23117-71-7

Usage

Uses

Used in Pharmaceutical Industry:
2-(bromomethyl)-9H-thioxanthen-9-one is used as a building block for the synthesis of various drugs, leveraging its unique structure to create a wide range of medicinal compounds.
Used in Antimicrobial Applications:
In the field of microbiology, 2-(bromomethyl)-9H-thioxanthen-9-one is used as an antimicrobial agent due to its ability to exhibit antimicrobial and antifungal properties, contributing to the development of new antimicrobial agents to combat resistant strains.
Used in Research and Development:
2-(bromomethyl)-9H-thioxanthen-9-one is utilized as a fluorescent probe for detecting and imaging biological molecules, taking advantage of its potential to interact with these molecules and provide visual or measurable signals for analysis.
Used in Organic Synthesis:
The bromomethyl group in 2-(bromomethyl)-9H-thioxanthen-9-one makes it a versatile intermediate for the synthesis of a broad spectrum of organic molecules, applicable across various industries including medicine and chemical research.

InChI:InChI=1/C14H9BrOS/c15-8-9-5-6-13-11(7-9)14(16)10-3-1-2-4-12(10)17-13/h1-7H,8H2

Synthetic route

2-methyl-9H-thioxanthen-9-one (15774-82-0) → 2-bromomethyl-9H-thioxanthene-9-one (23117-71-7)

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide
With N-Bromosuccinimide; dibenzoyl peroxide In cyclohexane for 4h; Reflux;
With N-Bromosuccinimide; dibenzoyl peroxide In cyclohexane for 4h; Reflux;	1.8 g

toluene (108-88-3) → 2-bromomethyl-9H-thioxanthene-9-one (23117-71-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / 1 h / 25 °C 1.2: 2 h / 20 - 25 °C 2.1: N-Bromosuccinimide / dibenzoyl peroxide / cyclohexane / 4 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: sulfuric acid / 1 h / 20 °C 1.2: 2 h / 20 °C 2.1: N-Bromosuccinimide; dibenzoyl peroxide / cyclohexane / 4 h / Reflux View Scheme

2,2'-dithiobenzoic acid (119-80-2) → 2-bromomethyl-9H-thioxanthene-9-one (23117-71-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / 1 h / 25 °C 1.2: 2 h / 20 - 25 °C 2.1: N-Bromosuccinimide / dibenzoyl peroxide / cyclohexane / 4 h / Reflux View Scheme

dithiosalicylic acid (527-89-9) → 2-bromomethyl-9H-thioxanthene-9-one (23117-71-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / 1 h / 20 °C 1.2: 2 h / 20 °C 2.1: N-Bromosuccinimide; dibenzoyl peroxide / cyclohexane / 4 h / Reflux View Scheme

methyl (2-nitrophenyl)acetate (30095-98-8) + 2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → C23H17NO5S (957003-97-3)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 18h;	93%

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) + Thiosalicylic acid (147-93-3) → 2-[(9-oxo-9H-thioxanthen-2-yl)methylthio]benzoic acid

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	93%

N,N-bis(p-nitrophenyl)amine (1821-27-8) + 2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 2-[bis(4-nitrophenyl)aminomethyl]-9H-thioxanthene-9-one

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 5h;	90%

pyridine (110-86-1) + 2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 1-(9-oxo-9H-thioxanthen-2-ylmethyl)pyridinium bromide

Conditions	Yield
In chloroform at 20 - 25℃; for 48h;	84%

4-mercaptobenzoic acid (1074-36-8) + 2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 4-[(9-oxo-9H-thioxanthen-2-yl)methylthio]benzoic acid

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	83%

methanol (67-56-1) + 2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 2-(methoxymethyl)thioxanthone (93825-19-5)

Conditions	Yield
With potassium hydroxide for 3h; Heating;	77%

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) + triphenylphosphine (603-35-0) → (9-oxo-9H-thioxanthen-2-ylmethyl)triphenylphosphonium bromide

Conditions	Yield
In toluene for 1h; Heating;	76%

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) + sodium thiomethoxide (5188-07-8) → 2-(methylthiomethyl)thioxanthone (93825-12-8)

Conditions	Yield
In methanol; acetone for 2h; Heating;	75%

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 2-bromomethyl-9H-thioxanthen-9-one 10-oxide (912968-30-0)

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile at 20 - 25℃; for 2h;	75%

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) + triethylamine (121-44-8) → triethyl(9-oxo-9H-thioxanthen-2-ylmethyl)ammonium bromide

Conditions	Yield
In chloroform at 20 - 25℃; for 48h;	75%

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 2-bromomethyl-9H-thioxanthen-9-one 10,10-dioxide

Conditions	Yield
With dihydrogen peroxide In water; acetic acid for 2h; Heating;	62%

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 2-bromomethyl-9-oxo-10-(4-heptoxyphenyl)-9H-thioxanthenium

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / cerium ammonium nitrate / acetonitrile; H2O / 2 h / 20 - 25 °C 2: P2O5; methanesulfonic acid View Scheme

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 2-(methoxymethyl)-9-(3-dimethylaminopropyl)thioxanthene-9-ol (93825-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / KOH / 3 h / Heating 2: Mg / 1.) ether, reflux 8 h; 2.) reflux 20 h View Scheme

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 9-(3-dimethylaminopropyl)-2-(methylthiomethyl)thioxanthene-9-ol (93825-13-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / acetone; methanol / 2 h / Heating 2: Mg / 1.) THF; 2.) benzene, reflux 12 h View Scheme

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 9-(3-dimethylaminopropylidene)-2-(methylthiomethyl)thioxanthene (93825-14-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 75 percent / acetone; methanol / 2 h / Heating 2: Mg / 1.) THF; 2.) benzene, reflux 12 h 3: 90 percent / 1.25M-H2SO4 / 1 h / 100 °C View Scheme

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) + 1,8-diazabicyclo[5.4.0]undec-7-ene (6674-22-2) → 8-(9-oxo-9H-thioxanthen-2-yl)methyl-1,8-diazabicyclo[5.4.0]-7-undecenium bromide (1190431-05-0)

Conditions	Yield
In dichloromethane at 25℃; for 1h;

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) + 1,8-diazabicyclo[5.4.0]undec-7-ene (6674-22-2) → 8-(9-oxo-9H-thioxanthen-2-yl)methyl-1,8-diazabicyclo[5.4.0]-7-undecenium tetraphenylborate

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 1 h / 25 °C 2: chloroform; water / 1 h / 25 °C View Scheme

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 2-mercaptomethylthioxanthone

Conditions	Yield
Stage #1: 2-bromomethyl-9H-thioxanthene-9-one With potassium thioacetate In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: With potassium carbonate at 20℃; for 1h;	5 g

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → C40H32BO3S(1-)*C16H23N2(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / N,N-dimethyl-formamide / 20 h 2: water; chloroform / 3 h / 20 °C View Scheme

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → C40H32BO3S(1-)*C17H23N2O(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / N,N-dimethyl-formamide / 20 h 2: water; chloroform / 3 h / 20 °C View Scheme

potassium (4-hydroxyethyloxy)phenyltriphenylborate + 2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → C40H32BO3S(1-)*K(1+)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide for 20h;	11 g

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → 2-[bis(4-aminophenyl)aminomethyl]-9H-thioxanthene-9-one

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 5 h / 80 °C 2: palladium 10% on activated carbon; hydrazine hydrate / tetrahydrofuran / 24 h / 66 °C / Inert atmosphere View Scheme

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → C26H23N3S

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 5 h / 80 °C 2: acetic acid; zinc / 0.5 h / 20 °C View Scheme

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → C24H21NO2S2

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2.1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / acetonitrile / 0 °C 2.2: 0 °C View Scheme

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → C24H21NO6S2

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2.1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / acetonitrile / 0 °C 2.2: 0 °C 3.1: acetic acid; dihydrogen peroxide / Reflux View Scheme

2-bromomethyl-9H-thioxanthene-9-one (23117-71-7) → C24H21NO6S2

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2.1: acetic acid; dihydrogen peroxide / Reflux 3.1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / acetonitrile / 0 °C 3.2: 0 °C View Scheme

Upstream product

• 527-89-9 dithiosalicylic acid 
• 108-88-3 toluene 
• 119-80-2 2,2'-dithiobenzoic acid 
• 15774-82-0 2-methyl-9H-thioxanthen-9-one 

Downstream Products

• 957003-97-3 C₂₃H₁₇NO₅S 

Relevant academic research and scientific papers

PHOTOBASE GENERATOR

Provided are a photobase generator having higher sensitivity to light than do conventional photobase generators, and a photosensitive resin composition containing the photobase generator. The present invention is a photobase generator characterized in containing a salt represented by general formula (1). (In formula (1), R 1 -R 4 are mutually independent groups represented by general formula (2), C1-18 alkyl groups, or Ar, with at least one being a group represented by general formula (2); in formula (2), (D) is a divalent group bonded on at least one side to elemental boron, and Ar 1 is the same as the aforementioned Ar; and Q + is a monovalent onium cation.) €?€?€?€?€?€?€?€?-(D)-Ar 1 €?€?€?€?€?(2)

PHOTOSENSITIVE COMPOSITION

The present invention refers to attenuation or light irradiated number colored masking a substance such as a high-density film transmitting thick presence the nozzles less even in a case of a low energy dose curable a photosensitive composition and gives a cured article is defined to be in the, these compositions comprise photosensitive of the present invention (1) ～ (4) as disclosed is a photosensitive composition containing, radical disclosure number (A), number (C) base generation and number (B) acid generator at least 1 by the irradiation of the light active dog generates active species (H), (H) active species thereof disclosure number (A) radical is, number (B) acid generator or base generation number (C) reacts with the new active species (I) the registrant produces new active species by polymeric material (I) is performed by polymerization of (D), (I) or (H) active species thereof acid or base is characterized in that; (1) radical disclosure number (A) (2) acid generator or base generation number (C) number (B) (3) polymeric material (D) (4) number (E) colored, metal oxide powder (F) or metal powder (G).

Photobase generator

The object of the present invention is to provide a photobase generator capable of efficiently generating amines (tertiary amines and amidine) high in catalytic activity by sensing light with a wavelength of from 350 to 500 nm (especially, from 400 to 500 nm). The present invention is a photobase generator characterized in being represented by general formula (1) or (2). Y+ is a quaternary ammonio group of general formula (3) to (5), and X? is a counter anion selected from among a borate anion, a phenolate anion, and a carboxylate anion.