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Basic Information
CAS No.: 15139-21-6
Name: thionitrobenzoic acid
Article Data: 46
Molecular Structure:
Molecular Structure of 15139-21-6 (thionitrobenzoic acid)
Formula: C7H5NO4S
Molecular Weight: 199.187
Synonyms: 2-Nitro-5-mercaptobenzoicacid;2-Nitro-5-thiobenzoic acid;2-Nitro-5-thiolbenzoic acid;3-Carboxy-4-nitrobenzenethiol;5-Mercapto-2-nitrobenzoic acid;
Density: 1.575 g/cm3
Boiling Point: 419.2 °C at 760 mmHg
Flash Point: 207.4 °C
PSA: 121.92000
LogP: 2.10490
Synthetic route
69-78-3

5,5'-dithiobis-(2-nitrobenzoic acid)

15139-21-6

5-thio-2-nitrobenzoic acid

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol; water at 0 - 20℃;97%
With dithionite(2-); cetyltrimethylammonim bromide In water Kinetics; Equilibrium constant; further reagents, catalysts;
With 2-(N,N-dimethylamino)ethanol; 2-mercaptoethylamine hydrochloride In water at 25℃; for 1h; Yield given;

5,5’-dithiobis-(2-nitrobenzoic acid)

15139-21-6

5-thio-2-nitrobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride; 2-amino-2-hydroxymethyl-1,3-propanediol; diothiothreitol In water at 20℃; for 2h; pH=8;55%
69-78-3

5,5'-dithiobis-(2-nitrobenzoic acid)

A

15139-21-6

5-thio-2-nitrobenzoic acid

B

5-(2-Amino-2-carboxy-ethyldisulfanyl)-2-nitro-benzoic acid

Conditions
ConditionsYield
In water at 25℃; Rate constant; spectroscopic method, variation of the pH: the rate constant for the thiol-disulfide exchange (kSH) and for the thiolate ion-disulfide exchange (Ks-) as well as the activation energy were determined;
52-90-4

L-Cysteine

149997-68-2

5-(2-cyanoethyldithio)-2-nitrobenzoic acid

A

15139-21-6

5-thio-2-nitrobenzoic acid

B

(R)-2-Amino-3-(2-cyano-ethyldisulfanyl)-propionic acid

Conditions
ConditionsYield
With sodium phosphate buffer In ethanol Rate constant;
69-78-3

5,5'-dithiobis-(2-nitrobenzoic acid)

A

B

5-(2-Acetylamino-2-carboxy-ethyldisulfanyl)-2-nitro-benzoic acid

Conditions
ConditionsYield
In water at 25℃; Rate constant; spectroscopic method, variation of the pH: the rate constant for the thiol-disulfide exchange (kSH) and for the thiolate ion-disulfide exchange (Ks-) as well as the activation energy were determined;
52-66-4

DL-Penicillamin

69-78-3

5,5'-dithiobis-(2-nitrobenzoic acid)

A

15139-21-6

5-thio-2-nitrobenzoic acid

B

5-(2-Amino-2-carboxy-1,1-dimethyl-ethyldisulfanyl)-2-nitro-benzoic acid

Conditions
ConditionsYield
In water at 25℃; Rate constant; spectroscopic method, variation of the pH: the rate constant for the thiol-disulfide exchange (kSH) and for the thiolate ion-disulfide exchange (Ks-) as well as the activation energy were determined;
552-24-9

5,5’-dithiobis(2-nitrobenzoate)

A

15139-21-6

5-thio-2-nitrobenzoic acid

B

77874-90-9

3-carboxylate-4-nitrothiophenoxide ion

Conditions
ConditionsYield
With sodium dithionite; di-C18 vesicles; Tris buffer; potassium chloride at 25℃; Rate constant; also Di-C16 vesicles, also laced with varying ammounts cholesterol;
69-78-3

5,5'-dithiobis-(2-nitrobenzoic acid)

A

15139-21-6

5-thio-2-nitrobenzoic acid

B

5-(2-Amino-2-ethoxycarbonyl-ethyldisulfanyl)-2-nitro-benzoic acid

Conditions
ConditionsYield
In water at 25℃; Rate constant; spectroscopic method, variation of the pH: the rate constant for the thiol-disulfide exchange (kSH) and for the thiolate ion-disulfide exchange (Ks-) as well as the activation energy were determined;

5-(2-Cyano-ethylsulfanyl)-2-nitro-benzoic acid

A

15139-21-6

5-thio-2-nitrobenzoic acid

B

107-13-1

acrylonitrile

Conditions
ConditionsYield
hydroxide In water; dimethyl sulfoxide at 25℃; Rate constant; elimination, other base;

5-(1,2-Dicyano-ethylsulfanyl)-2-nitro-benzoic acid

A

15139-21-6

5-thio-2-nitrobenzoic acid

B

764-42-1

1,2-Dicyanoethylene

Conditions
ConditionsYield
piperidine In water; dimethyl sulfoxide at 25℃; Rate constant; elimination, other bases;
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Specification

The Thionitrobenzoic acid, with the CAS registry number 15139-21-6, is also known as 5-Mercapto-2-nitrobenzoate. This chemical's molecular formula is C7H5NO4S and molecular weight is 199.1839. Its systematic name is called 2-nitro-5-sulfanylbenzoic acid.

Physical properties of Thionitrobenzoic acid: (1)ACD/LogP: 2.30; (2)ACD/LogD (pH 5.5): -1.38; (3)ACD/LogD (pH 7.4): -1.84; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 5; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.682; (12)Molar Refractivity: 47.9 cm3; (13)Molar Volume: 126.4 cm3; (14)Surface Tension: 76.1 dyne/cm; (15)Density: 1.575 g/cm3; (16)Flash Point: 207.4 °C; (17)Enthalpy of Vaporization: 70.94 kJ/mol; (18)Boiling Point: 419.2 °C at 760 mmHg; (19)Vapour Pressure: 8.87E-08 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=[N+]([O-])c1c(cc(S)cc1)C(=O)O
(2)InChI: InChI=1/C7H5NO4S/c9-7(10)5-3-4(13)1-2-6(5)8(11)12/h1-3,13H,(H,9,10)
(3)InChIKey: GANZODCWZFAEGN-UHFFFAOYAP