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

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

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

Downstream Products

• 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 
• 482662-60-2 2-isopropylthioxanthone sulphoxide 

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.

Ultraviolet-light-induced aerobic oxidation of benzylic C(sp3)-H of alkylarenes under catalyst- and additive-free conditions

A mild and efficient system has been discovered for the synthesis of α-aryl carbonyl compounds via oxidation of benzylic C–H to C[dbnd]O bonds. This ultraviolet-light-mediated oxygenation reaction exhibited excellent substrate scope including various xanthenes, thioxanthenes and 9, 10-dihydroacridines and afforded the corresponding ketones with good to excellent yields under catalyst- and additive-free conditions at room temperature.

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.

Ultraviolet light promoted synthesis method of thioxanthone compounds

The invention discloses an ultraviolet light promoted synthesis method of a thioxanthone compound. The preparation method comprises the following steps: carrying out a reaction in 1,2-dichloroethane at normal temperature under the condition of 380-385 nm ultraviolet irradiation by taking a thioxanthone compound as a reaction substrate and taking oxygen in air as an oxidizing agent, and after the reaction is finished, carrying out separation treatment to obtain the thioxanthone compound. According to the synthesis method disclosed by the invention, the traditional heating reaction is replaced by an illumination reaction, so that energy sources can be saved, and any catalyst is not used.

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.

Preparation method of 2-isopropylthioxanthone

The invention relates to a preparation method of a photoinitiator 2-isopropylthioxanthone. The method is concretely characterized in that 2-(4-isopropylthiophenyl)benzoic acid undergoes a ring-closingreaction under a refluxing dehydration condition to prepare the 2-isopropylthioxanthone. The method has the advantages of small use amount of concentrated sulfuric acid, small environmental pressureand good product appearance.

Visible-Light-Induced Aerobic Oxidation of Benzylic C(sp 3)-H of Alkylarenes Promoted by DDQ, tert -Butyl Nitrite, and Acetic Acid

A visible-light photocatalytic aerobic oxidation of benzylic C(sp 3)-H bonds proceeded in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tert -butyl nitrite, and acetic acid. Advantages of this aerobic oxidation method include its relatively mild conditions, the use of visible-light irradiation instead of conventional thermal methods, the use of a low catalyst loading, and the ability to oxidize a range of alkylarenes, including xanthenes, thioxanthenes, and 9,10-dihydroacridines, to the corresponding ketones in excellent yields.

A sulfur mixed anthracene compound photocatalytic oxidation synthesis method (by machine translation)

The present invention discloses a sulfur mixed anthracene compound photocatalytic oxidation synthesis method, sulfur mixed anthracene compound as a reaction substrate, in order to 2, 3 - dichloro - 5, 6 - dinitrile - 1, 4 - benzoquinone (DDQ) and tert-butyl nitrite (TBN) as catalyst, in order to acetic acid as the reaction additive, to oxygen as the oxidizing agent, the reaction substrate in 1, 2 - dichloroethane in the solvent, and the blue light illumination at normal temperature and under the conditions of reaction, after the reaction is completed after the separation and processed to obtain the sulfur mixed anthracene compound. The synthesizing method of the invention, in order to light the reaction to replace the traditional heating reaction, the energy can be saved; without the use of a transition metal catalyst; under the condition of optimizing, the yield is high. (by machine translation)

Preparation methods of acyl chloride and thioxanthone

The present invention relates to the field of fine chemicals and pharmaceutical chemicals, particularly to new economical preparation process technologies of ortho-chlorosulfenyl aroyl chloride and thioxanthone compounds, and applications of the thioxanthone compounds in synthesis of photoinitiators or other new material chemicals.

Method for catalytic oxidization synthesis of anthone compound

The invention discloses a method for catalytic oxidation synthesis of an anthone compound. The method is carried out according to the following steps: adding an anthene compound, Fe(NO3)3*9H2O and a fluorine-containing inorganic salt into an acetonitrile solvent, and performing a reaction for 2-12h at 75-85 DEG C under a normal pressure oxygen condition to obtain the anthone compound, wherein the mass ratio of the reaction substrate namely the anthone compound, Fe(NO3)3*9H2O and the fluorine-containing inorganic salt is 100:(8-15):(15-30), and after the completion of the reaction, the anthone compound can be obtained by adopting conventional column separation purification. The method provided by the invention is simple, convenient and safe to operate, and has the following beneficial effects: A) clean oxygen is used as an oxidant in the method, so that the environmental cost is greatly reduced; and B) Fe(NO3)3*9H2O is used as a catalyst in the method, so that the cost is low.