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142770-42-1

1-Chloro-4-propoxythioxanthone, also known as CPTX, is a thioxanthone derivative that is widely used in the field of organic synthesis and as a photoinitiator for polymerization reactions. It is characterized by the presence of a chlorine atom at the first position and a propoxy group at the fourth position of the thioxanthone ring. This versatile chemical compound is known for its ability to initiate polymerization when exposed to UV light, making it a valuable component in the production of coatings, adhesives, and printing inks. Furthermore, CPTX has been studied for its potential application in photodynamic therapy for cancer treatment, showcasing its potential in both industrial and biomedical fields.

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  • 142770-42-1 Structure

  • Basic information

    1. Product Name: 1-Chloro-4-propoxythioxanthone
    2. Synonyms: 1-CHLORO-4-PROPOXY-9H-THIOXANTHEN-9-ONE;1-CHLORO-4-PROPOXYTHIOXANTHONE;SPEEDCURE CPTX;9H-Thioxanthen-9-one, 1-chloro-4-propoxy-;1-Chloro-4-propoxy-9H-thioxanthen-9-one 97%;1-Chloro-4-propoxythioxanthone, CPTX
    3. CAS NO:142770-42-1
    4. Molecular Formula: C16H13ClO2S
    5. Molecular Weight: 304.79
    6. EINECS: N/A
    7. Product Categories: Thioxanthones;Organic Photoinitiators;Polymerization Initiators
    8. Mol File: 142770-42-1.mol

  • Chemical Properties

    1. Melting Point: 99-103 °C(lit.)
    2. Boiling Point: 467.402 °C at 760 mmHg
    3. Flash Point: 236.477 °C
    4. Appearance: /
    5. Density: 1.319 g/cm3
    6. Vapor Pressure: 6.53E-09mmHg at 25°C
    7. Refractive Index: 1.637
    8. Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. Water Solubility: 80.6μg/L at 20℃
    11. CAS DataBase Reference: 1-Chloro-4-propoxythioxanthone(CAS DataBase Reference)
    12. NIST Chemistry Reference: 1-Chloro-4-propoxythioxanthone(142770-42-1)
    13. EPA Substance Registry System: 1-Chloro-4-propoxythioxanthone(142770-42-1)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 142770-42-1(Hazardous Substances Data)

142770-42-1 Usage

Uses

Used in Coatings Industry:
1-Chloro-4-propoxythioxanthone is used as a photoinitiator for [application type] in the coatings industry for [application reason] its ability to initiate polymerization when exposed to UV light, which is essential for the curing process of various coatings.
Used in Adhesives Industry:
1-Chloro-4-propoxythioxanthone is used as a photoinitiator in the adhesives industry for [application reason] its capability to promote rapid curing of adhesives upon exposure to UV light, enhancing their bonding strength and durability.
Used in Printing Inks Industry:
1-Chloro-4-propoxythioxanthone is used as a photoinitiator in the printing inks industry for [application reason] its effectiveness in initiating the polymerization process, which is crucial for the drying and curing of inks on various substrates.
Used in Photodynamic Therapy for Cancer Treatment:
1-Chloro-4-propoxythioxanthone is used as a potential agent in photodynamic therapy for cancer treatment for [application reason] its ability to generate reactive oxygen species upon exposure to light, which can selectively destroy cancer cells while minimizing damage to surrounding healthy tissues. This application is still under research and development, but it holds promise for advancing cancer treatment options.

Check Digit Verification of cas no

The CAS Registry Mumber 142770-42-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,2,7,7 and 0 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 142770-42:
(8*1)+(7*4)+(6*2)+(5*7)+(4*7)+(3*0)+(2*4)+(1*2)=121
121 % 10 = 1
So 142770-42-1 is a valid CAS Registry Number.
InChI:InChI=1/C16H13ClO2S/c1-2-9-19-12-8-7-11(17)14-15(18)10-5-3-4-6-13(10)20-16(12)14/h3-8H,2,9H2,1H3

142770-42-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-chloro-4-propoxythioxanthen-9-one

1.2 Other means of identification

Product number -
Other names 1-chloro-4-propyloxy-thioxanthone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:142770-42-1 SDS

142770-42-1Synthetic route

1-chloro-4-hydroxy-9H-thioxanthen-9-one
59803-22-4

1-chloro-4-hydroxy-9H-thioxanthen-9-one

propyl bromide
106-94-5

propyl bromide

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With potassium carbonate at 80℃;95.4%
1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

1-chloro-4-hydroxy-9H-thioxanthen-9-one
59803-22-4

1-chloro-4-hydroxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
Stage #1: 1-chloro-4-propoxy-9H-thioxanthen-9-one With boron tribromide In dichloromethane at -70℃;
Stage #2: With methanol		88%
With boron tribromide Ullmann Condensation;
1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

4-propoxy-1-chloro-9H-thioxanthen-9-one 10-oxide
591773-95-4

4-propoxy-1-chloro-9H-thioxanthen-9-one 10-oxide

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile at 20 - 25℃; for 2h;87%
With ammonium cerium(IV) nitrate In water; acetonitrile at 50℃; for 1h;72.7%
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃; for 2h;
1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

4-propoxy-1-chloro-9H-thioxanthen-9-one 10,10-dioxide

4-propoxy-1-chloro-9H-thioxanthen-9-one 10,10-dioxide

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetic acid for 2h; Heating;56%
methanol
67-56-1

methanol

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

A

1-methoxy-4-propoxy-9H-thioxanthen-9-one
1351934-50-3

1-methoxy-4-propoxy-9H-thioxanthen-9-one

B

1-[(3-hydroxypropyl)amino]-4-propoxy-9H-thioxanthen-9-one
1351934-52-5

1-[(3-hydroxypropyl)amino]-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(I) oxide at 100℃; for 48h; Ullmann cross-coupling;A n/a
B 30%
(2R)-hydroxypropylamine
2799-16-8

(2R)-hydroxypropylamine

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

(R)-1-((2-hydroxypropyl)amino)-4-propoxy-9H-thioxanthen-9-one

(R)-1-((2-hydroxypropyl)amino)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In methanol at 100℃; for 48h;23.62%
(S)-2-amino-4-methylpentan-1-ol
7533-40-6

(S)-2-amino-4-methylpentan-1-ol

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

(S)-1-((1-hydroxy-4-methylpentan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

(S)-1-((1-hydroxy-4-methylpentan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In methanol at 100℃; for 48h;19.59%
2-amino-4-methyl-1-pentanol
7533-40-6, 16369-17-8, 53448-09-2, 502-32-9

2-amino-4-methyl-1-pentanol

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

(R)-1-((1-hydroxy-4-methylpentan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

(R)-1-((1-hydroxy-4-methylpentan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In methanol at 100℃; for 48h;10.4%
(R)-2-amino-3-methylbutanol
4276-09-9

(R)-2-amino-3-methylbutanol

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

(R)-1-((1-hydroxy-3-methylbutan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

(R)-1-((1-hydroxy-3-methylbutan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In methanol at 100℃; for 48h;10.24%
(S)-valinol
2026-48-4

(S)-valinol

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

(S)-1-((1-hydroxy-3-methylbutan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

(S)-1-((1-hydroxy-3-methylbutan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In methanol at 100℃; for 48h;10.12%
(S)-1-amino-2-propanol
2799-17-9

(S)-1-amino-2-propanol

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

(S)-1-((2-hydroxypropyl)amino)-4-propoxy-9H-thioxanthen-9-one

(S)-1-((2-hydroxypropyl)amino)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In methanol at 100℃; for 48h;7.86%
(R)-2-aminopropan-1-ol
35320-23-1

(R)-2-aminopropan-1-ol

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

(R)-1-((1-hydroxypropan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

(R)-1-((1-hydroxypropan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In methanol at 100℃; for 48h;5.91%
(S)-Alaninol
2749-11-3

(S)-Alaninol

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

(S)-1-((1-hydroxypropan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

(S)-1-((1-hydroxypropan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In methanol at 100℃; for 48h;1.97%
1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

4-propoxy-1-chloro-9-oxo-10-(4-heptoxyphenyl)-9H-thioxanthenium

4-propoxy-1-chloro-9-oxo-10-(4-heptoxyphenyl)-9H-thioxanthenium

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 87 percent / cerium ammonium nitrate / acetonitrile; H2O / 2 h / 20 - 25 °C
2: P2O5; methanesulfonic acid
View Scheme
4,4'-didodecyloxyphenyl sulfoxide
134216-06-1

4,4'-didodecyloxyphenyl sulfoxide

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

C52H70ClO4S2(1+)*F6Sb(1-)

C52H70ClO4S2(1+)*F6Sb(1-)

Conditions
ConditionsYield
Stage #1: 4,4'-didodecyloxyphenyl sulfoxide; 1-chloro-4-propoxy-9H-thioxanthen-9-one With sulfuric acid In chloroform; acetic anhydride at 10 - 20℃; for 48h;
Stage #2: With sodium hexafluoroantimonate In chloroform; water; acetic anhydride at 20℃; for 12h;
piperidine
110-89-4

piperidine

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

1-(piperidin-1-yl)-4-propoxy-9H-thioxanthen-9-one
1351934-53-6

1-(piperidin-1-yl)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(I) oxide Ullmann cross-coupling;
DL-threonine
72-19-5, 80-68-2, 144-98-9, 632-20-2, 2676-21-3, 7004-04-8, 24830-94-2, 28954-12-3, 36676-50-3

DL-threonine

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

3-Hydroxy-2-[(9-oxo-4-propoxy-9H-thioxanthen-1-yl)amino]butanoic acid
1351934-55-8

3-Hydroxy-2-[(9-oxo-4-propoxy-9H-thioxanthen-1-yl)amino]butanoic acid

Conditions
ConditionsYield
With copper(I) oxide In 1-methyl-pyrrolidin-2-one; water Ullmann cross-coupling;
N-acetylpiperidine
13889-98-0

N-acetylpiperidine

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

1-(4-acetylpiperazin-1-yl)-4-propoxy-9H-thioxanthen-9-one
1351934-58-1

1-(4-acetylpiperazin-1-yl)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(I) oxide; potassium carbonate In 1-methyl-pyrrolidin-2-one at 205℃; for 0.833333h; Ullmann cross-coupling; Microwave irradiation;
isoniazid
54-85-3

isoniazid

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

N'-(9-oxo-4-propoxy-9H-thioxanthen-1-yl)isonicotinohydrazide
1351934-61-6

N'-(9-oxo-4-propoxy-9H-thioxanthen-1-yl)isonicotinohydrazide

Conditions
ConditionsYield
With copper(I) oxide Ullmann cross-coupling;
valinol
16369-05-4

valinol

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

C21H25NO3S

C21H25NO3S

Conditions
ConditionsYield
With copper(I) oxide; potassium carbonate In methanol at 100℃; for 48h; Ullmann cross-coupling;
2-(1H-benzimidazol-2-yl)ethylamine
29518-68-1

2-(1H-benzimidazol-2-yl)ethylamine

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

1-[2-(1H-benzimidazole-2-yl)ethylamino]-4-propoxy-9H-thioxanthen-9-one
1351934-65-0

1-[2-(1H-benzimidazole-2-yl)ethylamino]-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(I) oxide In 1-methyl-pyrrolidin-2-one; water Ullmann cross-coupling;
1,2,3,4-tetrahydroisoquinolin-5-amine
115955-90-3

1,2,3,4-tetrahydroisoquinolin-5-amine

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

1-(5-Amino-3,4-dihydroisoquinolin-2(1H)-yl)-4-propoxy-9H-thioxanthen-9-one
1351934-63-8

1-(5-Amino-3,4-dihydroisoquinolin-2(1H)-yl)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(I) oxide; potassium carbonate In 1-methyl-pyrrolidin-2-one at 205℃; for 0.833333h; Ullmann cross-coupling; Microwave irradiation;
C12H17NO6

C12H17NO6

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

C28H29NO8S

C28H29NO8S

Conditions
ConditionsYield
With copper(I) oxide In 1-methyl-pyrrolidin-2-one; water Ullmann cross-coupling;
sulfuric acid mono-(2-amino-ethyl ester)
926-39-6

sulfuric acid mono-(2-amino-ethyl ester)

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

2-[(9-Oxo-4-propoxy-9H-thioxanthen-1-yl)amino]ethyl hydrogen sulfate
1351934-62-7

2-[(9-Oxo-4-propoxy-9H-thioxanthen-1-yl)amino]ethyl hydrogen sulfate

Conditions
ConditionsYield
With copper(I) oxide Ullmann cross-coupling;
O-(p-nitrobenzyl)hydroxylamine
1944-96-3

O-(p-nitrobenzyl)hydroxylamine

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

1-(((4-nitrobenzyl)oxy)amino)-4-propoxy-9H-thioxanthen-9-one
1351934-69-4

1-(((4-nitrobenzyl)oxy)amino)-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(I) oxide Ullmann cross-coupling;
p-xylylidenediamine
539-48-0

p-xylylidenediamine

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

1-{[4-(Aminomethyl)benzyl]amino}-4-propoxy-9H-thioxanthen-9-one
1351934-59-2

1-{[4-(Aminomethyl)benzyl]amino}-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(I) oxide Ullmann cross-coupling;
2-(p-nitrophenyl)ethylamine
24954-67-4

2-(p-nitrophenyl)ethylamine

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

1-{[2-(4-nitrophenyl)ethyl]amino}-4-propoxy-9H-thioxanthen-9-one
1351934-68-3

1-{[2-(4-nitrophenyl)ethyl]amino}-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(I) oxide Ullmann cross-coupling;
2-nitro-4-ethoxyaniline
616-86-4

2-nitro-4-ethoxyaniline

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

1-[(4-Ethoxy-2-nitrophenyl)amino]-4-propoxy-9H-thioxanthen-9-one
1351934-70-7

1-[(4-Ethoxy-2-nitrophenyl)amino]-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(I) oxide; potassium carbonate In 1-methyl-pyrrolidin-2-one at 205℃; for 0.833333h; Ullmann cross-coupling; Microwave irradiation;
3,4-methylenedioxyphenylethylamine
1484-85-1

3,4-methylenedioxyphenylethylamine

1-chloro-4-propoxy-9H-thioxanthen-9-one
142770-42-1

1-chloro-4-propoxy-9H-thioxanthen-9-one

1-{[2-(1,3-benzodioxol-5-yl)ethyl]amino}-4-propoxy-9H-thioxanthen-9-one
1351934-66-1

1-{[2-(1,3-benzodioxol-5-yl)ethyl]amino}-4-propoxy-9H-thioxanthen-9-one

Conditions
ConditionsYield
With copper(I) oxide Ullmann cross-coupling;
Ullmann Condensation; Alkaline conditions; Microwave irradiation;

142770-42-1Relevant articles and documents

Preparation method of photoinitiator 1-chloro-4-propoxythioxanthone

-

Paragraph 0035; 0037; 0038, (2018/09/12)

The invention discloses a preparation method of a photoinitiator 1-chloro-4-propoxythioxanthone. The method comprises the following steps: step 1, carrying out condensation ring formation reaction: adding 2-mercaptobenzoic acid and p-chlorophenol into concentrated sulfuric acid and extracting to obtain a corresponding organic product; step 2, directly carrying out etherification reaction, withoutthe need of separation and purification: adding 1-halogenated propane and alkali into an obtained organic layer; finally, carrying out decompression and desolvation, de-coloring, filtering and vacuumdrying on an etherified product to obtain a final product, i.e., the photoinitiator 1-chloro-4-propoxythioxanthone. Compared with the prior art, the yield is greatly improved, reaction conditions aremoderate and post-treatment is simple; the preparation method is a production method suitable for industrialization.

Thioxanthone derivatives

-

, (2008/06/13)

Thioxanthone derivatives of the general formula I STR1 wherein R1 wherein R1 represents a halogen atom or a C1-10 alkoxy group, R2 and R4 each represent a hydrogen atom, a halogen atom or a C1 -C6 alkyl group, X represents oxygen or sulphur, and R3 represents a C1 -C10 alkyl group optionally substituted by a hydroxy group which hydroxy group may be alkylated by an optionally substituted C1-6 alkyl, C1-6 alkenyl or a benzyl group or acylated by a C1-8 alkanoyl or C1-8 alkenoyl group, a C1-10 alkenyl group, a C3 -C6 cycloalkyl group, a C1 -C8 alkanoyl group, a C1-8 alkenoyl group, an optionally substituted phenyl group, an optionally substituted benzyl group or an optionally substituted benzoyl group. Process for the preparation of the above thioxanthones, their use as photoinitiators, photopolymerisable compositions containing them, the use of such compositions for the production of photocured surface coating and products on which these photocured compositions have been applied.

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