97-07-4

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-Chloro-3-nitrophenyl methyl sulfone is utilized as an intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides. Its role in these industries is crucial for the production of effective and safe products.
Used in Organic Chemistry:
As a reagent in organic chemistry, 4-Chloro-3-nitrophenyl methyl sulfone is employed in a range of chemical reactions, facilitating the synthesis of complex organic compounds and contributing to advancements in chemical research and development.
Used in Dye and Pigment Production:
4-Chloro-3-nitrophenyl methyl sulfone is used in the production of dyes and pigments, providing colorants for various applications such as textiles, plastics, and printing inks. Its presence in these industries is essential for creating vibrant and stable color products.

InChI:InChI=1/C7H6ClNO4S/c1-14(12,13)5-2-3-6(8)7(4-5)9(10)11/h2-4H,1H3

Synthetic route

4-chlorophenyl methyl sulfone (98-57-7) → 1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4)

Conditions	Yield
With sulfuric acid; nitric acid at 25℃; for 2h;	99.7%
(nitration);

4-chlorobenzenesulfonyl chloride (98-60-2) → 1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium sulfite; sodium hydrogencarbonate / water / 4 h / 75 °C 1.2: 15 h / 105 - 107 °C 2.1: sulfuric acid; nitric acid / 2 h / 25 °C View Scheme

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) → C12H13NO8S (917562-22-2)

Conditions	Yield
Stage #1: malonic acid dimethyl ester With potassium tert-butylate In tert-butyl alcohol Stage #2: 1-chloro-4-methanesulfonyl-2-nitrobenzene In tert-butyl alcohol at 20℃; for 15h; Heating / reflux;	100%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 2-bromothiophenol (6320-02-1) → 2'-Brom-2-nitro-4-methylsulfonyl-diphenylsulfid

Conditions	Yield
In ethanol at 40 - 80℃; for 0.5h;	99%
With sodium hydroxide

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + methyl 2-cyanoacetate (105-34-0) → methyl 2-cyano-2-(4-(methylsulfonyl)-2-nitrophenyl)acetate

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 60℃; for 1h;	96%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 3-Amino-1,2-propanediol (616-30-8, 13552-31-3) → 4-(β,γ-dihydroxypropylamino-3-nitro)phenyl methyl sulfone (120381-40-0)

Conditions	Yield
In dimethyl sulfoxide	95%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 2-fluorothiophenol (2557-78-0) → 2-(2-fluorophenylthio)-5-(methylsulfonyl)nitrobenzene (129846-91-9)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 4h;	95%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + N-(2-cyanoethyl)-N-methylamine (693-05-0) → 3-[(4-Methanesulfonyl-2-nitro-phenyl)-methyl-amino]-propionitrile (81689-46-5)

Conditions	Yield
In butan-1-ol at 118℃; for 2h;	91%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + toluene (108-88-3) → C14H14ClNO2S

Conditions	Yield
With tert.-butylhydroperoxide; hydrogen In water; toluene at 160℃; under 30003 Torr; for 36h; Autoclave;	84%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + (3-chlorophenyl)(pyridin-2-yl)methanamine (39930-15-9) → (rac)-N-((3-chlorophenyl)(pyridin-2-yl)methyl)-4-(methylsulfonyl)-2-nitroaniline

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 130℃; for 0.5h; Sealed tube; Microwave irradiation;	83%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9) → 2,2-dimethyl-5-[4-(methylsulfonyl)-2-nitrophenoxy]-4H-1,3-benzodioxin-4-one (862298-42-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 7h;	80%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + N,N-dimethylethylenediamine (108-00-9) → 4-(β-dimethylaminoethyl)amino-3-nitrophenyl methyl sulfone (120381-41-1)

Conditions	Yield
In dimethyl sulfoxide; ethyl acetate	78%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 1-methoxycarbonyl-3-methylbenzene (99-36-5) → C16H16ClNO4S

Conditions	Yield
With tert.-butylhydroperoxide; hydrogen In water; toluene at 160℃; under 30003 Torr; for 36h; Autoclave;	73%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 2-fluorothiophenol (2557-78-0) → 4-(ethylthio)-3-nitrophenyl methyl sulfone (129846-93-1) + 2-(2-fluorophenylthio)-5-(methylsulfonyl)nitrobenzene (129846-91-9) + 3,4-bis(2-fluorophenylthio)phenyl methyl sulfone (129846-92-0) + di(4-(methylsulfonyl)-2-nitrophenyl) sulfide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3.5h;	A 4.96% B 63% C 8.03 g D 1.50 g
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3.5h;	A 4.96 g B 63% C 8.03 g D 1.50 g

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 3-ethylamino propionitrile (21539-47-9) → 3-nitro-4-ethylaminophenyl methyl sulfone (21355-97-5) + 2-nitro-4-methylsulfonyl-N-ethyl-N-β-cyanoethylaniline (81676-76-8)

Conditions	Yield
In methanol for 42h; Heating;	A 43% B 56%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2-{4-[4-(methylsulfonyl)-2-nitroanilino]phenyl}ethanol

Conditions	Yield
With sodium carbonate In ethanol at 100℃; for 16h;	34%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 3,4-dihydroxythiophene-2,5-dicarboxylic acid diethyl ester (1822-66-8) → 6-(methylsulfonyl)benzo[b]thieno[3,4-e][1,4]dioxine

Conditions	Yield
With potassium carbonate; lithium bromide In N,N-dimethyl acetamide at 200℃; for 1h; Microwave irradiation; Sealed tube; Inert atmosphere;	20.9%

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + ethanol (64-17-5) + sodium methansulfinate (20277-69-4) → 1,4-bis-methanesulfonyl-2-nitro-benzene

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 2-(4-aminophenoxy)ethanol (6421-88-1) → 2-[4-(4-methanesulfonyl-2-nitro-anilino)-phenoxy]-ethanol

Conditions	Yield
With ethanol; sodium carbonate

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + sodium methansulfinate (20277-69-4) → 1,4-bis-methanesulfonyl-2-nitro-benzene

Conditions	Yield
With ethanol

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + sodium methylate (124-41-4) → 4-methanesulfonyl-1-methoxy-2-nitro-benzene (20945-69-1)

Conditions	Yield
With methanol

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) → 1-ethoxy-4-methanesulfonyl-2-nitro-benzene (21081-73-2)

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) → 1-fluoro-4-methanesulfonyl-2-nitrobenzene (453-72-5)

Conditions	Yield
With potassium fluoride at 180℃;

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) → bis-(4-methanesulfonyl-2-nitro-phenyl)-sulfide (100620-98-2)

Conditions	Yield
With alkali sulfide

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 4-methoxy-aniline (104-94-9) → (4-methanesulfonyl-2-nitro-phenyl)-(4-methoxy-phenyl)-amine (92192-70-6)

Conditions	Yield
With ethanol

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + aniline (62-53-3) → (4-methanesulfonyl-2-nitro-phenyl)-phenyl-amine (16588-01-5)

Conditions	Yield
With ethanol

carbon disulfide (75-15-0) + 1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) → 2-chloro-5-methanesulfonyl-benzothiazole (61700-73-0)

Conditions	Yield
(i) Na2S3, (ii) /BRN= 1098293/, (iii) SO2Cl2; Multistep reaction;

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) → 1-(4-(methylsulfonyl)-2-nitrophenyl)piperidine (18543-01-6)

Conditions	Yield
With /BRN= 102438/ In dimethyl sulfoxide at 45℃; Rate constant;

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + N-(2-cyanoethyl)-N-methylamine (693-05-0) → methyl 4-methyl-amino-3-nitrophenyl sulfone (30388-44-4) + 3-[(4-Methanesulfonyl-2-nitro-phenyl)-methyl-amino]-propionitrile (81689-46-5)

Conditions	Yield
In butan-1-ol at 118℃; for 40h;

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + 3-diethylaminopropionitrile (5351-04-2) → hydrochloride of 3-diethylaminopropionitrile (37899-75-5) + N,N-diethyl-4-(methylsulfonyl)-2-nitroaniline (81676-67-7) + acrylonitrile (107-13-1)

Conditions	Yield
In i-Amyl alcohol

1-chloro-4-methanesulfonyl-2-nitrobenzene (97-07-4) + potassium ethyl xanthogenate (140-89-6) → Dithiocarbonic acid O-ethyl ester S-(4-methanesulfonyl-2-nitro-phenyl) ester

Conditions	Yield
In ethanol for 18h; Ambient temperature;

Upstream product

• 98-57-7 4-chlorophenyl methyl sulfone 
• 98-60-2 4-chlorobenzenesulfonyl chloride 

Downstream Products

• 18543-01-6 1-(4-(methylsulfonyl)-2-nitrophenyl)piperidine 
• 30388-44-4 methyl 4-methyl-amino-3-nitrophenyl sulfone 
• 81689-46-5 3-[(4-Methanesulfonyl-2-nitro-phenyl)-methyl-amino]-propionitrile 
• 37899-75-5 hydrochloride of 3-diethylaminopropionitrile 
• 81676-67-7 N,N-diethyl-4-(methylsulfonyl)-2-nitroaniline 
• 107-13-1 acrylonitrile 
• 129846-93-1 4-(ethylthio)-3-nitrophenyl methyl sulfone 
• 129846-91-9 2-(2-fluorophenylthio)-5-(methylsulfonyl)nitrobenzene 
• 129846-92-0 3,4-bis(2-fluorophenylthio)phenyl methyl sulfone 
• 21355-97-5 3-nitro-4-ethylaminophenyl methyl sulfone 
• 81676-76-8 2-nitro-4-methylsulfonyl-N-ethyl-N-β-cyanoethylaniline 
• 81676-65-5 Methyl-<3-nitro-4-dimethylamino-phenyl>-sulfon 
• 18076-02-3 hydrochloride of 3-dimethylaminopropionitrile 
• 20945-69-1 4-methanesulfonyl-1-methoxy-2-nitro-benzene 

Relevant academic research and scientific papers

Design, synthesis, anticancer activity, molecular docking and ADME studies of novel methylsulfonyl indole-benzimidazoles in comparison with ethylsulfonyl counterparts

Cancer poses a world-wide healthcare problem, demanding selective and effective therapy protocols. To address that, a vast amount of therapeutic candidates are being investigated in the field of medicinal chemistry. Accordingly, indole-benzimidazole structures have recently gained considerable interest because of their anticancer properties and estrogen receptor (ER) modulatory actions. In this study, novel methylsulfonyl indole-benzimidazole derivatives have been synthesized upon substitution of respectively the first (R1) and fifth (R2) positions of benzimidazole and indole groups. Structure and activity relationships were then studied via1H NMR, 13C NMR, mass spectral and in silico docking analyses, as well as cell viability measurements. We found that the compounds exhibited substantial affinity levels towards ER alpha (ERα). In addition, the correlation analysis of cytotoxicity profiles between ethyl- and methyl-sulfonyl indole-benzimidazoles revealed a collection of effective and consistent R1 and R2 substitutions. However, for some candidate derivatives, distinctive cytotoxicity levels and varying viability versus ERα affinity correlations were observable across the studies, suggesting that the sulfonyl side chain modifications themselves can also influence the ERα binding levels. These results demonstrated that our novel methylsulfonyl indole-benzimidazole derivatives, similar to their ethylsulfonyl counterparts, exhibit anticancer effects with potential estrogen receptor modulatory actions. This journal is

Preparation method of 2-(methyl sulphonyl)-10H-phenothiazine

The invention relates to a preparation method of 2-(methyl sulphonyl)-10H-phenothiazine and belongs to the technical field of medical intermediate preparation. According to the method, parachlorobenzenesulfonyl chloride and sodium salt of 2-bromothiophenol are taken as starting materials, two novel intermediates M1 and M3 not reported are involved, ideal schemes different from related references are explored in all experimental procedures, and particularly the cyclization process for synthesis of the final product 2-(methyl sulphonyl)-10H-phenothiazine completely breaks through various restrictions in literatures. The method has the advantages that the whole process is simple in step, convenient to operate, mild in reaction condition and easy to control, product yield in all the steps is high and the like, thereby being suitable for industrial production and having high value in use and social and economic benefits.

Substituted 1-sulfonylbenzimidazoles

Certain 1-sulfonyl-2,5(6)-substituted-benzimidazole compounds are useful as antiviral agents.