1948-39-6

Basic information

• Product Name: 4-Hydroxy-3,5-diiodophenylacetic acid
• Synonyms: 3,5-DIIODO-4-HYDROXY PHENYLACETIC ACID;4-hydroxy-3,5-diiodophenylacetic acid;4-Hydroxy-3,5-diiodobenzeneacetic acid
• CAS NO: 1948-39-6
• Molecular Formula: C₈H₆I₂O₃
• Molecular Weight: 403.94
• EINECS: 217-753-8
• Product Categories: Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1948-39-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 217.5-219.5 °C(Solv: acetone (67-64-1); water (7732-18-5))
• Boiling Point: 370.3 °C at 760 mmHg
• Flash Point: 177.8 °C
• Appearance: /
• Density: 2.533 g/cm³
• Vapor Pressure: 3.87E-06mmHg at 25°C
• Refractive Index: 1.751
• PKA: 4.20±0.10(Predicted)
• CAS DataBase Reference: 4-Hydroxy-3,5-diiodophenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-3,5-diiodophenylacetic acid(1948-39-6)
• EPA Substance Registry System: 4-Hydroxy-3,5-diiodophenylacetic acid(1948-39-6)

Safety Data

• Hazardous Substances Data: 1948-39-6(Hazardous Substances Data)

Usage

Uses

3,5-Diiodo-4-hydroxyphenylacetic acid is an impurity of Thyroxine (T425600).

InChI:InChI=1/C8H6I2O3/c9-5-1-4(3-7(11)12)2-6(10)8(5)13/h1-2,13H,3H2,(H,11,12)

Upstream product

• 156-38-7 4-hydroxyphenylacetate 

Downstream Products

• 54291-88-2 methyl 2-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)acetate 
• 1155-40-4 2-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)acetic acid 
• 56460-36-7 methyl 2-(4-hydroxy-3,5-diiodophenyl)acetate 
• 73149-15-2 4-Hydroxy-3,5-diiod-phenylessigsaeure-(2,4,5-trichlor-phenylester) 
• 100130-56-1 (4-hydroxy-3,5-diiodo-phenyl)-acetic acid amide 

Relevant articles and documents

Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes

Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products.