23117-71-7

Basic information

• Product Name: 2-(bromomethyl)-9H-thioxanthen-9-one
• Synonyms: 2-(bromomethyl)-9H-thioxanthen-9-one;Einecs 245-435-9
• CAS NO: 23117-71-7
• Molecular Formula: C₁₄H₉BrOS
• Molecular Weight: 305.18966
• EINECS: 245-435-9
• Mol File: 23117-71-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 194-195 °C(Solv: acetone (67-64-1))
• Boiling Point: 450.2°Cat760mmHg
• Flash Point: 226°C
• Appearance: /
• Density: 1.593g/cm³
• Vapor Pressure: 2.7E-08mmHg at 25°C
• Refractive Index: 1.708
• CAS DataBase Reference: 2-(bromomethyl)-9H-thioxanthen-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(bromomethyl)-9H-thioxanthen-9-one(23117-71-7)
• EPA Substance Registry System: 2-(bromomethyl)-9H-thioxanthen-9-one(23117-71-7)

Safety Data

• Hazardous Substances Data: 23117-71-7(Hazardous Substances Data)

Usage

General Description

2-(bromomethyl)-9H-thioxanthen-9-one is a chemical compound that consists of a thioxanthene core with a bromomethyl group attached to it. It is an organic compound that is commonly used in the pharmaceutical industry as a building block for the synthesis of various drugs. 2-(bromomethyl)-9H-thioxanthen-9-one has been found to exhibit antimicrobial and antifungal properties, making it useful in the development of new antimicrobial agents. Additionally, it has also been investigated for its potential as a fluorescent probe for detecting and imaging biological molecules. The bromomethyl group makes this compound a versatile intermediate for the synthesis of a wide range of organic molecules with various applications in medicine and 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

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

Downstream Products

• 957003-97-3 C₂₃H₁₇NO₅S 

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