7499-07-2

Basic information

• Product Name: 4-CHLORO-2-METHYLBENZOIC ACID
• Synonyms: RARECHEM AL BO 0472;2-METHYL-4-CHLOROBENZOIC ACID;4-CHLORO-O-TOLUIC ACID;4-CHLORO-2-METHYLBENZOIC ACID;2-Carboxy-5-chlorotoluene, 4-Chloro-o-toluic acid;4-Chloro-2-Methylbenzoic Acid, 97+%;4-Chloro-2-methylbenzoicacid,98%;Benzoic acid,4-chloro-2-methyl-
• CAS NO: 7499-07-2
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzene series;Benzoic acid;C8;Carbonyl Compounds;Carboxylic Acids
• Mol File: 7499-07-2.mol

Chemical Properties

• Melting Point: 167-171 °C(lit.)
• Boiling Point: 300.3 °C at 760 mmHg
• Flash Point: 135.4 °C
• Appearance: /
• Density: 1.31 g/cm³
• Vapor Pressure: 0.000504mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.63±0.25(Predicted)
• CAS DataBase Reference: 4-CHLORO-2-METHYLBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-METHYLBENZOIC ACID(7499-07-2)
• EPA Substance Registry System: 4-CHLORO-2-METHYLBENZOIC ACID(7499-07-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-41
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 7499-07-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Chloro-2-methylbenzoic acid is used as a key intermediate in the synthesis of various organic compounds, including:
1. 4-chloro-2-methylbenzophenone: 4-CHLORO-2-METHYLBENZOIC ACID is synthesized via Friedel-Crafts acylation with benzene, which is a versatile method for the formation of carbon-carbon bonds in organic chemistry.
2. 4-chloro-2-methyl-5-(methylsulfonyl)benzoic acid: This derivative can be used in the development of pharmaceuticals and other chemical products.
3. 4-chloro-2-methyl-3-nitrobenzoic acid methyl ester: This ester can be utilized in the synthesis of various organic compounds and may have potential applications in the pharmaceutical or chemical industries.

InChI:InChI=1/C8H7ClO2/c1-5-4-6(9)2-3-7(5)8(10)11/h2-4H,1H3,(H,10,11)

Upstream product

• 50712-68-0 4-chloro-2-methylbenzonitrile 
• 3274-12-2 4-methyl-4-(trichloromethyl)cyclohexa-2,5-dien-1-one 
• 594-19-4 tert.-butyl lithium 
• 74-11-3 para-chlorobenzoic acid 
• 74-88-4 methyl iodide 
• 598-30-1 sec.-butyllithium 
• 762-49-2 2-fluoroethyl bromide 
• 75319-02-7 4-chloro-2-methylbenzohydrazide 
• 124-38-9 carbon dioxide 
• 129716-11-6 2-methyl-4-chlorobenzyl alcohol 
• 1048025-62-2 4-chloro-2-iodo-6-methylbenzoic acid 
• 14495-51-3 2-bromo-5-chlorotoluene 
• 766-80-3 1-bromomethyl-3-chlorobenzene 
• 108-41-8 1-chloro-3-methylbenzene 

Downstream Products

• 15393-58-5 4-chloro-2-methyl-benzoic acid ethyl ester 
• 75870-97-2 4-chloro-2-methylbenzoyl fluoride 
• 129716-11-6 2-methyl-4-chlorobenzyl alcohol 
• 40319-46-8 3,5-dinitro-4-chloro-o-toluic acid 
• 190368-22-0 5-Methanesulfonyl-2-methyl-4-(pyrimidin-2-ylamino)-benzoic acid methyl ester 
• 190367-93-2 3-Methanesulfonyl-2-methyl-4-(pyridin-3-yloxy)-benzoic acid methyl ester 
• 190368-32-2 4-Chloro-5-methanesulfonyl-2-methyl-3-pyrrol-1-yl-benzoic acid methyl ester 
• 1025835-61-3 4-Benzoimidazol-1-yl-5-methanesulfonyl-2-methyl-benzoic acid 
• 190368-08-2 4-Benzoimidazol-1-yl-5-methanesulfonyl-2-methyl-benzoic acid methyl ester 

Relevant articles and documents

Catalytic Reductions Without External Hydrogen Gas: Broad Scope Hydrogenations with Tetrahydroxydiboron and a Tertiary Amine

Facile reduction of aryl halides with a combination of 5% Pd/C, B2(OH)4, and 4-methylmorpholine is reported. Aryl bromides, iodides, and chlorides were efficiently reduced. Aryl dihalides containing two different halogen atoms underwent selective reduction: I over Br and Cl, and Br over Cl. Beyond these, aryl triflates were efficiently reduced. This combination was broadly general, effectuating reductions of benzylic halides and ethers, alkenes, alkynes, aldehydes, and azides, as well as for N-Cbz deprotection. A cyano group was unaffected, but a nitro group and a ketone underwent reduction to a low extent. When B2(OD)4 was used for aryl halide reduction, a significant amount of deuteriation occurred. However, H atom incorporation competed and increased in slower reactions. 4-Methylmorpholine was identified as a possible source of H atoms in this, but a combination of only 4-methylmorpholine and Pd/C did not result in reduction. Hydrogen gas has been observed to form with this reagent combination. Experiments aimed at understanding the chemistry led to the proposal of a plausible mechanism and to the identification of N,N-bis(methyl-d3)pyridin-4-amine (DMAP-d6) and B2(OD)4 as an effective combination for full aromatic deuteriation. (Figure presented.).

Dehydrogenation of Alcohols to Carboxylic Acid Catalyzed by in Situ-Generated Facial Ruthenium- CPP Complex

A selective catalytic system for the dehydrogenation of primary alcohols to carboxylic acids using a facial ruthenium complex generated in situ from the [Ru(COD)Cl2]n and a hybrid N-heterocyclic carbene (NHC)-phosphine-phosphine ligand (CPP) has been first reported. The facial coordination model was unveiled by NMR analysis of the reaction mixture. Such a fac-ruthenium catalyst system exhibited high catalytic activity and stability, and a high turnover number of 20 000 could be achieved with catalyst loading as low as 0.002 mol %. The exceedingly high catalyst stability was tentatively attributed to both the anchoring role of NHC and the hemi-lability of phosphines. The catalytic system also features a wide substrate scope. In particular, the facial coordination of CPP ligands was found to be beneficial for sterically hindered alcohols, and ortho-substituted benzylic alcohols and bulky adamantanyl methanol as well as cholesterol were all found to be viable dehydrogenation substrates.

Synthetic method of 1-(4-iodophenyl)-5-chlorinisobenzofuran

The invention relates to a synthetic method of a compound, in particular to a synthetic method of 1-(4-iodophenyl)-5-chlorinisobenzofuran.By means of the method, the 1-(4-iodophenyl)-5-chlorinisobenzofuran is obtained through a series of reactions of oxidation, condensation and the like.The method is mild in reaction condition and high in yield.

DIPEPTIDYL PEPTIDASE-IV INHIBITORS

The present invention relates generally to pyrrolidine and thiazolidine DPP-IV inhibitor compounds. The present invention also provides synthetic methods for preparation of such compounds, methods of inhibiting DPP-IV using such compounds and pharmaceutical formulations containing them for treatment of DPP-IV mediated diseases, in particular, Type-2 diabetes.

Doxepin analogs and methods of use thereof

The invention relates to novel antihistamines and methods of modulating sleep by administering a doxepin analog or a pharmaceutically effective salt thereof.

METHODS OF TREATING SLEEP DISORDERS

The invention relates to novel antihistamines and methods of modulating sleep by administering a doxepin analog or a pharmaceutically effective salt thereof.

The first regioselective metalation and functionalization of unprotected 4-halobenzoic acids

(Chemical Equation Presented) By treatment with s-BuLi, s-BuLi/TMEDA, or t-BuLi at ～-78°C, 4-fluoro- and 4-chlorobenzoic acids (1a,b) are metalated preferentially in the position adjacent to the carboxylate. A complete reversal in regioselectivity is observed for 1a when treated with LTMP; a sequential process involving a rapid intraaggregate lithiation through a quasi dianion complex "QUADAC" is postulated to explain the unusual reactivity of Me2S2 and I2.

Viral polymerase inhibitors

An isomer, enantiomer, diastereoisomer, or tautomer of a compound, represented by formula I: wherein R1 is selected from: H, haloalkyl, (C1-6)alkyl, (C2-6)alkenyl, (C3-7)cycloalkyl, (C2-6)alkynyl, (C5-7)cycloalkenyl, 6 or 10-membered aryl, Het all optionally substituted; R2 is selected from (C1-6)alkyl, (C3-7)cycloalkyl, (C6-10)bicycloalkyl, 6- or 10-membered aryl, or Het all optionally substituted; B is N or CR5, wherein R5 is H, halogen, haloalkyl, (C1-6)alkyl, (C3-7)cycloalkyl or (C1-6)alkyl-(C3-7)cycloalkyl; X is N or CR5; D is N or CR5; each of Y1 and Y2 is independently O or S; Z is O, N, or NRz wherein Rz is H, (C1-6)alkyl, (C3-7)cycloalkyl or (C1-6)alkyl-(C3-7)cycloalkyl; R3 and R4 are each independently H, (C1-6)alkyl, first (C3-7)cycloalkyl or 6- or 10-membered aryl, Het (C1-6)alkyl-6- or 10-membered aryl, (C1-6)alkyl-Het; or each R3 and R4 are independently covalently bonded together to form second (C3-7)cycloalkyl, or heterocycle, all optionally substituted; or when Z is N, either R3 or R4 are independently covalently bonded thereto to form a nitrogen-containing heterocycle; R7 is H, (C1-6 alkyl), (C3-7)cycloalkyl or (C1-6)alkyl-(C3-7)cycloalkyl; or R7 is covalently bonded to either of R3 or R4 to form a heterocycle; A is (C1-6) alkyl-CONHR8 wherein R8 is-6- or 10-membered aryl, or Het; or A is a 6- or 10-membered aryl, or Het said aryl or Het being optionally substituted; or a salt or a derivative thereof; such compounds being potent inhibitors of HCV NS5B polymerase.

Viral polymerase inhibitors

A compound of the formula I: wherein: X is CH or N; Y is O or S; Z is OH, NH2, NMeR3, NHR3; OR3 or 5- or 6-membered heterocycle, having 1 to 4 heteroatoms selected from 0, N and S, said heterocycle being optionally substituted with from 1 to 4 substituents; A is N, COR7 or CR5, wherein R5 is H, halogen, or (C1-6) alkyl and R7 is H or (C1-6 alkyl), with the proviso that X and A are not both N; R6 is H, halogen, (C1-6 alkyl) or OR7, wherein R7 is H or (C1-6 alkyl); R1 is selected from the group consisting of 5- or 6-membered heterocycle having 1 to 4 heteroatoms selected from O, N, and S, phenyl, phenyl(C1-3)alkyl, (C2-6)alkenyl, phenyl(C2-6)alkenyl, (C3-6)cycloalkyl, (C1-6)alkyl, CF3, 9- or 10-membered heterobicycle having 1 to 4 heteroatoms selected from O, N and S, wherein said heterocycle, phenyl, phenyl(C2-6)alkenyl and phenyl(C1-3)alkyl), alkenyl, cycloalkyl, (C1-6)alkyl, and heterobicycle are all optionally substituted with from 1 to 4 substituents R2 is selected from (C1-6)alkyl, (C3-7)cycloalkyl, (C3-7)cycloalkyl(C1-3)alkyl, (C6-10)bicycloalkyl, adamantyl, phenyl, and pyridyl, all of which is optionally substituted with from1 to 4 substituents; R3 is selected from H, (C1-6)alkyl, (C3-6)cycloalkyl, (C36)cycloalkyl(C1-6)alkyl, (C6-10)aryl, (C6-10)aryl(C1-6)alkyl, (C2-6)alkenyl, (C3-6)cycloalkyl(C2-6)alkenyl, (C6-10)aryl(C2-6)alkenyl, N{(C1-6)alkyl}2, NHCOO(C1-6)alkyl(C6-10)aryl, NHCO(C6-10)aryl, (C1-6)alkyl-5- or 10-atom heterocycle, having 1 to 4 heteroatoms selected from O, N and S, and 5- or 10-atom heterocycle having 1 to 4 heteroatoms selected from O, N and S; wherein said alkyl, cycloalkyl, aryl, alkenyl and heterocycle are all optionally substituted with from 1 to 4 substituents; n is zero or 1; or a detectable derivative or salt thereof. The compounds of the invention may be used as inhibitors of hepatitis C virus replication. The invention further provides a method for treating or preventing hepatitis C virus infection.

Method for producing ortho-alkylated benzoic acid derivatives

The invention relates to a process for the preparation of ortho-alkylated benzoic acid derivatives of the formula I characterized in that an aryl bromide of the formula II is reacted with a secondary or tertiary organolithium compound and CO2.