Chloroacetic acid

Base Information

• Chemical Name: Chloroacetic acid
• CAS No.: 79-11-8
• Molecular Formula: C2H3ClO2
• Molecular Weight: 94.4976
• Hs Code.: 29154000
• European Community (EC) Number: 201-178-4
• ICSC Number: 0235
• NSC Number: 42970,142
• UN Number: 1751,1750
• UNII: 5GD84Y125G
• DSSTox Substance ID: DTXSID4020901
• Nikkaji Number: J2.409K
• Wikipedia: Chloroacetic acid
• Wikidata: Q409013
• RXCUI: 2374
• Metabolomics Workbench ID: 1754
• ChEMBL ID: CHEMBL14090
• Mol file: 79-11-8.mol

Synonyms:Acetocaustin;chloroacetate;chloroacetic acid;chloroacetic acid, aluminum salt;chloroacetic acid, ammonium (2:1) salt;chloroacetic acid, ammonium salt;chloroacetic acid, calcium (3:1) salt;chloroacetic acid, calcium salt;chloroacetic acid, potassium (2:1) salt;chloroacetic acid, potassium salt;chloroacetic acid, silver salt;chloroacetic acid, sodium (2:1) salt;chloroacetic acid, sodium (5:2) salt;chloroacetic acid, sodium salt;monochloroacetic acid;SODIUM CHLOROACETATE

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Chemical Property of Chloroacetic acid

Chemical Property:

• Appearance/Colour: colourless or white crystals
• Vapor Pressure: 0.75 mm Hg ( 20 °C)
• Melting Point: 61 °C
• Refractive Index: 1.4330
• Boiling Point: 188.999 °C at 760 mmHg
• PKA: 2.85(at 25℃)
• Flash Point: 71.538 °C
• PSA: 37.30000
• Density: 1.399 g/cm³
• LogP: 0.30980
• Storage Temp.: 0-6°C
• Sensitive.: Hygroscopic
• Solubility.: Soluble in methanol, acetone, diethyl ether, benzene, chloroform
• Water Solubility.: SOLUBLE
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 93.9821570
• Heavy Atom Count: 5
• Complexity: 42.9
• Transport DOT Label: Poison Corrosive

Purity/Quality:

Safty Information:

• Pictogram(s): T,N,Xi,F
• Hazard Codes: T,N,Xi,F
• Statements: 25-34-50-40-36/37/38-23/24/25-38
• Safety Statements: 23-37-45-61-36-26-16-63-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(C(=O)O)Cl
• Recent EU Clinical Trials: Monochloroacetic acid versus cryotherapy in the treatment of warts: A Randomised Clinical Trial (WARTS-2)
• Inhalation Risk: A harmful contamination of the air will be reached slowly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Inhalation of high concentrations may cause lung oedema, but only after initial corrosive effects on the eyes and the upper respiratory tract have become manifest. The substance may cause effects on the metabolism. This may result in metabolic acidosis and multiple organ failure. Exposure could cause death. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged inhalation may cause effects on the lungs.
• General Description: **Chloroacetic acid** is a halogenated derivative of acetic acid, where one hydrogen atom is replaced by chlorine, forming a highly reactive and versatile compound. It is commonly used as a reagent in organic synthesis, particularly in the formation of heterocyclic compounds like thiazolidinones and thiazoles, as well as in the preparation of biologically active derivatives such as 2-mercaptobenzothiazole-based molecules. Its reactivity with thiols, amines, and other nucleophiles makes it valuable for constructing pharmacologically relevant scaffolds. However, due to its corrosive and toxic nature, careful handling is required. Chloroacetic acid's utility is highlighted in green chemistry approaches, where it participates in efficient, high-yielding reactions under mild conditions, often with recoverable catalysts.

Technology Process of Chloroacetic acid

There total 229 articles about Chloroacetic 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: 37.0%

tetrachloromethane (56-23-5) + acetic acid (64-19-7,77671-22-8) → chloroform (67-66-3,8013-54-5) + succinic acid (110-15-6) + chloroacetic acid (79-11-8)

Guidance literature:

acetic acid; With lithium diisopropyl amide; In tetrahydrofuran; at 0 - 40 ℃; Inert atmosphere;

tetrachloromethane; In tetrahydrofuran; at 20 - 25 ℃; for 2h; Inert atmosphere;

DOI:10.1134/S1070428019010068

Reference yield:

chloroacetic acid 4-nitrophenyl ester (777-84-4) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + chloroacetic acid (79-11-8)

Guidance literature:

With 1H-imidazole; water; In ethanol; at 25 ℃; Mechanism; Kinetics; phosphate buffer (pH=8.05);

Reference yield:

water (7732-18-5) + S-chloroacetyl-isothiourea; hydrobromide → hydrogen bromide (10035-10-6,12258-64-9) + thiourea (17356-08-0) + chloroacetic acid (79-11-8)

Guidance literature:

upstream raw materials:

dichloro-acetic acid

2-nitro-1-ethanol

ethene

chloroacetylene

Downstream raw materials:

1,2-bis(chloroacetoxy)ethane

piperidinoacetic acid

tetrahydrofurfuryl chloroacetate

1-(carboxymethyl)pyridinium chloride

Refernces

Expedient and green synthesis of some novel 4-thiazolidinones and new 2,4-disubstituted thiazoles with tetrahydro carbazole pendant

10.2174/157017812803521081

The research focuses on the expedited and green synthesis of novel 4-thiazolidinones and new 2,4-disubstituted thiazoles with a tetrahydro carbazole pendant. The purpose of this study is to develop an efficient and environmentally friendly method for synthesizing these heterocyclic compounds, which are known for their biological activities and potential applications in pharmaceuticals and optoelectronic devices. The researchers utilized N-methylpyridinium tosylate, an ionic liquid, as a catalyst for the cyclocondensation reaction of 2-(2,3-dihydro1H-carbazol-4(9H)-ylidene)hydrazinecarbothioamide with α-haloacids, achieving quantitative yields in a short time. They also reported a solvent-free grinding method for the synthesis of 2,4-disubstituted thiazoles. The chemicals used in the process include 2,3-dihydro-1H-carbazol-4(9H)-one, thiosemicarbazide, chloroacetic acid, 2-bromopropionic acid, and substituted phenacyl bromides. The study concludes that the use of the ionic liquid not only simplifies the work-up process but also results in faster reactions and higher yields compared to conventional methods, with the added benefit of being recoverable and reusable for multiple reaction cycles without affecting product yield.

Synthesis and Reactions of 2-Mercaptobenzothiazole Derivatives of Expected Biological Activity. 2

10.1021/je00028a032

The research focuses on the synthesis and reactions of 2-mercaptobenzothiazole derivatives, which are expected to have biological activity. The study involves the preparation of various compounds, including amides and anilides of benzothiazole-2-ylthioacetate and 3-(benzothiazol-2-ylthio)propanoate, arylhydrazones, cycloalkanone hydrarones, and pyridine derivatives. Key chemicals used in the research include 2-mercaptobenzothiazole, chloroacetic acid, bromopropanoic acid, sodium metal, thionyl chloride, aniline, and other reagents for the synthesis processes. The compounds were synthesized through reactions such as refluxing mixtures of starting materials in solvents like ethanol and benzene, followed by purification steps like crystallization. The synthesized compounds were characterized by their melting points, yields, and spectroscopic data (IR and NMR), which confirmed their structures. The research aims to explore the potential biological activity of these synthesized compounds, building on previous literature indicating that substituted benzothiazoles possess anticonvulsant activity and inhibit monoamine oxidase activity.

Reaction of 1-germatranol hydrate with carboxylic acids

10.1134/S1070363215120154

Chloroacetic Acid is a halogenated carboxylic acid used to form 1-(chloroacetoxy)germatrane. Cinnamic Acid is an aromatic carboxylic acid used to form 1-(benzylideneacetato)germatrane. 2-Fluorobenzoic Acid is a fluorinated aromatic carboxylic acid used to form 1-(2'-fluorobenzoyloxy)germatrane. 3-Bromobenzoic Acid is a brominated aromatic carboxylic acid used to form 1-(3'-bromobenzoyloxy)germatrane. 3-Hydroxybenzoic Acid is a hydroxylated aromatic carboxylic acid used to form 1-(3'-hydroxybenzoyloxy)germatrane. 3-Ethoxybenzoic Acid is an ethoxylated aromatic carboxylic acid used to form 1-(3'-ethoxybenzoyloxy)germatrane. These acids react with 1-germatranol hydrate to form the corresponding 1-acyloxygermatranes. The nature of the substituent (R) on the carboxylic acid affects the yield and properties of the resulting product.