84996-11-2

Basic information

• Product Name: 4-(ethylsulphonyl)-2-nitrophenol
• Synonyms: 4-(ethylsulphonyl)-2-nitrophenol;4-Hydroxy-3-nitrophenyl ethylsulfone;Einecs 284-947-7;Ethyl 4-hydroxy-3-nitrophenyl sulphone, 5-(Ethylsulphonyl)-2-hydroxynitrobenzene
• CAS NO: 84996-11-2
• Molecular Formula: C₈H₉NO₅S
• Molecular Weight: 231.22576
• EINECS: 284-947-7
• Mol File: 84996-11-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 137-139
• Boiling Point: 410.3°Cat760mmHg
• Flash Point: 201.9°C
• Appearance: /
• Density: 1.463g/cm³
• Vapor Pressure: 2.57E-07mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: 4-(ethylsulphonyl)-2-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(ethylsulphonyl)-2-nitrophenol(84996-11-2)
• EPA Substance Registry System: 4-(ethylsulphonyl)-2-nitrophenol(84996-11-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 84996-11-2(Hazardous Substances Data)

Usage

General Description

4-(Ethylsulphonyl)-2-nitrophenol is a chemical compound with the molecular formula C8H9NO5S. It is a yellow crystalline solid that is used as an intermediate in the synthesis of pharmaceuticals and organic compounds. The compound is primarily used as a building block in the production of dyes, pigments, and other organic chemicals. It is also known for its antibacterial and antifungal properties, making it a potential ingredient in antimicrobial products. Additionally, 4-(Ethylsulphonyl)-2-nitrophenol is used in research as a reagent in various chemical reactions. However, it is important to handle this compound with caution due to its potential toxicity and environmental impact.

InChI:InChI=1/C8H9NO5S/c1-2-15(13,14)6-3-4-8(10)7(5-6)9(11)12/h3-5,10H,2H2,1H3

Synthetic route

4-hydroxy-phenyl-ethylsulfone (859537-79-4) → 4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2)

Conditions	Yield
With nitric acid; acetic acid at 80℃; for 3h;	100%

1-chloro-4-(ethylsulphonyl)-2-nitrobenzene (74159-80-1) → 4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2)

Conditions	Yield
With sodium hydroxide at 95℃; for 3h; Temperature; Autoclave;	97%

4-(ethylsulfonyl)-1-methoxy-2-nitrobenzene (51572-44-2) → 4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2)

Conditions	Yield
With formic acid; hydrogen bromide at 90℃; for 30h; Temperature;	92%

4-(ethylthio)phenol (1195-46-6) → 4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: Oxone / water; ethanol / 18 h / 20 °C 2: nitric acid; acetic acid / 3 h / 80 °C View Scheme

4-sulfanylphenol (637-89-8) → 4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 2 h / 20 °C 2: Oxone / water; ethanol / 18 h / 20 °C 3: nitric acid; acetic acid / 3 h / 80 °C View Scheme

4-chlorophenyl ethyl sulfide (5120-72-9) → 4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: dihydrogen peroxide; sodium tungstate (VI) dihydrate / ethyl acetate / 5 h / 30 - 55 °C / Large scale 2: nitric acid; sulfuric acid / 2 h / 0 - 20 °C / Large scale 3: sodium hydroxide / 3 h / 95 °C / Autoclave View Scheme

1-(ethylsulfonyl)-4-chlorobenzene (7205-80-3) → 4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 2 h / 0 - 20 °C / Large scale 2: sodium hydroxide / 3 h / 95 °C / Autoclave View Scheme

4-methoxy-phenyl-sulphonyl chloride (98-68-0) → 4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium sulfite / water; tetrahydrofuran / 20 h / -5 - 0 °C 2: methanol / 2 h / 65 °C 3: nitric acid / 70 °C 4: hydrogen bromide; formic acid / 30 h / 90 °C View Scheme
Multi-step reaction with 4 steps 1: sodium sulfite / water; tetrahydrofuran / 20 h / -5 - 0 °C 2: ethanol / 2 h / 80 °C 3: nitric acid / 70 °C 4: hydrogen bromide; formic acid / 30 h / 90 °C View Scheme

sodium 4-methoxybenzenesulfinate (6462-50-6) → 4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / 2 h / 65 °C 2: nitric acid / 70 °C 3: hydrogen bromide; formic acid / 30 h / 90 °C View Scheme
Multi-step reaction with 3 steps 1: ethanol / 2 h / 80 °C 2: nitric acid / 70 °C 3: hydrogen bromide; formic acid / 30 h / 90 °C View Scheme

1-(ethylsulfonyl)-4-methoxybenzene (7205-79-0) → 4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / 70 °C 2: hydrogen bromide; formic acid / 30 h / 90 °C View Scheme

4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2) → 2-amino-4-(ethylsulfonyl)phenol (43115-40-8)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol at 60 - 70℃; under 15001.5 Torr; Temperature; Solvent; Autoclave;	86%
With palladium 10% on activated carbon; hydrogen In isopropyl alcohol at 50℃; under 2280.15 Torr; for 24h;	73%

4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2) → 2-bromo-4-(ethylsulfonyl)-6-nitrophenol

Conditions	Yield
With iron(III) chloride; bromine; acetic acid In water at 20℃; for 4h;	80%

4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2) → 2-amino-6-bromo-4-(ethylsulfonyl)phenol

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; iron(III) chloride; acetic acid / water / 4 h / 20 °C 2: hydrogen / ethanol / 2 h / Inert atmosphere View Scheme

4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2) → 8-bromo-6-(ethylsulfonyl)-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine; iron(III) chloride; acetic acid / water / 4 h / 20 °C 2: hydrogen / ethanol / 2 h / Inert atmosphere 3: potassium carbonate / acetonitrile / 3 h / 80 °C View Scheme

4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2) → 8-bromo-6-(ethylsulfonyl)-2,2,4-trimethyl-2H-1,4-benzoxazin-3(4H)-one

Conditions	Yield
Multi-step reaction with 4 steps 1.1: bromine; iron(III) chloride; acetic acid / water / 4 h / 20 °C 2.1: hydrogen / ethanol / 2 h / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 3 h / 80 °C 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C 4.2: 0.5 h / 0 - 20 °C View Scheme

4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2) → 6-(ethylsulfonyl)-2,2,4-trimethyl-8-{6-methyl-1-[(4-methylphenyl)sulfonyl]-7-oxo-6-dihydro-1H-pyrrolo[2,3-c]pyrid-4-yl}-2H-1,4-benzoxazin-3(4H)-one

Conditions

Yield

Multi-step reaction with 5 steps 1.1: bromine; iron(III) chloride; acetic acid / water / 4 h / 20 °C 2.1: hydrogen / ethanol / 2 h / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 3 h / 80 °C 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C 4.2: 0.5 h / 0 - 20 °C 5.1: cesium fluoride; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere View Scheme

4-(ethylsulfonyl)-2-nitro-phenol (84996-11-2) → 6-(ethylsulfonyl)-2,2,4-trimethyl-8-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-2H-1,4-benzoxazin-3(4H)-one

Conditions

Yield

Multi-step reaction with 6 steps 1.1: bromine; iron(III) chloride; acetic acid / water / 4 h / 20 °C 2.1: hydrogen / ethanol / 2 h / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 3 h / 80 °C 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C 4.2: 0.5 h / 0 - 20 °C 5.1: cesium fluoride; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere 6.1: sodium hydroxide; water / ethanol / 2 h / 80 °C View Scheme

Upstream product

• 51572-44-2 4-(ethylsulfonyl)-1-methoxy-2-nitrobenzene 
• 7205-79-0 1-(ethylsulfonyl)-4-methoxybenzene 
• 6462-50-6 sodium 4-methoxybenzenesulfinate 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 74159-80-1 1-chloro-4-(ethylsulphonyl)-2-nitrobenzene 
• 7205-80-3 1-(ethylsulfonyl)-4-chlorobenzene 
• 5120-72-9 p-chlorophenyl ethyl sulfide 
• 859537-79-4 4-hydroxy-phenyl-ethylsulfone 
• 637-89-8 4-sulfanylphenol 
• 1195-46-6 4-(ethylthio)phenol 

Downstream Products

• 43115-40-8 2-amino-4-(ethylsulfonyl)phenol 

Relevant articles and documents

A 2 - amino - (4 - ethyl sulfonyl) phenol synthesis method (by machine translation)

The invention discloses a 2 - amino - (4 - ethyl sulfonyl) phenolic synthetic method, to 4 - methoxybenzene sulfonyl chloride as the starting material, by reduction, ethyl substituted, nitration, de-methyl, 2 - amino - (4 - ethyl sulfonyl) phenol to prepare five-step reaction to obtain the final product 2 - amino - (4 - ethyl sulfonyl) phenol. The present invention the used raw materials are cheap and easily obtained, mild and easy to control the process, the reaction apparatus and after treatment is simple, low cost, easy to industrial production. (by machine translation)

1H-PYRROLO[2,3-c]PYRIDIN-7(6H)-ONES AND PYRAZOLO[3,4-c]PYRIDIN-7(6H)-ONES AS INHIBITORS OF BET PROTEINS

The present invention relates to substituted pyrrolopyridinones and substituted pyrazolopyridinones which are inhibitors of BET proteins such as BRD2, BRD3, BRD4, and BRD-t and are useful in the treatment of diseases such as cancer.