84740-98-7

Basic information

• Product Name: Benzoic acid, 4-ethenyl-, 1,1-diMethylethyl ester
• Synonyms: Benzoic acid, 4-ethenyl-, 1,1-diMethylethyl ester;Tert-butyl 4-ethenylbenzoate
• CAS NO: 84740-98-7
• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.26494
• Mol File: 84740-98-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoic acid, 4-ethenyl-, 1,1-diMethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-ethenyl-, 1,1-diMethylethyl ester(84740-98-7)
• EPA Substance Registry System: Benzoic acid, 4-ethenyl-, 1,1-diMethylethyl ester(84740-98-7)

Safety Data

• Hazardous Substances Data: 84740-98-7(Hazardous Substances Data)

Upstream product

• 1075-49-6 4-ethenylbenzoic acid 
• 36805-97-7 N,N-dimethylformamide di-tert-butyl acetal 
• 2627-95-4 tetramethyldivinyldisiloxane 
• 59247-47-1 tert-butyl-4-bromobenzoate 
• 6232-88-8 4-bromomethylbenzoic Acid 
• 1565-41-9 p-vinylbenzoyl chloride 
• 865-47-4 potassium tert-butylate 
• 105580-41-4 4-acetylbenzoic acid tert-butyl ester 
• 586-89-0 4-acetyl-benzoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 52062-92-7 4-(2-bromoethyl)benzoic acid 
• 151587-58-5 2-<<(N,N-Dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidine 
• 149325-41-7 tert-Butyl 4-(2-bromoethyl)benzoate 
• 65874-27-3 4-(tert-butoxycarbonyl)benzaldehyde 

Downstream Products

• 856680-26-7 tert-butyl 4-(oxiran-2-yl)benzoate 
• 1003862-21-2 tert-butyl 4-[2-(4-methoxyphenyl)-1-ethenyl]benzoate 
• 1160518-78-4 C₂₁H₂₃NO₄ 
• 1160518-80-8 C₁₇H₁₅NO₄ 
• 1307784-34-4 C₄₉H₅₂N₅O₅⁽¹⁺⁾*Cl^(1-) 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1565-41-9 p-vinylbenzoyl chloride 
• 1393542-59-0 C₂₂H₂₆O₃ 
• 1054646-79-5 (S)-2-{4-[2-(2-Amino-4-hydroxy-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester 
• 158214-28-9 (S)-2-{4-[2-(2,4-Diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester 
• 149325-63-3 tert-butyl 4-<2-(2-amino-6,7-dihydro-4-oxo-5H-cyclopentapyrimidin-5-yl)ethyl>benzoate 
• 149325-45-1 tert-butyl 4-<2-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)ethyl>benzoate 
• 149325-62-2 tert-butyl 4-<2-<2-(methoxycarbonyl)-3-oxocyclopentanyl>ethyl>benzoate 
• 149325-46-2 4-<2-(2,4-diamino-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)ethyl>benzoic acid 

Relevant articles and documents

Structural and mechanistic studies of the base-induced Sommelet-Hauser rearrangement of: N -α-branched benzylic azetidine-2-carboxylic acid-derived ammonium salts

The base-induced Sommelet-Hauser rearrangement of N-α-branched benzylic azetidine-2-carboxylic acid ester-derived ammonium salts to obtain α-arylazetidine-2-carboxylic acid esters was investigated. The substrates, two diastereomeric salts (1S,2S,1′S)- and (1R,2R,1′S)-2, showed different reactivities. The rearrangement of (1S,2S,1′S)-2a proceeded with a perfect N-to-C chirality transfer to provide (R)-3a in 74% yield with 99% ee. However, the rearrangement of (1R,2R,1′S)-2a under the same conditions afforded (S)-3a in only 15% yield with a lower 66% ee, along with the competitive [1,2] Stevens rearrangement product 4a. Structural and mechanistic studies of this rearrangement were carried out to clarify the exact reason. Our results define the scope and limitations of the Sommelet-Hauser rearrangement and provide unique synthetic access to α-aryl amino acid derivatives.

Precision polyelectrolytes

Charged macromolecules with controlled microstructures were prepared. Well-defined non-ionic precursors were first synthesized by sequence-controlled radical polymerization of tert-butyl 4-vinyl benzoate with various N-substituted maleimides. Afterwards, these macromolecules were hydrolyzed into polyanions.

Vinylation of aromatic halides using inexpensive organosilicon reagents. Illustration of design of experiment protocols

The preparation of styrenes by palladium-catalyzed cross-coupling of aromatic iodides and bromides with divinyltetramethyldisiloxane (DVDS) in the presence of inexpensive silanolate activators has been developed. To facilitate the discovery of optimal reaction conditions, Design of Experiment (DoE) protocols were used. By the guided selection of reagents, stoichiometries, temperatures, and solvents, the vinylation reaction was rapidly optimized with three stages consisting of ca. 175 experiments (of a possible 1440 combinations). A variety of aromatic iodides undergo cross-coupling at room temperature in the presence of potassium trimethylsilanoate using Pd(dba) 2 in DMF in good yields. Triphenylphosphine oxide is needed to extend catalyst lifetime. Application of these conditions to aryl bromides was accomplished by the development of two complementary protocols. First, the direct implementation of the successful reaction conditions using aryl iodides at elevated temperature in THF provided the corresponding styrenes in good to excellent yields. Alternatively, the use of potassium triethylsilanolate and a bulky "Buchwald-type" ligand allows for the vinylation reactions to occur at or just above room temperature. A wide range of bromides underwent coupling in good yields for each of the protocols described.