66107-30-0

Basic information

• Product Name: 4-Bromophenyl triflate
• Synonyms: 4-Bromophenyl triflate
• CAS NO: 66107-30-0
• Molecular Formula: C₇H₄BrF₃O₃S
• Molecular Weight: 305.0690696
• Mol File: 66107-30-0.mol

Chemical Properties

• Boiling Point: 100-102 °C(Press: 3.2 Torr)
• Appearance: /
• Density: 1.826±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4-Bromophenyl triflate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromophenyl triflate(66107-30-0)
• EPA Substance Registry System: 4-Bromophenyl triflate(66107-30-0)

Safety Data

• Hazardous Substances Data: 66107-30-0(Hazardous Substances Data)

Upstream product

• 106-41-2 4-bromo-phenol 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 17763-67-6 Phenyl triflate 
• 5467-74-3 4-Bromophenylboronic acid 
• 2926-30-9 sodium triflate 

Downstream Products

• 10541-38-5 1,4-dioctylbenzene 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 72758-69-1 (E)-1-(4-bromophenyl)-3-phenylprop-2-en-1-one 
• 54118-75-1 4-bromo-4'-methoxybenzophenone 
• 79784-58-0 1,1'-(1,4-phenylene)bis(pentan-1-one) 
• 112533-16-1 1-<4-(4-methoxybenzoyl)>-1-pentanone 
• 92-69-3 4-Phenylphenol 
• 92-94-4 [1,1';4',1'']terphenyl 
• 108-86-1 bromobenzene 
• 53092-64-1 2,2”-dimethyl-1,1‘:4’,1“-terphenyl 
• 106475-19-8 4'-bromo-2-methyl-1,1'-biphenyl 
• 21711-52-4 4,4''-dichloro-1,1':4',1''-terphenyl 
• 23055-77-8 4'-chloro-4-bromo-biphenyl 

Relevant articles and documents

Palladium-Catalyzed Reductive Carbonylation of (Hetero) Aryl Halides and Triflates Using Cobalt Carbonyl as CO Source

An efficient protocol for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas-free conditions using Pd/Co2(CO)8 and triethylsilane has been developed. The mild reaction conditions, enhanced chemoselectivity and, easy access to heterocyclic and vinyl carboxaldehydes highlights its importance in organic synthesis.

Palladium-Catalyzed Synthesis of N, N-Dimethylanilines via Buchwald-Hartwig Amination of (Hetero)aryl Triflates

This work delineates the synthesis of N,N-dimethylaniline derivatives from dimethylamines and aryl triflates. The palladium-catalyzed C-N bond formation proceeds in excellent yields, using an unsophisticated catalytic system, a mild base, and triflates as electrophiles, which are readily available from inexpensive phenols. N,N-Dimethylanilines are multifunctional reaction partners and represent useful but underutilized building blocks in organic synthesis.

Base-promoted selective O-phosphorylation of aryl triflates with P(O)-H compounds

Compared to previous transition metal-catalyzed C-phosphorylation reactions for constructing C–P bonds, in the absence of transition metal catalysts and ligands, a direct O-phosphorylation of aryl triflates selectively occurred with P(O)-H compounds in the presence of a base via the construction of O–P bonds. This transformation proceeds under simple and mild conditions, and provides a new method for the preparation of valuable organophosphoryl compounds from readily available P(O)-H compounds and triflates.

Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts

Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp2)-O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies as well as theoretical investigations reveal the intermediacy of a highly electrophilic Bi(V) species, which rapidly eliminates phenyl triflate.

Catalytic Geminal Difluorination of Styrenes for the Construction of Fluorine-rich Bioisosteres

A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-TolI as the organocatalyst, turnover is enabled by Selectfluor-mediated oxidation to generate the ArIF2 species in situ. Extension to include α-substituted styrenes bearing fluorine-containing groups is disclosed and provides an expansive platform for the generation of fluorine-rich architectures.

Remote migratory cross-electrophile coupling and olefin hydroarylation reactions enabled by in situ generation of nih

A highly efficient strategy for remote reductive cross-electrophile coupling has been developed through the ligand-controlled nickel migration/arylation. This general protocol allows the use of abundant and bench-stable alkyl bromides and aryl bromides for the synthesis of a wide range of structurally diverse 1, 1-diarylalkanes in excellent yields and high regioselectivities under mild conditions. We also demonstrated that alkyl bromide could be replaced by the proposed olefin intermediate while using n-propyl bromide/Mn0 as a potential hydride source.

Rapid Room-Temperature, Chemoselective Csp2?Csp2Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air

While chemoselectivities in Pd0-catalyzed coupling reactions are frequently non-intuitive and a result of a complex interplay of ligand/catalyst, substrate, and reaction conditions, we herein report a general method based on PdIthat allows for an a priori predictable chemoselective Csp2?C Csp2coupling at C?Br in preference to C?OTf and C?Cl bonds, regardless of the electronic or steric bias of the substrate. The C?C bond formations are extremely rapid (Idimer under open-flask conditions.

Ligand- and Solvent-Tuned Chemoselective Carbonylation of Bromoaryl Triflates

The palladium-catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The selective C?Br bond versus C?OTf (OTf=triflate) bond functionalization can be remarkably tuned by the combination of the ligand [4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) vs. 1,1′-bis(diphenylphosphino)ferrocene (DPPF)] and the solvent (toluene vs. DMSO). The respective ligand and solvent effects are rationalized by DFT calculations. In contrast, the monodentate ligands BuPAd2 and tBu3P prefer the selective C?Br bond activation and are solvent insensitive.

Reactions of triflate esters and triflamides with an organic neutral super-electron-donor

The bis-pyridinylidene 13 converts aliphatic and aryl triflate esters to the corresponding alcohols and phenols respectively, using DMF as solvent, generally in excellent yields. While the deprotection of aryl triflates has been seen with other reagents and by more than one mechanism, the deprotection of alkyl triflates is a new reaction. Studies with 18O labelled DMF indicate that the C-O bond stays intact and hence it is the S-O bond that cleaves, underlining that the cleavage results from the extraordinary electron donor capability of 13. Trifluoromethanesulfonamides are converted to the parent amines in like manner, representing the first cleavage of such substrates by a ground-state organic reducing reagent.

Zinc chloride-promoted aryl bromide-alkyne cross-coupling reactions at room temperature

(Chemical Equation Presented) Substoichiometric amounts of ZnCl2 promote the room temperature, Pd/P(t-Bu)3-catalyzed cross-coupling of aryl bromides with alkynes. Pd(I) dimer 1 is demonstrated to be a particularly active precatalyst for this reaction. The reaction is general for a wide variety of aryl bromides.