7148-03-0

Basic information

• Product Name: 4'-Methylbiphenyl-2-carboxylic acid
• Synonyms: 4'-METHYL[1,1'-BIPHENYL]-2-CARBOXYLIC ACID;4'-METHYL-2-BIPHENYLCARBOXYLIC ACID;4'-METHYLBIPHENYL-2-CARBOXYLIC ACID;AKOS BAR-0260;2-(4-METHYLPHENYL)BENZOIC ACID;2-(P-TOLYL)BENZOIC ACID;2-BIPHENYL-4'-METHYL-CARBOXYLIC ACID;1’-biphenyl]-2-carboxylicacid,4’-methyl-[
• CAS NO: 7148-03-0
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.24
• EINECS: 230-462-0
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;INTERMEDIATESOF;Biphenyl & Diphenyl ether;Organic acids;Hypertension;C13 to C42+;Carbonyl Compounds;Carboxylic Acids
• Mol File: 7148-03-0.mol

Chemical Properties

• Melting Point: 146-148°C
• Boiling Point: 354.5 °C at 760 mmHg
• Flash Point: 165.3 °C
• Appearance: /
• Density: 1.156 g/cm³
• Storage Temp.: Room temperature.
• Solubility: DMSO, Methanol
• PKA: 3.90±0.36(Predicted)
• CAS DataBase Reference: 4'-Methylbiphenyl-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Methylbiphenyl-2-carboxylic acid(7148-03-0)
• EPA Substance Registry System: 4'-Methylbiphenyl-2-carboxylic acid(7148-03-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 7148-03-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4'-Methylbiphenyl-2-carboxylic acid is used as a key intermediate in the synthesis of angiotensin II receptor antagonists, which are potent orally active antihypertensives. These antagonists play a crucial role in treating hypertension by blocking the effects of angiotensin II, a hormone responsible for narrowing blood vessels and increasing blood pressure.

Purification Methods

Crystallise the acid from toluene or *C6H6 (m 147-148o). [Beilstein 9 H 677, 9 IV 2523.]

Upstream product

• 114772-34-8 methyl 4'-methylbiphenyl-2-carboxylate 
• 84392-32-5 4,4-dimethyl-2-(4'-methyl-biphenyl-2-yl)-4,5-dihydrooxazole 
• 146017-83-6 2,6-di-tert-butyl-4-methylphenyl 4'-methylbiphenyl-2-carboxylate 
• 108-88-3 toluene 
• 611-61-0 2,4'-dimethylbiphenyl 
• 64-19-7 acetic acid 
• 131-62-4 1-hydroxy-1,2-benzodioxol-3-(1H)-one 
• 5720-05-8 4-methylphenylboronic acid 
• 40881-45-6 4-tolylboronic dimethyl ester 
• 114772-53-1 2-Cyano-4'-methylbiphenyl 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 118-92-3 anthranilic acid 
• 106-38-7 para-bromotoluene 
• 137600-69-2 2,6-diisopropylphenyl 2-methoxybenzoate 

Downstream Products

• 114772-34-8 methyl 4'-methylbiphenyl-2-carboxylate 
• 114772-36-0 tert-butyl 4'-methyl-2-biphenylcarboxylate 
• 150766-86-2 4'-bromomethylbiphenyl-2-carboxylic acid 
• 897446-35-4 4'-methylbiphenyl-2-carboxylic acid (2-aminophenyl)amide 
• 114772-38-2 Methyl 4'-(bromomethyl)biphenyl-2-carboxylate 
• 306271-96-5 3'',3'''-dichloro-5'',5'''-di(methoxycarbonyl)-4'',4'''-di[p-(2-methoxycarbonylphenyl)benzyloxy]-4',4'-diphenyl-3β-(3'-buten-1'-yl)cholestane 
• 168626-55-9 2-(4-methyl)phenyl-4'-(5-oxo-2,3,4,5-tetrahydro-1H-1-benzoazepine-1-carbonyl)benzanilide 
• 168046-06-8 2-<2,6-diaza-6-<<4<<2-(4-methylphenyl)phenyl>carbonyl-amino>phenyl>carbonyl>-3-oxobicyclo<5.4.0>undeca-1(7),8,10-trien-2-yl>acetic acid 
• 168047-46-9 ethyl 2-<2,6-diaza-6-<<4<<2-(4-methylphenyl)phenyl>carbonyl-amino>phenyl>carbonyl>-3-oxobicyclo<5.4.0>undeca-1(7),8,10-trien-2-yl>acetate 

Relevant articles and documents

Synthesis method of 4-bromomethyl-2-methyl formate biphenyl

The invention discloses a synthesis method of 4-bromomethyl-2-methyl formate biphenyl. The method comprises the following steps: performing bromination reaction in a mode of synchronously dropwise adding bromine and hydrogen peroxide, re-oxidizing hydrobromic acid formed after the reaction into bromine, and performing bromination reaction again, so that the bromine can fully participate in the reaction so as to reduce the use amount of bromine raw materials and improve the yield of the 4-bromomethyl-2-methyl formate biphenyl, waste difficult to treat cannot be generated, hydrogen peroxide is cheap and easy to obtain, and the production cost is remarkably saved.

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Mechanochemical-Cascaded C-N Cross-Coupling and Halogenation Using N-Bromo- And N-Chlorosuccinimide as Bifunctional Reagents

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Remote and Selective C(sp2)-H Olefination for Sequential Regioselective Linkage of Phenanthrenes

Biphenylcarboxylic acid with two competing C(sp2)-H sites was designed for site selective C(sp2)-H functionalization by developing carboxylic acids assisted remote and selective olefination via 7-membered palladacycle. Mechanism investigation and DFT calculations reveal a kinetics-determined process, which could be utilized to explore a variety of remote site selectivity. The practicability of this method was highlighted by the precise construction of phenathrene under sequential site selectivity.

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

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Synthesis and Biological Activity of Novel Succinate Dehydrogenase Inhibitor Derivatives as Potent Fungicide Candidates

In searching for novel fungicidal leads, the novel bioactive succinate dehydrogenase inhibitor (SDHI) derivatives were designed and synthesized by the inversion of carbonyl and amide groups. Bioassay indicated that compound 5i stood out with a broad spectrum of in vitro activity against five fungi. Its EC50 value (0.73 μg/mL) was comparable to that of boscalid (EC50 of 0.51 μg/mL) and fluxapyroxad (EC50 of 0.19 μg/mL) against Sclerotinia sclerotiorum. For Rhizoctonia cerealis, 5i and 5p with EC50 values of 4.61 and 6.48 μg/mL, respectively, showed significantly higher activity than fluxapyroxad with the EC50 value of 16.99 μg/mL. In vivo fungicidal activity of 5i exhibited an excellent inhibitory rate (100%) against Puccinia sorghi at 50 μg/mL, while the positive control boscalid showed only a 70% inhibitory rate. Moreover, 5i showed promising fungicidal activity with a 60% inhibitory rate against Rhizoctonia solani at 1 μg/mL, which was better than that of boscalid (30%). Compound 5i possessed better in vivo efficacy against P. sorghi and R. solani than boscalid. Molecular docking showed that even the carbonyl oxygen atom of 5i was far from the pyrazole ring. It could also form hydrogen bonds toward the hydroxyl hydrogen and amino hydrogen of TYR58 and TRP173 on SDH, respectively, which consisted of the positive control fluxapyroxad. Fluorescence quenching analysis and SDH enzymatic inhibition studies also validated its mode of action. Our studies showed that 5i was worthy of further investigation as a promising fungicide candidate.

Method for preparing high-purity 4'-methylbiphenyl-2-carboxylic acid methyl ester by using waste residues of 4'-methylbiphenyl-2-carboxylic acid methyl ester

The invention relates to a method for preparing high-purity 4'-methylbiphenyl-2-carboxylic acid methyl ester by using waste residues of 4'-methylbiphenyl-2-carboxylic acid methyl ester, and belongs tothe technical field of pharmaceutical synthesis. According to the method, the waste residues of 4'-methylbiphenyl-2-carboxylic acid methyl ester are taken as starting materials, after alkali hydrolysis, acidolysis and then layering are carried out after solvent extraction, after the solvent extraction, layering and re-esterification processes are carried out to synthesize the high-purity 4'-methylbiphenyl-2-carboxylic acid methyl ester. By using the method, the waste residues are recycled, the reuse of the waste residues is realized, the overall yield of the reaction is improved, and the pollution is reduced; and the method is low in cost, easy in operation and easy to realize industrial production.

Electrochemical C?O Bond Formation: Facile Access to Aromatic Lactones

An efficient and robust methodology based on electrochemical techniques for the direct synthesis of aromatic lactones through dehydrogenative C?O cyclization is described. This new and useful electrochemical reaction can tolerate a variety of functional groups, and is scalable to 100 g under mild conditions. Remarkably, heterocycle-containing substrates can be employed, thus expanding the scope of radical C?O cyclization reactions.

Synthetic method of 4'-bromomethylbiphenyl-2-carboxylate

The invention discloses a synthetic method of 4'-bromomethylbiphenyl-2-carboxylate. The synthetic method comprises the following steps: 1, hydrolyzing 4'-methyl-2-cyanobiphenyl to obtain 4'-methyl-2-biphenyl formic acid; 2, esterifying 4'-methyl-2-biphenyl formic acid to obtain 4'-methyl-2-biphenyl formate; and 3, reacting 4'-methyl-2-biphenyl formate under the illumination of 15000-20000lx at 20-30DEG C for 4-6h to obtain 4'-bromomethylbiphenyl-2-carboxylate. The synthetic method of 4'-bromomethylbiphenyl-2-carboxylate allows 4'-bromomethylbiphenyl-2-carboxylate to be obtained after hydrolysis, esterification and bromination of 4'-methyl-2-cyanobiphenyl used as an initial material. The route of the method is short, so the problem of raw material waste caused by bromine removal and bromo group introduction is avoided; and a bromination reaction is an illumination reaction, so 4'-bromomethylbiphenyl-2-carboxylate can be directly used in telmisartan synthesis without purifying, thereby the cost is reduced.