5807-30-7

Basic information

• Product Name: 3,4-Dichlorophenylacetic acid
• Synonyms: TIMTEC-BB SBB003501;RARECHEM AL BO 0123;2-(3,4-DICHLOROPHENYL)ACETIC ACID;3,4-DICHLOROBENZENE ACETIC ACID;3,4-DICHLOROPHENYLACETIC ACID;LABOTEST-BB LT00455049;Benzeneacetic acid, 3,4-dichloro-;3,4-Dichlorophenylaceticacid,98%
• CAS NO: 5807-30-7
• Molecular Formula: C₈H₆Cl₂O₂
• Molecular Weight: 205.04
• EINECS: 227-368-7
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;C8;Carbonyl Compounds;Carboxylic Acids;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 5807-30-7.mol

Chemical Properties

• Melting Point: 89-91 °C(lit.)
• Boiling Point: 294.45°C (rough estimate)
• Flash Point: 152.1 °C
• Appearance: white to light yellow crystalline powder
• Density: 1.3806 (rough estimate)
• Vapor Pressure: 7.9E-05mmHg at 25°C
• Refractive Index: 1.5490 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.99±0.10(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 1953781
• CAS DataBase Reference: 3,4-Dichlorophenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dichlorophenylacetic acid(5807-30-7)
• EPA Substance Registry System: 3,4-Dichlorophenylacetic acid(5807-30-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25
• WGK Germany: 3
• Hazardous Substances Data: 5807-30-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dichlorophenylacetic acid is used as an intermediate in the synthesis of various pharmaceutical compounds. Its chemical structure allows for the creation of a range of drugs with different therapeutic properties.
Used in Chemical Synthesis:
3,4-Dichlorophenylacetic acid is used as a building block in the parallel solid phase synthesis of tetra-substituted diethylenetriamines. This process involves selective amide alkylation and exhaustive reduction of N-acylated dipeptides, which are essential for the development of complex organic molecules with specific functions.
Used in Research and Development:
Due to its unique chemical properties, 3,4-Dichlorophenylacetic acid is also utilized in research and development for the creation of new compounds and materials. Its reactivity and structural features make it a valuable component in the design and synthesis of novel molecules for various applications.

InChI:InChI=1/C8H6Cl2O2/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3H,4H2,(H,11,12)/p-1

Upstream product

• 3218-49-3 3,4-dichloro-benzeneacetonitrile 
• 23722-52-3 2-diazo-1-(3,4-dichlorophenyl)ethan-1-one 
• 1805-32-9 3,4-dichlorobenzyl alcohol 
• 51-44-5 3,4-dichlorbenzoic acid 
• 102-47-6 3,4-Dichlorophenylmethyl chloride 
• 201230-82-2 carbon monoxide 
• 18414-58-9 diphenylmethylsilanecarboxylic acid 
• 18880-04-1 3,4-dichlorobenzyl bromide 
• 3024-72-4 3,4-dichlorobenzoyl chloride 

Downstream Products

• 6725-45-7 ethyl 3,4-dichlorophenylacetate 
• 101273-28-3 (3,4-dichloro-phenyl)-acetic acid-(3,4-dichloro-phenethylamide) 
• 101495-08-3 chloro-(3,4-dichloro-phenyl)-acetyl chloride 
• 35364-79-5 2-(3,4-dichlorophenyl)ethanol 
• 150208-59-6 1-[1,4]Diazepan-1-yl-2-(3,4-dichloro-phenyl)-ethanone 
• 138356-63-5 2-(3,4-Dichloro-phenyl)-N-(2-pyrrolidin-1-yl-ethyl)-acetamide 
• 128103-38-8 1-<(3,4-dichlorophenyl)acetyl>-2-piperidinemethanol 
• 184637-53-4 2-<<(3,4-dichlorophenyl)acetamido>methyl>-1-ethylpyrrolidine 
• 116763-50-9 N-[2-(3,4-dichlorophenyl)acetyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine 
• 138357-12-7 2-(3,4-Dichloro-phenyl)-N-methyl-N-(2-piperidin-1-yl-ethyl)-acetamide 
• 150208-68-7 2-(3,4-Dichloro-phenyl)-1-(octahydro-pyrido[1,2-a]pyrazin-2-yl)-ethanone 
• 131815-14-0 2-(3,4-Dichloro-phenyl)-N-(1-piperidin-1-yl-cyclohexylmethyl)-acetamide 
• 150208-58-5 1-<(3,4-dichlorophenyl)acetyl>-4-(1-propyl)piperazine 
• 138356-85-1 2-(3,4-Dichloro-phenyl)-N-(2-diethylamino-ethyl)-N-methyl-acetamide 

Relevant articles and documents

Palladium-catalyzed synthesis of aromatic carboxylic acids with silacarboxylic acids

Aryl iodides and bromides were easily converted to their corresponding aromatic carboxylic acids via a Pd-catalyzed carbonylation reaction using silacarboxylic acids as an in situ source of carbon monoxide. The reaction conditions were compatible with a wide range of functional groups, and with the aryl iodides, the carbonylation was complete within minutes. The method was adapted to the double and selective isotope labeling of tamibarotene.

Exceptionally simple catalytic system for the carbonylation of benzyl halides

A ligand-less catalytic system, Pd(OAc)2 immobilized in NBu4Hal melt is suggested for the synthesis of arylacetic acids by the carbonylation of benzyl bromides.

Novel polymorphs of azabicyclohexane

The invention provides polymorphic crystalline forms of acid addition salts of (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane designated as polymorph form A, polymorph form B and polymorph form C, where polymorph form A is more thermodynamically stable than the other forms, methods for preparing and using such polymorph forms and pharmaceutical compositions containing such polymorph forms.

NOVEL POLYMORPHS OF AZABICYCLOHEXANE

The invention provides polymorphic crystalline forms of acid addition salts of (+)-1-(3, 4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane designated as polymorph form A, polymorph form B and polymorph form C, where polymorph form A is more thermodynamically stable than the other forms, methods for preparing and using such polymorph forms and pharmaceutical compositions containing such polymorph forms.

Synthesis, selective aldose reductase inhibitory profile and antihyperglycaemic potential of certain parabanic acid derivatives

Synthesis and aldose reductase inhibitory profile of certain parabanic acid derivatives 1a-p is described. Also, the antihyperglycaemic potential of these compounds was studied. The most active inhibitors in this series were compounds 1 g, 1p, and 1o which showed inhibitory activity, 36.6, 90 and 91% respectively, at concentration 1 × 10-4. Their IC50 were 2 × 10-6, 7.5 × 10-8 and 5 × 10-8, respectively. Compound 1o exhibited pronounced antihyperglycaemic effect.

Quinolones as gonadotropin releasing hormone (GnRH) antagonists: Simultaneous optimization of the C(3)-aryl and C(6)-substituents

A series of 3-arylquinolones was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. A variety of substitution patterns of the 3-aryl substituent are described. The 3,4,5-trimethylphenyl substituent (23h) was found to be optimal. (C) 2000 Elsevier Science Ltd. All rights reserved.

METABOLISM OF CHLOROPHENYLALANINES IN CROP AND WEED PLANTS IN RELATION TO THE FORMATION OF POTENTIAL HERBICIDAL END PRODUCTS

Metabolism of 12 synthetic D,L-chlorophenylalanines has been examined in several crop and weed plants.Twenty-five gram samples of excised shoots or leaves of bushbean, soybean, corn, pigweed, lambsquarters, and giant foxtail were allowed to metabolize 10-4 M solutions of the D,L-chlorophenylalanines for 24 hr in continuous light.The plant samples were then extracted in 80percent methanol and the soluble acidic metabolites fractionated into ether.Each ether concentrate was partially purified by fractional elution from a PrepSep C18 coloumn and then analysed by HPLC.Collected fractions were esterified with pentafluorobenzylbromide and examined by GC-MS to demonstrate the presence of PFB-esters of chlorophenylacetic, chlorobenzoic and/or chlorocinnamic acids.Since certain of these metabolites are known to be potent plant growth-regulators and herbicides, the results are discussed in relation to the potantial herbicidal action of certain chlorophenylalanines by the mechanism of 'lethal synthesis'.Key Word Index - Phaseolus vulgaris; Glycine max.; Leguminosae; Zea mays; Amaranthus retroflexus; Chenopodium album; Setaria faberii; metabolism; D,L-chlorophenylalanines; chlorophenylacetic acids; chlorobenzoic acids; chlorocinnamic acids; growth regulators.

Synthesis and Antineoplastic Activity of Bisoxy>methyl>-Substituted 3-Pyrrolines as Prodrugs of Tumor Inhibitory Pyrrole Bis(carbamates)

A series of bispyrrolines 2-4 were synthesized from either the appropriate α-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1,3-dipolar cycloaddition reactions.The antineoplastic activities of the pyrrolines were compared to the corresponding pyrroles.The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive.The activity of the 2-phenyl-substituted pyrrolines 3 was markedly dependent on the nature of the phenyl substituent, although the correspondingphenylpyrroles all showed comparable activity.The differences in the activities of the pyrrolines 3 may be due to the rate of metabolic conversion of the pyrroline to the pyrrole.Electron-withdrawing substituents on the phenyl ring appear to retard this process.

Aminotetralin derivatives

This invention related to new aminotetralin derivatives of formula I STR1 wherein STR2 B is methylene or, when A is --CH2 --CH2 --, --CH=CH--, --NH--CO-- or --CH2 --CO--, B can also be carbonyl or thiocarbonyl; E is a C2 -C4 straight-chain alkylene, optionally substituted by a C1 -C3 alkyl, or is 2-hydroxy-n-propylene, 2-hydroxy-n-butylene or 3-hydroxy-n-butylene; R1 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, nitro, amino, C1 -C3 alkylamino, C1 -C3 dialkylamino, C1 -C3 alkyl, C1 -C3 alkylthio, hydroxy, C1 -C3 alkoxy or phenyl C1 -C3 alkoxy; R2 is hydrogen, chlorine, bromine, hydroxy, C1 -C3 alkoxy phenyl C1 -C3 alkoxy, or C1 -C3 alkyl or, together with R1, can be a C1 -C2 alkylenedioxy; R3 and R4 are each independently selected from hydrogen, fluorine, chlorine, bromine, C1 -C3 alkyl, hydroxy, C1 -C3 alkoxy, nitro, amino, C1 -C3 alkylamino, or C1 -C3 dialkylamino, or together can be methylenedioxy; and R5 is hydrogen, C3 -C5 alkenyl, C1 -C3 alkyl, or phenyl C1 -C3 alkyl, and nontoxic, pharmaceutically acceptable addition salts thereof which have valuable pharmacological properties, particularly a long-lasting heart rate lowering effect and the effect of reducing the O2 requirement of the heart.