimethoxybiphenyl and 4-methoxyphenyl phosphonate.This interesting biaryl elimination was confirmed to proceed via a singlet intramolecular excimer by means of fluorescence spectra and Stern-Volmer analysis.

Activation of Reducing Agents. Sodium Hydride Containing Complex Reducing Agents. 32. NiCRAL's as Very Efficient Agents in Promoting Cross-Coupling of Aryl Halides

Nickel-containing complex reducing agents NiCRA-bpy are shown to be the first nickel reagents able to efficiently perform cross-coupling of aryl halides.The presence of KI in the reaction medium generally improves the procedure.The mechanism and influence of the structures of the substrates are discused.