1077-58-3

Usage

Uses

Used in Chemical Synthesis:
4-tert-Butylbenzoic acid is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a valuable building block for creating a wide range of molecules with different functional groups and properties.
Used in Research and Development:
As a useful research chemical, 4-tert-Butylbenzoic acid is employed in the development of new chemical processes and methodologies. It can be utilized to study reaction mechanisms, optimize reaction conditions, and explore the potential of new synthetic routes.
Used in Pharmaceutical Industry:
4-tert-Butylbenzoic acid may also find applications in the pharmaceutical industry, where it can be used as a starting material for the synthesis of drug candidates or as a component in the development of new drug delivery systems.
Used in Material Science:
The compound's structural properties make it a potential candidate for use in material science, where it could be employed in the design and synthesis of novel materials with specific characteristics, such as improved stability or enhanced performance in various applications.

Synthesis Reference(s)

Synthetic Communications, 22, p. 13, 1992 DOI: 10.1080/00397919208021074

InChI:InChI=1/C11H14O2/c1-11(2,3)9-7-5-4-6-8(9)10(12)13/h4-7H,1-3H3,(H,12,13)

Upstream product

• 594-19-4 tert.-butyl lithium 
• 445-29-4 o-fluoro-benzoic acid 
• 1074-92-6 1-tert-butyl-2-methyl-benzene 
• 2252-37-1 2-bromo-6-fluorobenzoic acid 
• 1073-06-9 3-fluorobromobenzene 
• 579-75-9 2-Methoxybenzoic acid 
• 198206-03-0 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 124-38-9 carbon dioxide 
• 21190-35-2 (tert-butylphenyl)methyl alcohol 
• 253185-03-4 tert-butylbenzene 
• 66464-20-8 2-(2-fluorophenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 
• 87306-63-6 2-<2-(1,1-dimethylethyl)phenyl>-4,4-dimethyl-2-oxazoline 
• 15719-64-9 methylammonium carbonate 
• 139287-38-0 2-tert-Butyl-benzoic acid 2-methyl-2-(methyl-trifluoromethanesulfonyl-amino)-propyl ester 

Downstream Products

• 14034-90-3 2-tert-butyl-5-nitrobenzoic acid 
• 16372-51-3 2-tert-butylbenzoyl chloride 
• 14034-91-4 5-Amino-2-tert.-butyl-benzoesaeure 
• 1369778-47-1 2-iodo-6-(1,1-dimethylethyl)benzoic acid 
• 1382472-04-9 (3S,10R,13S)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13-decahydro-1H-cyclopenta[a]phenanthren-3-yl 2-(tert-butyl)benzoate 
• 1365150-20-4 (R)-methyl 3-(2-tert-butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate 
• 1365151-96-7 (R)-3-(2-tert-Butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acid 
• 1188380-10-0 5'-O-2-(tert-butyl)benzoylthymidine 
• 220848-18-0 4-[[(2,6-Dichlorophenyl)carbonyl]amino]-N-[[2-(1,1-dimethylethyl)phenyl]carbonyl]-L-phenylalanine methyl ester 
• 16372-57-9 2,2'-Di-tert.-butyl-benzophenon 
• 16372-64-8 di(2-tert-butylphenyl)methanol 
• 106567-23-1 2-tert-Butyl-N,N-dimethyl-benzamide 
• 22679-53-4 2-tert-butylbenzophenone 
• 27334-45-8 methyl 2-(tert-butyl)benzoate 

Relevant academic research and scientific papers

Cobalt- and Nickel-Catalyzed Carboxylation of Alkenyl and Sterically Hindered Aryl Triflates Utilizing CO2

A highly efficient cobalt-catalyzed reductive carboxylation reaction of alkenyl trifluoromethanesulfonates (triflates) has been developed. By employing Mn powder as a reducing reagent under 1 atm pressure of CO2 at room temperature, diverse alkenyl triflates can be converted to the corresponding α,β-unsaturated carboxylic acids. Moreover, the carboxylation of sterically hindered aryl triflates proceeds smoothly in the presence of a nickel or cobalt catalyst.

Uncatalyzed CO2Li-Mediated SNAr Reaction of Unprotected Benzoic Acids via Silicon Trickery

The alkyl and aryllithium nucleophilic aromatic substitution (SNAr) displacement of a fluoro or methoxy group from unprotected 2-fluoro/methoxybenzoic acids is discussed. It was discovered that a TMS group located at the C6-position ortho to the carboxyl group shields effectively the carboxylate against nucleophilic attack, thus reducing dramatically ketone formation, and reorients nucleophilic substitution to the C2-position. The reactions with fluoro-substituted substrate 7 proceed efficiently; in contrast, the use of methoxy-functionalized benzoic acid 8 only affords moderate yields with s-BuLi and PhLi. This uncatalyzed coupling reaction, which provides a direct access to biaryl compounds, presumably proceeds by an addition-elimination sequence via intermediate formation of a resonance-stabilized pentavalent silalactone-Meisenheimer complex.

Meta -Non-flat substituents: A novel molecular design to improve aqueous solubility in small molecule drug discovery

Aqueous solubility is a key requirement for small-molecule drug candidates. Here, we investigated the regioisomer-physicochemical property relationships of disubstituted benzenes. We found that meta-isomers bearing non-flat substituents tend to possess the lowest melting point and the highest thermodynamic aqueous solubility among the regioisomers. The examination of pharmaceutical compounds containing a disubstituted benzene moiety supported the idea that the introduction of a non-flat substituent at the meta position of a benzene substructure would be a promising approach for medicinal chemists aiming to improve the thermodynamic aqueous solubility of drug candidates, even though it might not be universally effective. This journal is

Structural optimization and structure–activity relationship of 4-thiazolidinone derivatives as novel inhibitors of human dihydroorotate dehydrogenase

Human dihydroorotate dehydrogenase (hDHODH), one of the attractive targets for the development of immunosuppressive drugs, is also a potential target of anticancer drugs and anti-leukemic drugs. The development of promising hDHODH inhibitors is in high demand. Based on the unique binding mode of our previous reported 4-thiazolidinone derivatives, via molecular docking method, three new series 4-thiazolidinone derivatives were designed and synthesized as hDHODH inhibitors. The preliminary structure–activity relationship was investigated. Compound 9 of biphenyl series and compound 37 of amide series displayed IC50 values of 1.32 μM and 1.45 μM, respectively. This research will provide valuable reference for the research of new structures of hDHODH inhibitors.

Facile benzo-ring construction via palladium-catalyzed functionalization of unactivated sp3 C-H bonds under mild reaction conditions

(Equation Presented). A practical synthetic method for the annulation of benzo-rings by the intramolecular coupling of an aryl iodide and a methylene C-H bond is described. The palladium-catalyzed C-H functionalization is directed by an aminoquinoline carboxamide group, which can be easily installed and removed. High yields and broad substrate scope were achieved. An additive of ortho-phenyl benzoic acid, identified from a systematic screening, functions as a critical ligand for the catalytic process under mild condition, even at near room temperature.

Selectivities in reactions of organolithium reagents with unprotected 2-halobenzoic acids

(Matrix presented) Exposing 2-fluorobenzoic acid (1a) to 2.2 equiv of LTMP at ca. -78°C leads to deprotonation at the 3-position whereas 2-chloro/bromobenzoic acids (1b,c) are lithiated adjacent to the carboxylate. The resulting dianions 3Li-1a and 6Li-1b

Fungicides for the control of take-all disease of plants

A method of controlling Take-All disease of plants by applying a fungicide of the formula STR1 wherein Z1 and Z2 are C and are part of an aromatic ring which is benzothiophene; and A is selected from --C(X)-amine wherein the amine is an unsubstituted, monosubstituted or disubstituted amino radical, --C(O)--SR3, --NH--C(X)R4, and --C(=NR3)--XR7 ; B is --Wm --Q(R2)3 or selected from O-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4 ; Q is C, Si, Ge, or Sn; W is --C(R3)p H(2-p) --; or when Q is C, W is selected from --C(R3)p H(2-p), --N(R3)m H(1-m)--, --S(O)p--, and --O--; X is 0 or S; n is 0, 1, 2, or 3; m is 0 or 1; p is 0, 1, or 2; each R and R2 is independently defined herein; R3 is C1 -C4 alkyl; R4 is C1 -C4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R7 is C1 -C4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R4 ; or an agronomic salt thereof.

Directed lithiations: The effect of varying directing group orientation on competitive efficiencies for a series of tertiary amide, secondary amide, and alkoxide directed ortho lithiations

Significant differences for competitive efficiencies in directed ortho lithiations for single functional groups in three series, the secondary benzamides 1-4, the tertiary benzamides 5-11, and the benzylic alcohols 12-17, are reported. For both amide seri

N-imidaxo[1,2-b]pyridazinyl carbamates

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A new method for hydrolyzing 2-aryl-4,4-dimethyl-2-oxazolines to aryl carboxylic acids

A method of hydrolyzing 2-aryl-4,4-dimethyl-2-oxazolines with trifluoromethanesulfonic anhydride is described which works well even for highly hindered systems where alternate methods fail.