63549-55-3

Basic information

• Product Name: 4-bromophenyl 2,2-dimethylpropanoate
• Synonyms: 4-Bromophenyl pivalate; propanoic acid, 2,2-dimethyl-, 4-bromophenyl ester
• CAS NO: 63549-55-3
• Molecular Formula: C₁₁H₁₃BrO₂
• Molecular Weight: 257.1237
• Mol File: 63549-55-3.mol

Chemical Properties

• Boiling Point: 288.1°C at 760 mmHg
• Flash Point: 128.1°C
• Density: 1.333g/cm³
• Vapor Pressure: 0.00238mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: 4-bromophenyl 2,2-dimethylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromophenyl 2,2-dimethylpropanoate(63549-55-3)
• EPA Substance Registry System: 4-bromophenyl 2,2-dimethylpropanoate(63549-55-3)

Safety Data

• Hazardous Substances Data: 63549-55-3(Hazardous Substances Data)

Upstream product

• 1187442-17-6 tert-butyl 2,4-dibromophenyl carbonate 
• 401-81-0 m-trifluoromethylphenyl iodide 
• 106-41-2 4-bromo-phenol 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 3282-30-2 pivaloyl chloride 
• 4920-92-7 pivalic acid phenyl ester 

Downstream Products

• 112004-82-7 4-phenylcabonylphenyl pivalate 
• 1269510-22-6 4-bromo-2-(phenylthio)phenol 
• 909038-19-3 2,2-dimethylpropionic acid 4-(phenylethynyl)phenyl ester 

Relevant articles and documents

Regioselective Ortho‐C–H sulfenylation of free phenols catalyzed by Co(II)-immobilized on silica-coated magnetic nanoparticles

Fe3O4?SiO2-UT?CoII is prepared by the silica-coated magnetic nanoparticles, urea-triazole, and CoCl2. This organic-inorganic hybride composite showed a good to excellent catalytic activity toward regioselective ortho-sulfenylation of free phenols and naphthols using pivalic anhydride as a directing group, also K2S2O8 and PPh3 were employed as oxidant and additive respectively. The newly synthesized catalyst was fully characterized by using different techniques such as FT-IR, TGA, DTG, TEM, SEM, EDS, ICP and VSM analyses. The competitive price, accessibility and lower toxicity of cobalt compared to expensive transition metals using for C–H bond activation and functionalization constitute precious advantages for this method. Moreover, this heterogeneous catalyst could be magnetically recovered and reused without significant loss of its catalytic activity after five cycles.

Nickel-catalyzed reductive cleavage of aryl-oxygen bonds in alkoxy- and pivaloxyarenes using hydrosilanes as a mild reducing agent

A nickel-catalyzed reductive deoxygenation of aryl alkyl ethers and aryl pivalates has been developed. Hydrosilanes serve as a mild reducing agent. The present protocol allows the use of a pivalate group as a robust and traceless steering group in arene functionalization reactions. The Royal Society of Chemistry.

Nickel-catalyzed cross-coupling of aryl bromides with tertiary grignard reagents utilizing donor-functionalized N-heterocyclic carbenes (NHCs)

Metal-catalyzed cross-coupling reactions are among the most important transformations in organic synthesis, allowing the efficient construction of complex structures from simpler, readily available building blocks.Many applications in large and small-scale synthesis can be found in different areas such as agrochemicals, pharmaceuticals and supramolecular chemistry. Whereas the coupling of sp2-hybridized carbon atoms in either reaction partner is well established, the use of CACHTUNGTRENUNG(sp3)-hybridized substrates presents some challenges. Catalytic cross-coupling of sterically hindered tertiary alkyl substrates is especially difficult, generally resulting in low yields, and thus, only few reports exist.[27] A big challenge in this field is not only to get the required level of reactivity, but also to overcome competing pathways like β-hydride elimination, hydrodehalogenation or isomerization

Preparation of polyfunctional arylmagnesium, arylzinc, and benzylic zinc reagents by using magnesium in the presence of LiCl

The presence of LiCl considerably facilitates the insertion of magnesium into various aromatic and heterocyclic bromides. Several functional groups, such as -OBoc, -OTs, -Cl, -F, -CF3, -OMe, -NMe2, and -N 2NR2, are well tolerated. The presence of a cyano group leads in some cases to competitive reduction of the organic halide to the corresponding ArH compound. The presence of sensitive groups such as methyl or ethyl ester is tolerated upon in situ trapping of the intermediate magnesium reagent with ZnCl2. This method can also be applied to the preparation of functionalized benzylic zinc reagents from benzylic chlorides. In the case of di- or tribromoaryl derivatives, directing groups such as -OPiv, -OTs, -N2NR2, or -OAc orient the zinc insertion (Zn/LiCl) to the ortho-position, while the reaction with Mg/LiCl or Mg/LiCl/ZnCl 2 leads to regioselective insertion into the para-carbon-bromine bond. Large-scale experiments (20-100 mmol) for all of the metalation procedures are described.

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