5495-84-1

Basic information

• Product Name: 2-Isopropylthioxanthone
• Synonyms: SPEEDCURE ITX;QUANTACURE ITX;SPEEDCURE 2-ITX;2-Isopropylthioxanthon;Photocure-Itx;2-Isopropylthioxanthen-9-one;9H-Thioxanthen-9-one, 2-(1-methylethyl)-;2-isopropylthioxantone
• CAS NO: 5495-84-1
• Molecular Formula: C₁₆H₁₄OS
• Molecular Weight: 254.35
• EINECS: 226-827-9
• Product Categories: Functional Materials;Photopolymerization Initiators;Aromatics;Sulfur & Selenium Compounds
• Mol File: 5495-84-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 76 °C
• Boiling Point: 398.9 °C at 760 mmHg
• Flash Point: 210 °C
• Appearance: /
• Density: 1.199 g/cm³
• Vapor Pressure: 1.43E-06mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: 340μg/L at 20℃
• CAS DataBase Reference: 2-Isopropylthioxanthone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Isopropylthioxanthone(5495-84-1)
• EPA Substance Registry System: 2-Isopropylthioxanthone(5495-84-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 20/21-58
• WGK Germany: 3
• Hazardous Substances Data: 5495-84-1(Hazardous Substances Data)

Usage

Description

2-Isopropylthioxanthone is a thioxanthone derivative, characterized as a light yellow solid with general solubility. It is effective at low concentrations and has an absorption wavelength ranging from 250 to 400nm. 2-Isopropylthioxanthone is known for its role as a sulfur type photoinitiator in various industries.

Uses

Used in Printing and Packaging Industries:
2-Isopropylthioxanthone is used as a photoinitiator for UV-cured inks in the printing industry, particularly for food packaging materials. Its application reason is to facilitate the curing process of inks under ultraviolet light, ensuring fast and efficient printing.
Used in Analytical Chemistry:
2-Isopropylthioxanthone serves as an analytical standard for determining specific analytes in packaged food materials. It is utilized in liquid chromatography-tandem mass spectrometry (LC–MS/MS) to accurately measure and identify target compounds in the samples.
Additionally, it is used as an analytical standard in high performance liquid chromatography (HPLC) coupled to MS/MS and micellar electrokinetic chromatography (MEKC) techniques for the determination of analytes in milk, fruit drinks, and other packaged beverages. The application reason is to provide a reliable and accurate reference for the quantification and identification of specific substances in these products.

InChI:InChI=1/C16H14OS/c1-10(2)11-7-8-15-13(9-11)16(17)12-5-3-4-6-14(12)18-15/h3-10H,1-2H3

Synthetic route

Isopropylbenzene (98-82-8) + 2,2'-dithiobenzoic acid (119-80-2) → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With sulfuric acid at 20℃; for 0.5h;	99%
With methanesulfonic acid; zinc In chlorobenzene at 115℃;	89.5%

2-isopropyl thioxanthene → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 12h; Irradiation;	98%
With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 12h; Sealed tube; Irradiation;	98%
With potassium hexafluorophosphate; iron(III) nitrate monohydrate; oxygen In acetonitrile at 80℃; for 2h; Reagent/catalyst; Temperature; Concentration;	96%
In 1,2-dichloro-ethane at 20℃; for 2h; UV-irradiation;	75%
With air In 1,2-dichloro-ethane at 20℃; for 2h; UV-irradiation;	75%

2-(4-isopropylphenylthio)benzoic acid (5495-75-0) → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With sulfuric acid In cyclohexane Solvent; Temperature; Reflux;	91%

Isopropylbenzene (98-82-8) + 2-chlorosulfenylbenzoyl chloride (3950-02-5) → 4-isopropylthioxanthone + 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 0.5h; Product distribution / selectivity; Friedel Crafts Acylation;	A 9.8% B 88.2%
aluminum (III) chloride In 1,2-dichloro-ethane at -10 - 25℃; for 1 - 1.25h; Product distribution / selectivity; Friedel Crafts Acylation;	A 11.2% B 76%

Isopropylbenzene (98-82-8) + 2,2'-dithiobenzoic acid (119-80-2) + Benzotrichlorid (98-07-7) → 4-isopropylthioxanthone + 2-isopropyl-9H-thioxanthen-9-one (5495-84-1) + 3-isopropylthioxanthone

Conditions	Yield
Stage #1: 2,2'-dithiobenzoic acid; Benzotrichlorid With iron(III) chloride In chlorobenzene at 100℃; for 1h; Inert atmosphere; Stage #2: Isopropylbenzene With aluminum (III) chloride In trans-1,2-dichloroethylene at 20℃; for 1h; Inert atmosphere; Overall yield = 32.8 g;

2-chloro-2'-ethoxy-5'-isopropylbenzophenone → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With copper; sodium carbonate; sulfur In 1,2-dichloro-ethane Solvent; Reagent/catalyst; Reflux;	20.8 g

2-chloro-2'-methoxy-5'-isopropylbenzophenone → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With copper; sulfur; sodium hydroxide In 1,2-dichloro-ethane Solvent; Reagent/catalyst; Reflux;	20 g

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 2-isopropyl-9H-thioxanthen-9-one 10,10-dioxide (210295-96-8)

Conditions	Yield
With Oxone In methanol; water Heating / reflux;	82%

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 2-isopropylthioxanthone sulphoxide (482662-60-2)

Conditions	Yield
With cerium(IV)diammonium nitrate In water; acetonitrile at 20℃; for 2.5h;	52.3%
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃; for 2.5h;	52.3%
With dihydrogen peroxide; trifluoroacetic acid In water at 0 - 23℃; for 12.25h;

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C29H26OS

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol 2.1: perchloric acid / toluene; water 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -84 °C / Sealed tube; Inert atmosphere 3.2: 1 h / 20 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C30H28OS

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanol 2: perchloric acid / toluene; water 3: 0.5 h / 20 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C24H24OS

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol 2.1: thionyl chloride / Inert atmosphere; Cooling with ice 2.2: Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -84 °C / Inert atmosphere 3.2: 1 h / 120 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C25H26OS

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol 2.1: thionyl chloride / Inert atmosphere; Cooling with ice 2.2: Inert atmosphere 3.1: 2 h / 20 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C16H16OS

Conditions	Yield
With methanol; sodium tetrahydroborate

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 9-(phenylthio)-2-isopropyl-9H-thioxanthene

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol 2: perchloric acid / toluene; water View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 9-(methylthio)-2-isopropyl-9H-thioxanthene

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; methanol 2.1: thionyl chloride / Inert atmosphere; Cooling with ice 2.2: Inert atmosphere View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C27H27O6S(1+)*CF3O3S(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C26H24O6S

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C 3.1: sodium hydroxide; water / chloroform / 1.5 h / 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C25H22O6S

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C 3.1: sodium hydroxide; water / chloroform / 1.5 h / 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C26H25O6S(1+)*CF3O3S(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C25H22O4S

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: trifluorormethanesulfonic acid / chloroform / 0.5 h / 23 °C 2.2: 6.25 h / 5 - 23 °C View Scheme

Upstream product

• 98-82-8 Isopropylbenzene 
• 119-80-2 2,2'-dithiobenzoic acid 
• 3950-02-5 2-chlorosulfenylbenzoyl chloride 
• 98-07-7 Benzotrichlorid 
• 5495-75-0 2-(4-isopropylphenylthio)benzoic acid 

Downstream Products

• 482662-60-2 2-isopropylthioxanthone sulphoxide 
• 210295-96-8 2-isopropyl-9H-thioxanthen-9-one 10,10-dioxide 
• 162881-26-7 phenyl bis(2,4,6-trimethylbenzoyl)phosphine oxide 
• 474510-57-1 2-hydroxy-1-(4-(4-(2-hydroxy-2-methylpropionyl)-benzyl)-phenyl)-2-methylpropan-1-one 

Relevant articles and documents

Preparation process of photoinitiator 2-/4-isopropyl thioxanthone

The invention provides a preparation process of a photoinitiator 2-/4-isopropyl thioxanthone, which comprises the following steps: by taking dithiobenzoic acid as a raw material, and carrying out substitution condensation on an intermediate 2-chloromercaptobenzoyl chloride and isopropyl benzene under an anhydrous condition by taking a boron trifluoride complexing agent as a condensing agent; after condensation, carrying out reduced-pressure solvent removal, water washing treatment and high-vacuum distillation to obtain a 2-/4-isopropyl thioxanthone crude product, and refining the crude product to obtain a 2-/4-isopropyl thioxanthone refined product. The method has the advantages that generation of three wastes is greatly reduced, the production cost is reduced, the sewage treatment pressure is reduced, the production efficiency is improved, and the method is suitable for mass production of products.

Preparation method of thioxanthone photoinitiator

The invention relates to a preparation method of a thioxanthone photoinitiator, particularly relates to a preparation method of 2,4-diethyl thioxanthone and isopropyl thioxanthone, and is characterized in that the 2,4-diethyl thioxanthone and isopropyl thioxanthone are prepared by taking dithiosalicylic acid as a raw material and adopting a combined catalyst, and the 2,4-diethyl thioxanthone and isopropyl thioxanthone are both thioxanthone photoinitiators. According to the method, the catalyst can be recycled and reused, and meanwhile, the defects that a large amount of sulfuric acid is used and a large amount of sulfonation byproducts are generated in the reaction in the traditional process are avoided. According to the method, the raw materials are cheap and easy to obtain, the yield is high, the catalyst can be recycled and continuously used, and the preparation method is cheap, environmentally friendly, easy to operate and suitable for industrialization.

2 - Isopropyl thioxanthone preparation method

The invention relates to and provides a method for preparing 2-isopropyl thioxanthone by enabling raw material 2-chloro-2'-methoxy-5'-isopropyl diphenyl ketone or 2-chloro-2'-ethoxy-5'-isopropyl diphenyl ketone to react with powdered sulfur in the presence of an alkaline substance and copper powder. The method provided by the invention is a process for preparing 2-isopropyl thioxanthone with the advantages of no use of a solvent difficult to recycle, high content, few impurities, fast reaction, low raw material consumption and simple and convenient aftertreatment.