4875-10-9

Basic information

• Product Name: 2-NITROTHIOPHENOL
• Synonyms: 2-NITROTHIOPHENOL;2-Nitro-benzenethiol;o-Nitrothiophenol;o-Nitromercaptobenzene;2-Nitrobenzene-1-thiol;2-Nitrobenzenethiol, 2-Sulphanylnitrobenzene, 2-Thionitrobenzene
• CAS NO: 4875-10-9
• Molecular Formula: C₆H₅NO₂S
• Molecular Weight: 155.17
• EINECS: 225-483-7
• Mol File: 4875-10-9.mol
• Article Data: 26

Chemical Properties

• Melting Point: 56 °C
• Boiling Point: 262.5°Cat760mmHg
• Flash Point: 112.6°C
• Appearance: /
• Density: 1.362g/cm³
• Vapor Pressure: 0.0177mmHg at 25°C
• Refractive Index: 1.638
• PKA: 5.10±0.43(Predicted)
• CAS DataBase Reference: 2-NITROTHIOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROTHIOPHENOL(4875-10-9)
• EPA Substance Registry System: 2-NITROTHIOPHENOL(4875-10-9)

Safety Data

• Hazardous Substances Data: 4875-10-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 498, 1984 DOI: 10.1055/s-1984-30880

InChI:InChI=1/C6H5NO2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H

Synthetic route

bis(2-nitrophenyl)disulfide (1155-00-6) → 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran	100%
With triisopropoxyborohydride In tetrahydrofuran at 0℃; for 0.25h;	92%
With triphenylphosphine; 2-hydroxyethanethiol In tetrahydrofuran; water at 50℃; for 21h; Inert atmosphere;	90%

bis(2-nitrophenyl)disulfide (1155-00-6) → 2-nitrothiophenol (4875-10-9) + 2-amino-benzenethiol (137-07-5)

Conditions	Yield
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.5h; Reduction;	A 10% B 90%
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.166667h; Reduction;	A 80% B 20%

2-Chloronitrobenzene (88-73-3) → 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With sodium sulfide In N,N-dimethyl-formamide for 62h; Ambient temperature;	87%
With thiourea In ethanol Heating;	60%
With ethanol; sodium disulfide

4-o-nitrophenylthio-1,2-naphthoquinone (108732-56-5) → 2-Hydroxy-1,4-naphthoquinone (83-72-7) + 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With sodium hydroxide In ethanol; water for 0.0333333h;	A 80% B n/a

sodium sulfide (Na2 S.9H2 O) + 2-Chloronitrobenzene (88-73-3) → 2-nitrothiophenol (4875-10-9)

Conditions	Yield
In hydrogenchloride	61%

2-Chloronitrobenzene (88-73-3) → bis(2-nitrophenyl)disulfide (1155-00-6) + 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With sodium sulfide In N,N-dimethyl-formamide for 62h; Ambient temperature;	A 60% B 25%
With sodium sulfide In dimethyl sulfoxide at 50℃; for 0.5h; Product distribution; further reagents, further solvent, further substituted o-chloronitrobenzenes, further times and temp.;	A 10% B 50%

bis(2-nitrophenyl)disulfide (1155-00-6) + ethanol (64-17-5) + glucose (50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5) + furan-2,3,5(4H)-trione pyridine (1:1) → 2-nitrothiophenol (4875-10-9)

methanol (67-56-1) + bis(phenylsulfonyl)methane (3406-02-8) + sodium methylate (124-41-4) → 2-nitrothiophenol (4875-10-9) + Bis(phenylsulfonyl)(phenylthio)methane (73622-50-1)

Conditions	Yield
anschliessendes Behandeln mit <2-Nitro-phenyl>-phenyl-disulfid;

ethanol (64-17-5) + (2-nitro-phenyl)-phenyl disulfide (28215-02-3) + potassium thiophenolate (3111-52-2) → bis(2-nitrophenyl)disulfide (1155-00-6) + 2-nitrothiophenol (4875-10-9) + diphenyldisulfane (882-33-7)

2-nitrobenzenesulfenyl bromide (22024-99-3) → 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With phosphorus tribromide Verduennen mit Aether und anschliessendes Versetzen mit Wasser;

2-(2-nitro-phenylsulfanyl)-1-phenyl-ethanone (20940-09-4) + sodium methylate (124-41-4) → 2-benzoylbenzothiazole (1629-75-0) + 2-nitrothiophenol (4875-10-9) + benzoic acid (65-85-0)

(2-nitro-phenyl)-phenyl disulfide (28215-02-3) → 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With ethanol; potassium thiophenolate

2-nitrobenzenesulfenyl chloride (7669-54-7) → 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With DL-thiomalic acid; acetic acid Erwaermen des Reaktionsprodukts mit Natriumcyanid und wss. Alkalilauge;
Multi-step reaction with 2 steps 1: diethyl ether 2: potassium thiophenolate; alcohol View Scheme

1,2-Dinitrobenzene (528-29-0) → 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With methanol; sodium hydrogensulfide

2-(2-nitro-phenylsulfanyl)-1-phenyl-ethanone (20940-09-4) + potassium tert-butylate (865-47-4) + tert-butyl alcohol (75-65-0) → 2-benzoylbenzothiazole (1629-75-0) + 2-nitrothiophenol (4875-10-9) + benzoic acid (65-85-0)

2-Nitrobenzenesulfonyl chloride (1694-92-4) → 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With sulfuric acid; zinc at 10℃;

[Dimethylamino-(2-nitro-phenylsulfanyl)-methylene]-dimethyl-ammonium; iodide → 2-nitrothiophenol (4875-10-9) + tetramethylurea (632-22-4)

Conditions	Yield
at 20℃; Rate constant; pH=11;

(2-nitro-phenylsulfanyl)-acetic acid (6375-65-1) → 2-nitrothiophenol (4875-10-9) + Glyoxilic acid (298-12-4)

Conditions	Yield
With perchloric acid; sodium perborate; acetic acid at 24.9℃; Rate constant; Thermodynamic data; Mechanism; var. temp., ΔH(excit.), ΔS(excit.);

(2-nitro-phenylsulfanyl)-acetic acid (6375-65-1) → 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With perchloric acid; pyridinium chlorochromate In water; acetic acid at 24.85 - 44.85℃; Kinetics; Oxidation;

1,2-Dinitrobenzene (528-29-0) + Na2S → 2-nitrothiophenol (4875-10-9)

ethanol (64-17-5) + 2-Chloronitrobenzene (88-73-3) + sodium disulfide → bis(2-nitrophenyl)disulfide (1155-00-6) + 2-nitrothiophenol (4875-10-9)

methanol (67-56-1) + 1,2-Dinitrobenzene (528-29-0) + NaHS → bis(2-nitrophenyl)disulfide (1155-00-6) + bis-(2-nitro-phenyl)-sulfide (22100-66-9) + 2-nitrothiophenol (4875-10-9)

water (7732-18-5) + 2-Chloronitrobenzene (88-73-3) + sodium sulfide → bis-(2-nitro-phenyl)-sulfide (22100-66-9) + 2-nitrothiophenol (4875-10-9) + 2-amino-benzenethiol (137-07-5) + 2-Chloroaniline (95-51-2)

2-Chloronitrobenzene (88-73-3) + furan-2,3,5(4H)-trione pyridine (1:1) + sodium sulfide → bis-(2-nitro-phenyl)-sulfide (22100-66-9) + 2-nitrothiophenol (4875-10-9) + 2-amino-benzenethiol (137-07-5) + 2-Chloroaniline (95-51-2)

2-nitrobenzenesulfenyl bromide (22024-99-3) + phosphorus tribromide (7789-60-8) → 2-nitrothiophenol (4875-10-9)

Conditions	Yield
anschliessendes Verduennen mit Aether und Versetzen mit Wasser;

sodium-salt of thiosulfuric acid S-<2-nitro-phenyl ester> → 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With hydrogenchloride

2-nitro-benzene-sulfonic acid-(1)-bromide → bis(2-nitrophenyl)disulfide (1155-00-6) + 2-nitrothiophenol (4875-10-9)

Conditions	Yield
With phosphorus tribromide Behandeln des in Aether geloesten Reaktionsgemisches mit Wasser;

2-(2-nitro-phenylsulfanyl)-1-phenyl-ethanone (20940-09-4) + methanol.KOH → 2-benzoylbenzothiazole (1629-75-0) + 2-nitrothiophenol (4875-10-9) + benzoic acid (65-85-0)

2-(2-nitro-phenylsulfanyl)-1-phenyl-ethanone (20940-09-4) + methanol.Na2CO3 → 2-benzoylbenzothiazole (1629-75-0) + 2-nitrothiophenol (4875-10-9) + benzoic acid (65-85-0)

1-Bromopentane (110-53-2) + 2-nitrothiophenol (4875-10-9) → (2-nitrophenyl) (pentyl) sulfane (76697-40-0)

Conditions	Yield
With sodium hydroxide In ethanol 1.) 15 min 2.) reflux, 14 h;	99.1%

2-nitrothiophenol (4875-10-9) + methyl 3-bromo-2,6-dinitro-5-methoxybenzoate (56709-74-1) → methyl 2-nitro-3,6-di(2-nitrophenylthio)-5-methoxybenzoate (75355-04-3)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 10℃; for 0.25h;	99%

2-nitrothiophenol (4875-10-9) + methyl 3-bromo-2,6-dinitro-5-methoxy-4-methylbenzoate (67973-31-3) → methyl 2-nitro-3,6-di(2-nitrophenylthio)-5-methoxy-4-methylbenzoate (75355-07-6)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 10℃; for 0.25h;	99%

2-nitrothiophenol (4875-10-9) + C13H17BrO2 (1202041-29-9) → benzyl 5-(2-nitrophenylthio)hexanoate (1202041-20-0)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone at 56℃;	99%

1-(4-nitrophenylthio)-6-bromo-hexane + 2-nitrothiophenol (4875-10-9) → 1-(6-(4-nitrophenylthio)hexylthio)-2-nitrobenzene (1202041-25-5)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone at 56℃;	98%

2-nitrothiophenol (4875-10-9) + N-ethyl-N-phenylamine (103-69-5) → 2-Amino-N-ethyl-N-phenyl-benzenesulfonamide (81-10-7)

Conditions	Yield
In 1,4-dioxane at 87℃; Rate constant;	97.8%
In 1,4-dioxane at 87℃;	97.8%

2-nitrothiophenol (4875-10-9) + (S)-2-[(1R,3S,4aR,5R,8aS)-3-(tert-Butyl-diphenyl-silanyloxy)-5-((R)-1-methanesulfonyloxymethyl-2-methyl-propyl)-7-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl]-propionic acid (831235-46-2) → (S)-2-{(1R,3S,4aR,5R,8aS)-3-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-5-[(R)-2-methyl-1-(2-nitro-phenylsulfanylmethyl)-propyl]-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl}-propionic acid (831235-51-9)

Conditions	Yield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 55℃; for 8h;	97%

2-nitrothiophenol (4875-10-9) → bis(2-nitrophenyl)disulfide (1155-00-6)

Conditions	Yield
With water; dihydrogen peroxide In various solvent(s) at 20℃; for 0.166667h; Oxidation; Dimerization;	96%
With sodium hydroxide; iodine for 6h; Heating;	90%
With bipyridinium hydrobromide perbromide In acetonitrile at 20℃; for 0.25h;	90%

2-nitrothiophenol (4875-10-9) + benzyl chloride (100-44-7) → 1-(benzylsulfanyl)-2-nitrobenzene (22057-44-9)

Conditions	Yield
With sodium hydroxide In ethanol 1.) 15 min 2.) reflux, 14 h;	95.2%
With C40H30Cl2N2NiO2S2; sodium hydroxide In N,N-dimethyl-formamide at 70℃; for 1h;	95%
With alkali

2-nitrothiophenol (4875-10-9) + α-bromoacetophenone (70-11-1) → 2-(2-nitro-phenylsulfanyl)-1-phenyl-ethanone (20940-09-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;	95%
With sodium methylate In methanol	73%
With sodium carbonate

2-[2-(chloroethoxy)ethoxy]ethanol (5197-62-6) + 2-nitrothiophenol (4875-10-9) → 8-[(2-nitrophenylthio)]-3,6-dioxaoctanol (366470-09-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 6h; Heating;	95%

2-nitrothiophenol (4875-10-9) + (2S)-2-benzyloxycarbonylamino-4-bromo-butyric acid methyl ester (15159-67-8) → benzyl (S)-1-(methoxycarbonyl)-3-(2-nitrophenylthio)propylcarbamate (1187361-39-2)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone at 90℃; Sealed tube;	94.9%

2-nitrothiophenol (4875-10-9) + 1-Chloro-2-propanol (127-00-4) → bis[β-(2-nitrophenylthio)-α-methyl-ethyl]-terephthalate + 1-(2-nitro-phenylsulfanyl)-propan-2-ol (28097-57-6)

Conditions	Yield
With sodium hydroxide In water	A n/a B 94.8%

2-nitrothiophenol (4875-10-9) + benzaldehyde (100-52-7) → 2-Phenylbenzothiazole (883-93-2)

Conditions	Yield
Stage #1: o-nitrothiophenol; benzaldehyde In 1,4-dioxane; water at 90℃; for 0.0833333h; Stage #2: With formic acid In 1,4-dioxane; water at 90℃; for 8h; Temperature; Sealed tube;	94%

1-bromo-hexane (111-25-1) + 2-nitrothiophenol (4875-10-9) → Hexyl-(2-nitrophenyl)-sulfid (76697-41-1)

Conditions	Yield
With sodium hydroxide In ethanol 1.) 15 min 2.) reflux, 14 h;	93.5%

2-nitrothiophenol (4875-10-9) + benzyl 3-bromo-2,6-dinitro-5-benzyloxybenzoate (67973-25-5) → benzyl 2-nitro-3,6-di(2-nitrophenylthio)-5-benzyloxybenzoate (75355-08-7)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 10℃; for 0.25h;	93%

2-nitrothiophenol (4875-10-9) + 1-bromo-11-(phenylthio)undecane (148773-54-0) → 1-(11-(2-nitrophenylthio)undecylthio)benzene (1202041-22-2)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone at 56℃;	93%

Cyclopentyl bromide (137-43-9) + 2-nitrothiophenol (4875-10-9) → Cyclopentyl-(2-nitrophenyl)-sulfid (77053-23-7)

Conditions	Yield
With sodium hydroxide In ethanol 1.) 15 min 2.) reflux, 14 h;	92.7%

2-nitrothiophenol (4875-10-9) + methyl (3,4,5-tri-O-acetyl-β-D-arabino-hex-2-ulopyranosyl)onate bromide (225937-33-7) → methyl 2-S-(2-nitrophenyl)-3,4,5-tri-O-acetyl-α-D-arabino-2-hexulopyranosonate (225794-00-3)

Conditions	Yield
With potassium carbonate In acetone for 2h; Heating;	92%

2-nitrothiophenol (4875-10-9) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 2-<2-<2-nitrophenyl(thio)>ethoxy>ethanol (240131-55-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 6h; Heating;	92%

2-nitrothiophenol (4875-10-9) + heptakis(6-bromo-6-deoxy)-β-cyclodextrin (53784-83-1) → Heptakis-[6-thio(2'-nitrophenyl)-6-deoxy]-β-cyclodextrin

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide Ambient temperature;	90%

2-nitrothiophenol (4875-10-9) + 2-chloro-ethanol (107-07-3) → bis(2-aminophenylthioethyl)terephthalate + 2-((2-nitrophenyl)thio)ethan-1-ol (13287-78-0)

Conditions	Yield
With sodium hydroxide In water	A n/a B 89.8%

1-iodo-2,4-dimethylbenzene (4214-28-2) + 2-nitrothiophenol (4875-10-9) → 2,4-dimethyl-1-[(2-nitro-phenyl)-sulfanyl]-benzene

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst; Solvent;	89.6%

2-nitrothiophenol (4875-10-9) + methyl ethynyl ketone (1423-60-5) → E/Z-4-(2-nitrophenylthio)-3-buten-2-one

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Substitution;	89%

2-nitrothiophenol (4875-10-9) + allyl bromide (106-95-6) → allyl(2-(nitrophenyl))sulfane (54848-79-2)

Conditions	Yield
Stage #1: o-nitrothiophenol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.666667h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	89%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere; Cooling with ice;	3.1 g

2-nitrothiophenol (4875-10-9) + benzyl 11‐bromoundecanoate (78277-30-2) → benzyl 11-(2-nitrophenylthio)undecanoate (1202041-14-2)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone at 56℃;	88%
With potassium carbonate; sodium iodide In acetone at 56℃; Reflux;	88%

2-nitrothiophenol (4875-10-9) + prenyl bromide (870-63-3) → 1-(3-methyl-but-2-enylsulfanyl)-2-nitro-benzene (1187627-61-7)

Conditions	Yield
Stage #1: o-nitrothiophenol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.666667h; Inert atmosphere; Stage #2: prenyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	88%
Stage #1: o-nitrothiophenol With sodium hydride In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere; Stage #2: prenyl bromide In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere;	79%

Upstream product

• 7669-54-7 2-nitrobenzenesulfenyl chloride 
• 528-29-0 1,2-Dinitrobenzene 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 64-17-5 ethanol 
• 88-73-3 2-Chloronitrobenzene 
• 67-56-1 methanol 
• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 3406-02-8 bis(phenylsulfonyl)methane 
• 124-41-4 sodium methylate 
• 50-99-7 glucose 
• 13511-84-7 S-(2-nitrophenyl)-N,N-dimethylcarbamothioate 
• 833-20-5 o-(2-nitrophenyl)-N,N-dimethylthiocarbamate 
• 88-75-5 2-hydroxynitrobenzene 
• 861784-94-3 2,5-dichloro-benzenethiosulfonic acid S-(2-nitro-phenyl ester) 

Downstream Products

• 5324-52-7 3-[(2-nitrophenyl)thio]propanoic acid 
• 858433-97-3 2,3-bis-(2-nitro-phenylsulfanyl)-[1,4]naphthoquinone 
• 93049-46-8 chlorothiocarbonic acid S-(2-nitro-phenyl ester) 
• 110251-43-9 2-nitro-benzenethioselenenic acid-(2-nitro-phenyl ester) 
• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 92463-14-4 o-nitrophenyl phenylselenyl sulfide 
• 536-57-2 p-toluene sulfinic acid 
• 100-03-8 4-chlorobenzenesulfinic acid 
• 10342-50-4 bis(2-nitrophenyl) trisulfide 
• 861571-71-3 1,2-bis-(2-nitro-phenylsulfanyl)-ethene 
• 859074-19-4 benzophenone-[bis-(2-nitro-phenyl)-dithioacetal] 
• 26246-21-9 chloro-(2-nitro-phenyl)-disulfane 
• 91823-10-8 formaldehyde-[bis-(2-nitro-phenyl)-dithioacetal] 
• 125904-72-5 mercury o-nitrophenyl mercaptide 

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