33697-81-3

Basic information

• Product Name: 3-CHLORO-4-HYDROXYPHENYLACETIC ACID
• Synonyms: vufb9649;3-CHLORO-4-HYDROXYPHENYLACETIC ACID;m-chloro-p-hydroxyphenylacetic acid;Benzeneacetic acid, 3-chloro-4-hydroxy.;3-Chloro-4-hydroxyphenylacetic acid,99%;Chloro hydroxyphenylacetic acid;2-(3-chloro-4-hydroxyphenyl)acetic acid;4-(Carboxymethyl)-2-chlorophenol
• CAS NO: 33697-81-3
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 186.59
• EINECS: 251-643-0
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;C8;Carbonyl Compounds;Carboxylic Acids
• Mol File: 33697-81-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 108-110 °C(lit.)
• Boiling Point: 348.6 °C at 760 mmHg
• Flash Point: 164.6 °C
• Appearance: /
• Density: 1.466 g/cm³
• Vapor Pressure: 1.87E-05mmHg at 25°C
• Refractive Index: 1.61
• PKA: 4.33±0.10(Predicted)
• CAS DataBase Reference: 3-CHLORO-4-HYDROXYPHENYLACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-HYDROXYPHENYLACETIC ACID(33697-81-3)
• EPA Substance Registry System: 3-CHLORO-4-HYDROXYPHENYLACETIC ACID(33697-81-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 2
• RTECS: CY1576300
• Hazardous Substances Data: 33697-81-3(Hazardous Substances Data)

Usage

Description

3-Chloro-4-hydroxyphenylacetic acid, also known as an auxin influx inhibitor, is a hydroxy monocarboxylic acid derived from chlorotyrosine. It is characterized by its orange to tan powder form and is recognized as a major chlorinated metabolite of chlorotyrosine.

Uses

Used in Plant Biology:
3-Chloro-4-hydroxyphenylacetic acid is used as a phytohormone for the inhibition of auxin influx, which plays a crucial role in plant growth and development. By regulating the movement of auxins, this compound can influence various aspects of plant physiology, including cell elongation, division, and differentiation.
Used in Pharmaceutical Research:
As a major chlorinated metabolite of chlorotyrosine, 3-chloro-4-hydroxyphenylacetic acid holds potential for pharmaceutical research. Its unique chemical structure and properties may contribute to the development of new drugs or therapies targeting various medical conditions.
Used in Chemical Synthesis:
3-CHLORO-4-HYDROXYPHENYLACETIC ACID's distinctive structure also makes it a valuable intermediate in the synthesis of other complex organic molecules. It can be utilized in the development of novel chemical compounds for various applications, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C8H7ClO3/c9-6-3-5(4-8(11)12)1-2-7(6)10/h1-3,10H,4H2,(H,11,12)

Upstream product

• 13721-20-5 2-(3-chloro-4-methoxyphenyl)acetic acid 
• 156-38-7 4-hydroxyphenylacetate 
• 72198-15-3 (R,S)-3-chloro-4-hydroxymandelic acid 
• 95-57-8 2-monochlorophenol 
• 7569-58-6 2-(3-chloro-4-methoxyphenyl)acetonitrile 

Downstream Products

• 50972-63-9 2-(3-chloro-4-hydroxyphenyl)ethanol 
• 93245-87-5 (3-bromo-5-chloro-4-hydroxyphenyl)acetic acid 
• 199930-20-6 3-chloro-4-hydroxyphenylacetic acid 2,4,5-trichlorophenyl ester 
• 193357-36-7 3-chloro-4-hydroxyphenylacetic acid ethyl ester 
• 53577-58-5 2-(3-Chlor-4-hydroxyphenyl)essigsaeureamid 
• 57017-95-5 methyl 3-chloro-4-hydroxyphenylacetate 
• 494865-21-3 ethyl {4-[3,3-bis-(4-bromo-phenyl)-allyloxy]-3-chloro-phenyl}-acetate 

Relevant articles and documents

A new system for the reduction of 4-hydroxymandelic acids

We describe a new reduction of 4-hydroxymandelic acids which is easy to perform with available, cheap and environmentally clean reagents.The reduction of these acids is an important method for the synthesis of (4-hydroxyphenyl)-acetic acids.The new reducing system is constituted of sodium bisulfite or dithionite in catalytic quantities and formic acid in slight excess. - Keywords: 4-hydroxymandelic acid; reduction; sodium bisulfite; sodium dithionite; formic acid

Process for preparation of alkanoic acids

A process for preparation of substituted acetic acids having the general formula I: in which R is selected from the group consisting in one hydrogen atom and C1 -C4 -alkyl radicals, and Ar is selected from the group consisting in radicals of aromatic nature selected from the following radicals: 2-thienyl, 2-methoxy-1-naphthyl, 3,4-methylenedioxy-phenyl, and the substituted phenyls of the general formula II: STR1 where R1 is selected from the group consisting in hydrogen and C1 -C4 -alkyl groups, and R2 is selected from the group consisting in hydrogen, halogen, alkyl, alkoxy and hydroxy-groups, such process comprising the step of reacting under heat in an acid medium, in the presence of red phosphorus and catalytic quantities of iodine or hydriodic acid, an alpha carbonylated carboxylic acid having the general formula III: in which R has the same meaning as above with an unsaturated derivative of aromatic nature selected from the group consisting in thiophene, 2-methoxynaphthalene, 1,2-methylenedioxy-benzene, and the substituted aromatic hydrocarbons having the general formula IV: STR2 in which R1, R2 have the same meanings as above, possibly within a compatible organic solvent.

Antiinflammatory substituted phenylacetic acids

Antiinflammatory substituted phenylacetic acids of low toxicity are prepared by reaction of a salt of an alkyl 3 chloro-4-hydroxyphenylacetate with a substituted benzyl halide in the presence of an inert organic solvent at elevated temperatures.