4273-98-7

Basic information

• Product Name: 2-(Phenylsulfonyl)aniline
• Synonyms: 2-(PHENYLSULFONYL)ANILINE;2-AMINOPHENYL PHENYL SULFONE;2-AMINOPHENYL PHENYL SULPHONE;2-AMINODIPHENYL SULFONE;O-AMINODIPHENYL SULFONE;O-(PHENYLSULFONYL)ANILINE;TIMTEC-BB SBB000718;2-(phenylsulfonyl)-benzenamin
• CAS NO: 4273-98-7
• Molecular Formula: C₁₂H₁₁NO₂S
• Molecular Weight: 233.29
• EINECS: 224-271-1
• Product Categories: Intermediates of Dyes and Pigments;Amines
• Mol File: 4273-98-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 120-122 °C(lit.)
• Boiling Point: 439.6 °C at 760 mmHg
• Flash Point: 219.7 °C
• Appearance: off-white to beige powder
• Density: 1.295 g/cm³
• Vapor Pressure: 6.3E-08mmHg at 25°C
• Refractive Index: 1.627
• PKA: -1.06±0.10(Predicted)
• CAS DataBase Reference: 2-(Phenylsulfonyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Phenylsulfonyl)aniline(4273-98-7)
• EPA Substance Registry System: 2-(Phenylsulfonyl)aniline(4273-98-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 4273-98-7(Hazardous Substances Data)

Usage

Description

2-(Phenylsulfonyl)aniline is an organic compound with the chemical formula C12H11NO2S. It is an off-white to beige powder and is used in chemical synthesis due to its unique properties.

Uses

Used in Chemical Synthesis:
2-(Phenylsulfonyl)aniline is used as a chemical intermediate for the synthesis of various compounds. Its application reason is its reactivity and ability to form new chemical bonds with other molecules.
Used in Textile Industry:
2-(Phenylsulfonyl)aniline is used as a coupling component in the textile industry for improving the fastness properties of dyes on cotton. It enhances the light, soda boiling, oxygen bleaching, ironing, chlorine bleaching, and washing fastness of dyed fabrics, ensuring their durability and color retention.
The fastness properties of cotton treated with 2-(Phenylsulfonyl)aniline are as follows:
Fast light: 6-7
Soda boiling: 4
Oxygen bleaching: 2
Ironing: 3-4
Chlorine bleaching: 4-5
Washing fastness (ISO): 24
Washing fastness (AATCC): 5
These properties indicate the level of resistance to various conditions, with higher numbers representing better fastness.

Preparation

Preparation?of?the?chromophore : Will 1-(2-Nitrophenylsulfonyl)benzene?restored.

Coupling?components

Fast light

ISO

AATCC

1/3N

2N

8

5

11

5

12

5

20

5

24

5

InChI:InChI=1/C12H11NO2S/c13-11-8-4-5-9-12(11)16(14,15)10-6-2-1-3-7-10/h1-9H,13H2

Synthetic route

2-phenylsulfanyl-aniline (1134-94-7) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
With urea hydrogen peroxide adduct In ethanol at 20℃; for 0.25h;	98%

N-phenylbenzenesulfonamide (1678-25-7) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
With aluminium trichloride for 0.0166667h; Fries rearrangement; Irradiation;	95%

1-nitro-2-(phenylsulfonyl)benzene (31515-43-2) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
With iron; acetic acid at 70℃; for 3h;	92%
With hydrogenchloride; iron In ethanol; water 1.) 75-80 deg C, 40 min 2.) reflux, 2 h;	77.6%
With hydrogenchloride; iron

sodium benzenesulfonate (873-55-2) + 2-bromoaniline (615-36-1) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
With potassium phosphate; copper(l) iodide; (2S,4R)-N-(2,6-dimethylphenyl)-4-hydroxypyrrolidine-2-carboxamide In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;	72%

N-phenylbenzenesulfonamide (1678-25-7) → p-aminophenyl phenyl sulfone (7019-01-4) + 2-aminophenyl phenyl sulfone (4273-98-7) + aniline (62-53-3)

Conditions	Yield
With β‐cyclodextrin In water Product distribution; Irradiation; other solvents, absence of cyclodextrin and/or solvent;	A 62.4% B 21.4% C 17.9%
Fries rearrangement; Irradiation; electron beam;	A 10 % Chromat. B 24 % Chromat. C n/a

sodium benzenesulfonate (873-55-2) + aniline (62-53-3) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
With dihydrogen peroxide; copper diacetate In water at 20℃; for 2h; Reagent/catalyst; Green chemistry;	47%

N-phenylbenzenesulfonamide (1678-25-7) → biphenyl (92-52-4) + p-aminophenyl phenyl sulfone (7019-01-4) + 2-aminophenyl phenyl sulfone (4273-98-7) + 4-Aminobiphenyl (92-67-1) + 2-phenylaniline (90-41-5) + aniline (62-53-3) + SO2

Conditions	Yield
at 300℃; for 15h; Mechanism; other substrate, also in the presence of isoquinoline or aniline;	A 17.15% B n/a C n/a D n/a E n/a F 31% G n/a

acetic acid-(2-benzenesulfonyl-anilide) (16714-29-7) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
With potassium hydroxide

2-Nitrosophenyl-phenylsulfon (29787-25-5) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane

2'-benzenesulfonyl-4-hydroxy-azobenzene-carboxylic acid-(3) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
With tin(ll) chloride

2-nitrophenyl phenyl sulfide (4171-83-9) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94.8 percent / H2O2 / acetic acid / 1.) 35-40 deg C, 30 min 2.) 80 deg C, 1 h 2: 77.6 percent / Fe powder, HCl / ethanol; H2O / 1.) 75-80 deg C, 40 min 2.) reflux, 2 h View Scheme
Multi-step reaction with 2 steps 1: aq. H2O2 / acetic acid / Heating 2: Sn, aq. HCl View Scheme

thiophenol (108-98-5) + alkali → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99.9 percent / KOH / dimethylformamide; H2O / 1.) between -3 and +2 deg C, 40 min, 2.) 80 deg C, 1 h 2: 94.8 percent / H2O2 / acetic acid / 1.) 35-40 deg C, 30 min 2.) 80 deg C, 1 h 3: 77.6 percent / Fe powder, HCl / ethanol; H2O / 1.) 75-80 deg C, 40 min 2.) reflux, 2 h View Scheme

2-Chloronitrobenzene (88-73-3) + magnesium → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99.9 percent / KOH / dimethylformamide; H2O / 1.) between -3 and +2 deg C, 40 min, 2.) 80 deg C, 1 h 2: 94.8 percent / H2O2 / acetic acid / 1.) 35-40 deg C, 30 min 2.) 80 deg C, 1 h 3: 77.6 percent / Fe powder, HCl / ethanol; H2O / 1.) 75-80 deg C, 40 min 2.) reflux, 2 h View Scheme

2-Chloronitrobenzene (88-73-3) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate; alcohol / 160 °C / im Einschlussrohr 2: alcoholic tin dichloride View Scheme

benzenesulfonyl chloride (98-09-9) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether; zinc; water / Man kocht 1-2 Stdn., bis die Masse breiartig und grauweiss wird; das ausgeschiedene Zinksalz wird nach dem Waschen mit Wasser durch Soda in das Natriumsalz uebergefuehrt 2: sodium acetate; alcohol / 160 °C / im Einschlussrohr 3: alcoholic tin dichloride View Scheme

Benzenesulfinic acid (618-41-7) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate; alcohol / 160 °C / im Einschlussrohr 2: alcoholic tin dichloride View Scheme

thiophenol (108-98-5) + disodium dodecyl phosphate → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. Na2CO3 / ethanol / Heating 2: aq. H2O2 / acetic acid / Heating 3: Sn, aq. HCl View Scheme

2-Chloronitrobenzene (88-73-3) + CS2 → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. Na2CO3 / ethanol / Heating 2: aq. H2O2 / acetic acid / Heating 3: Sn, aq. HCl View Scheme

(2-Hydroxyamino-phenyl)-phenyl-sulfon (5194-27-4) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. K2Cr2O7, H2SO4 2: aq. NaOH / dioxane View Scheme

N-(2-(phenylthio)phenyl)acetamide (1489-23-2) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. H2O2, AcOH 2: aq. KOH View Scheme

C12H11NO2S*C42H70O35 (135218-54-1) → p-aminophenyl phenyl sulfone (7019-01-4) + 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
for 0.0958333h; Irradiation;

N-phenylbenzenesulfonamide (1678-25-7) → p-aminophenyl phenyl sulfone (7019-01-4) + 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
for 0.0958333h; Irradiation;

4-Chlorophenyl phenyl sulfone (80-00-2) + (o-chlorophenyl)phenylsulfone (17051-72-8) → p-aminophenyl phenyl sulfone (7019-01-4) + 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
With ammonia; copper(l) chloride at 220℃; for 6h; Product distribution / selectivity;

ortho-nitrofluorobenzene (1493-27-2) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 2: dihydrogen peroxide; acetic acid / 2 h / 55 °C 3: iron; acetic acid / 3 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: 10% Pd/C; hydrogen / methanol View Scheme

benzenesulfonic acid (98-11-3) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: 10% Pd/C; hydrogen / methanol View Scheme

thiophenol (108-98-5) → 2-aminophenyl phenyl sulfone (4273-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 2: dihydrogen peroxide; acetic acid / 2 h / 55 °C 3: iron; acetic acid / 3 h / 70 °C View Scheme

2-phenylsulfanyl-aniline (1134-94-7) → 2-aminophenyl phenyl sulfone (4273-98-7) + phenyl-2-amine-phenylsulfoxide (16714-31-1)

Conditions	Yield
With nano-sized mesoporous sodium iron hydroxyphosphate supported gold; dihydrogen peroxide In methanol; water at 60℃; for 10h; Green chemistry;

2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride (289686-69-7) + 2-aminophenyl phenyl sulfone (4273-98-7) → N-(2-benzenesulfonyl-phenyl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	95%

o-benzenedisulfonimide (4482-01-3) + 2-aminophenyl phenyl sulfone (4273-98-7) → 2-phenylsulfonylbenzenediazonium o-benzenedisulfonimide

Conditions	Yield
With isopentyl nitrite In acetic acid at 0 - 5℃; Diazotization;	92%

2-pyrrole aldehyde (1003-29-8) + 2-aminophenyl phenyl sulfone (4273-98-7) → C17H14N2O2S

Conditions	Yield
With formic acid In methanol for 24h;	89%

2-aminophenyl phenyl sulfone (4273-98-7) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(2-(phenylsulfonyl)phenyl)acetamide

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 8h;	87%

2-aminophenyl phenyl sulfone (4273-98-7) + acenaphthene quinone (82-86-0) → C36H24N2O4S2

Conditions	Yield
With acetic acid; zinc(II) chloride at 60 - 120℃; for 0.5h;	81%

2-aminophenyl phenyl sulfone (4273-98-7) + benzyl alcohol (100-51-6) → N-benzyl-2-(phenylsulfonyl)aniline

Conditions	Yield
With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; Catalytic behavior; Sealed tube; Green chemistry;	75%

2-cyanomethylbenzothiazole (56278-50-3) + 2-aminophenyl phenyl sulfone (4273-98-7) → C21H14N4O2S2

Conditions	Yield
Stage #1: 2-aminophenyl phenyl sulfone With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.75h; Stage #2: 2-cyanomethylbenzothiazole With sodium acetate In ethanol; water at 20℃;	75%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + 2-aminophenyl phenyl sulfone (4273-98-7) → C27H31NO3S

Conditions	Yield
With acetic acid In ethanol for 6h; Reflux; Inert atmosphere; Schlenk technique;	69%

aqueous sodium nitrite + 2-aminophenyl phenyl sulfone (4273-98-7) + sodium hydrogensulfite → 2-(phenylsulfonyl)benzenesulfonyl chloride (6462-15-3)

Conditions	Yield
In hydrogenchloride; dichloromethane; water	66%

2-aminophenyl phenyl sulfone (4273-98-7) + 3-Bromopropionyl chloride (15486-96-1) → N-(3-Bromopropionyl)-2-(phenylsulfonyl)aniline

Conditions	Yield
With dmap; triethylamine In N,N-dimethyl-formamide	42%

5-chloro-2-hydroxybenzoic acid (321-14-2) + 2-aminophenyl phenyl sulfone (4273-98-7) → C19H14ClNO4S (1417658-16-2)

Conditions	Yield
With pyridine; phosphorus trichloride In toluene for 12h; Inert atmosphere; Reflux;	24%

2-aminophenyl phenyl sulfone (4273-98-7) + 4-(methylsulfonyl)benzonitrile (22821-76-7) → N-(2-benzenesulfonyl-phenyl)-4-methanesulfonyl-benzamidine

2-aminophenyl phenyl sulfone (4273-98-7) → 1-bromo-2-(phenylsulfonyl)benzene (5324-79-8)

Conditions	Yield
With hydrogen bromide; sodium nitrite anschliessend Behandeln mit Kupfer(I)-bromid;
Multi-step reaction with 2 steps 1: 92 percent / isopentyl nitrite / acetic acid / 0 - 5 °C 2: 85 percent / tetrabutylammonium bromide; Cu / acetonitrile / 0.75 h / 20 °C View Scheme

2-aminophenyl phenyl sulfone (4273-98-7) → 2-azidophenyl phenyl sulphone

Conditions	Yield
With hydrogenchloride; sodium nitrite anschliessendes Behandeln mit Natriumazid;
With hydrogenchloride; sodium azide; sodium acetate; sodium nitrite 1.) 1.) 0-5 deg C; Yield given. Multistep reaction;

2-aminophenyl phenyl sulfone (4273-98-7) → 2-benzenesulfonyl-benzenediazonium; tetrachlorocobaltate (II)

Conditions	Yield
With nitrosylsulfuric acid; sulfuric acid Versetzen die wss.Reaktionsloesung mit Kobalt(II)-sulfat und NaCl;

2-aminophenyl phenyl sulfone (4273-98-7) + acetic anhydride (108-24-7) → acetic acid-(2-benzenesulfonyl-anilide) (16714-29-7)

Conditions	Yield
With sodium acetate

2-aminophenyl phenyl sulfone (4273-98-7) + urea (57-13-6) → dibenzothiophene sulfone (1016-05-3)

Conditions	Yield
With hydrogenchloride; acetic acid; sodium nitrite anschliessend mit Kupfer behandeln;

2-aminophenyl phenyl sulfone (4273-98-7) + N-<2-benzenesulfonyl-phenyl>-benzamimidoyl chloride → N,N'-bis-(2-benzenesulfonyl-phenyl)-benzamidine

Conditions	Yield
With nitrobenzene

2,5-bis-[4-(5-oxo-2-trifluoromethyl-4,5-dihydro-oxazol-4-yl)-phenoxymethyl]-benzoyl chloride + 2-aminophenyl phenyl sulfone (4273-98-7) → N-(2-benzenesulfonyl-phenyl)-2,5-bis-[4-(5-oxo-2-trifluoromethyl-4,5-dihydro-oxazol-4-yl)-phenoxymethyl]-benzamide

Conditions	Yield
In dichloromethane at 4℃;

Upstream product

• 31515-43-2 1-nitro-2-(phenylsulfonyl)benzene 
• 1678-25-7 N-phenylbenzenesulfonamide 
• 16714-29-7 acetic acid-(2-benzenesulfonyl-anilide) 
• 29787-25-5 2-Nitrosophenyl-phenylsulfon 
• 4171-83-9 2-nitrophenyl phenyl sulfide 
• 108-98-5 thiophenol 
• 88-73-3 2-Chloronitrobenzene 
• 98-09-9 benzenesulfonyl chloride 
• 618-41-7 Benzenesulfinic acid 
• 5194-27-4 (2-Hydroxyamino-phenyl)-phenyl-sulfon 
• 1489-23-2 N-(2-(phenylthio)phenyl)acetamide 
• 135218-54-1 C₁₂H₁₁NO₂S*C₄₂H₇₀O₃₅ 
• 80-00-2 4-Chlorophenyl phenyl sulfone 
• 17051-72-8 (o-chlorophenyl)phenylsulfone 

Downstream Products

• 5324-79-8 1-bromo-2-(phenylsulfonyl)benzene 
• 16714-29-7 acetic acid-(2-benzenesulfonyl-anilide) 
• 1016-05-3 dibenzothiophene sulfone 
• 17051-72-8 (o-chlorophenyl)phenylsulfone 
• 53347-49-2 2,2'-diaminodiphenyl sulfone 
• 6462-15-3 2-(phenylsulfonyl)benzenesulfonyl chloride 

Relevant articles and documents

Effect of cyclodextrin encapsulation on photo-fries rearrangement of benzensulphonanilide

Photolysis of benzenesulphonanilide upon cyclodextrin encapsulation in solid phase yields exclusively 2-aminodiphenyl sulphone.

A Class of Amide Ligands Enable Cu-Catalyzed Coupling of (Hetero)aryl Halides with Sulfinic Acid Salts under Mild Conditions

The amide derived from 4-hydroxy-l-proline and 2,6-dimethylaniline is a powerful ligand for Cu-catalyzed coupling of (hetero)aryl halides with sulfinic acid salts, allowing the formation of a wide range of (hetero)aryl sulfones from the corresponding (hetero)aryl halides at considerably low catalytic loadings. The coupling of (hetero)aryl iodides and sodium methanesulfinate proceeds at room temperature with only 0.5 mol % CuI and ligand, representing the first example for Cu-catalyzed arylation at both low catalytic loading and room temperature.

Nano-sized mesoporous sodium iron hydroxyphosphate supported gold: An effective catalyst for the oxidation of sulfides

New nano-sized mesoporous sodium iron hydroxyphosphate (SIHP, Na4.55Fe(PO4)2H0.45O), synthesized by a microemulsion-hydrothermal synthesis method, with supported gold nanoparticles (AuNPs) could be a very effective catalyst for the selective oxidation of sulfides. The results showed that the SIHP material was an excellent catalyst support due to its special structure and the interactions between the AuNPs and the surface hydroxyl groups.