Conditions | Yield |
---|---|
Stage #1: 2-Iodobenzoic acid With copper(l) iodide; potassium carbonate; sulfur In N,N-dimethyl-formamide at 90℃; for 12h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In N,N-dimethyl-formamide at 40℃; Inert atmosphere; Cooling with ice; | 88% |
Conditions | Yield |
---|---|
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; |
2-phenylbenzo[d]-1,3-oxathiin-4-one
sodium phenoxide
A
diphenyl 2,2'-disulfanediyldibenzoate
B
benzaldehyde
C
Thiosalicylic acid
Conditions | Yield |
---|---|
In benzene for 9h; Heating; | A 51% B n/a C n/a |
2-phenylbenzo[d]-1,3-oxathiin-4-one
sodium ethanolate
A
bis(2-ethoxycarbonylphenyl) disulfide
B
benzaldehyde
C
Thiosalicylic acid
Conditions | Yield |
---|---|
In benzene for 9h; Heating; | A 46% B n/a C n/a |
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; potassium thioacetate In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere; | A 27% B 10% |
2-thiocyanatobenzoic acid
Thiosalicylic acid
Conditions | Yield |
---|---|
With sodium sulfide |
Conditions | Yield |
---|---|
With acetic acid; zinc |
1-thioflavone
sodium ethanolate
A
2,2'-dithiobenzoic acid
B
1-(2-mercaptophenyl)ethan-1-one
C
Thiosalicylic acid
D
acetophenone
o-Carboxybenzenediazonium
Thiosalicylic acid
Conditions | Yield |
---|---|
With alkali polysulfide Behandeln der sodaalkalischen Loesung mit Eisen oder Zinkstaub; |
Conditions | Yield |
---|---|
Irradiation; |
3-(3-oxo-3H-benzo[b]thiophen-2-ylidene)-1,3-dihydro-indol-2-one
sodium ethanolate
A
3-formyloxindole
B
Thiosalicylic acid
2-benzoylimino-benzo[b]thiophen-3-one
Thiosalicylic acid
o-(hydroxysulfinyl)benzoic acid
Thiosalicylic acid
Conditions | Yield |
---|---|
With water; zinc weiteres Reagens: Salzsaeure; | |
With ethanol; zinc weiteres Reagens: Salzsaeure; |
2-but-2t-enylmercapto-benzoic acid
B
2-Ethyl-2,3-dihydrobenzothiophene
C
Thiosalicylic acid
Conditions | Yield |
---|---|
at 250℃; |
2-(1,3-dioxo-indan-2-ylidene)-benzo[b]thiophen-3-one
A
2-formylindane-1,3-dione
B
Thiosalicylic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water; sodium nitrite Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge; |
tetrachloromethane
thiophenol
A
Thiosalicylic acid
B
diphenyldisulfane
Conditions | Yield |
---|---|
With potassium hydroxide at 100 - 110℃; im Rohr; |
Conditions | Yield |
---|---|
Irradiation; |
Conditions | Yield |
---|---|
hydroxide In water; dimethyl sulfoxide at 25℃; Rate constant; elimination; |
Conditions | Yield |
---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine 1.) cyclohexane, hexane, 0 deg C, 30 min, r.t., 22 h, 2.) cyclohexane, 0 deg C, 30 min, r.t., 24 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 30℃; Kinetics; Rate constant; Mechanism; other temperature, other pH; |
Thiosalicylic acid
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 30℃; further temperature; |
Thiosalicylic acid
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 30℃; further temperature; | |
With sodium hydroxide In 1,4-dioxane; water at 30℃; Kinetics; Rate constant; Mechanism; other temperature, other pH; |
Conditions | Yield |
---|---|
2-amino-2-hydroxymethyl-1,3-propanediol In water; dimethyl sulfoxide at 25℃; Rate constant; other base; |
Thiosalicylic acid
Conditions | Yield |
---|---|
With buffer (pH=11) at 20℃; | |
With buffer (pH=11) at 20℃; Rate constant; |
ortho-chlorobenzoic acid
A
2,2'-dithiobenzoic acid
B
Thiosalicylic acid
C
benzoic acid
D
salicylic acid
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; sulfur 1.) 270 deg C, NaOH-KOH melt, 3 min.; 2.) water; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; | |
With hydrogenchloride; sodium disulfide; acetic acid; zinc; sodium nitrite Multistep reaction; | |
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water 1.2: 80 °C 2.1: hydrogenchloride; sodium hydroxide; sodium dithionite / water View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 20℃; for 15h; | 100% |
With sodium hydroxide In ethanol at 20℃; for 15h; | 100% |
With sodium hydroxide In ethanol; water for 72h; | 98% |
Conditions | Yield |
---|---|
With boric acid In water at 100℃; for 0.25h; Heating / reflux; | 100% |
Conditions | Yield |
---|---|
With sulfuric acid In toluene for 6h; Heating / reflux; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide; copper In water Heating; | 100% |
Thiosalicylic acid
p-methoxybenzyl chloride
2-(4-methoxy-benzylsulfanyl)-benzoic acid
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 10h; Heating; | 99.7% |
Thiosalicylic acid
α-bromoacetophenone
2-[(2-oxo-2-phenylethyl)thio]-benzoic acid
Conditions | Yield |
---|---|
With sodium acetate In methanol at 20℃; for 1h; | 99.1% |
With potassium hydroxide In ethanol for 2h; Heating; | 39.9% |
Stage #1: Thiosalicylic acid; α-bromoacetophenone With potassium hydroxide In ethanol for 2h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In ethanol; water Cooling with ice; |
Conditions | Yield |
---|---|
With xenon difluoride In dichloromethane at 25℃; | 99% |
With 1-oxa-2-azaspiro[2.5]octane In toluene | 99% |
With polyvinylpolypyrrolidonium tribromide In ethanol at 20℃; for 1.5h; Green chemistry; | 99% |
Thiosalicylic acid
1-Bromo-2-bromomethyl-benzene
2‑(2‑bromobenzylsulfanyl)benzoic acid
Conditions | Yield |
---|---|
With potassium carbonate In water; acetone for 8h; Reflux; Inert atmosphere; | 99% |
With potassium hydroxide In ethanol; water at 50 - 60℃; for 4h; | 8 g |
Conditions | Yield |
---|---|
With sodium hydroxide for 1h; Ambient temperature; | 99% |
3-phenyl-5-chloro-4-chloromethyl-1-methyl-1H-pyrazole
Thiosalicylic acid
2-(3-phenyl-5-chloro-1-methyl-1H-pyrazol-4-ylmethylsulphanyl)benzoic acid
Conditions | Yield |
---|---|
Stage #1: 3-phenyl-5-chloro-4-chloromethyl-1-methyl-1H-pyrazole; Thiosalicylic acid With potassium carbonate In ethanol; water for 2h; Heating / reflux; Stage #2: With hydrogenchloride In water pH=2; | 99% |
Conditions | Yield |
---|---|
Stage #1: Thiosalicylic acid With sodium hydroxide In methanol; water at 20℃; for 0.333333h; Stage #2: isopropyl bromide In methanol; water at 70℃; | 99% |
With potassium carbonate In ethanol at 78℃; for 12h; | 46% |
With potassium hydroxide In ethanol for 6h; | 30% |
N-Benzylidenemethylamine
Thiosalicylic acid
3-methyl-2-phenyl-2H-benzo[e][1,3]thiazin-4(3H)-one
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In toluene at 90℃; for 20h; Inert atmosphere; | 99% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In toluene at 90℃; for 20h; | 99% |
p-nitrobenzene iodide
Thiosalicylic acid
2-((4-nitrophenyl)thio)benzoic acid
Conditions | Yield |
---|---|
With [Ce((L)-proline)2]2(oxalate); potassium carbonate In ethanol at 80℃; for 6h; | 99% |
Thiosalicylic acid
Conditions | Yield |
---|---|
With chlorine | 98.5% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In xylene | 98% |
2,4-dichloro-N-hydroxybenzenecarboximidoyl chloride
Thiosalicylic acid
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 2h; | 98% |
With potassium carbonate In acetone at 25℃; for 1h; | 97% |
Stage #1: Thiosalicylic acid With potassium carbonate In acetone Stage #2: methyl iodide In acetone at 20℃; for 1h; | 96% |
Conditions | Yield |
---|---|
With potassium carbonate; copper In water at 130 - 140℃; for 3h; Product distribution / selectivity; Ullmann Condensation; | 98% |
With copper; potassium carbonate In water at 130 - 140℃; for 3h; | 96% |
With potassium carbonate In water | 52.8 g (97%) |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h; | 98% |
With lithium aluminium tetrahydride | 97% |
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 1h; | 96% |
Aliquat 336
Thiosalicylic acid
tricaprylmethylammonium thiosalicylate
Conditions | Yield |
---|---|
With sodium hydroxide at 60℃; for 4h; | 98% |
With sodium hydroxide In water at 40℃; for 4h; Inert atmosphere; | 98% |
1,3-bis-(diphenylphosphino)propane
nickel(II) acetate tetrahydrate
Thiosalicylic acid
[Ni(SC6H4CO2)(C27H26P2)]
Conditions | Yield |
---|---|
With pyridine In methanol dissoln. of the Ni salt and the ligand in MeOH with warming, addn. of thiosalicylic acid, then pyridine, short reflux; filtration, washing (cold MeOH; Et2O), drying, recrystn. (CH2Cl2/Et2O); elem. anal.; | 98% |
pyridine
dichloro( 1,5-cyclooctadiene)platinum(ll)
sodium tetraphenyl borate
Thiosalicylic acid
triphenylphosphine
[(triphenylphosphine)2Pt(thiosalicylate)...pyridinium][tetraphenylborate]
Conditions | Yield |
---|---|
In methanol mixt. (PtCl2(cod)), PPh3, thiosalicylic acid, and pyridine in MeOH was heated to reflux for 10 min, Na(BPh4) was added to refluxing soln.; elem. anal.; | 98% |
Conditions | Yield |
---|---|
Stage #1: tris-(trifluoroacetylacetonato)iron(III); Thiosalicylic acid In ethylene glycol at 120℃; Inert atmosphere; Stage #2: With hydrogenchloride In water; ethylene glycol at 20℃; Inert atmosphere; | 98% |
2-ethynylpyridine
Thiosalicylic acid
2-(pyridin-2-ylmethyl)-4H-3,1-benzoxathiin-4-one
Conditions | Yield |
---|---|
With palladium diacetate In toluene at 120℃; for 1h; Inert atmosphere; regioselective reaction; | 98% |
Conditions | Yield |
---|---|
Stage #1: Thiosalicylic acid With trichloroisocyanuric acid In acetonitrile at -20℃; Green chemistry; Stage #2: 3-mercaptopropionic acid In acetonitrile at -20℃; for 0.0833333h; Green chemistry; | 98% |
With trichloroisocyanuric acid In acetonitrile at -20℃; for 0.0833333h; | 97.8% |
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; iron(II) acetylacetonate In toluene at 120℃; for 16h; Inert atmosphere; Glovebox; | 98% |
With potassium phosphate In toluene at 110℃; for 20h; Inert atmosphere; Schlenk technique; Green chemistry; | 90% |
1-(tert-butyl)-4-(3,3,3-trifluoroprop-1-yn-1-yl)-benzene
Thiosalicylic acid
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; iron(II) acetylacetonate In toluene at 120℃; for 16h; Inert atmosphere; Glovebox; | 98% |
Conditions | Yield |
---|---|
With sodium acetate In methanol at 23℃; for 0.5h; | 98% |
With sodium acetate In methanol at 23℃; for 0.5h; |
2-Mercaptopyridine
Thiosalicylic acid
2-(pyridin-2-yl-disulfanyl) benzoic acid
Conditions | Yield |
---|---|
With thionyl chloride | 98% |
With thionyl chloride In chloroform at 20℃; for 1h; | 82.4% |
Conditions | Yield |
---|---|
Stage #1: Thiosalicylic acid With sodium hydroxide In water Stage #2: mercury dichloride In water at 20℃; for 3h; | 98% |
The IUPAC name of o-Mercaptobenzoic acid is 2-sulfanylbenzoic acid. With the CAS registry number 147-93-3, it is also named as 2-Thiosalicylic acid; Benzoic acid, 2-mercapto-. The product's categories are aromatic carboxylic acids, amides, anilides, anhydrides & salts; phenol & thiophenol & mercaptan; metal isotopes; sulfur & selenium compounds. It is white to light yellow crystal powder which is soluble in water, ethanol and diethyl ether, and slightly soluble in DMSO and ligroin. And it is sensitive to air and light. In addition, o-Mercaptobenzoic acid is obtained by the reaction of halogenbenzoicacid and sulfhydrate in the presence of copper catalyst.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.39; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.12; (4)ACD/LogD (pH 7.4): -0.79; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.47; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.641; (13)Molar Refractivity: 41.35 cm3; (14)Molar Volume: 114.5 cm3; (15)Polarizability: 16.39×10-24 cm3; (16)Surface Tension: 59.2 dyne/cm; (17)Enthalpy of Vaporization: 56.87 kJ/mol; (18)Vapour Pressure: 0.000563 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Tautomer Count: 4; (21)Exact Mass: 154.00885; (22)MonoIsotopic Mass: 154.00885; (23)Topological Polar Surface Area: 38.3; (24)Heavy Atom Count: 10; (25)Complexity: 136.
Uses of o-Mercaptobenzoic acid: It is used as intermediate in organic synthesis, medicine and dye. And it is also a trapping agent used in the desulfenylation of 3-indolyl sulfides. Furthermore, this chemical is prepared for the reagent for determining iron.
When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. And it is also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES: O=C(O)c1ccccc1S;
2. InChI: InChI=1/C7H6O2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H,(H,8,9).
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 50mg/kg (50mg/kg) | National Technical Information Service. Vol. AD277-689, |
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