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68-11-1

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68-11-1 Usage

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.

Chemical Properties

Different sources of media describe the Chemical Properties of 68-11-1 differently. You can refer to the following data:
1. Thioglycolic acid is a colorless liquid with a strong unpleasant odor like rotten eggs.
2. Also known as mercaptoacetic acid, HSCH2COOH is a colorless liquid with a strong unpleasant odor. Used as a reagent for metals such as iron, molybdenum, silver, and tin,and in bacteriology.

Uses

Different sources of media describe the Uses of 68-11-1 differently. You can refer to the following data:
1. 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.
2. 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.
3. Mercaptoacetic acid is used as a reagent formetals analysis; in the manufacture of thioglycolates, pharmaceuticals, and permanentwave solutions; and as a vinyl stabilizer.

Application

Thioglycolic 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. Thioglycolic 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. Thioglycolic 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. Thioglycolic 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, it is used for cleaning and derusting of equipment and rails. It 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. Thioglycolic acid is used as a color developer for the photometric determination of molybdenum, rhenium and iron, and as a compounding masking agent.

General Description

A colorless liquid with an unpleasant odor. Density 1.325 g / cm3. Used to make permanent wave solutions and depilatories. Corrosive to metals and tissue.

Air & Water Reactions

Readily oxidized by air. Water soluble.

Reactivity Profile

Mercaptoacetic acid is readily oxidized by air . Reacts readily with other oxidizing agents as well in reactions that may generate toxic gases. Incompatible with diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials may generate heat and toxic and flammable gases. May react with acids to liberate hydrogen sulfide. Neutralizes bases in exothermic reactions. Reacts with cyanides, sulfites, nitrites, thiosulfates to generate flammable and toxic gases and heat. Reacts with carbonates and bicarbonates.

Hazard

Toxic by ingestion and inhalation, strong irritant to tissue, eyes, and skin.

Health Hazard

Different sources of media describe the Health Hazard of 68-11-1 differently. You can refer to the following data:
1. TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
2. Mercaptoacetic acid is a highly toxic and ablistering compound. Even a 10% solutionwas lethal to most experimental animals by dermal absorption. The oral LD50 value ofundiluted acid is less than 50 mg/kg (Patty1963). The lethal dose in rabbits by skinabsorption is 300 mg/kg. The acute toxicsymptoms in test animals include weakness,respiratory distress, convulsions, irritation ofthe gastrointestinal tract, and liver damage.Mercaptoacetic acid is a severe irritant.Contact with eyes can cause conjunctivalinflammation and corneal opacity. Skin contact can result in burns and necrosis.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Safety Profile

Poison by ingestion, skin contact, intraperitoneal, and intravenous routes. Moderately toxic by subcutaneous route. A corrosive irritant to skin, eyes, and mucous membranes. When heated to decomposition it emits toxic fumes of SOx. See also MERCAPTANS and HYDROGEN SULFIDE.

Potential Exposure

Thioglycolic acid is used to make thioglycolates; in sensitivity tests for iron; in formulations of permanent wave solutions and depilatories; in pharmaceutical manufacture; as a stabilizer in vinyl plastics.

Carcinogenicity

Thioglycolic acid was not mutagenic in a number of Salmonella typhimurium strains with or without metabolic activation.

Shipping

UN1940 Thyoglycolic acid, Hazard class: 8; Labels: 8-Corrosive material.

Purification Methods

Mix the acid with an equal volume of *benzene; the *benzene is then distilled off to dehydrate the acid. After heating to 100o to remove most of the *benzene, the residue is distilled under vacuum and stored in sealed ampoules at 3o. [Eshelman et al. Anal Chem 22 844 1960, Beilstein 3 IV 1130.]

Incompatibilities

Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur). Air, strong oxidizers; bases, active metals, for example, sodium potassium, magnesium, and calcium. Readily oxidized by air. Thermal decomposition causes release of hydrogen sulfide. May attack various metals.

Waste Disposal

Dissolve in flammable solvent and burn in furnace equipped with afterburner and alkaline scrubber.

Check Digit Verification of cas no

The CAS Registry Mumber 68-11-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 8 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 68-11:
(4*6)+(3*8)+(2*1)+(1*1)=51
51 % 10 = 1
So 68-11-1 is a valid CAS Registry Number.
InChI:InChI=1/C2H4O2S/c3-2(4)1-5/h5H,1H2,(H,3,4)/p-1

68-11-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (M0052)  Thioglycolic Acid  >98.0%(T)

  • 68-11-1

  • 25g

  • 125.00CNY

  • Detail
  • TCI America

  • (M0052)  Thioglycolic Acid  >98.0%(T)

  • 68-11-1

  • 500g

  • 380.00CNY

  • Detail
  • Alfa Aesar

  • (B20391)  Mercaptoacetic acid, 97+%   

  • 68-11-1

  • 100g

  • 210.0CNY

  • Detail
  • Alfa Aesar

  • (B20391)  Mercaptoacetic acid, 97+%   

  • 68-11-1

  • 500g

  • 418.0CNY

  • Detail
  • Alfa Aesar

  • (B20391)  Mercaptoacetic acid, 97+%   

  • 68-11-1

  • 2500g

  • 1777.0CNY

  • Detail
  • Sigma-Aldrich

  • (T6750)  Thioglycolicacidsolution  ~70 % (w/w) in H2O

  • 68-11-1

  • T6750-50ML

  • 343.98CNY

  • Detail
  • Sigma-Aldrich

  • (T6750)  Thioglycolicacidsolution  ~70 % (w/w) in H2O

  • 68-11-1

  • T6750-100ML

  • 506.61CNY

  • Detail
  • Sigma-Aldrich

  • (T6750)  Thioglycolicacidsolution  ~70 % (w/w) in H2O

  • 68-11-1

  • T6750-500ML

  • 1,170.00CNY

  • Detail
  • Sigma-Aldrich

  • (88652)  Thioglycolicacidsolution  ~80% in H2O, for spectrophotometric det. of palladium, iron, uranium(VI), molybdates and nitrites

  • 68-11-1

  • 88652-250ML

  • 413.01CNY

  • Detail
  • Sigma-Aldrich

  • (88652)  Thioglycolicacidsolution  ~80% in H2O, for spectrophotometric det. of palladium, iron, uranium(VI), molybdates and nitrites

  • 68-11-1

  • 88652-1L

  • 1,110.33CNY

  • Detail
  • Sigma-Aldrich

  • (T3758)  Thioglycolicacid  ≥98%

  • 68-11-1

  • T3758-100ML

  • 469.17CNY

  • Detail
  • Sigma-Aldrich

  • (T3758)  Thioglycolicacid  ≥98%

  • 68-11-1

  • T3758-500ML

  • 937.17CNY

  • Detail

68-11-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name thioglycolic acid

1.2 Other means of identification

Product number -
Other names Thiovanic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Corrosion inhibitors and anti-scaling agents,Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:68-11-1 SDS

68-11-1Synthetic route

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

mercaptoacetic acid
68-11-1

mercaptoacetic acid

Conditions
ConditionsYield
With sulfuric acid at 40 - 43℃; Electrochemical reaction;96.7%
With Phenylalanine; pyrographite at 38℃;
With sulfuric acid; cadmium Reduktion mit elektrolytisch gefaelltem Cadmiumpulver;
glycolic Acid
79-14-1

glycolic Acid

bromoacetic acid
79-08-3

bromoacetic acid

A

2,2'-thiodiglycolic acid
705924-36-3

2,2'-thiodiglycolic acid

B

mercaptoacetic acid
68-11-1

mercaptoacetic acid

Conditions
ConditionsYield
With hydrogen sulfide; hydrogen bromide In waterA n/a
B 95%
(N-Phenyl-formimidoylsulfanyl)-acetic acid methyl ester
84495-75-0

(N-Phenyl-formimidoylsulfanyl)-acetic acid methyl ester

A

mercaptoacetic acid
68-11-1

mercaptoacetic acid

B

Methyl thioglycolate
2365-48-2

Methyl thioglycolate

Conditions
ConditionsYield
With hydrogenchloride In water Ambient temperature;A 3%
B 93%
2-(N-Phenyl-N-methyl-thiocarbamoylthio)acetic Acid
20069-27-6

2-(N-Phenyl-N-methyl-thiocarbamoylthio)acetic Acid

A

4-methyl-4-phenyl-3-thiosemicarbazide
21076-11-9

4-methyl-4-phenyl-3-thiosemicarbazide

B

mercaptoacetic acid
68-11-1

mercaptoacetic acid

Conditions
ConditionsYield
With hydrazine hydrate In water at 85℃; for 0.416667h;A 81%
B n/a
2-thioxo-4-thiazolidinone
141-84-4

2-thioxo-4-thiazolidinone

A

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

B

mercaptoacetic acid
68-11-1

mercaptoacetic acid

Conditions
ConditionsYield
With hydrogenchloride at 130℃;
2-thioxo-4-thiazolidinone
141-84-4

2-thioxo-4-thiazolidinone

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2-methylamino-Δ2-thiazolin-4-one
16312-19-9

2-methylamino-Δ2-thiazolin-4-one

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

mercaptoacetic acid
68-11-1

mercaptoacetic acid

3-methyl-thiazolidine-2,4-dione
16312-21-3

3-methyl-thiazolidine-2,4-dione

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

mercaptoacetic acid
68-11-1

mercaptoacetic acid

B

methylamine
74-89-5

methylamine

2-imino-4-oxo-thiazolidine-3-carboxylic acid amide

2-imino-4-oxo-thiazolidine-3-carboxylic acid amide

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

mercaptoacetic acid
68-11-1

mercaptoacetic acid

thiazolidine-2,4-dione-2-semicarbazone
39130-96-6

thiazolidine-2,4-dione-2-semicarbazone

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

mercaptoacetic acid
68-11-1

mercaptoacetic acid

(1,4,5,6-tetrahydro-pyrimidin-2-ylmercapto)-acetic acid ethyl ester

(1,4,5,6-tetrahydro-pyrimidin-2-ylmercapto)-acetic acid ethyl ester

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2-imino-4-oxo-thiazolidine-3-carboxylic acid methylamide

2-imino-4-oxo-thiazolidine-3-carboxylic acid methylamide

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2-imino-4-oxo-thiazolidine-3-carboxylic acid ethyl ester

2-imino-4-oxo-thiazolidine-3-carboxylic acid ethyl ester

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

mercaptoacetic acid
68-11-1

mercaptoacetic acid

ethanol
64-17-5

ethanol

2,2'-sulfinyldiacetic acid
33388-14-6

2,2'-sulfinyldiacetic acid

mercaptoacetic acid
68-11-1

mercaptoacetic acid

Conditions
ConditionsYield
With hydrogenchloride der Aethylester entsteht;
L-Cysteine
52-90-4

L-Cysteine

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

mercaptoacetic acid
68-11-1

mercaptoacetic acid

Conditions
ConditionsYield
Kinetics; Gleichgewicht unter verschiedenen Bedingungen;
L-Cysteine
52-90-4

L-Cysteine

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

A

L-cystine
56-89-3

L-cystine

B

mercaptoacetic acid
68-11-1

mercaptoacetic acid

Conditions
ConditionsYield
polarometrische Untersuchung der Gleichgewichtsreaktion;
1,1-dithio-thiasuccinic acid
90439-55-7

1,1-dithio-thiasuccinic acid

mercaptoacetic acid
68-11-1

mercaptoacetic acid

Conditions
ConditionsYield
durch Selbstzersetzung;
1,1-dithio-thiasuccinic acid
90439-55-7

1,1-dithio-thiasuccinic acid

A

carbon disulfide
75-15-0

carbon disulfide

B

mercaptoacetic acid
68-11-1

mercaptoacetic acid

dimethylcarbamoylsulfanyl-acetic acid
29596-84-7

dimethylcarbamoylsulfanyl-acetic acid

1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

A

mercaptoacetic acid
68-11-1

mercaptoacetic acid

B

dimethyl amine
124-40-3

dimethyl amine

2,2'-sulfinyldiacetic acid
33388-14-6

2,2'-sulfinyldiacetic acid

A

mercaptoacetic acid
68-11-1

mercaptoacetic acid

B

Glyoxilic acid
298-12-4

Glyoxilic acid

Conditions
ConditionsYield
at 120 - 130℃; Mechanism;
bis(carboxymethyl)trithiocarbonate
6326-83-6

bis(carboxymethyl)trithiocarbonate

mercaptoacetic acid
68-11-1

mercaptoacetic acid

Conditions
ConditionsYield
With water
With ammonia
ethoxy-sulfanediyldi-acetic acid diethyl ester

ethoxy-sulfanediyldi-acetic acid diethyl ester

A

mercaptoacetic acid
68-11-1

mercaptoacetic acid

B

Glyoxilic acid
298-12-4

Glyoxilic acid

Conditions
ConditionsYield
bei der Einw. von Saeuren;
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

S-benzoylthioglycolic acid
6398-74-9

S-benzoylthioglycolic acid

A

mercaptoacetic acid
68-11-1

mercaptoacetic acid

B

benzoic acid
65-85-0

benzoic acid

1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

2-(3-oxo-1,3-diphenylpropylsulfanyl)acetic acid
16111-22-1

2-(3-oxo-1,3-diphenylpropylsulfanyl)acetic acid

A

mercaptoacetic acid
68-11-1

mercaptoacetic acid

B

1,3-diphenyl-propen-3-one
614-47-1

1,3-diphenyl-propen-3-one

1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

benzimidoylsulfanyl-acetic acid; hydrobromide

benzimidoylsulfanyl-acetic acid; hydrobromide

A

mercaptoacetic acid
68-11-1

mercaptoacetic acid

B

benzonitrile
100-47-0

benzonitrile

2-imino-4-oxo-thiazolidine-3-carboxylic acid isopentyl ester

2-imino-4-oxo-thiazolidine-3-carboxylic acid isopentyl ester

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

mercaptoacetic acid
68-11-1

mercaptoacetic acid

ethyl bromide
74-96-4

ethyl bromide

ethanol
64-17-5

ethanol

pseudothiohydantoin
556-90-1

pseudothiohydantoin

A

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

B

mercaptoacetic acid
68-11-1

mercaptoacetic acid

C

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

Conditions
ConditionsYield
at 130 - 140℃;
pseudothiohydantoin
556-90-1

pseudothiohydantoin

A

mercaptoacetic acid
68-11-1

mercaptoacetic acid

B

N-Cyanoguanidine
127099-85-8, 780722-26-1

N-Cyanoguanidine

Conditions
ConditionsYield
With barium dihydroxide
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

mercaptoacetic acid
68-11-1

mercaptoacetic acid

(benzhydrylthio)acetic acid
63547-22-8

(benzhydrylthio)acetic acid

Conditions
ConditionsYield
With trifluoroacetic acid for 0.5h; Ambient temperature;100%
With trifluoroacetic acid at 20℃; for 3h;99%
99%
triphenylmethyl alcohol
76-84-6

triphenylmethyl alcohol

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2-(triphenylmethylthio)ethanoic acid
34914-36-8

2-(triphenylmethylthio)ethanoic acid

Conditions
ConditionsYield
With trifluoroacetic acid at 20℃; for 0.5h;100%
With trifluoroacetic acid In chloroform at 20℃; for 1h;98%
With trifluoroacetic acid In chloroform at 20℃; for 3h;95%
mercaptoacetic acid
68-11-1

mercaptoacetic acid

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
With 2,2'-dipyridyl disulfide bis-N-oxide In chloroform-d1 for 18h; Ambient temperature;100%
With xenon difluoride In dichloromethane at 25℃;99%
With nickel(II) chloride hexahydrate; cadmium selenide; sodium hydroxide In water at 20℃; for 4h; pH=9; Catalytic behavior; Irradiation; Inert atmosphere;99%
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

mercaptoacetic acid
68-11-1

mercaptoacetic acid

bis(5-mercapto-4-keto-3-oxa pentyl) terephthalate

bis(5-mercapto-4-keto-3-oxa pentyl) terephthalate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran; benzene for 24h; Heating;100%
N-methyl-N-(tert-butyldimethylsilyl)acetamide
82112-20-7

N-methyl-N-(tert-butyldimethylsilyl)acetamide

mercaptoacetic acid
68-11-1

mercaptoacetic acid

C14H32O2SSi2
82112-29-6

C14H32O2SSi2

Conditions
ConditionsYield
With tert-butyldimethylsilyl chloride In acetonitrile for 0.0833333h; Product distribution; Ambient temperature; other tert-butyldimethylsilyl- donors; var. hydroxy carboxylic acids;100%
2-n-propyldithiopyridine-N-oxide
136852-78-3

2-n-propyldithiopyridine-N-oxide

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

1-hydroxy-2(1H)-pyridinethione
1121-30-8

1-hydroxy-2(1H)-pyridinethione

B

n-propyldithioacetic acid
136852-81-8

n-propyldithioacetic acid

Conditions
ConditionsYield
In chloroform for 23h; Ambient temperature;A n/a
B 100%
3-(N,N-Dimethylamino)phenyl isocyanate
31125-04-9

3-(N,N-Dimethylamino)phenyl isocyanate

mercaptoacetic acid
68-11-1

mercaptoacetic acid

triethylamine
121-44-8

triethylamine

(3-dimethylaminophenylaminocarbonylthio)acetic acid triethylammonium salt
79479-15-5

(3-dimethylaminophenylaminocarbonylthio)acetic acid triethylammonium salt

Conditions
ConditionsYield
In chloroform for 16h;100%
1,6,15,20-Tetraoxa-2,5,16,19-tetraoxocyclooctacosa-3,17-diene
118495-80-0

1,6,15,20-Tetraoxa-2,5,16,19-tetraoxocyclooctacosa-3,17-diene

mercaptoacetic acid
68-11-1

mercaptoacetic acid

bis<3,17-(2-carboxy-1-thiaethyl)>-1,6,15,20-tetraoxa-2,5,16,19-tetraoxocyclooctacosane

bis<3,17-(2-carboxy-1-thiaethyl)>-1,6,15,20-tetraoxa-2,5,16,19-tetraoxocyclooctacosane

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine In tetrahydrofuran at 64℃; for 26h;100%
5-Hydroxy-1-(4-methoxybenzyl)-3,4-dimethyl-1,5-dihydropyrrol-2-one
732256-60-9

5-Hydroxy-1-(4-methoxybenzyl)-3,4-dimethyl-1,5-dihydropyrrol-2-one

mercaptoacetic acid
68-11-1

mercaptoacetic acid

[1-(4-Methoxybenzyl)-3,4-dimethyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylsulfanyl]-acetic acid
935689-18-2

[1-(4-Methoxybenzyl)-3,4-dimethyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylsulfanyl]-acetic acid

Conditions
ConditionsYield
With camphorsulphonic acid In dichloromethane at 0℃; for 1.5h;100%
5-hydroxy-1-(4-methoxy-benzyl)-3-methyl-1,5-dihydro-pyrrol-2-one
935689-64-8

5-hydroxy-1-(4-methoxy-benzyl)-3-methyl-1,5-dihydro-pyrrol-2-one

mercaptoacetic acid
68-11-1

mercaptoacetic acid

[1-(4-Methoxybenzyl)-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylsulfanyl]-acetic acid
935689-82-0

[1-(4-Methoxybenzyl)-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylsulfanyl]-acetic acid

Conditions
ConditionsYield
With camphorsulfonic acid In dichloromethane at 0℃; for 1.5h; Product distribution / selectivity;100%
bis(tri-n-propylstannyl)oxide
1067-29-4

bis(tri-n-propylstannyl)oxide

mercaptoacetic acid
68-11-1

mercaptoacetic acid

(C3H7)3SnOOCCH2SH
49864-58-6

(C3H7)3SnOOCCH2SH

Conditions
ConditionsYield
In neat (no solvent) byproducts: H2O; at 115°C for 2 h; removal of water formed and excess acid, vac. distn. or recrystn.;100%
1-chloro-4-pentyne
14267-92-6

1-chloro-4-pentyne

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2-(pent-4-ynylthio)acetic acid
1010447-29-6

2-(pent-4-ynylthio)acetic acid

Conditions
ConditionsYield
Stage #1: mercaptoacetic acid With potassium hydroxide In methanol at 0℃; for 0.333333h;
Stage #2: 1-chloro-4-pentyne In methanol at 40 - 50℃; for 2h; Inert atmosphere;
100%
3,7-dichloro-5,5-difluoro-10-phenyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide

3,7-dichloro-5,5-difluoro-10-phenyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide

mercaptoacetic acid
68-11-1

mercaptoacetic acid

3,5-dithioacetic acid-3a,4a-diaza-4,4-difluoro-8-phenyl boron dipyrromethene
1206782-90-2

3,5-dithioacetic acid-3a,4a-diaza-4,4-difluoro-8-phenyl boron dipyrromethene

Conditions
ConditionsYield
With triethylamine In acetonitrile for 7h; Reflux; Darkness; Inert atmosphere;100%
2-(1H-naphtho[2,3-d]imidazol-2-yl)acetonitrile

2-(1H-naphtho[2,3-d]imidazol-2-yl)acetonitrile

mercaptoacetic acid
68-11-1

mercaptoacetic acid

(E)-2-((1H-naphtho[2,3-d]imidazol-2-yl)methylene)thiazolidin-4-one

(E)-2-((1H-naphtho[2,3-d]imidazol-2-yl)methylene)thiazolidin-4-one

Conditions
ConditionsYield
In pyridine at 100℃; for 8h;100%
N'-[4-(trifluoromethyl)cyclohexylidene]-2-phenoxyacetohydrazide

N'-[4-(trifluoromethyl)cyclohexylidene]-2-phenoxyacetohydrazide

mercaptoacetic acid
68-11-1

mercaptoacetic acid

N‐[3‐oxo‐8‐(trifluoromethyl)‐1‐thia‐4‐azaspiro[4.5]dec‐4‐yl]‐2‐phenoxyacetamide

N‐[3‐oxo‐8‐(trifluoromethyl)‐1‐thia‐4‐azaspiro[4.5]dec‐4‐yl]‐2‐phenoxyacetamide

Conditions
ConditionsYield
In toluene Reflux; Dean-Stark;100%
C15H20N2O

C15H20N2O

mercaptoacetic acid
68-11-1

mercaptoacetic acid

N‐(3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)‐3‐phenylpropanamide

N‐(3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)‐3‐phenylpropanamide

Conditions
ConditionsYield
In toluene Reflux; Dean-Stark;100%
C16H22N2O

C16H22N2O

mercaptoacetic acid
68-11-1

mercaptoacetic acid

N‐(8‐methyl‐3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)‐3‐phenylpropanamide

N‐(8‐methyl‐3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)‐3‐phenylpropanamide

Conditions
ConditionsYield
In toluene Reflux; Dean-Stark;100%
C18H26N2O

C18H26N2O

mercaptoacetic acid
68-11-1

mercaptoacetic acid

N‐(3‐oxo‐8‐propyl‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)‐3‐phenylpropanamide

N‐(3‐oxo‐8‐propyl‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)‐3‐phenylpropanamide

Conditions
ConditionsYield
In toluene Reflux; Dean-Stark;100%
C19H28N2O

C19H28N2O

mercaptoacetic acid
68-11-1

mercaptoacetic acid

N‐(8‐tert‐butyl‐3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)‐3‐phenylpropanamide

N‐(8‐tert‐butyl‐3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)‐3‐phenylpropanamide

Conditions
ConditionsYield
In toluene Reflux; Dean-Stark;100%
C21H24N2O

C21H24N2O

mercaptoacetic acid
68-11-1

mercaptoacetic acid

N‐(8‐phenyl‐3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)‐3‐phenylpropanamide

N‐(8‐phenyl‐3‐oxo‐1‐thia‐4‐azaspiro[4.5]decan‐4‐yl)‐3‐phenylpropanamide

Conditions
ConditionsYield
In toluene Reflux; Dean-Stark;100%
9-fluorenylmethyl chloride
36375-77-6

9-fluorenylmethyl chloride

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2-(((9H-fluoren-9-yl)methyl)thio)acetic acid

2-(((9H-fluoren-9-yl)methyl)thio)acetic acid

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 17h;100%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2,2'-((4-chlorophenyl)methylene)bis(sulfanediyl)diacetic acid
99854-22-5

2,2'-((4-chlorophenyl)methylene)bis(sulfanediyl)diacetic acid

Conditions
ConditionsYield
With L-proline In neat (no solvent) at 70℃; for 0.2h;99%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2,2'-((3-nitrophenyl)methylene)bis(sulfanediyl)diacetic acid
34939-21-4

2,2'-((3-nitrophenyl)methylene)bis(sulfanediyl)diacetic acid

Conditions
ConditionsYield
With L-proline In neat (no solvent) at 70℃; for 0.166667h;99%
With zinc(II) chloride
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2,2'-((4-nitrophenyl)methylene)bis(sulfanediyl)diacetic acid
6623-25-2

2,2'-((4-nitrophenyl)methylene)bis(sulfanediyl)diacetic acid

Conditions
ConditionsYield
With L-proline In neat (no solvent) at 70℃; for 0.166667h;99%
With zinc(II) chloride
With toluene-4-sulfonic acid In benzene Heating;
With boron trifluoride diethyl etherate; acetic acid at 60℃; for 3h; Yield given;
With boron trifluoride; acetic acid 1.) 60 deg C, 20 min, 2.) 60 deg C, 3 h; Multistep reaction;
benzaldehyde
100-52-7

benzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

α,α'-(benzylidenedithio)diacetic acid
4265-49-0

α,α'-(benzylidenedithio)diacetic acid

Conditions
ConditionsYield
With L-proline In neat (no solvent) at 70℃; for 0.25h;99%
With toluene-4-sulfonic acid In pentane for 5h; Heating;82%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

4-methoxyphenyl-bis(carboxymethylthio)methane
100118-50-1

4-methoxyphenyl-bis(carboxymethylthio)methane

Conditions
ConditionsYield
With L-proline In neat (no solvent) at 70℃; for 0.25h;99%
benzoyl chloride
98-88-4

benzoyl chloride

mercaptoacetic acid
68-11-1

mercaptoacetic acid

S-benzoylthioglycolic acid
6398-74-9

S-benzoylthioglycolic acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile for 4h;99%
With sodium hydroxide In water; toluene at 10 - 28℃; for 2.5h;92%
With sodium hydrogencarbonate In water 15 min, 0 deg C; 15 min, RT;72%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2-mercapto-N-(4-methoxyphenyl)acetamide
34282-29-6

2-mercapto-N-(4-methoxyphenyl)acetamide

Conditions
ConditionsYield
at 130℃; for 5h; Inert atmosphere;99%
at 100℃; for 6h;89%
mercaptoacetic acid
68-11-1

mercaptoacetic acid

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

2-nitrophenyl-bis(carboxymethylthio)methane
34914-15-3

2-nitrophenyl-bis(carboxymethylthio)methane

Conditions
ConditionsYield
With L-proline In neat (no solvent) at 70℃; for 0.25h;99%
With hydrogenchloride
With boron trifluoride diethyl etherate; acetic acid at 60℃; for 3h; Yield given;
With boron trifluoride; acetic acid 1.) 60 deg C, 20 min, 2.) 60 deg C, 3 h; Yield given. Multistep reaction;
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2,2'-(p-tolylmethylene)bis(sulfanediyl)diacetic acid
34914-18-6

2,2'-(p-tolylmethylene)bis(sulfanediyl)diacetic acid

Conditions
ConditionsYield
With L-proline In neat (no solvent) at 70℃; for 0.25h;99%
With toluene-4-sulfonic acid In benzene Heating;
With boron trifluoride diethyl etherate; acetic acid at 60℃; for 3h; Yield given;

68-11-1Relevant articles and documents

Sastry, M. S.,Kulshreshtha, S. K.

, p. 95 - 100 (1989)

A new procedure for thioester deprotection using thioglycolic acid in both homogeneous and heterogeneous phase

Mahler, Graciela,Saiz, Cecilia,Villamil, Valentina

, (2021/07/20)

Classic acetyl thioester protection/deprotection methodologies are widely used in organic synthesis, but deprotection step usually requires harsh conditions not suitable for labile substrates. In this work, a new method for thioester deprotection using a thiotransesterification approach is described. Firstly, thioglycolic acid (TGA) was identified as a good deprotecting reagent in solution. In order to develop a thiol polymer-supported reagent, TGA was anchored to a PEG-based resin through an amide bond (TG-NCO-SH). Both homogeneous and heterogeneous approaches were conveniently carried out at room temperature, in aqueous buffer at pH 8. The mild conditions were suitable for alkyl and phenyl thioesters. Moreover labile thioesters containing thiazolidine and oxazolidine scaffolds, bearing amine, ester and acetal functionalities were also deprotected. The polymer-supported TGA gave better deprotection yields compared to TGA in solution, yields ranging from 61 to 90%. The feasibility of the recovery and reuse of TG-NCO-SH reagent was explored, showing it can be reused at least five times without lossing the activity.

Synthesis of an enantiopure thioester as key substrate for screening the sensitivity of penicillin binding proteins to inhibitors

Simon, Justine F.,Bouillez, André,Frère, Jean-Marie,Luxen, André,Zervosen, Astrid

, p. 22 - 31 (2016/10/31)

The synthesis of the enantiopure thioester (R)-2-(2-benzamidopropanoylthio)acetic acid was developed. After the exploration of several activation methods, reaction conditions were found for the formation of the thioester bond in the presence of propylphosphonic anhydride with high enantioselectivity (ee > 99%). The thioester activity of Penicillin Binding Proteins is helpful in research programs looking for new lead structures to overcome the problem of bacterial resistance.

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