27644-18-4

Basic information

• Product Name: 2,2-dimethylpropionyl bromide
• Synonyms: 2,2-dimethylpropionyl bromide;2,2-Dimethylpropanoic acid bromide;2,2-diMethylpropanoyl broMide;2,2-DIMETHYLPROPANOYL BROMIDE(WXG01758)
• CAS NO: 27644-18-4
• Molecular Formula: C₅H₉BrO
• Molecular Weight: 165.02836
• EINECS: 248-590-0
• Mol File: 27644-18-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 136.4°Cat760mmHg
• Flash Point: 46.3°C
• Appearance: /
• Density: 1.359g/cm³
• Vapor Pressure: 7.4mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: 2,2-dimethylpropionyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dimethylpropionyl bromide(27644-18-4)
• EPA Substance Registry System: 2,2-dimethylpropionyl bromide(27644-18-4)

Safety Data

• Hazardous Substances Data: 27644-18-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 7237, 1990 DOI: 10.1016/S0040-4039(00)97289-7

InChI:InChI=1/C5H9BrO/c1-5(2,3)4(6)7/h1-3H3

Upstream product

• 630-19-3 pivalaldehyde 
• 96185-31-8 C₁₁H₂₄O₂Si 
• 1034-39-5 dibromotriphenylphosphorane 
• 507-19-7 t-butyl bromide 
• 75-98-9 Trimethylacetic acid 
• 3282-30-2 pivaloyl chloride 
• 7324-58-5 silver pivalate 

Downstream Products

• 42867-40-3 pivaloyl cyanide 
• 112888-47-8 di-tert-butyl N-<4-(prop-2-ynylamino)benzoyl>-L-glutamate 
• 60718-19-6 S-phenyl 2,2-dimethylpropanethioate 
• 104310-46-5 N-[2-(3,4-Dimethoxy-phenyl)-ethyl]-3,3-dimethyl-2-oxo-butyrimidoyl bromide 
• 110164-46-0 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1-(2,2-dimethyl-1-oxopropyl)thieno[3,2-d]pyrimidine-2,4-dione 
• 120345-61-1 O-2,2-dimethylbutyryl-2-hydroxy-2-phenylacetonitrile 
• 52571-19-4 2,2-Dimethyl-propionic acid isocyano-phenyl-methyl ester 
• 1346435-34-4 2,2-dimethyl-propionic acid 1-bromomethyl-2-(4-chloro-phenoxy)-ethyl ester 
• 1346435-31-1 2,2-dimethyl-propionic acid 1-bromomethyl-2-(4-methoxy-phenoxy)-ethyl ester 
• 1346435-28-6 2,2-dimethyl-propionic acid 1-bromomethyl-2-phenoxy-ethyl ester 

Relevant articles and documents

Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: No metal catalysts required

A practical direct method for the direct preparation of esters and thioesters from aldehydes is described. Esters and thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol, various esters and thioesters were prepared in high yields. This effective method offers a promising approach for the facile esterification and thioesterification of aldehydes.

Selective C(sp2)-H Halogenation of "click" 4-Aryl-1,2,3-triazoles

Selective bromination reactions of "click compounds" are described. Electron-neutral and electron-deficient arenes selectively undergo unprecedented Pd-catalyzed C-H ortho-halogenations assisted by simple triazoles as modular directing groups, whereas electron-rich arenes are regioselectively halogenated following an electrophilic aromatic substitution reaction pathway. These C-H halogenation procedures exhibit a wide group tolerance, complement existing bromination procedures, and represent versatile synthetic tools of utmost importance for the late-stage diversification of "click compounds". The characterization of a triazole-containing palladacycle and density functional theory studies supported the mechanism proposal.

Synthesis of n-alkyl terminal halohydrin esters from acid halides and cyclic ethers or thioethers under solvent- and catalyst-free conditions

An efficient and eco-friendly protocol has been developed for the preparation of n-alkyl terminal halohydrin esters under solvent- and catalyst-free conditions. Ring opening of cyclic ethers by organic acid halides affords the 1,4- and 1,5-halohydrins, OH-protected by different acyl groups. The green reaction conditions, simple work-up procedures, high yields and broad substrate scope of the reaction highlight the positive features of this method. This journal is