1642-81-5

Basic information

• Product Name: 4-(Chloromethyl)benzoic acid
• Synonyms: Benzoic acid, 4-(chloromethyl)-;4-(ChloroMethyl)benzoic acid 95%;4-(ChloroMethyl)benzoic Acid, 98.0%(GC&T;4 - chlorine Methyl benzoic acid;-Chloro-p-toluicacid;P-(CHLOROMETHYL)BENZOIC ACID;RARECHEM AL BO 0358;ALPHA-CHLORO-O-TOLUNITRILE
• CAS NO: 1642-81-5
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• EINECS: 216-697-1
• Product Categories: Piperidines;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Building Blocks;C8;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 1642-81-5.mol

Chemical Properties

• Melting Point: 201-202 °C(lit.)
• Boiling Point: 317.7 °C at 760 mmHg
• Flash Point: 145.9 °C
• Appearance: White to slightly yellow/Crystalline Powder
• Density: 1.315 g/cm³
• Vapor Pressure: 0.000159mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 4.11±0.10(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 1907970
• CAS DataBase Reference: 4-(Chloromethyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Chloromethyl)benzoic acid(1642-81-5)
• EPA Substance Registry System: 4-(Chloromethyl)benzoic acid(1642-81-5)

Safety Data

• Hazard Codes: C
• Statements: 34-42/43-36
• Safety Statements: 26-36/37/39-45-22-27-37/37/39
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 19
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1642-81-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(Chloromethyl)benzoic acid is used as a synthetic intermediate for the production of dihydroxy stilbene derivatives, which are known for their potential applications in the development of pharmaceuticals targeting various health conditions.
Used in Chemical Synthesis:
4-(Chloromethyl)benzoic acid is used as a building block in the synthesis of complex organic molecules, particularly in the creation of dihydroxy stilbene derivatives, which can be further utilized in various chemical and pharmaceutical applications.

InChI:InChI=1/C8H7ClO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4H,5H2,(H,10,11)/p-1

Upstream product

• 876-08-4 p-(chloromethyl)benzoyl chloride 
• 84545-14-2 tert-butyl 4-(chloromethyl)benzamide 
• 874-60-2 4-methyl-benzoyl chloride 
• 104-82-5 4-Methylbenzyl chloride 
• 99-94-5 p-Toluic acid 
• 17201-43-3 4-cyanobenzyl bromide 
• 874-86-2 4-cyanobenzyl chloride 
• 76-05-1 trifluoroacetic acid 
• 7647-01-0 hydrogenchloride 
• 619-66-9 4-Carboxybenzaldehyde 
• 104-85-8 para-methylbenzonitrile 
• 108-88-3 toluene 
• 2094-98-6 1,1'-azobis (cyclohexanecarbonitrile) 
• 258278-55-6 4-[(nitrooxy)methyl]benzoic acid 

Downstream Products

• 1201-90-7 ethyl 4-chloromethylbenzoate 
• 876-08-4 p-(chloromethyl)benzoyl chloride 
• 3006-96-0 3-hydroxymethyl-benzoic acid 
• 62642-59-5 4-diethylaminomethyl-benzoic acid 
• 34040-64-7 p-methyloxycarbonylbenzyl chloride 
• 62642-62-0 4-(morpholinomethyl)benzoic acid 
• 108179-81-3 (R,S)-4-(3-methyl-2-oxa-4-pentenyl)benzoic acid 
• 108179-79-9 (R)-4-(3-butyl-2-oxa-4-pentenyl)benzoic acid 
• 88382-51-8 4-(4chloro-phenylsulfanylmethyl)-benzoic acid 
• 110046-23-6 4-<(4'-Methoxyphenylthio)methyl>benzoic acid 
• 75472-97-8 4-(ethoxythiocarbonylthiomethyl)benzoic acid 
• 88382-49-4 4-<(Phenylthio)methyl>benzoic acid 
• 88382-50-7 4-p-Tolylsulfanylmethyl-benzoic acid 
• 110046-26-9 4-(4-Nitro-phenylsulfanylmethyl)-benzoic acid 

Relevant articles and documents

1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 under Clean Conditions

Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.

Preparation method of 4-formylbenzoic acid

The invention provides a preparation method of 4-formylbenzoic acid, and the method comprises the following steps: by using 4-methylbenzoyl chloride as a raw material, performing chlorinating to obtain 4-chloromethylbenzoyl chloride, performing hydrolyzing to obtain 4-chloromethyl benzoic acid, and reacting with urotropine to obtain 4-formylbenzoic acid. The method provided by the invention is simple in process, does not need special equipment and is relatively low in cost; moreover, the method provided by the invention is relatively high in product yield and purity, and large-scale industrialproduction is easy to realize. The result of the embodiment shows that the yield of each step of the preparation method of the 4-formylbenzoic acid provided by the invention is greater than or equalto 90%, and the purity of the finally obtained 4-formylbenzoic acid is greater than or equal to 99.7%.

Preparation method of aminomethylbenzoic acid

The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of aminomethylbenzoic acid. The method comprises the following steps: carrying outchlorination reaction on p-toluic acid and a chlorination reagent under the condition of a catalyst I to obtain an intermediate p-chloromethylbenzoic acid, and carrying out ammonolysis on the intermediate p-chloromethylbenzoic acid and ammonia water under the condition of a catalyst II to prepare aminomethylbenzoic acid. The purity of the obtained product aminomethylbenzoic acid is greater than 99.9%, the single impurity content is less than 0.1%, and the overall yield of the two-step reaction is greater than 63%. The method is short in synthetic route, free of highly toxic reagents or precious metals, low in production cost, less in environmental pollution, high in overall yield and suitable for large-scale industrial production.

Highly selective halogenation of unactivated C(sp3)-H with NaX under co-catalysis of visible light and Ag@AgX

The direct selective halogenation of unactivated C(sp3)-H bonds into C-halogen bonds was achieved using a nano Ag/AgCl catalyst at RT under visible light or LED irradiation in the presence of an aqueous solution of NaX/HX as a halide source, in air. The halogenation of hydrocarbons provided mono-halide substituted products with 95% selectivity and yields higher than 90%, with the chlorination of toluene being 81%, far higher than the 40% conversion using dichlorine. Mechanistic studies demonstrated that the reaction is a free radical process using blue light (450-500 nm), with visible light being the most effective light source. Irradiation is proposed to cause AgCl bonding electrons to become excited and electron transfer from chloride ions induces chlorine radical formation which drives the substitution reaction. The reaction provides a potentially valuable method for the direct chlorination of saturated hydrocarbons.

Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids Using α,α-Dichlorodiphenylmethane

A new method for chlorination of alcohols and carboxylic acids, using α,α-dichlorodiphenylmethane as the chlorinating agent and FeCl3 as the catalyst, was developed. The method enables conversions of various alcohols and carboxylic acids to their corresponding alkyl and acyl chlorides in high yields under mild conditions. Particulary interesting is the observation that the respective alkyl bromides and iodides can be generated from alcohols when either LiBr or LiI are present in the reaction mixtures.

A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions

A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.

One-Step Trimethylstannylation of Benzyl and Alkyl Halides

Trialkylstannanes are good leaving groups that have been used for the formation of carbon-metal bonds to electrode surfaces for analyses of single-molecule conductivity. Here, we report the multistep synthesis of two amide-containing compounds that are of interest in studies of molecular rectifiers. Each molecule has two trimethylstannyl units, one linked by a methylene and the other by an ethylene group. To account for the very different reactivities of the parent halides, a new methodology for one-step trimethylstannylation was developed and optimized.

Silver-catalyzed decarboxylative chlorination of aliphatic carboxylic acids

Decarboxylative halogenation of carboxylic acids, the Hunsdiecker reaction, is one of the fundamental functional group transformations in organic chemistry. As the initial method requires the preparations of strictly anhydrous silver carboxylates, several modifications have been developed to simplify the procedures. However, these methods suffer from the use of highly toxic reagents, harsh reaction conditions, or limited scope of application. In addition, none is catalytic for aliphatic carboxylic acids. In this Article, we report the first catalytic Hunsdiecker reaction of aliphatic carboxylic acids. Thus, with the catalysis of Ag(Phen)2OTf, the reactions of carboxylic acids with t-butyl hypochlorite afforded the corresponding chlorodecarboxylation products in high yields under mild conditions. This method is not only efficient and general, but also chemoselective. Moreover, it exhibits remarkable functional group compatibility, making it of more practical value in organic synthesis. The mechanism of single electron transfer followed by chlorine atom transfer is proposed for the catalytic chlorodecarboxylation.

PROCESS FOR PREPARING 4-NITRO-OXY-METHYL-BENZOIC ACID

This invention relates to a new process for preparing 4-nitro-oxy-methyl- benzoic acid, comprising the following steps: a) reaction of 4-chloromethyl-benzoic acid with silver nitrate and in the presence of an acid as a catalyst in acetonitrile at reflux temperature, followed by cooling and adding of a polar aprotic solvent; b) separation of the silver salts by filtration, followed by washout with a polar aprotic solvent; c) precipitation of the 4-nitro-oxy-methyl-benzoic acid with water from the filtrate obtained in step b); and d) drying of the 4-nitro-oxy-methyl-benzoic acid.