84434-05-9

Basic information

• Product Name: [(9-oxo-9H-thioxanthen-2-yl)oxy]acetic acid
• Synonyms: [(9-oxo-9H-thioxanthen-2-yl)oxy]acetic acid;(9-Oxo-9H-thioxanthene-2-yloxy)acetic acid;2-(Carboxymethoxy)-9H-thioxanthene-9-one;Einecs 282-803-8;Acetic acid, [(9-oxo-9H-thioxanthen-2-yl)oxy]-
• CAS NO: 84434-05-9
• Molecular Formula: C₁₅H₁₀O₄S
• Molecular Weight: 286.3025
• EINECS: 282-803-8
• Mol File: 84434-05-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 528.9 °C at 760 mmHg
• Flash Point: 273.7 °C
• Appearance: yellow powder
• Density: 1.415 g/cm³
• Vapor Pressure: 5.13E-12mmHg at 25°C
• Refractive Index: 1.685
• Water Solubility: 18.6mg/L at 20℃
• CAS DataBase Reference: [(9-oxo-9H-thioxanthen-2-yl)oxy]acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [(9-oxo-9H-thioxanthen-2-yl)oxy]acetic acid(84434-05-9)
• EPA Substance Registry System: [(9-oxo-9H-thioxanthen-2-yl)oxy]acetic acid(84434-05-9)

Safety Data

• Hazardous Substances Data: 84434-05-9(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C15H10O4S/c16-14(17)8-19-9-5-6-13-11(7-9)15(18)10-3-1-2-4-12(10)20-13/h1-7H,8H2,(H,16,17)

Synthetic route

2-hydroxy thioxanthone (31696-67-0) + ethyl bromoacetate (105-36-2) → 2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9)

Conditions	Yield
Stage #1: 2-hydroxy thioxanthone With sodium hydroxide In tetrahydrofuran for 1.5h; Reflux; Stage #2: ethyl bromoacetate In tetrahydrofuran at 40℃; for 4h; Reflux;	91.91%

Thiosalicylic acid (147-93-3) + 2-phenoxyacetic acid (122-59-8) → 2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9)

Conditions	Yield
Stage #1: Thiosalicylic acid With sulfuric acid for 0.0833333h; Stage #2: 2-phenoxyacetic acid at 80℃; for 2h;	80%
With sulfuric acid at 5 - 60℃; for 2h;	47%
Stage #1: Thiosalicylic acid With sulfuric acid In water Stage #2: 2-phenoxyacetic acid In water at 20 - 80℃; for 3.5h;
With sulfuric acid at 20℃; for 2h;

2,2'-dithiobenzoic acid (119-80-2) + 2-phenoxyacetic acid (122-59-8) → 2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9)

Conditions	Yield
With sulfuric acid at 0 - 25℃; for 1h;	76%

2-carboxymethoxythioxanthone ethyl ester → 2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran for 3h; Reflux;	28 g

Thiosalicylic acid (147-93-3) → 2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / 3 h / 20 - 100 °C 2.1: sodium hydroxide / tetrahydrofuran / 2 h / Reflux 2.2: 3 h / Reflux 3.1: sodium hydroxide / tetrahydrofuran / 3 h / Reflux View Scheme

phenol (108-95-2) → 2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / 3 h / 20 - 100 °C 2.1: sodium hydroxide / tetrahydrofuran / 2 h / Reflux 2.2: 3 h / Reflux 3.1: sodium hydroxide / tetrahydrofuran / 3 h / Reflux View Scheme

2-hydroxy thioxanthone (31696-67-0) → 2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / tetrahydrofuran / 2 h / Reflux 1.2: 3 h / Reflux 2.1: sodium hydroxide / tetrahydrofuran / 3 h / Reflux View Scheme

2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9) + C3H5O2Pol → C54H66O20S2

Conditions	Yield
at 150 - 180℃; for 18h; Polyoxyethylene;	100%

2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9) → 2-[(9-oxo-9H-thioxanthen-2-yl)oxy]acetyl chloride

Conditions	Yield
With thionyl chloride In tetrahydrofuran for 24h; Reflux;	100%
With thionyl chloride at 20℃; Inert atmosphere;

2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9) + C4H9O2Pol + p-N,N-dimethylaminobenzoic acid (619-84-1) → C36H43NO8S

Conditions	Yield
toluene-4-sulfonic acid at 200℃; for 5h; Polytetrahydrofuran; Neat (no solvent);	86%

Trimethyl orthoacetate (1445-45-0) + 2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9) → (9-oxo-9H-thioxanthen-2-yloxy)-acetic acid methyl ester (1129771-54-5)

Conditions	Yield
With sulfuric acid In methanol at 60℃; for 2h;	45%

2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → acrylic acid 4-{2-hydroxy-3-[2-(9-oxo-9H-thioxanthen-2-yloxy)-acetoxy]-propoxy}-butyl ester (1214748-81-8)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In ISOPROPYLAMIDE; acetonitrile for 16h; Reflux;
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In acetonitrile for 16h; Reflux;	1.8 g

2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9) → sodium (9-oxo-9H-thioxanthen-2-yloxy)-acetate (1233918-13-2)

Conditions	Yield
With sodium hydroxide at 100℃; for 24h;

2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → acrylic acid 4-{2-hydroxy-3-[2-(9-oxo-9H-thioxanthen-2-yloxy)-acetoxy]-propoxy}-butyl ester (1214748-81-8)

Conditions	Yield
With tetrabutylammomium bromide In ISOPROPYLAMIDE; acetonitrile

2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9) → Reaxys ID: 32192832

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / tetrahydrofuran / 24 h / Reflux 2: triethylamine / tetrahydrofuran / Reflux View Scheme

Upstream product

• 31696-67-0 2-hydroxy thioxanthone 
• 105-36-2 ethyl bromoacetate 
• 108-95-2 phenol 
• 147-93-3 Thiosalicylic acid 
• 119-80-2 2,2'-dithiobenzoic acid 
• 122-59-8 2-phenoxyacetic acid 

Relevant articles and documents

Erratum: A review of U.S. patents in the field of organic process development published during November and December 2005 (Organic Process Research and Development (2006) 2 (184-193))

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POLYMERIC PHOTO ACTIVE AGENTS

The present disclosure is drawn to polymeric photo active agents, photo curable inks containing the polymeric photo active agents, and methods of making the photo curable inks. A polymeric photo active agent can include a xanthone analog modified with a polyether chain connecting to the xanthone analog through an amide linkage.

NEW PHOTOINITIATORS

The present invention is related to novel photoinitiators, in particular to photoinitiators comprising amino groups within the molecule.