2122-61-4

Basic information

• Product Name: 4-Amino-3,5-diiodobenzoic acid
• Synonyms: 3,5-dijod-4-aminohippursaeure;4-amino-3,5-diiodo-benzoicaci;3,5-DIIODO-4-AMINOBENZOIC ACID;4-AMINO-3,5-DIIODOBENZOIC ACID;LABOTEST-BB LT00080707;4-Amino-3,5-diiodobenzoic acid, 98+%;4-AMINO-3,5-DIIODOBENZOIC ACID: TECH., 90%;4-Amino-3,5-diiodobenzoic acid,85%
• CAS NO: 2122-61-4
• Molecular Formula: C₇H₅I₂NO₂
• Molecular Weight: 388.93
• EINECS: 218-331-6
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Phenylacetic acid
• Mol File: 2122-61-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 448.7 °C at 760 mmHg
• Flash Point: 225.2 °C
• Appearance: beige-pink crystalline powder
• Density: 2.3815 (estimate)
• Vapor Pressure: 7.73E-09mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 4.16±0.10(Predicted)
• Water Solubility: Soluble in water (partly miscible).
• Sensitive: Light Sensitive
• BRN: 2103037
• CAS DataBase Reference: 4-Amino-3,5-diiodobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-3,5-diiodobenzoic acid(2122-61-4)
• EPA Substance Registry System: 4-Amino-3,5-diiodobenzoic acid(2122-61-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39-36/37/39
• WGK Germany: 3
• RTECS: DG2310000
• Hazardous Substances Data: 2122-61-4(Hazardous Substances Data)

Usage

Chemical Properties

beige-pink crystalline powder

Uses

4-Amino-3,5-diiodobenzoic acid is a very useful substituted benzene compound for use as a building block in synthesis. The carboxylic acid and amine functionalities can be used to form linkages through nucleophile-electrophile coupling and the iodides may be used as functional sites for cross-coupling transformations. 4-Amino-3,5-diiodobenzoic acid has been specifically used in the synthesis of an adduct to introduce into Tecoflex polymers to impart radiopaqueness to the material.

Purification Methods

Purify the iodo-acid by dissolving it in dilute NaOH and precipitating with dilute HCl. Alternatively, dissolve it in aqueous NH3 and acidify it with AcOH. Dry it in air. The solubility of the Na salt in H2O is 2.56% at 25o. [Klemme & Hunter J Org Chem 5 510 1940, Beilstein 14 H 439, 14 III 1161, 14 IV 1284.]

InChI:InChI=1/C7H5I2NO2/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2H,10H2,(H,11,12)/p-1

Upstream product

• 150-13-0 4-amino-benzoic acid 
• 7647-01-0 hydrogenchloride 
• 7790-99-0 Iodine monochloride 
• 190071-24-0 4-acetylamino-3-iodo-benzoic acid 
• 29289-16-5 N-(2-iodo-4-methylphenyl)acetamide 
• 29289-13-2 2-iodo-4-methylaniline 
• 94-09-7 p-aminoethylbenzoate 
• 5400-81-7 ethyl 4-amino-3.5-diiodobenzoate 

Downstream Products

• 945265-36-1 4-(5,6-dimethyl-1H-benzimidazol-2-yl)-3,5-diiodobenzoic acid 
• 3337-66-4 methyl 4-hydroxy-3,5-diiodobenzoate 
• 19094-48-5 3,5-diiodobenzoic acid 
• 1333334-28-3 4-amino-3,5-bis(pyridin-3-ylethynyl)benzoic acid 
• 1146629-50-6 3,5-diiodo-4-(2-methyl-1H-5-imidazolyl)benzoic acid 
• 717813-39-3 4-amino-3,5-diiodo-benzoic acid 2-diethylamino-ethyl ester 
• 14266-19-4 3,5‐diiodobenzoic acid methyl ester 
• 17352-25-9 3,5-diiodobenzaldehyde 
• 153390-73-9 3,5‐bis((trimethylsilyl)ethynyl)benzaldehyde 
• 153390-76-2 3,5-bis-(ethynyl)benzaldehyde 
• 945264-91-5 (CH₃)2C₇H₃N₂C₆H₂I₂CONHCHCH₂C₆H₅CONHCHCH(CH₃)2CONC₄H₇CO₂CH₃ 
• 945264-90-4 (CH₃)2C₇H₃N₂C₆H₂I₂CONHCHCH₃CONHCHCH₂C₆H₄OHCONHCH₂CO₂CH₃ 
• 945264-89-1 (CH₃)2C₇H₃N₂C₆H₂I₂CONHCHCH₂C₃H₃N₂CONC₄H₇CO₂CH₃ 
• 131755-87-8 methyl 4-amino-3,5-diiodobenzoate 

Relevant articles and documents

Convenient and efficient method for the iodination of aromatic amines by pyridinium iodochloride

A simple and efficient method for the iodination of aromatic amines using pyridinium iodochloride (PyICl) in methanol as solvent is reported. Mild reaction conditions, short reaction time, and good to excellent yields of the product are the noteworthy advantages of the method. Pyridinium iodochloride is an efficient solid iodinating reagent and can be handled safely. Copyright Taylor & Francis Group, LLC.

Synthetic studies on novel benzimidazolopeptides with antimicrobial, cytotoxic and anthelmintic potential

Four substituted benzimidazolyl-benzoic/salicylic acids 5-8 were synthesized by interaction of 5,6-dimethyl-/6-nitrobenzimidazoles with diazotized substituted/unsubstituted aminobenzoic acids in the presence of cupric chloride. The coupling of compounds 5-8 with different amino acid ester hydrochlorides/dipeptide/tripeptide/tetrapeptide methyl esters afforded novel benzimidazolopeptide derivatives 5a-f, 6a-h, 7a-g and 8a-g. The structures of all newly synthesized compounds were established on the basis of analytical, IR, 1H NMR, 13C NMR and mass spectral data. Selected peptide ester derivatives were further hydrolyzed by using lithium hydroxide (LiOH) to yield corresponding acid derivatives 5ba-da, 6ea-ga, 7ca-ea and 8ea-ga. All peptide derivatives were screened for their antimicrobial, anthelmintic and cytotoxic activities. Almost all newly synthesized benzimidazolopeptides have shown moderate to good anthelmintic activity against all three earthworm species and good antimicrobial activity against pathogenic fungal strains Candida albicans and Aspergillus niger, gram negative bacterial strains Pseudomonas aeruginosa and Escherichia coli. Compounds 8g and 8ga possessed significant cytotoxic activity against Dalton's lymphoma ascites (DLA) and Ehrlich's ascites carcinoma (EAC) cell lines.