79520-52-8

Usage

Uses

Used in Organic Synthesis:
Pentanoic acid, 5-bromo-2,2-dimethyl-, methyl ester is used as a building block in the production of various chemical compounds. Its unique structure and reactivity make it a valuable component in the synthesis of complex organic molecules.
Used in Chemical Reactions:
Pentanoic acid, 5-bromo-2,2-dimethyl-, methyl ester is used as a reagent in chemical reactions, facilitating the formation of desired products through its participation in various reaction mechanisms.
Used in Fragrance and Flavor Formulations:
Pentanoic acid, 5-bromo-2,2-dimethyl-, methyl ester can be used in the formulation of fragrances and flavors due to its characteristic odor. Its unique scent profile can contribute to the development of novel and distinct scents in the perfumery and flavor industries.
Used in Research and Industrial Settings:
This chemical is commonly found in research and industrial settings, where it is utilized for its properties and reactivity in the development and production of various chemical products.
Safety Precautions:
Due to its flammability and potential hazards, Pentanoic acid, 5-bromo-2,2-dimethyl-, methyl ester must be handled and stored with caution. Proper safety measures, such as using fire-resistant storage containers and avoiding exposure to heat or open flames, should be implemented to minimize risks associated with its use.

Upstream product

• 67-56-1 methanol 
• 82884-95-5 2,2-dimethyl-5-bromopentanoic acid 
• 16386-93-9 2,2-dimethylpent-4-enoic acid 
• 547-63-7 Methyl isobutyrate 
• 109-64-8 1,3-dibromo-propane 

Downstream Products

• 79520-57-3 5-[3-(4-Methoxycarbonyl-4-methyl-pentyloxy)-5-methyl-phenoxy]-2,2-dimethyl-pentanoic acid methyl ester 
• 85629-94-3 2,6-Bis-(4-methoxycarbonyl-4-methyl-pentyloxy)-benzoic acid methyl ester 
• 85629-90-9 5-(4-{1-[4-(4-Methoxycarbonyl-4-methyl-pentyloxy)-phenyl]-1-methyl-ethyl}-phenoxy)-2,2-dimethyl-pentanoic acid methyl ester 
• 79520-65-3 5-[2-Formyl-4-(4-methoxycarbonyl-4-methyl-pentyloxy)-phenoxy]-2,2-dimethyl-pentanoic acid methyl ester 
• 85630-03-1 5-[5-(4-Methoxycarbonyl-4-methyl-pentyloxy)-2-methyl-phenoxy]-2,2-dimethyl-pentanoic acid methyl ester 
• 85629-99-8 5-[2-Bromo-5-(4-methoxycarbonyl-4-methyl-pentyloxy)-phenoxy]-2,2-dimethyl-pentanoic acid methyl ester 
• 85630-08-6 5-[5-(4-Methoxycarbonyl-4-methyl-pentyloxy)-biphenyl-3-yloxy]-2,2-dimethyl-pentanoic acid methyl ester 
• 79521-08-7 dimethyl 5,5'-[(2-benzoyl-1,4-phenylene)bis(oxy)]bis[2,2-dimethylpentanoate] 
• 79520-54-0 dimethyl 5,5'-[(2-fluoro-1,4-phenylene)bis(oxy)]bis[2,2-dimethylpentanoate] 
• 79521-17-8 dimethyl 5,5'-[[2-(1-oxopropyl)-1,4-phenylene]bis(oxy)]bis[2,2-dimethylpentanoate] 
• 79521-12-3 dimethyl 5,5'-[[2-(1-oxobutyl)-1,4-phenylene]bis(oxy)]bis[2,2-dimethylpentanoate] 
• 79520-76-6 5-[5-(4-Methoxycarbonyl-4-methyl-pentyloxy)-biphenyl-2-yloxy]-2,2-dimethyl-pentanoic acid methyl ester 
• 79520-72-2 dimethyl 5,5'-[(2-methyl-1,4-phenylene)bis(oxy)]bis[2,2-dimethylpentanoate] 
• 79520-69-7 5-[4-(4-Methoxycarbonyl-4-methyl-pentyloxy)-2,5-dimethyl-phenoxy]-2,2-dimethyl-pentanoic acid methyl ester 

Relevant academic research and scientific papers

Erratum: Efficient Targeted Degradation via Reversible and Irreversible Covalent PROTACs (Journal American Chemical Society (2020) DOI: 10.1021/jacs.9b13907)

This addition corrects several errors in the chemical drawings in the article. The correction has no influence on the data or conclusions of the work. The configuration of the chiral carbon in Figure 1 in the main text was originally drawn as S. The corrected figure shown here depicts the R enantiomer used in this work. (Figure presented) In the Supporting Information PDF files, the configuration of the chiral carbon of the BTK binder in supplementary Table 1 (page S9), supplementary Figure 4 (page S13), and several of the synthetic schemes (pages S17-S42) was originally drawn and marked as S by error. The corrected supplementary file depicts the R enantiomer, which was the sole enantiomer used in the work. The linker in the right panel of supplementary Table 1 (page S9) was missing two carbons in the drawing, and the linker size written for compound PG15 (RC-0b) in the table was incorrect. The corrected supplementary file contains the correct drawings and linker sizes.

Efficient Targeted Degradation via Reversible and Irreversible Covalent PROTACs

Proteolysis targeting chimeras (PROTACs) represent an exciting inhibitory modality with many advantages, including substoichiometric degradation of targets. Their scope, though, is still limited to date by the requirement for a sufficiently potent target binder. A solution that proved useful in tackling challenging targets is the use of electrophiles to allow irreversible binding to the target. However, such binding will negate the catalytic nature of PROTACs. Reversible covalent PROTACs potentially offer the best of both worlds. They possess the potency and selectivity associated with the formation of the covalent bond, while being able to dissociate and regenerate once the protein target is degraded. Using Bruton's tyrosine kinase (BTK) as a clinically relevant model system, we show efficient degradation by noncovalent, irreversible covalent, and reversible covalent PROTACs, with 85% degradation. Our data suggest that part of the degradation by our irreversible covalent PROTACs is driven by reversible binding prior to covalent bond formation, while the reversible covalent PROTACs drive degradation primarily by covalent engagement. The PROTACs showed enhanced inhibition of B cell activation compared to ibrutinib and exhibit potent degradation of BTK in patient-derived primary chronic lymphocytic leukemia cells. The most potent reversible covalent PROTAC, RC-3, exhibited enhanced selectivity toward BTK compared to noncovalent and irreversible covalent PROTACs. These compounds may pave the way for the design of covalent PROTACs for a wide variety of challenging targets.

Ketamine esters and amides as short-acting anaesthetics: Structure-activity relationships for the side-chain

N-Aliphatic ester analogues of the non-opioid ketamine (1) retain effective anaesthetic/analgesic properties while minimising ketamine's psychomimetic side-effects. We show that the anaesthetic/analgesic properties of these ester analogues depend critically on the length (from 2 to 4 carbons), polarity and steric cross-section of the aliphatic linker chain. More stable amide and ethylsulfone analogues generally showed weaker anaesthetic/analgesic activity. There was no correlation between the anaesthetic/analgesic properties of the compounds and their binding affinities for the N-methyl-D-aspartate (NMDA) receptor.

An improved new path to synthesize gemfibrozil

A new route has been developed for synthesis of gemfibrozil in good yield with high purity. The obtained gemfibrozil was characterized by using IR, 1H NMR, 13C NMR and mass spectral studies. According to Biopharmaceutical Classification System, gemfibrozil is classified under class-II drugs (low solubility-high permeability) and an antihyperlipidimic. So it's admirable to synthesize the intention molecule in easy and economical way.

7-oxabicycloheptyl substituted heterocyclic amide or ester prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease

7-Oxabicycloheptane substituted prostaglandin analogs useful in treating thrombotic and vasopastic disease have the structural formula STR1 wherein m is 1, 2 or 3; n is 1, 2, 3 or 4; Z is --(CH2)2 --, --CH=CH-- or STR2 wherein Y is O, a single bond or vinyl, with the proviso that when n is 0, if Z is STR3 then Y cannot be O, and Z is --CH=CH--, n is 1, 2, 3 or 4; and when Y=vinyl, n=0; R is CO2 H, CO2 lower alkyl, CH2 OH, CO2 alkali metal, CONHSOR3, CONHR3a or --CH2 --5-tetrazolyl, X is O, S or NH; and where R1, R2, R3 and R3a are as defined herein.

Process for preparing 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid

An improved two-step process for preparing 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid (gemfibrozil) which regularly affords gembibrozil in overall yields in excess of 80% comprises reacting an alkali metal salt of a lower alkyl ester of 2-methylpropanoic acid with 1,3-dibromopropane or 1-bromo-3-chloropropane in a polar aprotic solvent such as tetrahydrofuran, and then reacting the intermediate thus formed with an alkali metal salt of 2,5-dimethylphenol in a mixed toluene/dimethylsulfoxide solvent system.