92254-03-0

Basic information

• Product Name: 5-METHYLBIPHENYL-2-CARBOXYLIC ACID
• Synonyms: 5-METHYLBIPHENYL-2-CARBOXYLIC ACID
• CAS NO: 92254-03-0
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.24388
• Mol File: 92254-03-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-METHYLBIPHENYL-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYLBIPHENYL-2-CARBOXYLIC ACID(92254-03-0)
• EPA Substance Registry System: 5-METHYLBIPHENYL-2-CARBOXYLIC ACID(92254-03-0)

Safety Data

• Hazardous Substances Data: 92254-03-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-METHYLBIPHENYL-2-CARBOXYLIC ACID is used as an intermediate in the synthesis of penicillins, which are a class of antibiotics known for their effectiveness against a wide range of bacterial infections. Specifically, it plays a crucial role in the preparation of penicillins that exhibit activity against staphylococci, a type of bacteria that can cause various infections, including skin infections, pneumonia, and food poisoning. The presence of the 5-methyl group in the biphenyl core of this compound contributes to the enhanced activity of the resulting penicillin derivatives against these resistant bacteria.

Upstream product

• 42308-22-5 5-methyl-[1,1'-biphenyl]-2-carbonitrile 
• 108-86-1 bromobenzene 
• 1829-21-6 4-methyl-2-iodobenzoic acid 
• 7372-85-2 2,5-dimethylbiphenyl 
• 106-42-3 para-xylene 
• 4501-52-4 2-cyclohexyl-p-xylene 
• 108-93-0 cyclohexanol 
• 68036-69-1 (E)-2-methyl-4-phenyl-1,3-butadiene 
• 99-94-5 p-Toluic acid 
• 191104-38-8 4-methyl-2-phenylbenzoic acid methyl ester 
• 98-80-6 phenylboronic acid 
• 7697-27-0 2-bromo-4-methylbenzoic acid 
• 191104-16-2 2-(trifluoromethanesulfonyloxy)4-methylbenzoic acid methyl ester 
• 50-85-1 2-hydroxy-p-toluic acid 

Downstream Products

• 19547-84-3 6β-(5-methyl-biphenyl-2-carbonylamino)-penicillanic acid 

Relevant articles and documents

Palladium-catalyzed intramolecular aromatic C-H acylation of 2-arylbenzoyl fluorides

The catalytic intramolecular cyclization of acyl fluorides using a Pd(OAc)2/PCy3 system is described. A wide range of 2-arylbenzoyl fluoride derivatives can be used as fluorenone precursors and the reaction proceeds via an intramolecular coupling between aromatic C-H bonds with acyl C-F bonds. The reaction can be applied to the synthesis of indenofluorenedione derivatives and to the construction of other molecules with fivemembered rings.

Visible-Light-Induced Arene C(sp 2)-H Lactonization Promoted by DDQ and tert -Butyl Nitrite

A visible-light photocatalytic aerobic oxidative lactonization of arene C(sp 2)-H bonds proceeds in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert -butyl nitrite (TBN). Under the optimized conditions, a range of 2-arylbenzoic acids is converted into the corresponding benzocoumarin derivatives in moderate to excellent yields. This method is characterized by its atom economy, mild reaction conditions, the use of a green oxidant and metal-free catalysis.

Electronic effects on the substitution reactions of benzhydrols and fluorenyl alcohols. Determination of mechanism and effects of antiaromaticity

A range of substituted benzhydrols and fluorenols were prepared and subjected to acid catalysed methanolysis. Analysis of the rates of each of these processes showed correlation with Hammett σ+ parameters as is consistent with the significant build-up of positive charge adjacent to the ring. In combination with the similarity of the electronic susceptibility of the processes, these data suggest that both reactions proceed through a unimolecular rate-determining step. This shows that the effect of fusion of the phenyl systems (and hence potentially introducing an antiaromatic carbocation intermediate) is only to slow the rate of reaction rather than change the mechanism of the process.

Photocatalytic Dehydrogenative Lactonization of 2-Arylbenzoic Acids

A metal-free dehydrogenative lactonization of 2-arylbenzoic acids at room temperature was developed. This work illustrates the first application of visible-light photoredox catalysis in the preparation of benzo-3,4-coumarins, an important structural motif in bioactive molecules. The combination of photocatalyst [Acr+-Mes] with (NH4)2S2O8 as a terminal oxidant provides an economical and environmentally benign entry to different substituted benzocoumarins. Preliminary mechanistic studies suggest that this reaction most likely occurs through a homolytic aromatic substitution pathway.

Pd-catalyzed C-H lactonization for expedient synthesis of biaryl lactones and total synthesis of cannabinol

A practical Pd(II)/Pd(IV)-catalyzed carboxyl-directed C-H activation/C-O cyclization to construct biaryl lactones has been developed. The synthetic utility of this new reaction was demonstrated in an atom-economical and operationally convenient total synthesis of the natural product cannabinol from commercially available starting materials, with the newly developed method used for two key steps.

Inhibitors of protein isoprenyl transferases

Compounds having the formula or a pharmaceutically acceptable salt thereof wherein R1 is (a) hydrogen, (b) loweralkyl, (c) alkenyl, (d) alkoxy, (e) thioalkoxy, (f) halo, (g) haloalkyl, (h) aryl-L2—, and (i) heterocyclic-L2—; R2 is selected from (a) (b) —C(O)NH—CH(R14)—C(O)OR15, (c) (d) —C(O)NH—CH(R14)—C(O)NHSO2R16 (e) —C(O)NH—CH(R14)-tetrazolyl, (f) —C(O)NH-heterocyclic, and (g) —C(O)NH—CH(R14)—C(O)NR17R18; R3 is heterocyclic, aryl, substituted or unsubstituted cycloalkyl; R4 is hydrogen, lower alkyl, haloalkyl, halogen, aryl, arylakyl, heterocyclic, or (heterocyclic)alkyl; L1 is absent or is selected from (a) —L4—N(R5)—L5—, (b) —L4—O—L5—, (c) —L4—S(O)n—L5— (d) —L4-L6—C(W)—N(R5)—L5—, (e) —L4-L6—S(O)m—N(R5)—L5—, (f) —L4—N(R5)—C(W)—L7-L5—, (g) —L4—N(R5)—S(O)p—L7—L5—, (h) optionally substituted alkylene, (i) optionally substituted alkenylene, and (j) optionally substituted alkynylene are inhibitors of protein isoprenyl transferases. Also disclosed are protein isoprenyl transferase inhibiting compositions and a method of inhibiting protein isoprenyl transferases.

Liquid-phase catalytic oxidation of 2,5-dimethylbiphenyl

Liquid-phase catalytic oxidation of 2,5-dimethylbiphenyl provided 2,5-biphenyldicarboxylic acid. The effect on reaction of temperature, catalyst type, and reagents concentration was investigated.