137-47-3

Basic information

• Product Name: 2-NITROCHLOROBENZENE-4-(N,N-DIMETHYL)-SULPHONAMIDE
• Synonyms: 4-CHLORO-N,N'-DIMETHYL-3-NITRO-BENZENE SULFONAMIDE;4-CHLORO-N,N-DIMETHYL-3-NITRO-BENZENESULFONAMIDE;2-NITROCHLOROBENZENE-4-(N,N-DIMETHYL)-SULPHONAMIDE;4-chloro-n,n-dimethyl-3-nitro-benzenesulfonamid;4-chloro-N,N-dimethyl-3-nitrobenzenesulphonamide;4-chloro-3-nitro-N,N-dimethylbenzenesulfonamide;4-CHLORO-3-NITRO-N,N-DIMETHYLBENZENESULFAMIDE;N,N-DIMETHYL-4-CHLORO-3-NITROBENZENE SULFONAMIDE
• CAS NO: 137-47-3
• Molecular Formula: C₈H₉ClN₂O₄S
• Molecular Weight: 264.69
• EINECS: 205-295-1
• Mol File: 137-47-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 103.5℃ (acetone water )
• Boiling Point: 387.3 °C at 760 mmHg
• Flash Point: 188 °C
• Appearance: /
• Density: 1.48 g/cm³
• Vapor Pressure: 3.32E-06mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-NITROCHLOROBENZENE-4-(N,N-DIMETHYL)-SULPHONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROCHLOROBENZENE-4-(N,N-DIMETHYL)-SULPHONAMIDE(137-47-3)
• EPA Substance Registry System: 2-NITROCHLOROBENZENE-4-(N,N-DIMETHYL)-SULPHONAMIDE(137-47-3)

Safety Data

• Hazardous Substances Data: 137-47-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H9ClN2O4S/c1-10(2)16(14,15)6-3-4-7(9)8(5-6)11(12)13/h3-5H,1-2H3

Synthetic route

3-(Dimethylaminomethyl)indole (87-52-5) + 3-nitro-4-chlorosulfonyl chloride (97-08-5) → 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3)

Conditions	Yield
With triethylamine In acetonitrile at 25℃; for 24h;	84%
With triethylamine In acetonitrile at 25℃; for 24h;	84%

3-nitro-4-chlorosulfonyl chloride (97-08-5) + dimethyl amine (124-40-3) → 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3)

Conditions	Yield
In tetrahydrofuran	20%

3-nitro-4-chlorosulfonyl chloride (97-08-5) + N,N-dimethylammonium chloride (506-59-2) → 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3)

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane at 20℃; for 2h;

3-nitro-4-chlorosulfonyl chloride (97-08-5) → 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3)

Conditions	Yield
With dimethyl amine In water; toluene

diethyl ether (60-29-7) + 2-chloro-3-nitrobenzenesulfonyl chloride (15945-25-2) → 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3)

Conditions	Yield
With dimethyl amine In methanol; water

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 3-hydroxy-5-tert-butylisoxazole (107403-12-3) → 5-t-butyl-2-(4-dimethylsulfamoyl-2-nitrophenyl)-4-isoxazolin-3-one (118938-18-4)

Conditions	Yield
With hydrogenchloride; potassium carbonate In dimethyl sulfoxide	89.5%

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + tert-butyl (3-(2-mercaptonicotinamido)propyl)carbamate → tert-butyl (3-(9-(N,N-dimethylsulfamoyl)-5-oxobenzo[b]pyrido-[3,2-f][1,4]thiazepin-6(5H)-yl)propyl)carbamate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; Smiles Aromatic Rearrangement;	89%

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + Thiosalicylic acid (147-93-3) → 2-((4-(N,N-dimethylsulfamoyl)-2-nitrophenyl)thio)benzoic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol for 18h; Reflux;	81%

2-(4,5-dihydro-1H-imidazol-2-yl)-benzenethiol (53440-31-6) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → N,N-dimethyl-2,3-dihydrodibenzo[b,f ]imidazo[1,2-d][1,4]-thiazepine-7-sulfonamide

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 75℃; Smiles Aromatic Rearrangement;	66%

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 3-ethylamino propionitrile (21539-47-9) → 2-nitro-4-dimethylsulfamoyl-N-ethylaniline (81676-81-5) + 2-nitro-4-dimethylsulfamoyl-N-ethyl-N-β-cyanoethylaniline (81676-78-0)

Conditions	Yield
In methanol at 65℃; for 10h;	A 30% B 65%
In i-Amyl alcohol at 130℃; Product distribution; Mechanism; other temperature, time, solvent;

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9) → 4-[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl)oxy]-N, N-dimethyl-3-nitrobenzenesulfonamide (862298-40-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃;	37%

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 1-amino-2-nitrobenzene-4-sulphonic acid dimethylamide (57824-29-0)

Conditions	Yield
With ammonia In methanol at 55℃;	16%

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 3,3'-dinitro-4,4'-sulfanediyl-bis-benzenesulfonic acid bis-dimethylamide (101430-57-3)

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 4-Ethoxyaniline (156-43-4) → 3-nitro-4-p-phenetidino-benzenesulfonic acid dimethylamide (67338-59-4)

Conditions	Yield
With sodium hydrogencarbonate

Cyclohexanone oxime (100-64-1) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 4-Cyclohexylideneaminooxy-N,N-dimethyl-3-nitro-benzenesulfonamide (13181-80-1)

Conditions	Yield
With sodium ethanolate In 1,4-dioxane

3-methyl-butan-2-one oxime (600-20-4) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 4-[1,2-Dimethyl-prop-(E)-ylideneaminooxy]-N,N-dimethyl-3-nitro-benzenesulfonamide (13194-09-7)

Conditions	Yield
With sodium ethanolate In ethanol; acetonitrile

(+/-)-camphor oxime (13559-66-5) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → N,N-Dimethyl-3-nitro-4-[1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylideneaminooxy]-benzenesulfonamide

Conditions	Yield
With sodium ethanolate In ethanol; acetonitrile

3,5-dichloro-4-hydroxy-benzaldehyde-oxime (26879-81-2) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 4-[1-(3,5-Dichloro-4-hydroxy-phenyl)-meth-(Z)-ylideneaminooxy]-N,N-dimethyl-3-nitro-benzenesulfonamide (61101-46-0)

Conditions	Yield
With sodium ethanolate In ethanol; acetonitrile

3,5-dibromo-4-hydroxy-benzaldehyde-oxime (25952-74-3) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 4-[1-(3,5-Dibromo-4-hydroxy-phenyl)-meth-(Z)-ylideneaminooxy]-N,N-dimethyl-3-nitro-benzenesulfonamide (13194-06-4)

Conditions	Yield
With sodium ethanolate In ethanol; acetonitrile

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 4-hydroxy-3,5-diiodo-benzaldehyde-oxime (2296-76-6) → 4-[1-(4-Hydroxy-3,5-diiodo-phenyl)-meth-(Z)-ylideneaminooxy]-N,N-dimethyl-3-nitro-benzenesulfonamide (13194-07-5)

Conditions	Yield
With sodium ethanolate In ethanol; acetonitrile

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + di-n-propylamine (142-84-7) → Dipropyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-51-7)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + dimethyl amine (124-40-3) → Dimethyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-49-3)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + diethylamine (109-89-7) → Diethyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-50-6)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + diisopropylamine (108-18-9) → Diisopropyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-52-8)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + N-cyclohexyl-cyclohexanamine (101-83-7) → Dicyclohexyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-53-9)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + dibenzylamine (103-49-1) → Dibenzyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-54-0)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 3-Nitro-4-methylamino-benzolsulfonsaeure-dimethylamid (68528-28-9) + 4-[(2-Cyano-ethyl)-methyl-amino]-N,N-dimethyl-3-nitro-benzenesulfonamide (81676-73-5)

Conditions	Yield
In i-Amyl alcohol at 130℃; Product distribution; Mechanism; other temperature, time, solvent;

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 4-[(2-Cyano-ethyl)-methyl-amino]-N,N-dimethyl-3-nitro-benzenesulfonamide (81676-73-5)

Conditions	Yield
In methanol Heating;

3-diethylaminopropionitrile (5351-04-2) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → hydrochloride of 3-diethylaminopropionitrile (37899-75-5) + 4-Diethylamino-N,N-dimethyl-3-nitro-benzenesulfonamide (81676-68-8) + acrylonitrile (107-13-1)

Conditions	Yield
In i-Amyl alcohol Product distribution; Heating;
In i-Amyl alcohol

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + sodium thiophenolate (930-69-8) → nitro-2 dimethylsulfamoyl-4 diphenylsulfure (83472-52-0)

Conditions	Yield
In N,N-dimethyl-formamide for 5h; Heating;

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 3-dimethylaminopropiononitrile (1738-25-6) → N,N-dimethyl-4-dimethylamino-3-nitrobenzenesulfonamide (81676-66-6) + hydrochloride of 3-dimethylaminopropionitrile (18076-02-3) + acrylonitrile (107-13-1)

Conditions	Yield
In i-Amyl alcohol

1,1-Dimethylurea (598-94-7) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → N,N-dimethyl-4-dimethylamino-3-nitrobenzenesulfonamide (81676-66-6)

Conditions	Yield
at 200℃;

N-(p-ethoxyphenyl)urea (150-69-6) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 3-nitro-4-p-phenetidino-benzenesulfonic acid dimethylamide (67338-59-4)

Conditions	Yield
at 200℃;

Upstream product

• 97-08-5 3-nitro-4-chlorosulfonyl chloride 
• 124-40-3 dimethyl amine 
• 60-29-7 diethyl ether 
• 15945-25-2 2-chloro-3-nitrobenzenesulfonyl chloride 
• 87-52-5 3-(Dimethylaminomethyl)indole 
• 506-59-2 N,N-dimethylammonium chloride 

Downstream Products

• 67338-59-4 3-nitro-4-p-phenetidino-benzenesulfonic acid dimethylamide 
• 25678-51-7 Dipropyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester 
• 25678-49-3 Dimethyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester 
• 25678-50-6 Diethyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester 
• 25678-53-9 Dicyclohexyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester 
• 25678-54-0 Dibenzyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester 
• 37899-75-5 hydrochloride of 3-diethylaminopropionitrile 
• 81676-68-8 4-Diethylamino-N,N-dimethyl-3-nitro-benzenesulfonamide 
• 107-13-1 acrylonitrile 
• 83472-52-0 nitro-2 dimethylsulfamoyl-4 diphenylsulfure 
• 81676-66-6 N,N-dimethyl-4-dimethylamino-3-nitrobenzenesulfonamide 
• 18076-02-3 hydrochloride of 3-dimethylaminopropionitrile 
• 68528-28-9 3-Nitro-4-methylamino-benzolsulfonsaeure-dimethylamid 
• 118938-18-4 5-t-butyl-2-(4-dimethylsulfamoyl-2-nitrophenyl)-4-isoxazolin-3-one 

Relevant articles and documents

Controlled synthesis of N, N-dimethylarylsulfonamide derivatives as nematicidal agents

Gramine can be intelligently and efficiently supplied with N, N-dimethylamino group and then reacted with the corresponding sulfonyl chlorides to synthesize N, N-dimethylarylsulfonamides. We herein designed and controlled synthesis of N, N-dimethylarylsulfonamide derivatives, and first reported the results of the nematicidal activity of 15 title compounds 3a-o against Meloidogyne incongnita in vitro, respectively. Among all of the title derivatives, compounds 3a, 3c, 3k, and 3o exhibited potent nematicidal activity with median lethal concentration (LC50) values ranging from 0.22 to 0.26 mg/L. Most noteworthy, N, N-dimethyl-4-methoxyphenylsulfonamide (3c) and N, N-dimethyl-8-quinolinesulfonamide (3o) showed the best promising and pronounced nematicidal activity, with LC50 values of 0.2381 and 0.2259 mg/L, respectively.

ARYLGLYCINE DERIVATIVES FOR USE AS GLYCINE TRANSPORT INHIBITORS

The present invention relates to compounds of Formula (I) and salts solvates and hydrates thereof. The invention further relates to pharmaceutical compositions containing said compounds and methods of treating neurological and neuropsychistric disorders using said compounds.

Heterocyclic compounds

The invention provides compounds of formula (I) having nematicidal, insecticidal, acaricidal and fungicidal properties, compositions comprising them and processes and intermediates for their preparation: STR1 wherein: X is oxygen or sulphur; n is 0, 1 or 2; R1, R2, R3, and R4 are as described in the specification.