77189-99-2

Usage

Uses

Used in Chemical Synthesis:
Benzenethiol, 2,4,6-trimethoxyis used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure with a phenol group, thiol group, and methoxy groups allows for versatile reactions and the formation of a wide range of derivatives.
Used in Pharmaceutical Industry:
Benzenethiol, 2,4,6-trimethoxyis used as a building block in the development of new pharmaceutical compounds. Its reactivity and stability make it a valuable component in the synthesis of potential drug candidates, particularly in the fields of medicinal chemistry and drug discovery.
Used in Material Science:
Benzenethiol, 2,4,6-trimethoxyis used as a component in the development of new materials with specific properties. Its molecular structure can be exploited to create materials with tailored characteristics, such as improved stability, reactivity, or other desirable traits, for use in various applications.
Used in Research and Development:
Benzenethiol, 2,4,6-trimethoxyis used as a research compound in academic and industrial laboratories. Its unique properties and potential applications make it an interesting subject for study, with the aim of uncovering new uses and understanding its behavior in different chemical contexts.

Synthetic route

Bis(2,4,6-trimethoxyphenyl) Trisulfide (77189-97-0) → 2,4,6-trimethoxybenzenethiol (77189-99-2)

Conditions	Yield
With hydrogenchloride; zinc In benzene	80%

1,2,3-trimethoxybenzene (621-23-8) → 2,4,6-trimethoxybenzenethiol (77189-99-2)

Conditions	Yield
Stage #1: 1,2,3-trimethoxybenzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: With sulfur In tetrahydrofuran; toluene at 20℃; for 6h; Inert atmosphere;	68%
Stage #1: 1,2,3-trimethoxybenzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at 0 - 20℃; for 1h; Stage #2: With sulfur In tetrahydrofuran; hexane; toluene at 20℃;	60%
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfur In hexane 1.) reflux, 2 h, 2.) reflux, 3 h;	49%

2,4,6-trimethoxybenzenethiol (77189-99-2) + 2-fluoro-N-phenethylacetamide → C19H23NO4S

Conditions	Yield
With tris(2-carboxyethyl)phosphine; 2-amino-2-hydroxymethyl-1,3-propanediol; sodium hydroxide In N,N-dimethyl-formamide at 37℃; pH=8.5; Kinetics;	83%

1,2-dithiane 1,1-dioxide (18321-15-8) + 2,4,6-trimethoxybenzenethiol (77189-99-2) → Sodium; 4-(2,4,6-trimethoxy-phenyldisulfanyl)-butane-1-sulfinate (111848-91-0)

Conditions	Yield
With sodium methylate In methanol at 25℃; for 0.0833333h;	78%

2,4,6-trimethoxybenzenethiol (77189-99-2) + Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine (135248-89-4) → Fmoc-Cys(S-TMP)-OH (1403834-74-1)

Conditions	Yield
With N-chloro-succinimide In tetrahydrofuran; dichloromethane at -78 - 25℃;	77%
With N-chloro-succinimide In tetrahydrofuran; dichloromethane at -78℃; for 1.5h; Inert atmosphere; Irradiation;	76%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + 2,4,6-trimethoxybenzenethiol (77189-99-2) → 2,4,6-trimethoxyphenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Conditions	Yield
Stage #1: 3,4,6-tri-O-benzyl-D-glucal With Oxone; sodium hydride; sodium hydrogencarbonate In dichloromethane; water; acetone at 0℃; for 0.75h; Stage #2: 2,4,6-trimethoxybenzenethiol In dichloromethane at -78℃; for 0.25h; Molecular sieve; Inert atmosphere; Stage #3: With zinc(II) chloride In diethyl ether; dichloromethane Molecular sieve; Inert atmosphere;	76%

2,4,6-trimethoxybenzenethiol (77189-99-2) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2',4',6'-Trimethoxyphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (172847-87-9)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1.) r.t., 10 min, 2.) 3 h;	73%

4,4'-dichlorodiphenyl disulfide (1142-19-4) + 2,4,6-trimethoxybenzenethiol (77189-99-2) → 2-(4-chlorophenylsulfanyl)-1,3,5-trimethoxybenzene (77189-92-5)

Conditions	Yield
With silver hexafluoroantimonate; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 100℃; for 12h; Inert atmosphere; regioselective reaction;	73%

2,4,6-trimethoxybenzenethiol (77189-99-2) → Bis(2,4,6-trimethoxyphenyl) Trisulfide (77189-97-0)

Conditions	Yield
With sulfur dichloride In diethyl ether at 0℃;	70%

3,4,6-tri-O-(4-chlorobenzyl)-D-glucal + 2,4,6-trimethoxybenzenethiol (77189-99-2) → 2,4,6-trimethoxyphenyl 3,4,6-tri-O-(4-chlorobenzyl)-1-thio-β-D-glucopyranoside

Conditions	Yield
Stage #1: 3,4,6-tri-O-(4-chlorobenzyl)-D-glucal With Oxone; sodium hydride; sodium hydrogencarbonate In dichloromethane; water; acetone at 0℃; for 0.75h; Stage #2: 2,4,6-trimethoxybenzenethiol In dichloromethane at -78℃; for 0.25h; Molecular sieve; Inert atmosphere; Stage #3: With zinc(II) chloride In diethyl ether; dichloromethane Molecular sieve; Inert atmosphere;	61%

3,4,6-tri-O-(4-chlorobenzyl)-β-D-galactal + 2,4,6-trimethoxybenzenethiol (77189-99-2) → 2,4,6-trimethoxyphenyl 3,4,6-tri-O-(4-chlorobenzyl)-1-thio-β-D-galactopyranoside

Conditions	Yield
Stage #1: 3,4,6-tri-O-(4-chlorobenzyl)-β-D-galactal With Oxone; sodium hydride; sodium hydrogencarbonate In dichloromethane; water; acetone at 0℃; for 0.75h; Stage #2: 2,4,6-trimethoxybenzenethiol In dichloromethane at -78℃; for 0.25h; Molecular sieve; Inert atmosphere; Stage #3: With zinc(II) chloride In diethyl ether; dichloromethane Molecular sieve; Inert atmosphere;	60%

3,4,6-tri-O-benzyl-D-galactal (80040-79-5) + 2,4,6-trimethoxybenzenethiol (77189-99-2) → 2,4,6-trimethoxyphenyl 3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

Conditions	Yield
Stage #1: 3,4,6-tri-O-benzyl-D-galactal With Oxone; sodium hydride; sodium hydrogencarbonate In dichloromethane; water; acetone at 0℃; for 0.75h; Stage #2: 2,4,6-trimethoxybenzenethiol In dichloromethane at -78℃; for 0.25h; Molecular sieve; Inert atmosphere; Stage #3: With zinc(II) chloride In diethyl ether; dichloromethane Molecular sieve; Inert atmosphere;	59%

formic acid (64-18-6) + 2,4,6-trimethoxybenzenethiol (77189-99-2) → S-(2,4,6-trimethoxy)phenyl thioformate

Conditions	Yield
Stage #1: formic acid With acetic anhydride at 45℃; for 2.5h; Schlenk technique; Stage #2: 2,4,6-trimethoxybenzenethiol With pyridine at 30℃; for 24h; Schlenk technique;	55%

3,4,6-tri-O-(2,4-dichlorobenzyl)-D-glucal + 2,4,6-trimethoxybenzenethiol (77189-99-2) → 2,4,6-trimethoxyphenyl 3,4,6-tri-O-(2,4-dichlorobenzyl)-1-thio-β-D-glucopyranoside

Conditions	Yield
Stage #1: 3,4,6-tri-O-(2,4-dichlorobenzyl)-D-glucal With Oxone; sodium hydride; sodium hydrogencarbonate In dichloromethane; water; acetone at 0℃; for 0.75h; Stage #2: 2,4,6-trimethoxybenzenethiol In dichloromethane at -78℃; for 0.25h; Molecular sieve; Inert atmosphere; Stage #3: With zinc(II) chloride In diethyl ether; dichloromethane Molecular sieve; Inert atmosphere;	50%

3,4,6-tri-O-(2,4-dichlorobenzyl)-β-D-galactal + 2,4,6-trimethoxybenzenethiol (77189-99-2) → 2,4,6-trimethoxyphenyl 3,4,6-tri-O-(2,4-dichlorobenzyl)-1-thio-β-D-galactopyranoside

Conditions	Yield
Stage #1: 3,4,6-tri-O-(2,4-dichlorobenzyl)-β-D-galactal With Oxone; sodium hydride; sodium hydrogencarbonate In dichloromethane; water; acetone at 0℃; for 0.75h; Stage #2: 2,4,6-trimethoxybenzenethiol In dichloromethane at -78℃; for 0.25h; Molecular sieve; Inert atmosphere; Stage #3: With zinc(II) chloride In diethyl ether; dichloromethane Molecular sieve; Inert atmosphere;	50%

2,4,6-trimethoxybenzenethiol (77189-99-2) → di(2,4,6-trimethoxyphenyl) disulphide (80279-40-9)

Conditions	Yield
In dimethyl sulfoxide for 24h; Ambient temperature; Yield given;
With iodine

2,4,6-trimethoxybenzenethiol (77189-99-2) → 2',4',6'-Trimethoxyphenyl 1-thio-β-D-glucopyranoside (172847-88-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / NaH / dimethylformamide / 1.) r.t., 10 min, 2.) 3 h 2: 91 percent / NaOMe / methanol / 3 h / Ambient temperature View Scheme

2,4,6-trimethoxybenzenethiol (77189-99-2) → 2',4',6'-Trimethoxyphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (172847-89-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 73 percent / NaH / dimethylformamide / 1.) r.t., 10 min, 2.) 3 h 2: 91 percent / NaOMe / methanol / 3 h / Ambient temperature 3: 67 percent / NaH / dimethylformamide / 1.) r.t., 10 min, 2.) 80 deg C, 10 h View Scheme

2,4,6-trimethoxybenzenethiol (77189-99-2) → Bis(2,4,6-trimethoxyphenyl)sulfid Radikalkation (80279-38-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: I2 2: AlCl3 / CH2Cl2 View Scheme

2,4,6-trimethoxybenzenethiol (77189-99-2) → C36H44N4O8S2 (1403834-78-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-chloro-succinimide / tetrahydrofuran; dichloromethane / 1.5 h / -78 °C / Inert atmosphere; Irradiation 2.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 1.08 h / 20 °C / Inert atmosphere 2.2: rink amide resin / Inert atmosphere View Scheme

2,4,6-trimethoxybenzenethiol (77189-99-2) → C21H34N4O6S2

Conditions

Yield

Multi-step reaction with 3 steps 1.1: N-chloro-succinimide / tetrahydrofuran; dichloromethane / 1.5 h / -78 °C / Inert atmosphere; Irradiation 2.1: diisopropyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime / N,N-dimethyl-formamide / 1.08 h / 20 °C / Inert atmosphere 2.2: rink amide resin / Inert atmosphere 3.1: dichloromethane; N,N-dimethyl-formamide / Inert atmosphere 3.2: Inert atmosphere View Scheme

Upstream product

• 621-23-8 1,2,3-trimethoxybenzene 
• 77189-97-0 Bis(2,4,6-trimethoxyphenyl) Trisulfide 

Downstream Products

• 111848-91-0 Sodium; 4-(2,4,6-trimethoxy-phenyldisulfanyl)-butane-1-sulfinate 
• 80279-38-5 Bis(2,4,6-trimethoxyphenyl)sulfid-Radikalkation 
• 1403834-78-5 C₃₆H₄₄N₄O₈S₂ 
• 1403834-74-1 Fmoc-Cys(S-TMP)-OH 
• 77189-92-5 2-(4-chlorophenylsulfanyl)-1,3,5-trimethoxybenzene 
• 172847-89-1 2',4',6'-Trimethoxyphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 172847-88-0 2',4',6'-Trimethoxyphenyl 1-thio-β-D-glucopyranoside 
• 80279-40-9 di(2,4,6-trimethoxyphenyl) disulphide 
• 77189-97-0 Bis(2,4,6-trimethoxyphenyl) Trisulfide 

Relevant academic research and scientific papers

Steric-Free Bioorthogonal Labeling of Acetylation Substrates Based on a Fluorine-Thiol Displacement Reaction

We have developed a novel bioorthogonal reaction that can selectively displace fluorine substitutions alpha to amide bonds. This fluorine-thiol displacement reaction (FTDR) allows for fluorinated cofactors or precursors to be utilized as chemical reporters, hijacking acetyltransferase-mediated acetylation both in vitro and in live cells, which cannot be achieved with azide- or alkyne-based chemical reporters. The fluoroacetamide labels can be further converted to biotin or fluorophore tags using FTDR, enabling the general detection and imaging of acetyl substrates. This strategy may lead to a steric-free labeling platform for substrate proteins, expanding our chemical toolbox for functional annotation of post-translational modifications in a systematic manner.

LINKING AMINO ACID SEQUENCES, MANUFACTURING METHOD THEREOF, AND USE THEREOF

This invention provides compositions comprising linked amino acid sequences, pharmaceutical compositions comprising linked amino acid sequences, and methods of making thereof. This invention also provides methods of delivering said compositions to subjects and methods of treating various disorders and diseases using the said compositions.

Trimethoxyphenylthio as a highly labile replacement for tert-butylthio cysteine protection in fmoc solid phase synthesis

Trimethoxyphenylthio (S-Tmp) is described as a novel cysteine protecting group in Fmoc solid phase peptide synthesis replacing the difficult to remove tert-butylthio. S-Tmp and dimethoxyphenylthio (S-Dmp) were successfully used for cysteine protection in a variety of peptides. Moreover, both groups can be removed in 5 min with mild reducing agents. S-Tmp is recommended for cysteine protection, as it yields crude peptides of high purity.

Trimethoxyphenylthio as a highly labile replacement for tert-butylthio cysteine protection in fmoc solid phase synthesis

Trimethoxyphenylthio (S-Tmp) is described as a novel cysteine protecting group in Fmoc solid phase peptide synthesis replacing the difficult to remove tert-butylthio. S-Tmp and dimethoxyphenylthio (S-Dmp) were successfully used for cysteine protection in a variety of peptides. Moreover, both groups can be removed in 5 min with mild reducing agents. S-Tmp is recommended for cysteine protection, as it yields crude peptides of high purity.

THIOGLYCOSIDES AS POTENTIAL GLYCOSYL DONORS IN ELECTROCHEMICAL GLYCOSYLATION REACTIONS. PART 1: THEIR PREPARATION AND REACTIVITY TOWARD SIMPLE ALCOHOLS

Costant potential electrolysis of several glycosyl donors such as substituted phenyl 2,3,4,6-tetra-O-acetyl, benzoyl or benzyl-1-thio-β-D-gluco or galactopyranosides in dry acetonitrile in the presence of various primary, secondary or tertiary alcohols performed in an undivided cell, gave preferentially β-linked saccharides in moderate to good yields according to the nature of the protective groups on the sugar moiety. 2-Deoxy-2-phthalimido-1-thio-β-D-gluco derivatives gave the β-glucosides selectively in excellent yields.It was found, as expected, that substitution of the phenyl group with methoxy or methyl radicals facilitates the electrochemical glycosylation reaction by lowering the oxidation potentials of the corresponding thioglycosides.