85100-62-5

Basic information

• Product Name: Benzoic acid, 4-butyl-, ethyl ester
• Synonyms: Benzoic acid, 4-butyl-, ethyl ester
• CAS NO: 85100-62-5
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.28082
• EINECS: -0
• Mol File: 85100-62-5.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoic acid, 4-butyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-butyl-, ethyl ester(85100-62-5)
• EPA Substance Registry System: Benzoic acid, 4-butyl-, ethyl ester(85100-62-5)

Safety Data

• Hazardous Substances Data: 85100-62-5(Hazardous Substances Data)

Upstream product

• 7335-27-5 ethyl 4-chlorobenzoate 
• 34219-54-0 n-butylzinc iodide 
• 4426-47-5 butylboronic acid 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 69190-62-1 pinacol butylboronate 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 42930-39-2 n-butylzinc chloride 
• 3692-81-7 tri-n-butylbismuthine 
• 693-04-9 butyl magnesium bromide 
• 693-03-8 n-butyl magnesium bromide 
• 124915-06-6 ethyl 4-(N,N,N-trimethylammonium)-1-benzoate triflate 
• 64-17-5 ethanol 
• 28788-62-7 4-butylbenzoyl chloride 
• 109-72-8 n-butyllithium 

Relevant articles and documents

Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands

Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.

Single-Electron-Transfer-Induced Coupling of Alkylzinc Reagents with Aryl Iodides

Alkylzinc reagents prepared from an alkyllithium and zinc iodide were found to undergo coupling with aryl and alkenyl iodides in the presence of LiI in a mixed solvent consisting of THF and diglyme (1:1). Alkyllithiums, prepared by halogen–lithium exchange between an alkyl iodide and tert-butyllithium, are also converted to alkylarenes through alkylzinc reagents.

Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides

We report a palladium-catalyzed method to synthesize acid chlorides by the chlorocarbonylation of aryl bromides. Mechanistic studies suggest the combination of sterically encumbered PtBu3 and CO coordination to palladium can rapidly equilibrate the oxidative addition/reductive elimination of carbon-halogen bonds. This provides a useful method to assemble highly reactive acid chlorides from stable and available reagents, and can be coupled with subsequent nucleophilic reactions to generate new classes of carbonylated products. The Good, the Bad and the Bulky! By employing a sterically encumbered phosphine ligand, tri-tert-butyl phosphine, under palladium catalysis inert aryl bromides are chlorocarbonylated to create reactive acid chlorides by reversible carbon-halogen bond reductive elimination. This general platform allows for an expanded scope of the Heck carbonylation reaction to include previously incompatible nucleophiles.