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2,2'-Dithiosalicylic acid

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Name

2,2'-Dithiosalicylic acid

EINECS 204-352-8
CAS No. 119-80-2 Density 1.53 g/cm3
PSA 125.20000 LogP 3.88240
Solubility insoluble in water Melting Point 287-290 °C
Formula C14H10O4S2 Boiling Point 493.1 °C at 760 mmHg
Molecular Weight 306.36 . Flash Point 252 °C
Transport Information Appearance off white to light yellow powder
Safety 26-36-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 119-80-2 (2,2'-Dithiosalicylic acid) Hazard Symbols IrritantXi
Synonyms

2, 2-Dithiobis[benzoic acid];Bis(o-carboxylphenyl) disulfide;Bis(2-carboxyphenyl) disulfide;Diphenyldisulfide-2,2-dicarboxylic acid;2,2-Dithiobis(benzoic acid);Benzoic acid, 2,2-dithiobis-;2,2-Dithiodi(benzoic acid);2-(2-carboxylatophenyl)disulfanylbenzoate;2-(2-carboxyphenyl)disulfanylbenzoic acid;Bis(o-carboxyphenyl) disulfide;2,2'-Dithiosalicy acid;Benzoic acid, 2,2-dithiodi-;2-[(2-Carboxyphenyl)disulfanyl]benzoic acid;2,2'-Dithio Dibenzoic Acid;2,2-Dithiosalicylic acid;

 

2,2'-Dithiosalicylic acid Synthetic route

147-93-3

Thiosalicylic acid

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With xenon difluoride In dichloromethane at 25℃;99%
With 1-oxa-2-azaspiro[2.5]octane In toluene99%
With polyvinylpolypyrrolidonium tribromide In ethanol at 20℃; for 1.5h; Green chemistry;99%
88-67-5

2-Iodobenzoic acid

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With nickel(II) chloride hexahydrate; morpholinium morpholine-1-carbodithioate; potassium hydroxide In water; ethylene glycol; N,N-dimethyl-formamide at 130℃;96%
With potassium sulfide; nickel(II) chloride hexahydrate; acetylacetone; potassium hydroxide In water; N,N-dimethyl-formamide at 110℃; for 24h;95%
88-65-3

2-bromobenzoic-acid

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With indium(III) oxide; ammonia; water; sulfur In ethanol at 60℃; Green chemistry;82%
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; sulfur In water at 80℃; for 48h; Inert atmosphere; Sealed tube; chemoselective reaction;
95-15-8

Benzo[b]thiophene

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With ozone; acetic acid at 16.84℃;26.7%
132-65-0

dibenzothiophene

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With ozone; acetic acid at 16.84℃;14%
19602-82-5

2,2'-dithiodibenzoic acid dichloride

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
bei laengerem Liegen an feuchter Luft;
493-57-2

benzo-[b]thiophene-2,3-dione

A

16807-21-9

1,2-benzisothiazole-3-carboxamide

B

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With ammonium hydroxide; dihydrogen peroxide
1677-27-6

3H-1,2-benzodithiol-3-one

141-52-6

sodium ethanolate

119-80-2

2,2'-dithiobenzoic acid

1677-27-6

3H-1,2-benzodithiol-3-one

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With sodium ethanolate
3354-42-5

3H-1,2-benzodithiole-3-thione

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

119-80-2

2,2'-dithiobenzoic acid

3354-42-5

3H-1,2-benzodithiole-3-thione

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With alkali
With ethanol; sodium
13993-58-3

4-chloro-3,5-diiodo-pyridine

64-17-5

ethanol

141-52-6

sodium ethanolate

147-93-3

Thiosalicylic acid

A

7153-08-4

4-hydroxy-3,5-diiodopyridine

B

4-ethoxy-3,5-diiodopyridine

C

119-80-2

2,2'-dithiobenzoic acid

D

2-(3,5-diiodo-[4]pyridylmercapto)-benzoic acid

784-62-3

1-thioflavone

141-52-6

sodium ethanolate

A

119-80-2

2,2'-dithiobenzoic acid

B

26824-02-2

1-(2-mercaptophenyl)ethan-1-one

C

147-93-3

Thiosalicylic acid

D

98-86-2

acetophenone

17333-86-7

o-Carboxybenzenediazonium

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With sodium disulfide
With sodium disulfide
623-11-0

1-methyl-4-nitrosobenzene

25803-71-8

2-[(2-oxo-2-phenylethyl)thio]-benzoic acid

119-80-2

2,2'-dithiobenzoic acid

13165-80-5

o-(hydroxysulfinyl)benzoic acid

A

632-25-7

2-sulfobenzoic acid

B

119-80-2

2,2'-dithiobenzoic acid

13165-80-5

o-(hydroxysulfinyl)benzoic acid

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride; water; tin(ll) chloride
118-92-3

anthranilic acid

119-80-2

2,2'-dithiobenzoic acid

109-72-8, 29786-93-4

n-butyllithium

60-29-7

diethyl ether

108-98-5

thiophenol

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
anschliessendes Behandeln mit festem CO2;
32147-20-9

(Z)-2-bromo-1,3-diphenylprop-2-en-1-one

147-93-3

Thiosalicylic acid

A

119-80-2

2,2'-dithiobenzoic acid

B

2-(1-benzoyl-2-phenyl-vinylmercapto)-benzoic acid

Conditions
ConditionsYield
With ethanol; sodium carbonate; acetone
147-93-3

Thiosalicylic acid

2032-35-1

Bromoacetaldehyde diethyl acetal

A

119-80-2

2,2'-dithiobenzoic acid

B

2-(2,2-diethoxy-ethylsulfanyl)-benzoic acid

Conditions
ConditionsYield
With ethanol; sodium acetate
109-72-8, 29786-93-4

n-butyllithium

60-29-7

diethyl ether

882-33-7

diphenyldisulfane

A

1126-80-3

(n-butylthio)benzene

B

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
anschliessendes Behandeln mit festem CO2;
333-20-0

potassium thioacyanate

88-65-3

2-bromobenzoic-acid

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; copper
36665-23-3

benzo[d]-1,3-oxathiin-4-one 1-oxide

A

50-00-0

formaldehyd

B

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 110℃; for 10h;
124-38-9

carbon dioxide

108-98-5

thiophenol

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With n-butyllithium 1.) hexane, r.t., overnight, 2.) r.t.; Yield given. Multistep reaction;
118-91-2

ortho-chlorobenzoic acid

A

119-80-2

2,2'-dithiobenzoic acid

B

147-93-3

Thiosalicylic acid

C

65-85-0

benzoic acid

D

69-72-7

salicylic acid

Conditions
ConditionsYield
With sulfur In melt at 270℃; Product distribution; effect of various molten salts, amount of sulfur, molar ratio of sulfur to molten salts, composition of molten salt and various mercaptylation agents;
124-38-9

carbon dioxide

622-38-8

Ethyl phenyl sulfide

629-19-6

Dipropyl disulfide

119-80-2

2,2'-dithiobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride; n-butyllithium Yield given. Multistep reaction;
7647-01-0

hydrogenchloride

1012-97-1

1,1-dioxo-2,3-dihydro-1λ6-benzo[e][1,2,3]thiadiazin-4-one-hydrazone

119-80-2

2,2'-dithiobenzoic acid

3354-42-5

3H-1,2-benzodithiole-3-thione

natrium carbonate

natrium carbonate

119-80-2

2,2'-dithiobenzoic acid

67-56-1

methanol

119-80-2

2,2'-dithiobenzoic acid

5459-63-2

bis[2-(methoxycarbonyl)phenyl]disulfide

Conditions
ConditionsYield
With triethylamine for 18h;100%
Stage #1: 2,2'-dithiobenzoic acid With thionyl chloride for 2h; Reflux;
Stage #2: methanol With triethylamine for 2h; Reflux;
92%
With sulfuric acid for 24h; Reflux;91%
122-88-3

4-Chlorophenoxyacetic acid

119-80-2

2,2'-dithiobenzoic acid

(1-chloro-9-oxo-9H-thioxanthen-4-yloxy)-acetic acid

Conditions
ConditionsYield
99.5%
With sulfuric acid at 10 - 40℃; for 4 - 5h;73.8%
With sulfuric acid at -5 - 50℃; for 58h;53.8%
With sulfuric acid at -5 - 50℃; for 58h;
With sulfuric acid at 20℃; for 2h;
119-80-2

2,2'-dithiobenzoic acid

106-48-9

4-chloro-phenol

59803-22-4

1-chloro-4-hydroxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With sulfuric acid at -5 - 70℃; for 21h;99%
Stage #1: 2,2'-dithiobenzoic acid With sulfuric acid In water for 0.5h;
Stage #2: 4-chloro-phenol In water at 40 - 100℃; for 5h;
77.9%
In sulfuric acid69.7%
119-80-2

2,2'-dithiobenzoic acid

3950-02-5

2-chlorosulfenylbenzoyl chloride

Conditions
ConditionsYield
With chlorine; sulfur In 1,1,2,2-tetrachloroethylene at 70℃; Temperature; Solvent;99%
Stage #1: 2,2'-dithiobenzoic acid With thionyl chloride; 1-methyl-pyrrolidin-2-one at 80℃; Heating / reflux;
Stage #2: With sulfuryl dichloride at 50℃; for 0.5h;
93%
With thionyl chloride; chlorine; N,N-dimethyl-formamide 1.) 1,2-dichloroethane, reflux, 1 h, 2.) 10 deg C, 20 min; Multistep reaction;
98-82-8

Isopropylbenzene

119-80-2

2,2'-dithiobenzoic acid

5495-84-1

2-isopropyl-9H-thioxanthen-9-one

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 0.5h;99%
With methanesulfonic acid; zinc In chlorobenzene at 115℃;89.5%
119-80-2

2,2'-dithiobenzoic acid

19602-82-5

2,2'-dithiodibenzoic acid dichloride

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide; toluene at 82℃; for 20h;97%
With thionyl chloride In N,N-dimethyl-formamide for 4h; Reflux;95%
With thionyl chloride; N,N-dimethyl-formamide In toluene at 82℃; for 20h;91.3%
120-72-9

indole

119-80-2

2,2'-dithiobenzoic acid

81471-22-9

2-((1H-indol-3-yl)thio)benzoic acid

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 130℃; for 48h; Reagent/catalyst; Solvent; Temperature; Green chemistry;95%
Stage #1: 2,2'-dithiobenzoic acid With ammonium peroxydisulfate In methanol at 70℃; for 3h;
Stage #2: indole In methanol at 20 - 70℃;
46%
119-80-2

2,2'-dithiobenzoic acid

3354-42-5

3H-1,2-benzodithiole-3-thione

Conditions
ConditionsYield
With tetraphosphorus decasulfide In 1,4-dioxane for 48h; Inert atmosphere; Reflux;93%
With phosphorous (V) sulfide; xylene
With Lawessons reagent In benzene Heating; Yield given;
With tetraphosphorus decasulfide In pyridine for 1h; Heating;
With pyridine; tetraphosphorus decasulfide
119-80-2

2,2'-dithiobenzoic acid

C14H10O5S2

Conditions
ConditionsYield
With dihydrogen peroxide In neat (no solvent) at 20℃; for 0.5h; Reagent/catalyst; chemoselective reaction;92%
With dihydrogen peroxide In neat (no solvent) at 20℃; for 0.5h; Reagent/catalyst; Green chemistry;92%
1076-38-6

4-hydroxy[1]benzopyran-2-one

119-80-2

2,2'-dithiobenzoic acid

3-(2-carboxyphenylthio)-4-hydroxy-coumarin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90 - 95℃; for 5h; Substitution;91%
399-51-9

6-fluoro-1H-indole

119-80-2

2,2'-dithiobenzoic acid

6-fluoro-3-[(2-carboxyphenyl)thio]-1H-indole

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 130℃; Green chemistry;91%
141-93-5

m-diethylbenzene

119-80-2

2,2'-dithiobenzoic acid

82799-44-8

2,4‐diethyl‐9H‐thioxanthene‐9‐one

Conditions
ConditionsYield
With sulfuric acid at 0 - 65℃; for 6h; Reagent/catalyst;90.2%
With aluminum oxide; iron; toluene-4-sulfonic acid at 130℃; Reagent/catalyst;89%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

119-80-2

2,2'-dithiobenzoic acid

497262-13-2

N,N'-disuccinimidyl-2,2'-dithiosalicylate

Conditions
ConditionsYield
With diisopropyl-carbodiimide In tetrahydrofuran; isopropyl alcohol at 20℃; for 4h;89%
With diisopropyl-carbodiimide In tetrahydrofuran; isopropyl alcohol at 25℃; for 4h;89%
With diisopropyl-carbodiimide In tetrahydrofuran; isopropyl alcohol at 25℃;
399-52-0

5-fluoro-1H-indole

119-80-2

2,2'-dithiobenzoic acid

C15H10FNO2S

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 130℃; Green chemistry;89%
1677-46-9

4-hydroxy-1-methyl-2(1H)-quinolone

119-80-2

2,2'-dithiobenzoic acid

3-(2-carboxyphenylthio)-4-hydroxy-1-methyl-2(1H)-quinolone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90 - 95℃; for 5h; Substitution;87%
1006-94-6

5-methoxylindole

119-80-2

2,2'-dithiobenzoic acid

5-methoxyl-3-[(2-carboxyphenyl)thio]-1H-indole

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 130℃; Green chemistry;86%
119-80-2

2,2'-dithiobenzoic acid

147-93-3

Thiosalicylic acid

Conditions
ConditionsYield
With hydrogenchloride; hydrogen iodide; hypophosphorous acid for 3h; Heating;85%
With hydrogenchloride; diphenylphosphinopolystyrene In tetrahydrofuran for 7h; Heating;73%
With tin; acetic acid weiteres Reagens: konz. Salzsaeure;
100-97-0

hexamethylenetetramine

119-80-2

2,2'-dithiobenzoic acid

C14H10O4S2*C6H12N4

Conditions
ConditionsYield
In ethanol at 20℃; for 336000h;85%
387-44-0

7-fluoro-1H-indole

119-80-2

2,2'-dithiobenzoic acid

C15H10FNO2S

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 130℃; Green chemistry;85%
66-71-7

1,10-Phenanthroline

copper(II) choride dihydrate

119-80-2

2,2'-dithiobenzoic acid

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

diaqua(1,10-phenanthroline)copper(II) sulfate

B

[Cu(2,2'-thiodibenzoic acid)(1,10-phenanthroline)(H2O)]2*2H2O*2DMF

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; pH=7.2;A 85%
B 15%
119-80-2

2,2'-dithiobenzoic acid

63-74-1

sulfanilamide

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h;83%
387-43-9

4-fluoroindole

119-80-2

2,2'-dithiobenzoic acid

C15H10FNO2S

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 130℃; Green chemistry;83%
119-80-2

2,2'-dithiobenzoic acid

A

19602-82-5

2,2'-dithiodibenzoic acid dichloride

B

1-(2,4,6-trichlorophenyl)-3-(2-chloro-5-tetradecanamido)-4-{[2-(2,4-di-t-amylphenoxy)-butylcarbamoyl]-phenylthio}-5-pyrazolone

1-(2,4,6-trichlorophenyl)-3-(2-chloro-5-tetradecanamido)-4-{[2-(2,4-di-t-amylphenoxy)-butylcarbamoyl]-phenylthio}-5-pyrazolone

Conditions
ConditionsYield
With thionyl chloride In n-heptaneA 80%
B n/a

gadolinium(III) nitrate hexahydrate

copper(II) chloride hexahydrate

119-80-2

2,2'-dithiobenzoic acid

[Cu(II)3Gd(III)(μ3-OH)(μ3-SH)(sulfate)(water)3]n

Conditions
ConditionsYield
With N(CH2CH3)3 In water High Pressure; heating mixt. of gadolinium compd., copper compd., benzoic acid deriv., deionized water and triethylamine at 170°C for 72 h; cooling to room temp. at rate of 5°C/h, isolation of crystals, washing deionized water, elem. anal.;80%
119-80-2

2,2'-dithiobenzoic acid

122-59-8

2-phenoxyacetic acid

84434-05-9

2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid

Conditions
ConditionsYield
With sulfuric acid at 0 - 25℃; for 1h;76%
119-80-2

2,2'-dithiobenzoic acid

13515-97-4

methyl 2-aminopropanoate monohydrochloride

2,2'-dithiodibenzoyl bis-alanine methyl ester

Conditions
ConditionsYield
Stage #1: 2,2'-dithiobenzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.666667h; Reflux;
Stage #2: methyl 2-aminopropanoate monohydrochloride With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 48h;
76%
119-80-2

2,2'-dithiobenzoic acid

35190-71-7

1,2-bis(2-(hydroxymethyl)phenyl)disulfane

Conditions
ConditionsYield
With borane-THF; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 18h;75%
With sodium bis(2-methoxyethoxy)aluminium dihydride In benzene

2,2'-Dithiosalicylic acid Chemical Properties

 Molecule structure of 2,2'-Dithiodibenzoic acid (CAS NO.119-80-2):

IUPAC Name: 2-(2-Carboxyphenyl)disulfanylbenzoic acid 
Molecular Weight: 306.3568 g/mol
Molecular Formula: C14H10O4S2 
Density: 1.53 g/cm3 
Melting Point: 287-290 °C(lit.)
Boiling Point: 493.1 °C at 760 mmHg 
Flash Point: 252 °C
Index of Refraction: 1.735
Molar Refractivity: 80.04 cm3
Molar Volume: 199.3 cm3
Polarizability: 31.73×10-24 cm3
Surface Tension: 83.8 dyne/cm 
Enthalpy of Vaporization: 80.06 kJ/mol
Vapour Pressure: 1.54E-10 mmHg at 25 °C 
Water Solubility: insoluble
XLogP3-AA: 3.1
H-Bond Donor: 2
H-Bond Acceptor: 4
Rotatable Bond Count: 5
Exact Mass: 306.00205
MonoIsotopic Mass: 306.00205
Topological Polar Surface Area: 74.6
Heavy Atom Count: 20
Complexity: 327
Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)SSC2=CC=CC=C2C(=O)O
InChI: InChI=1S/C14H10O4S2/c15-13(16)9-5-1-3-7-11(9)19-20-12-8-4-2-6-10(12)14(17)18/h1-8H,(H,15,16)(H,17,18)
InChIKey: LBEMXJWGHIEXRA-UHFFFAOYSA-N
EINECS: 204-352-8
Product Categories: pharmacetical; organic acids

2,2'-Dithiosalicylic acid Uses

 2,2'-Dithiodibenzoic acid (CAS NO.119-80-2) is used for intermediates of medicine, dyes, fungicides, and photoinitiators.

2,2'-Dithiosalicylic acid Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 367mg/kg (367mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 284, 1971.

2,2'-Dithiosalicylic acid Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: DG9660000
Hazard Note: Harmful / irritant

2,2'-Dithiosalicylic acid Specification

 2,2'-Dithiodibenzoic acid (CAS NO.119-80-2) is also named as 2,2'-Dithiobis(benzoic acid) ; 2,2'-Dithiodibenzoesaeure ; 2,2'-Dithiodibenzoesaeure [German] ; 4-10-00-00279 (Beilstein Handbook Reference) ; AI3-15534 ; BRN 2221810 ; Bis(2-carboxyphenyl) disulfide ; Bis(o-carboxylphenyl) disulfide ; Bis(o-carboxyphenyl) disulfide ; Diphenyldisulfide-2,2'-dicarboxylic acid . 2,2'-Dithiodibenzoic acid is brown powder. 2,2'-Dithiodibenzoic acid is high toxic. It is flammable. It will produce toxic sulfur oxides fumes when buring. So the storage environment should be ventilate, low-temperature and dry. Keep 2,2'-Dithiodibenzoic acid separate from raw materials of food.

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