5339-62-8

Basic information

• Product Name: fast red GTR base
• Synonyms: o-Anisidine, 5-(ethylsulfonyl)-;5-ethylsulphonyl-o-anisidine;fast red GTR base;5-(ethylsulfonyl)-2-methoxybenzenamine;C.I.37140(base);C.I.Azoic Diazo Component 29(base);[5-(ethylsulfonyl)-2-methoxyphenyl]amine;Benzenamine,5-(ethylsulfonyl)-2-methoxy-
• CAS NO: 5339-62-8
• Molecular Formula: C9H13NO3S
• Molecular Weight: 215.26942
• EINECS: 226-272-2
• Mol File: 5339-62-8.mol

Chemical Properties

• Boiling Point: 421.1°Cat760mmHg
• Flash Point: 208.5°C
• Appearance: /
• Density: 1.237g/cm³
• Vapor Pressure: 2.67E-07mmHg at 25°C
• Refractive Index: 1.542
• PKA: 2.61±0.10(Predicted)
• CAS DataBase Reference: fast red GTR base(CAS DataBase Reference)
• NIST Chemistry Reference: fast red GTR base(5339-62-8)
• EPA Substance Registry System: fast red GTR base(5339-62-8)

Safety Data

• Hazardous Substances Data: 5339-62-8(Hazardous Substances Data)

Usage

Uses

Used in Textile Industry:
Fast red GTR base is used as a dye for cotton in the textile industry for the following reasons:
1. Fastness to light: The color remains stable and does not fade easily when exposed to sunlight or artificial light.
2. Fastness to soda boiling: The color is resistant to fading or changing when the cotton is boiled in a soda solution.
3. Fastness to oxygen bleaching: The color does not fade or change when the cotton is treated with oxygen-based bleach.
4. Fastness to ironing: The color remains stable and does not change when the cotton is ironed.
5. Fastness to chlorine bleaching: The color is resistant to fading or changing when the cotton is treated with chlorine-based bleach.
The fastness properties of fast red GTR base are measured using various standards, such as ISO (International Organization for Standardization) and AATCC (American Association of Textile Chemists and Colorists). The ratings for these properties are as follows:
Fastness to light: 4-5 (ISO), 5 (AATCC)
Fastness to soda boiling: 3 (ISO), 4 (AATCC)
Fastness to oxygen bleaching: 5 (ISO), 4 (AATCC)
Fastness to ironing: 3 (ISO), 4 (AATCC)
Fastness to chlorine bleaching: 1/3N (ISO), 2N (AATCC)

Preparation

Sodium 3-acetamido-4-methoxybenzenesulfinate? with Chloroethane and the hydrolysis of ethyl?(BIOS 1149)

Coupling?components

Fast light

ISO

AATCC

1/3N

2N

12

5-6

InChI:InChI=1/C9H13NO3S/c1-3-14(11,12)7-4-5-9(13-2)8(10)6-7/h4-6H,3,10H2,1-2H3

Upstream product

• 100-66-3 methoxybenzene 
• 1432727-96-2 5-(ethylsulfonyl)-2-methoxy-1,3-dinitrobenzene 
• 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 

Downstream Products

• 628736-13-0 3-[(4-chlorophenyl)thio]-4-(ethylsulfonyl)-7-methoxy-2-methyl-1H-indole 
• 628736-12-9 3-[(4-chlorophenyl)thio]-4-(ethylsulfonyl)-7-methoxy-2-methyl-1H-indole-1-acetic acid 

Relevant articles and documents

Synthesis of 5-(ethylsulfonyl)-2-methoxyaniline: An important pharmacological fragment of VEGFR2 and other inhibitors

Background: 5-(Ethylsulfonyl)-2-methoxyaniline (5) is part of the structure in 131 compounds possessing different biological activities. In most cases, they have antitumor properties (112 compounds). Other compounds are described as cardiovascular agents, ion-channel blockers, nervous-system blockers, anti-inflammatory agents, or antidiabetic, antiosteoporotic and hypolipemic species. Compound 5 is a precursor of different protein-kinase inhibitors or enzyme modulators (EGFR, PDGFR, ckit, CDK 2 and 4, MMPs 2, 3, 9 and 13, etc.). The structure of 5 represents a fragment for several powerful inhibitors of VEGFR2, a key angiogenic receptor. Antiangiogenic inhibitors slow down or stop new blood-vessel formation from pre-existing vasculature. Some antiangiogenic drugs inhibiting the VEGFR2 receptor are successfully used in clinics for the treatment of several types of tumours in synergy with chemotherapy (e.g., Nexavar from Bayer, Sutent from Pfizer and Votrient from GlaxoSmithKline, approved by the FDA in 2005, 2006 and 2009, respectively). The structure of 5 is an important pharmacophoric fragment of potent VEGFR2 inhibitors (e.g., AAZ from PDB complex 1Y6A, enzymatic IC50 = 22 nM). Up to now, 25 VEGFR2 inhibitors possessing a fragment of 5 can be found in the literature. Despite the high significance of 5-(ethylsulfonyl)-2-methoxyaniline (5) its preparation has not yet been described. Results: Here we have developed a convenient synthesis of important polyheterosubstituted aniline 5 starting from commercially available 4-methoxybenzene-1-sulfonyl chloride (1) in four steps and 59% overall yield. The target 5-(ethylsulfonyl)-2-methoxyaniline (5) and its synthetic intermediates 2-4 together with a new compound 5-(ethylsulfonyl)-2-methoxy-1,3-dinitrobenzene (4a) have been precisely physicochemically characterised.