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Thiodiglycolic acid, with the molecular formula C4H8O3S, is a colorless, odorless liquid that is soluble in water. It is a chemical compound primarily used as a chemical intermediate in various industrial applications.

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  • 505-73-7 Structure
  • Basic information

    1. Product Name: THIODIGLYCOLIC ACID
    2. Synonyms: RARECHEM AL BO 1549;SYM-DICARBOXY DIMETHYL DISULFIDE;THIODIACETIC ACID;THIODIGLYCOLLIC ACID;2,2’-dithiobis-aceticaci;Dithioglycollicacid;MERCAPTODIACETIC ACID;DITHIOGLYCOLIC ACID
    3. CAS NO:505-73-7
    4. Molecular Formula: C4H6O4S2
    5. Molecular Weight: 182.22
    6. EINECS: 204-663-9
    7. Product Categories: Pharmaceutical Intermediates
    8. Mol File: 505-73-7.mol
  • Chemical Properties

    1. Melting Point: 128-131 °C(lit.)
    2. Boiling Point: 395.6°Cat760mmHg
    3. Flash Point: 193°C
    4. Appearance: /
    5. Density: 1,19 g/cm3
    6. Vapor Pressure: 2.32E-07mmHg at 25°C
    7. Refractive Index: 1.628
    8. Storage Temp.: −20°C
    9. Solubility: DMSO (Slightly), Methanol (Slightly)
    10. PKA: pK1:3.32;pK2:4.29 (25°C)
    11. Water Solubility: very faint turbidity
    12. CAS DataBase Reference: THIODIGLYCOLIC ACID(CAS DataBase Reference)
    13. NIST Chemistry Reference: THIODIGLYCOLIC ACID(505-73-7)
    14. EPA Substance Registry System: THIODIGLYCOLIC ACID(505-73-7)
  • Safety Data

    1. Hazard Codes: C,Xi
    2. Statements: 34-36/37/38
    3. Safety Statements: 26-36/37/39-45-36
    4. RIDADR: UN 3261 8/PG 2
    5. WGK Germany: 2
    6. RTECS: AJ6475000
    7. F: 13
    8. HazardClass: N/A
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 505-73-7(Hazardous Substances Data)

505-73-7 Usage

Uses

Used in Personal Care Industry:
Thiodiglycolic acid is used as a chemical intermediate for the production of mercaptoacetic acid, which is utilized in hair straightening formulations and permanent wave solutions. It helps in the restructuring of hair proteins, providing a smooth and straight appearance.
Used in Dye Industry:
Thiodiglycolic acid is used in the synthesis of dyes, contributing to the development of colorants for various applications, including textiles and printing inks.
Used in Pharmaceutical Industry:
As a chemical intermediate, thiodiglycolic acid plays a role in the synthesis of certain pharmaceuticals, aiding in the development of drugs for medical treatments.
Used in Plastics Industry:
Thiodiglycolic acid is utilized in the production of plastic stabilizers, which are essential for enhancing the durability and performance of plastic materials.
Used in Polymer, Adhesive, and Textile Industries:
Thiodiglycolic acid is used in the production of thioglycolic acid esters, which find applications in the manufacturing of polymers, adhesives, and textiles, improving their bonding and material properties.
Due to its strong reducing properties, thiodiglycolic acid is classified as a hazardous substance, and appropriate safety measures must be taken during its handling and use.

Check Digit Verification of cas no

The CAS Registry Mumber 505-73-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 5 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 505-73:
(5*5)+(4*0)+(3*5)+(2*7)+(1*3)=57
57 % 10 = 7
So 505-73-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O4S2/c5-3(6)1-9-10-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)

505-73-7Synthetic route

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%
Trichloroethylene
79-01-6

Trichloroethylene

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

(β,β-Dichlorovinylthio)acetic acid
77922-51-1

(β,β-Dichlorovinylthio)acetic acid

Conditions
ConditionsYield
for 36h; Heating; Irradiation;A n/a
B 54.1%
dimethyl 3,3'-disulfanediyl(2R,2'R)-bis(2-benzamidopropanoate)
5673-91-6

dimethyl 3,3'-disulfanediyl(2R,2'R)-bis(2-benzamidopropanoate)

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

(R)-2-((2-benzamido-3-methoxy-3-oxopropyl)disulfanyl)acetic acid

(R)-2-((2-benzamido-3-methoxy-3-oxopropyl)disulfanyl)acetic acid

Conditions
ConditionsYield
With triethylamine In methanolA 24%
B 42%
thiocyanato-acetic acid
4438-95-3

thiocyanato-acetic acid

potassium thioacyanate
333-20-0

potassium thioacyanate

A

ethanedinitrile
460-19-5

ethanedinitrile

B

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
das Kaliumsalz reagiert;
sodium monochloroacetic acid
3926-62-3

sodium monochloroacetic acid

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
With sodium polysulfide; water
With water; sodium thiosulfate Oxydieren des entstandenen Glykolsaeure-thiosulfats mit Jod;
With sodium tetrathioantimonate(V)
With sodium monothioarsenate
With sodium disulfide
2-iodopropionic acid
598-80-1

2-iodopropionic acid

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

propionic acid
802294-64-0

propionic acid

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

L-Cysteine
52-90-4

L-Cysteine

B

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
Equilibrium constant; unter verschiedenen Bedingungen;
Kinetics; unter verschiedenen Bedingungen;
Iodoacetic acid
64-69-7

Iodoacetic acid

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

thiodiacetic acid
123-93-3

thiodiacetic acid

B

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
in wss.Loesung;
iodacetamide
144-48-9

iodacetamide

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

thiodiacetic acid
123-93-3

thiodiacetic acid

B

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
in wss.Loesung;
3,3'-sulfinyldipropionic acid
3680-08-8

3,3'-sulfinyldipropionic acid

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

4-thiaheptane-1,7-dioic acid
111-17-1

4-thiaheptane-1,7-dioic acid

B

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
at 60℃; Rate constant;
diethyl ether
60-29-7

diethyl ether

mercaptoacetic acid
68-11-1

mercaptoacetic acid

α-bromoacetophenone
70-11-1

α-bromoacetophenone

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

2-((2-oxo-2-phenylethyl)thio)acetic acid
22536-46-5

2-((2-oxo-2-phenylethyl)thio)acetic acid

C

acetophenone
98-86-2

acetophenone

tetrachloromethane
56-23-5

tetrachloromethane

diethyl ether
60-29-7

diethyl ether

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2-Naphthalenesulfonyl chloride
93-11-8

2-Naphthalenesulfonyl chloride

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

naphthalene-2-sulfinic acid
613-49-0

naphthalene-2-sulfinic acid

mercaptoacetic acid
68-11-1

mercaptoacetic acid

p-benzoquinone
106-51-4

p-benzoquinone

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

hydroquinone
123-31-9

hydroquinone

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

trisulfanediyldi-acetic acid
16002-31-6

trisulfanediyldi-acetic acid

Conditions
ConditionsYield
With thionyl chloride; diethyl ether
ethyl bromoacetate
105-36-2

ethyl bromoacetate

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
With ethanol; sodium thiosulfate anschliessend Elektrolisieren die entstehenden Gemische im Kathodenraum in Gegenwart von Kaliumdicarbonat; Verseifen den entstandenen Ester durch Erhitzen mit Salzsaeure;
methyl bis(thioacetate)
1665-64-1

methyl bis(thioacetate)

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
With water Product distribution;
C4H5O4S2(1+)

C4H5O4S2(1+)

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

methyl viologen cation radical
26985-31-9

methyl viologen cation radical

Conditions
ConditionsYield
Rate constant; ph=12;
[(4-Bromo-phenyl)-methoxycarbonylmethylsulfanyl-methylsulfanyl]-acetic acid methyl ester
153258-85-6

[(4-Bromo-phenyl)-methoxycarbonylmethylsulfanyl-methylsulfanyl]-acetic acid methyl ester

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide In water; acetic acid for 48h; Mechanism; Heating; other compounds with electron withdrawing substituents;
2-benzylidenehydrazino-3-methyl-1,3-thiazolidin-4-one
96984-81-5

2-benzylidenehydrazino-3-methyl-1,3-thiazolidin-4-one

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

1-benzylidene-4-methylsemicarbazide
40848-87-1

1-benzylidene-4-methylsemicarbazide

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 6h; Heating;
1,1,1,2,2,3,3-heptafluoro-3-iodo-propane

1,1,1,2,2,3,3-heptafluoro-3-iodo-propane

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

heptafluoropropylthioacetic acid

heptafluoropropylthioacetic acid

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20 - 22℃; for 3h;A 6.6 % Spectr.
B 50.9 % Spectr.
mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

B

heptafluoropropylthioacetic acid

heptafluoropropylthioacetic acid

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20 - 22℃; for 2h;A 17.1 % Spectr.
B 41.2 % Spectr.
nitrosothioglycolic acid
58024-22-9

nitrosothioglycolic acid

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
In water at 25℃; Rate constant; pH: 7.4;
sulfuryl dichloride
7791-25-5

sulfuryl dichloride

mercaptoacetic acid
68-11-1

mercaptoacetic acid

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

sulfuric acid
7664-93-9

sulfuric acid

mercaptoacetic acid
68-11-1

mercaptoacetic acid

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
at 45℃;
mercaptoacetic acid
68-11-1

mercaptoacetic acid

air

air

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

mercaptoacetic acid
68-11-1

mercaptoacetic acid

hydrogen stream

hydrogen stream

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
at 120℃;
ethanol
64-17-5

ethanol

chloroacetic acid
79-11-8

chloroacetic acid

Na2S2

Na2S2

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

vitamin K5
83-70-5

vitamin K5

mercaptoacetic acid
68-11-1

mercaptoacetic acid

phosphate-buffer solution

phosphate-buffer solution

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
pH 7.8;
mercaptoacetic acid
68-11-1

mercaptoacetic acid

potassium peroxo disulfate

potassium peroxo disulfate

iron-salt

iron-salt

acidic water

acidic water

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Conditions
ConditionsYield
at 25℃; Kinetics;
at 25℃; Mechanism;
mercaptoacetic acid
68-11-1

mercaptoacetic acid

sulfur

sulfur

aqueous methanolic NaOH

aqueous methanolic NaOH

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

methanol
67-56-1

methanol

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

methyl bis(thioacetate)
1665-64-1

methyl bis(thioacetate)

Conditions
ConditionsYield
With sulfuric acid for 3h; Reflux;98%
With acetyl chloride for 16h; Heating;96%
With sulfuric acid at 20℃;96%
With toluene-4-sulfonic acid
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;
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

isopropyl alcohol
67-63-0

isopropyl alcohol

diisopropyl 2,2'-disulfanediyldiacetate
132685-31-5

diisopropyl 2,2'-disulfanediyldiacetate

Conditions
ConditionsYield
With sulfuric acid for 3h; Reflux;95%
ethanol
64-17-5

ethanol

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

diethyl 2,2'-disulfanediyldiacetate
1665-65-2

diethyl 2,2'-disulfanediyldiacetate

Conditions
ConditionsYield
With sulfuric acid for 3h; Reflux;93%
With hydrogenchloride
With hydrogenchloride at 20℃;
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

benzyl alcohol
100-51-6

benzyl alcohol

dibenzyl 2,2'-disulfanediyldiacetate

dibenzyl 2,2'-disulfanediyldiacetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Reflux;90%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

5-tert-butoxycarbonylamino-1-aminopentane
51644-96-3

5-tert-butoxycarbonylamino-1-aminopentane

di-tert-butyl(((2,2’-disulfanediylbis(acetyl))bis(azanediyl))bis(pentane-5,1-diyl))dicarbamate

di-tert-butyl(((2,2’-disulfanediylbis(acetyl))bis(azanediyl))bis(pentane-5,1-diyl))dicarbamate

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h;87%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h;87%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere;87%
In N,N-dimethyl-formamide87%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

Tocopherol
59-02-9

Tocopherol

C33H54O5S2

C33H54O5S2

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane85%
Stage #1: disulfanediyldiacetic acid With acetic anhydride at 30℃; for 2h;
Stage #2: Tocopherol With dmap In dichloromethane at 20℃; for 1h;
56.3%
Stage #1: disulfanediyldiacetic acid With acetic anhydride at 30℃; for 2h;
Stage #2: Tocopherol With dmap In dichloromethane; toluene at 20℃; for 0.0833333h;
114 mg
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

2,2'-disulfanediyldiacetylchloride
10021-77-9

2,2'-disulfanediyldiacetylchloride

Conditions
ConditionsYield
With thionyl chloride for 48h; Ambient temperature;84%
With thionyl chloride In 1,4-dioxane for 4h; Heating;59%
With diethyl ether; phosphorus pentachloride
2,6-Diaminopyridine
141-86-6

2,6-Diaminopyridine

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

1,3,5,12,14,16-hexeaza-6,11,17,22-tetraoxo-8,9,19,20-tetrathia-2,3,4:13,14,15-dipyridine cyclodocosane
1120337-11-2

1,3,5,12,14,16-hexeaza-6,11,17,22-tetraoxo-8,9,19,20-tetrathia-2,3,4:13,14,15-dipyridine cyclodocosane

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 85℃;82%
Oxidized glutathione
27025-41-8

Oxidized glutathione

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

carboxymethyl N-(N-γ-glutamylcysteinyl)glycyl disulfide

carboxymethyl N-(N-γ-glutamylcysteinyl)glycyl disulfide

Conditions
ConditionsYield
rhodium(III) chloride In water at 40℃; for 1h;81%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

tert–butyl (2–aminophenyl)carbamate
146651-75-4

tert–butyl (2–aminophenyl)carbamate

di-tert-butyl(((2,2'-disulfanediylbis(acetyl))bis(azanediyl))bis(2,1-phenylene))dicarbamate

di-tert-butyl(((2,2'-disulfanediylbis(acetyl))bis(azanediyl))bis(2,1-phenylene))dicarbamate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;81%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

di((Z)-octadec-9-enyl)amine
40165-68-2

di((Z)-octadec-9-enyl)amine

C40H75NO3S2

C40H75NO3S2

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 12h;80%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

dithiobis(succinimidyl acetate)
863649-56-3

dithiobis(succinimidyl acetate)

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane; acetone at 20℃;74%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;72%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 1.5h;49%
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

3,10-dimethylisoalloxazine
4074-59-3

3,10-dimethylisoalloxazine

A

6-(((carboxymethyl)dithio)methyl)-3,10-dimethylisoalloxazine
89322-35-0

6-(((carboxymethyl)dithio)methyl)-3,10-dimethylisoalloxazine

B

4a-(((carboxymethyl)dithio)methyl)-4a,5-dihydro-3,10-dimethylisoalloxazine
89322-33-8

4a-(((carboxymethyl)dithio)methyl)-4a,5-dihydro-3,10-dimethylisoalloxazine

Conditions
ConditionsYield
In water; acetonitrile for 6h; Irradiation; anaerobic;A 1%
B 72%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

deacetylthiocolchicine
2731-16-0

deacetylthiocolchicine

2,2'-dithiobis[N-(N-deacetylthiocolchicinyl)acetamide]
885501-69-9

2,2'-dithiobis[N-(N-deacetylthiocolchicinyl)acetamide]

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 72h;67%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;67%
benzoguanamine
91-76-9

benzoguanamine

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

1,10(2,6)-ditriazina-2,9,11,18-tetraaza-3,8,12,17-tetraoxo-5,6,14,15-tetrathia-cycloocta-decaphan-1(4),10(4)-diphenyl
1198294-58-4

1,10(2,6)-ditriazina-2,9,11,18-tetraaza-3,8,12,17-tetraoxo-5,6,14,15-tetrathia-cycloocta-decaphan-1(4),10(4)-diphenyl

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water Heating;67%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

N-Trifluoromethyl-N-nitrosobenzenesulfonamide
80783-62-6

N-Trifluoromethyl-N-nitrosobenzenesulfonamide

[(trifluoromethyl)sulfanyl]acetic acid
2408-17-5

[(trifluoromethyl)sulfanyl]acetic acid

Conditions
ConditionsYield
With dimethylglyoxal In acetone for 14h; Irradiation;63%
7-hydroxy-4-methyl-chromen-2-one
90-33-5, 79566-13-5

7-hydroxy-4-methyl-chromen-2-one

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

bis(4-methyl-2-oxo-2H-chromen-7-yl) 2,2'-disulfanediyldiacetate

bis(4-methyl-2-oxo-2H-chromen-7-yl) 2,2'-disulfanediyldiacetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;63%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

O,O’-diacetyl-dopa-methyl ester hydrochloride

O,O’-diacetyl-dopa-methyl ester hydrochloride

methyl 3-[3,4-bis(acetyloxy)phenyl]-2-{2-[({[3-[3,4-bis(acetyloxy)phenyl]-1-methoxy-1-oxopropan-2-yl]carbamoyl}methyl)disulfanyl]acetamido}propanoate

methyl 3-[3,4-bis(acetyloxy)phenyl]-2-{2-[({[3-[3,4-bis(acetyloxy)phenyl]-1-methoxy-1-oxopropan-2-yl]carbamoyl}methyl)disulfanyl]acetamido}propanoate

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 4℃; for 18h;54%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine hydrochloride

4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine hydrochloride

C13H12F3N3O3S2

C13H12F3N3O3S2

Conditions
ConditionsYield
Stage #1: disulfanediyldiacetic acid With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃;
Stage #2: With triethylamine In dichloromethane for 2h;
Stage #3: 4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine hydrochloride
53.1%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

benzylamine
100-46-9

benzylamine

Bis-(N-benzyl-carbamoylmethyl)-disulfid
1047-94-5

Bis-(N-benzyl-carbamoylmethyl)-disulfid

Conditions
ConditionsYield
Stage #1: disulfanediyldiacetic acid With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 2h; Reflux;
Stage #2: benzylamine In dichloromethane at 0 - 20℃; for 4h;
52%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

tributyltin chloride
1461-22-9

tributyltin chloride

[(n-Bu3Sn)2(O2CCH2S)2]n

[(n-Bu3Sn)2(O2CCH2S)2]n

Conditions
ConditionsYield
Stage #1: disulfanediyldiacetic acid With potassium hydroxide In methanol for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: tributyltin chloride In methanol at 45℃; for 12h; Schlenk technique; Inert atmosphere;
52%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

C39H67N5O7

C39H67N5O7

C43H71N5O10S2

C43H71N5O10S2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 5h;51%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

1-oxo-{1-{[4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl]amino}pent-4-yn-2-yl}amine

1-oxo-{1-{[4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl]amino}pent-4-yn-2-yl}amine

2-((2-oxo-2-(1-oxo-(1-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)amino)pent-4-yn-2-yl)amino)ethyl)disulfanyl)acetic acid

2-((2-oxo-2-(1-oxo-(1-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)amino)pent-4-yn-2-yl)amino)ethyl)disulfanyl)acetic acid

Conditions
ConditionsYield
Stage #1: disulfanediyldiacetic acid With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0℃; for 3h;
Stage #2: 1-oxo-{1-{[4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl]amino}pent-4-yn-2-yl}amine In dichloromethane at 20℃; for 24h;
50.9%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

methyldisulfanyl-acetic acid
60033-23-0

methyldisulfanyl-acetic acid

Conditions
ConditionsYield
With air; nitrogen(II) oxide In [D3]acetonitrile at 20℃; for 1h;50%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

podofilox
518-28-5

podofilox

dipodophyllotoxin-4-yl 2,2'-dithiobisacetate
885501-71-3

dipodophyllotoxin-4-yl 2,2'-dithiobisacetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 72h;50%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;50%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

[(Me3Sn)2(O2CCH2S)2]n

[(Me3Sn)2(O2CCH2S)2]n

Conditions
ConditionsYield
Stage #1: disulfanediyldiacetic acid With potassium hydroxide In methanol for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: trimethyltin(IV)chloride In methanol at 45℃; for 12h; Schlenk technique; Inert atmosphere;
50%
disulfanediyldiacetic acid
505-73-7

disulfanediyldiacetic acid

H-Phe-Val-Trp-Ile-NH2
439613-95-3

H-Phe-Val-Trp-Ile-NH2

H-Phe-Val-Trp(2'-SCH2COOH)-Ile-NH2

H-Phe-Val-Trp(2'-SCH2COOH)-Ile-NH2

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In trifluoroacetic acid at 20℃; for 48h;42%

505-73-7Relevant articles and documents

Cu(II)-catalyzed oxidation of thiols by superoxide ligated to Co III2

Mishra, Ritu,Banerjee, Rupendranath,Mukhopadhyay, Subrata

, p. 1193 - 1197 (2012)

Copper(II) dramatically catalyzes the oxidation of thiols by a superoxide bridging two CoIII ions. The catalyzed path overwhelmingly dominates over the uncatalysed path and is first order in the superoxo complex concentration. The first-order rate constants show a first-order dependence in [Cu2+], a second-order dependence in [thiol] and linearly varies with [H+]-3. On the basis of observed kinetics reported here, it is proposed that Cu(II) reacts with two thiol molecules to form a Cu II(thiol)2 complex, an electron is transferred from one ligated thiol to the CuII center to form CuI(thiol) and a thiyl radical. The copper(I)-thiol complex is oxidized by the conjugate base of the title complex to regenerate CuII(thiol). A CuII/I catalytic cycle is thus believed to be responsible for the observed catalysis. Copyright

Improvement of a process for synthesis of thioglycolic acid

Islamgulova,Shitova,Akhmerova,Tomilov

, p. 1438 - 1440 (2002)

An environmentally clean process was proposed for synthesis of thioglycolic acid by condensation of monochloroacetic acid with sodium disulfide, followed by electrochemical reduction of the resulting mixture.

Cu(II) catalyzed oxidation of mercaptoacetic acid by methylene blue in acidic medium: Influence of solvent and morphology

Sharma, Ranjana,Pal, Mahender,Mishra

, p. 41 - 47 (2016)

Kinetic studies on the Cu(II) catalyzed oxidation of mercaptoacetic acid (thioglycolic acid, TGA) by the model electron receptor methylene blue in acidic medium show that the reaction follows a second order kinetics in TGA. The order in methylene blue is unity but at higher [TGA], the order is 3/4. The rate shows an inverse relationship with [H+] and a second order dependence on [Cu(II)]. The reaction conforms to Arrhenius behavior in aqueous medium but resorts to anti-Arrhenius behavior in aqueous methanol and in aqueous acetone media. The reaction involves the in situ participation of nanoparticles which has been confirmed by SEM, XRD, and FTIR techniques. In aqueous medium, cauliflower shaped nanoparticles (44.21-74.33 nm) are obtained but in the presence of acetone and methanol, nanogranules (38.96-70.73 nm) and nanodisks (47.30-72.16 nm), respectively, are produced at 35°C as revealed by SEM images and XRD data. The reaction is characterized by the participation of two transition states in aqueous acetone medium and the kinetics of the reaction, especially the temperature dependence, is governed by the adsorption of methylene blue on copper nanoparticles as influenced by morphology inter alia dielectric constant of the reaction medium.

Determination of Thioglycolic Acid and Dithiodiglycolic Acid in Mineral Flotation Systems

McLean, McLean,Wagenen, Stan Van,Wiedemann, Donna,Fernando, Quintus,Raghavan, Srini

, p. 965 - 969 (1986)

When aqueous solution of thioglycolic acid are equilibrated with sphalerite, a zinc sulfide mineral, a large fraction of the thioglycolic acid is either adsorbed on the sphalerite surface or oxidized ot dithiodiglycolic acid.The total concentration of thioglycolic and dithioglycolic acid in solution has been determined by molecular emission cavity analysis (MECA).The fraction of the thioglycolic acid that is not adsorbed on the mineral surface and remains in solution has been determined by a coulometric titration in which iodine is electrogenerated in situ and the endpoint located by an amperometric method.Attempts to determine the thioglycolic acid that was adsorbed on the mineral surface directly by MECA gave unreliable results.This has been attributed to the wide variation in the surface area as well as the surface chemical composition of small samples (1-2 mg) of the mineral that must be useed in the sample cup in MECA.Thioglycolic acid also leaches traces of metal ions from the mineral surface.The concentration of zinc(II) in solution reflects the extent of leaching that has occurred.

Soft template induced phase selective synthesis of Fe2O3 nanomagnets: One step towards peroxidase-mimic activity allowing colorimetric sensing of thioglycolic acid

Roy, Anindita,Sahoo, Ramkrishna,Ray, Chaiti,Dutta, Soumen,Pal, Tarasankar

, p. 32308 - 32318 (2016)

Different Schiff's base (SB) templates have been obtained to mediate phase selective synthesis of α- or γ-Fe2O3 from the same temperature condition. The inherent phase transformation tendency (γ-Fe2O3 to α-Fe2O3) is found to be inhibited. Again, the phase selective evolution emerges out of the binding modes of SBs which has been illustrated here. The nature of SBs governs the shape and size distribution of Fe2O3 NPs. As both the phases are magenetically active, easy magnetic separation of them widens their applicability in catalysis. Magnetically active both α- and γ-Fe2O3 mimic interesting peroxidase like activity by oxidising colourless 3,3′,5,5′-tetramethylbenzidine (TMB) to blue coloured oxidised product (Ox-TMB) in aqueous H2O2. These results prompted us to improvise further to detect thioglycolic acid (TGA) at a micromolar level which provides commercial applicability.

l-Arginine complex of copper on modified core–shell magnetic nanoparticles as reusable and organic–inorganic hybrid nanocatalyst for the chemoselective oxidation of organosulfur compounds

Nikoorazm, Mohsen,Moradi, Parisa,Noori, Nourolah,Azadi, Gouhar

, p. 467 - 478 (2020/09/01)

In this paper, we report the fabrication and characterization of a stable heterogeneous nanostructure catalyst of copper immobilized on Fe3O4@SiO2@l-Arginine, for the oxidation of sulfides and oxidative coupling of thiols. The prepared nanocatalyst has been characterized by different techniques such as FTIR, XRD, SEM, TEM and TGA. These nanoparticles were the effective catalyst for selective oxidation of sulfides and oxidative coupling of thiols using 30% H2O2. The suggested method offers several prominent advantages such as mild condition, use of magnetically reusable catalyst, simple workup procedure, good to high yields of products and great selectivity.

Synthesis and Characterization of Magnetic Functionalized Ni and Cu Nano Catalysts and Their Application in Oxidation, Oxidative Coupling and Various Multi-Component Reactions

Hajjami, Maryam,Sheikhaei, Shiva,Gholamian, Fatemeh,Yousofvand, Zakieh

, p. 2420 - 2435 (2021/01/04)

Abstract: Two magnetic nano catalysts of nickel and copper, Fe3O4@SiO2@DOP-BenPyr-M(II), (M=Ni and Cu) have been synthesized. These catalysts were applied as recoverable, efficient and new heterogeneous catalysts for the high yielding and room temperature one-pot procedure of selective oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides. In addition, the catalytic activity of Fe3O4@SiO2@DOP-BenPyr-Ni(II) was investigated as heterogeneous nanocatalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones, 5-substituted 1H-tetrazoles and polyhydroquinolines. The synthesized catalysts were characterized by FT-IR, TGA, XRD, VSM, EDX, ICP and SEM techniques. These catalysts were recovered by an external magnet and reused several times without significant loss of catalytic efficiency. Graphic Abstract: [Figure not available: see fulltext.]

Fe3O4@MCM-41@Zn-Arg: as a novel, magnetically recoverable and ecofriendly nanocatalyst for the synthesis of disulfides, sulfoxides and 2,3-dihydroquinazolin?4(1H)?ones

Nikoorazm, Mohsen,Erfani, Zahra

, p. 642 - 655 (2020/08/19)

The direct supporting of Zn-arginine complex on magnetic core-shell nanostructures (Fe3O4@MCM-41@Zn-Arg) was reported as a novel, heterogeneous and excellent nanocatalyst, which applied for the oxidation reaction of sulfides to sulfoxides, oxidative coupling of thiols to their corresponding disulfides and the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives under mild conditions. The structure of the catalyst was studied by X-Ray diffraction, Fourier transform-infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, atomic absorption spectroscopy, and vibrating sample magnetometry techniques. The simple experimental procedure, very good catalytic activity, low cost, and excellent recycling are the noteworthy features of the currently employed heterogeneous catalytic system.

Synthesis and characterization of VO–vanillin complex immobilized on MCM-41 and its facile catalytic application in the sulfoxidation reaction, and synthesis of 2,3-dihydroquinazolin-4(1H)-ones and disulfides in green media

Nikoorazm, Mohsen,Khanmoradi, Maryam

, p. 1477 - 1489 (2020/03/11)

In this work, a vanillin complex is immobilized onto MCM-41 and characterized by FT-IR, X-ray diffraction, scanning electron microscopy, energy dispersive spectroscopy, thermogravimetric analysis, and BET techniques. This supported Schiff base complex was found to be an efficient and recoverable catalyst for the chemoselective oxidation of sulfides into sulfoxides and thiols into their corresponding disulfides (using hydrogen peroxide as a green oxidant) and also a suitable catalyst for the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in water at 90°C. Using this protocol, we show that a variety of disulfides, sulfoxides, and 2,3-dihydroquinazolin-4(1H)-one derivatives can be synthesized in green conditions. The catalyst can be recovered and recycled for further reactions without appreciable loss of catalytic performance.

SUPER-HYDROPHOBIC ELECTROTHERMAL EPOXY RESIN COMPOSITE MATERIAL AND PREPARATION AND SELF-REPAIRING METHOD THEREFOR

-

, (2020/12/25)

Superhydrophobic electrothermal epoxy composites, their preparation and a self-healing method are disclosed. 1,4,5-oxadithiepane-2,7-dione and methylhexahydrophthalic anhydride were mixed and cured with epoxides to get self-healable epoxy resins; carbon nanotube/self-healable epoxy resin prepolymers were coated on self-healable epoxy resins and cured to get electrothermal epoxy composites; modified superhydrophobic copper powders were adhered on electrothermal epoxy composites and cured to get a kind of superhydrophobic electrothermal epoxy composites. The thermal resistance of superhydrophobic electrothermal epoxy composites is superior to existed technical solutions and they can simultaneously repair cracking and delamination and the healed samples still exhibit excellent superhydrophobicity. These merits of superhydrophobic electrothermal epoxy composites provided in this invention can meet the harsh requirements of self-healing and removing ice on surfaces of wind turbine blades, suggesting good abilities of guaranteeing service safety and lifespan of wind turbine blades.

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