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TGA Mercaptoacetic acid is a sulfur-containing carboxylic acid.
TGA Mercaptoacetic acid is a conjugate acid of a thioglycolate(1-).
A colorless liquid with an unpleasant odor.
CAS: 68-11-1
MF: C2H4O2S
MW: 92.12
EINECS: 200-677-4
Synonyms
2-thio-glycolicaci;2-thioglycolicacid;Aceticacid,mercapto-;Acide thioglycolique;acidethioglycolique;acidethioglycolique(french);alpha-Mercaptoacetic acid;thio-glycolicaci
Density 1.325 g / cm3. Used to make permanent wave solutions and depilatories.
Corrosive to metals and tissue.
The TGA Mercaptoacetic acid also called Mercaptoacetic acid (MAA) (CAS 68-11-1) is a high-performance chemical containing mercaptan and carboxylic acid functionalities.
TGA Mercaptoacetic acid is completely miscible in water and in general polar organic solvents.
TGA Mercaptoacetic acid is a strong reducing agent especially at high pH and forms powerful complexes with metals that give it specific characteristics.
TGA Mercaptoacetic acid is used in industries and applications as diverse as cosmetics, oil and gas, polymerization, fine chemistry, leather processing, cleaning, and metals receovery.
TGA Mercaptoacetic acid, with the CAS number 68-11-1, is a colorless to pale yellow liquid that is characterized by its strong, sulfurous odor.
TGA Mercaptoacetic acid is a thiol compound, which means it contains a sulfhydryl (-SH) group, making it a key reagent in various chemical reactions.
TGA Mercaptoacetic acid is highly soluble in water and organic solvents, which enhances its utility in diverse applications.
TGA Mercaptoacetic acid is primarily used in the cosmetic industry for hair perming and straightening, as it can break disulfide bonds in keratin, allowing for the restructuring of hair.
Additionally, TGA Mercaptoacetic acid serves as a reducing agent in organic synthesis and is employed in the production of thiol-containing compounds.
Due to its reactivity, TGA Mercaptoacetic acid can also participate in the formation of esters and amides.
However, TGA Mercaptoacetic acid is important to handle this substance with care, as it can be irritating to the skin and eyes, and proper safety precautions should be observed during its use.
TGA Mercaptoacetic acid is used as a chemical depilatory and is still used as such, especially in salt forms, including calcium thioglycolate and sodium thioglycolate.
TGA Mercaptoacetic acid is the precursor to ammonium thioglycolate that is used for permanents.
TGA Mercaptoacetic acid is also used as an acidity indicator, manufacturing of thioglycolates, and in bacteriology for preparation of thioglycolate media.
In fact thioglycolysis reactions used on condensed tannins to study their structure.
TGA Mercaptoacetic acid is the organic compound HSCH2CO2H.
TGA Mercaptoacetic acid contains both a thiol (mercaptan) and a carboxylic acid.
TGA Mercaptoacetic acid is a clear liquid with a strong unpleasant odor.
TGA Mercaptoacetic acid is readily oxidized by air to the corresponding disulfide [SCH2CO2H]2.
TGA Mercaptoacetic acid 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 Mercaptoacetic acid is the precursor to ammonium thioglycolate that is used for permanents.
TGA Mercaptoacetic acid 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.
TGA Mercaptoacetic acid is also used as an acidity indicator, manufacturing of thioglycolates, and in bacteriology for preparation of thioglycolate media.
TGA Mercaptoacetic acid is also used in the making of tin stabilizers often used in certain polyvinyl chloride products (such as vinyl siding).
TGA Mercaptoacetic acid is used as nucleophile in thioglycolysis reactions used on condensed tannins to study their structure.
TGA Mercaptoacetic acid Chemical Properties
Melting point: −16 °C(lit.)
Boiling point: 96 °C5 mm Hg(lit.)
density: 1.326 g/mL at 20 °C(lit.)
vapor density: 3.2 (vs air)
vapor pressure: 0.4 mm Hg ( 25 °C)
refractive index: n20/D 1.505(lit.)
Fp: 126 °C
storage temp.: Store at +2°C to +8°C.
solubility: Chloroform (Sparingly), Methanol (Sparingly)
form: Liquid
pka: 3.68(at 25℃)
color: clear clear, colorless
PH: 1 (H2O, 20℃)
Odor: strong unpleasant odor
Water Solubility: soluble
Sensitive: Air Sensitive
Merck: 14,9336
BRN: 506166
Henry's Law Constant: 5.2×102 mol/(m3Pa) at 25℃, HSDB (2015)
Exposure limits: TLV-TWA 1 ppm (～3.8 mg/m3) (ACGIH).
Stability: Air Sensitive
Cosmetics Ingredients Functions: DEPILATORY
REDUCING
ANTIOXIDANT
HAIR WAVING OR STRAIGHTENING
InChI: 1S/C2H4O2S/c3-2(4)1-5/h5H,1H2,(H,3,4)
InChIKey: CWERGRDVMFNCDR-UHFFFAOYSA-N
LogP: 0.090
CAS DataBase Reference: 68-11-1(CAS DataBase Reference)
NIST Chemistry Reference: TGA Mercaptoacetic acid(68-11-1)
EPA Substance Registry System: TGA Mercaptoacetic acid (68-11-1)
TGA Mercaptoacetic acid is a colorless liquid with a strong unpleasant odor like rotten eggs.
TGA Mercaptoacetic acid is a 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.
TGA Mercaptoacetic acid is a strong antimicrobial agent that has been shown to be effective against bacteria and fungi.
TGA Mercaptoacetic acid is used in the preparation of biological samples for titration calorimetry studies.
Thioglycolic acid reacts with proteins by forming covalent linkages, which can be identified using laser ablation techniques.
The redox potential of TGA Mercaptoacetic acid makes it an ideal candidate for chemiluminescent reactions.
Uses
TGA Mercaptoacetic acid is an organic compound containing both a thiol and a carboxylic acid. TGA Mercaptoacetic 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.
TGA Mercaptoacetic acid is used as a reagent formetals analysis; in the manufacture of thioglycolates, pharmaceuticals, and permanentwave solutions; and as a vinyl stabilizer.
TGA Mercaptoacetic acid is an intermediate in the production of thiomethoprol (caputril), biotin, thiozinc acid, sodium dithiosuccinate and other pharmaceuticals, and is also an intermediate in the synthesis of cysteine, hormonal agent, and industrial disinfectant.
And an important raw material for the synthesis of sulfuric acid.
TGA Mercaptoacetic acid is used as antioxidant and stabilizer in pharmaceuticals to enhance the stability of the main drug and prolong the validity period of pharmaceutical preparations.
Ammonium and sodium salts of thioglycolic acid are mainly used as curling agents, calcium salts can be used as depilatory agents, polymerization initiators, accelerators and chain transfer agents, and can be used for hair removal before cosmetic surgery and animal experiments.
TGA Mercaptoacetic acid is used to make epoxy resin, catalyst of bisphenol A, and it can also be used as the basic raw material for synthesizing PVC transparent plastic and organic antimony and organic tin heat stabilizer.
TGA Mercaptoacetic acid is a sensitive reagent for the determination of iron, molybdenum, aluminum, tin, etc., and is an inhibitor of copper sulfide and iron sulfide minerals in beneficiation.
In the petrochemical industry and the railway sector, TGA Mercaptoacetic acid is used for cleaning and derusting of equipment and rails.
TGA Mercaptoacetic acid can be used as a crystallization nucleating agent in polypropylene processing and molding, as a modifier for coatings and fibers, as a blanket quickening agent, as a stabilizer raw material for polyvinyl chloride and rubber, as a cold perm agent, and as a pharmaceutical intermediate.
TGA Mercaptoacetic acid is used as a color developer for the photometric determination of molybdenum, rhenium and iron, and as a compounding masking agent.
TGA Mercaptoacetic acid is used as a chemical depilatory and is still used as such, especially in salt forms, including calcium thioglycolate and sodium thioglycolate.
TGA Mercaptoacetic acid is the precursor to ammonium thioglycolate, which is used for permanents.
TGA Mercaptoacetic acid 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.
TGA Mercaptoacetic acid is also used as an acidity indicator, manufacturing of thioglycolates, and in bacteriology for preparation of thioglycolate media.
TGA Mercaptoacetic acid reactions are used on condensed tannins to study their structure.
TGA Mercaptoacetic acid has also been used to soften nails, either to reshape pincer nails into the correct position or to help the topical antifungal agent terbinafine penetrate the nail.
Organotin derivatives of TGA Mercaptoacetic acid isooctyl esters are widely used as stabilizers for PVC.
These species have the formula R2Sn(SCH2CO2C8H17)2.
Sodium thioglycolate is a component of thioglycolate broth, a special bacterial growth media.
TGA Mercaptoacetic acid is also used in so-called "fallout remover" or "wheel cleaner" to remove iron oxide residue from wheels.
Ferrous iron combines with thioglycolate to form red-violet ferric thioglycolate.
Production
TGA Mercaptoacetic acid is prepared by reaction of sodium or potassium chloroacetate with alkali metal hydrosulfide in aqueous medium.
TGA Mercaptoacetic acid can be also prepared via the Bunte salt obtained by reaction of sodium thiosulfate with chloroacetic acid:
ClCH2CO2H + Na2S2O3 → Na[O3S2CH2CO2H] + NaCl
Na[O3S2CH2CO2H] + H2O → HSCH2CO2H + NaHSO4
Reactions
TGA Mercaptoacetic acid with a pKa of 3.83 is an acid about 8.5 times stronger than acetic acid (pKa 4.76):
HSCH2CO2H → HSCH2CO2− + H+
The second ionization has a pKa of 9.3:
HSCH2CO2− → −SCH2CO2− + H+
TGA Mercaptoacetic acid is a reducing agent, especially at higher pH.
TGA Mercaptoacetic acid oxidizes to the corresponding disulfide (2-[(carboxymethyl)disulfanyl]acetic acid or dithiodiglycolic acid):
2 HSCH2CO2H + "O" → [SCH2CO2H]2 + H2O
With metal ions
TGA Mercaptoacetic acid, usually as its dianion, forms complexes with metal ions.
Such complexes have been used for the detection of iron, molybdenum, silver, and tin.
TGA Mercaptoacetic acid reacts with diethyl acetylmalonate to form acetylmercaptoacetic acid and diethyl malonate, the reducing agent in the conversion of Fe(III) to Fe(II).
