4-Amino-6-chlorobenzene-1,3-disulfonamide
[CAS# 121-30-2]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 4-Amino-6-chlorobenzene-1,3-disulfonamide
• Synonyms: 3-Chloro-4,6-disulfamoylaniline; 5-Chloro-2,4-disulfamoylaniline
• Molecular Formula: C₆H₈ClN₃O₄S₂
• Molecular Weight: 285.72
• CAS Registry Number: 121-30-2
• EC Number: 204-463-1
• SMILES: C1=C(C(=CC(=C1Cl)S(=O)(=O)N)S(=O)(=O)N)N

Properties

• Density: 1.8±0.1 g/cm³ Calc.^*
• Melting point: 257 - 261 °C (Expl.)
• Boiling point: 614.4±65.0 °C 760 mmHg (Calc.)^*
• Flash point: 325.4±34.3 °C (Calc.)^*
• Index of refraction: 1.666 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H315-H319-H335-H373
• Safety Statements: P260-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H331

Discovery and Applications

4-Amino-6-chlorobenzene-1,3-disulfonamide is an aromatic sulfonamide compound with the molecular formula C₆H₆ClN₃O₄S₂. It features a benzene ring substituted with an amino group (–NH₂) at position 4, a chlorine atom at position 6, and sulfonamide groups (–SO₂NH₂) at positions 1 and 3. This compound is part of the broader class of sulfonamides, which have been widely studied for their biological activity and pharmaceutical relevance.

The synthesis of 4-amino-6-chlorobenzene-1,3-disulfonamide typically begins with appropriately substituted aniline derivatives or sulfonation of halogenated aromatic amines. The presence of two sulfonamide groups increases the molecule's hydrophilicity and potential for hydrogen bonding, making it a candidate for further derivatization in medicinal chemistry.

This compound has historically been used as an intermediate in the synthesis of sulfonamide-based drugs, especially carbonic anhydrase inhibitors and antibacterial agents. Sulfonamides with structural similarity to this molecule form the core scaffold of many early antibiotics, including sulfamethoxazole and related compounds. While 4-amino-6-chlorobenzene-1,3-disulfonamide itself is not commonly used as a therapeutic agent, its substitution pattern provides a framework for drug design targeting enzymes or receptors that interact with sulfonamide or aniline functionalities.

In addition to pharmaceutical relevance, sulfonamides like this compound have been studied for their potential application in coordination chemistry, materials science, and chemical sensors. The two sulfonamide groups offer sites for metal coordination or further chemical modification, such as acylation or diazotization reactions, which can yield more complex aromatic systems.

The compound’s structural features are typically characterized using spectroscopic methods. Infrared (IR) spectroscopy reveals strong absorption bands corresponding to N–H stretching and S=O stretching vibrations of the sulfonamide groups. Proton nuclear magnetic resonance (NMR) spectroscopy shows the aromatic proton signals, amino group, and sulfonamide protons, confirming the substitution pattern on the aromatic ring. Mass spectrometry and elemental analysis are also used to verify molecular composition and purity.

Due to its chemical properties, 4-amino-6-chlorobenzene-1,3-disulfonamide should be handled with care. Though it is generally considered stable under normal laboratory conditions, standard safety precautions—such as use of gloves, goggles, and working under a fume hood—are recommended. There is limited toxicity data specific to this compound, but structurally related sulfonamides may cause irritation or allergic reactions in sensitive individuals.

In summary, 4-amino-6-chlorobenzene-1,3-disulfonamide is a functionalized aromatic sulfonamide valued as a chemical intermediate in the synthesis of biologically active molecules. Its dual sulfonamide groups and specific substitution pattern make it relevant in medicinal chemistry and organic synthesis research.

References

2015. Sulfonamide inhibition studies of the ζ-class carbonic anhydrase from the malaria pathogen Plasmodium falciparum. Bioorganic & Medicinal Chemistry, 23(3).
DOI: 10.1016/j.bmc.2014.12.009

2016. Sulfonamide inhibition studies of the α-carbonic anhydrase from the gammaproteobacterium Thiomicrospira crunogena XCL-2, TcruCA. Bioorganic & Medicinal Chemistry Letters, 26(2).
DOI: 10.1016/j.bmcl.2015.11.104

2015. Sulfonamide inhibition studies of the γ-carbonic anhydrase from the Antarctic cyanobacterium Nostoc commune. Bioorganic & Medicinal Chemistry, 23(8).
DOI: 10.1016/j.bmc.2015.02.045