3-Chloro-4-hydroxyphenylacetic acid

Base Information

• Chemical Name: 3-Chloro-4-hydroxyphenylacetic acid
• CAS No.: 33697-81-3
• Molecular Formula: C8H7ClO3
• Molecular Weight: 186.595
• Hs Code.: 29182900
• European Community (EC) Number: 251-643-0
• DSSTox Substance ID: DTXSID60187381
• Nikkaji Number: J47.610B
• Wikidata: Q27120768
• ChEMBL ID: CHEMBL592010
• Mol file: 33697-81-3.mol

Synonyms:3-chloro-4-hydroxyphenylacetic acid;3-chloro-4-hydroxyphenylacetic acid, monosodium salt

Chemical Property of 3-Chloro-4-hydroxyphenylacetic acid

Chemical Property:

• Vapor Pressure: 1.87E-05mmHg at 25°C
• Melting Point: 108-110 °C(lit.)
• Refractive Index: 1.61
• Boiling Point: 348.6 °C at 760 mmHg
• PKA: 4.33±0.10(Predicted)
• Flash Point: 164.6 °C
• PSA: 57.53000
• Density: 1.466 g/cm³
• LogP: 1.67270
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 186.0083718
• Heavy Atom Count: 12
• Complexity: 172

Purity/Quality:

98% ^*data from raw suppliers

3-Chloro-4-hydroxyphenylacetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC(=O)O)Cl)O
• Uses: 3-Chloro-4-hydroxyphenylacetic Acid is a phytohormone responsible for the inhibition of auxin influx.

Technology Process of 3-Chloro-4-hydroxyphenylacetic acid

There total 8 articles about 3-Chloro-4-hydroxyphenylacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

4-hydroxyphenylacetate (156-38-7) → (3-chloro-4-hydroxy-phenyl)-acetic acid (33697-81-3) + (3,5-dichloro-4-hydroxyphenyl)acetic acid (89894-49-5)

Guidance literature:

With chlorine; In acetic acid; Yields of byproduct given; Ambient temperature;

DOI:10.1002/hlca.19840670610

Reference yield:

4-hydroxy-3-chloro-mandelic acid → (3-chloro-4-hydroxy-phenyl)-acetic acid (33697-81-3)

Guidance literature:

With formic acid; sodium hydrogensulfite; at 100 ℃; for 9h; under 3750.3 Torr;

Reference yield:

2-(3-chloro-4-methoxyphenyl)acetic acid (13721-20-5) → (3-chloro-4-hydroxy-phenyl)-acetic acid (33697-81-3)

Guidance literature:

With sodium methylate; at 185 ℃;

upstream raw materials:

2-(3-chloro-4-methoxyphenyl)acetic acid

4-hydroxyphenylacetate

(R,S)-3-chloro-4-hydroxymandelic acid

2-monochlorophenol

Downstream raw materials:

3-chloro-4-hydroxyphenylacetic acid ethyl ester

Refernces

• 1、 Sugita, Shin-Ichi,Toda, Susumu,Yoshiyasu, Takashi,Teraji, Tsutomu. "Synthesis and Properties of Optically Active Phenoxypropionates. Effect of Halogeno Substituent in the Core on Physical Properties". . p. 399 - 406. Retrieved 2007/10/02.
• 2、 D'Ambrosio,Guerriero,Pietra. "Novel, racemic or nearly-racemic antibacterial bromo- and chloroquinols and γ-lactams of the verongiaquinol and the cavernicolin type from the marine sponge Aplysina (= Verongia) cavernicola". . p. 1484 - 1492. Retrieved 2007/10/02.