Thioglycolic acid

Base Information

• Chemical Name: Thioglycolic acid
• CAS No.: 68-11-1
• Deprecated CAS: 57755-20-1,7283-42-3,7283-42-3
• Molecular Formula: C2H4O2S
• Molecular Weight: 92.1186
• Hs Code.: H 2COOH MOL WT. 92.12
• European Community (EC) Number: 200-677-4
• ICSC Number: 0915
• NSC Number: 1894
• UN Number: 1940
• UNII: 7857H94KHM
• DSSTox Substance ID: DTXSID8026141
• Nikkaji Number: J4.856I
• Wikipedia: Thioglycolic_acid
• Wikidata: Q414738
• NCI Thesaurus Code: C77510
• Metabolomics Workbench ID: 51986
• ChEMBL ID: CHEMBL116455
• Mol file: 68-11-1.mol

Synonyms:2-mercaptoacetate;2-mercaptoacetate, bismuth (3+), sodium salt (3:1:3);2-mercaptoacetate, calcium salt (1:1);2-mercaptoacetate, calcium salt (2:1);2-mercaptoacetate, calcium salt (2:1) salt, trihydrate;2-mercaptoacetate, monoammonium salt;2-mercaptoacetate, monopotassium salt;2-mercaptoacetate, monosodium salt;2-thioglycolic acid;ammonium thioglycolate;calcium thioglycolate;mercaptoacetic acid;sodium thioglycolate;sodium thioglycollate;thioglycolic acid

Chemical Property of Thioglycolic acid

Chemical Property:

• Appearance/Colour: Clear liquid
• Vapor Pressure: 0.4 mm Hg ( 25 °C)
• Melting Point: -16 °C(lit.)
• Refractive Index: 1.503
• Boiling Point: 225.481 °C at 760 mmHg
• PKA: 3.68(at 25℃)
• Flash Point: 99.841 °C
• PSA: 76.10000
• Density: 1.312 g/cm³
• LogP: 0.00080
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: soluble
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 91.99320054
• Heavy Atom Count: 5
• Complexity: 42.9
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

ThioglycolicAcid(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, T+
• Hazard Codes: T,T+
• Statements: 23/24/25-34-26-24/25
• Safety Statements: 25-27-28-45-36/37-28C-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C(C(=O)O)S
• Recent ClinicalTrials: Treatment of Periorbicular Hyperchromia Comparing 10% Thioglycolic Acid Peeling Versus Pulsed Intense Light
• Inhalation Risk: A harmful contamination of the air can be reached very quickly 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 the vapour may cause lung oedema. Exposure could cause death. The effects may be delayed. Medical observation is indicated.
• Description: Thio glycolic acid (TGA) is the organic compound HSCH2CO2H . It contains both a thiol (mercaptan) and a carboxylic acid. It is a clear liquid with a strong unpleasant odor. It is readily oxidized by air to the corresponding disulfide [SCH2CO2H]2. TGA was developed in the 1940s for use as a chemical depilatory and is still used as such, especially in salt forms, including calcium thioglycolate and sodium thioglycolate. TGA is the precursor to ammonium thioglycolate that is used for permanents. TGA and its derivatives break the disulfide bonds in the cortex of hair. One reforms these broken bonds in giving hair a "perm." Alternatively and more commonly, the process leads to depilation as is done commonly in leather processing. It is also used as an acidity indicator, manufacturing of thioglycolates, and in bacteriology for preparation of thioglycolate media. TGA is also used in the making of tin stabilizers often used in certain polyvinyl chloride products (such as vinyl siding). TGA, usually as its dianion, forms complexes with metal ions. Such complexes have been used for the detection of iron, molybdenum, silver, and tin. Thioglycolic acid is used as nucleophile in thioglycolysis reactions used on condensed tannins to study their structure.
• Uses: Thioglycolic Acid is an organic compound containing both a thiol and a carboxylic acid. Thioglycolic Acid is a precursor to ammonium thioglycolate, a chemical used for permanents. Thioglycolic Acid is used in organic synthesis as a nucleophile in thioglycolysis reactions and is used as a S transfer agent for sulfonyl chloride synthesis. Sensitive reagent for iron, molybdenum, silver, tin. With ferric iron a blue color appears, and when an alkali hydroxide is added to a solution contg ferrous salts and thioglycolic acid, a yellow precipitate forms. Used in the manufacture of thioglycolates. The ammonium and sodium salts are commonly used for cold waving and the calcium salt is a depilatory. The sodium salt also is used in bacteriology in the preparation of thioglycolate media. Mercaptoacetic acid is used as a reagent formetals analysis; in the manufacture of thioglycolates, pharmaceuticals, and permanentwave solutions; and as a vinyl stabilizer.

Technology Process of Thioglycolic acid

There total 155 articles about Thioglycolic 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:

(α-carboxymethylsulfanyl-benzylidene)-dimethyl-ammonium; bromide → S-benzoylthioglycolic acid (6398-74-9) + mercaptoacetic acid (68-11-1) + N,N-dimethylbenzamide (611-74-5)

Guidance literature:

Reference yield:

(α-carboxymethylsulfanyl-benzylidene)-dimethyl-ammonium; bromide → S-benzoylthioglycolic acid (6398-74-9) + mercaptoacetic acid (68-11-1) + N,N-dimethylbenzamide (611-74-5)

Guidance literature:

Reference yield:

→ O-ethyl thiocarbamate (625-57-0) + mercaptoacetic acid (68-11-1)

Guidance literature:

With ammonia;

upstream raw materials:

2-thioxo-4-thiazolidinone

2-methylamino-Δ²-thiazolin-4-one

3-methyl-thiazolidine-2,4-dione

thiazolidine-2,4-dione-2-semicarbazone

Downstream raw materials:

S-(2-pyridyl)thioglycolic acid

2-(piperidin-1-yl)thiazole-4(5H)-one

(4-amino-2-methyl-5-pyrimidylmethyl)thioacetic acid

(6-bromo-3-methyl-[4]quinolylmercapto)-acetic acid

Refernces

• 1、 -. "LOW-ODOR THIOGLYCOLIC ACID COMPOSITION". . . Retrieved 2022/03/02.
• 2、 -. "A mercapto-acetic acid (by machine translation)". Paragraph 0030; 0031. . Retrieved 2017/05/26.