3-[(Aminoiminomethyl)amino]-4-methylbenzoic acid ethyl ester mononitrate
[CAS# 641569-96-2]

Identification

• Name: 3-[(Aminoiminomethyl)amino]-4-methylbenzoic acid ethyl ester mononitrate
• Molecular Formula: C₁₁H₁₅N₃O₂.HNO₃
• Molecular Weight: 284.27
• CAS Registry Number: 641569-96-2
• EC Number: 808-104-5
• SMILES: CCOC(=O)C1=CC(=C(C=C1)C)N=C(N)N.[N+](=O)(O)[O-]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

3-[(Aminoiminomethyl)amino]-4-methylbenzoic acid ethyl ester mononitrate is a functionalized aromatic compound in which a substituted benzoic acid ester is modified with both a guanidine-type aminoiminomethyl group and a nitrate ester. This combination of functional groups makes it of interest in medicinal chemistry and chemical research due to its potential reactivity, hydrogen-bonding capacity, and capacity for bioactive interactions. The guanidine-type functionality can act as a strong base and hydrogen-bond donor, while the nitrate ester introduces electrophilicity and potential nitric oxide–releasing properties. Structurally, the molecule consists of a benzene ring bearing a methyl substituent at the 4-position, an ethyl ester of the carboxylic acid at the 1-position, and a 3-position-substituted aminoiminomethylamino group. The nitrate group is associated with one of the nitrogen atoms in the guanidine-like moiety, forming a mononitrate. The conjugation between the aromatic ring and the aminoiminomethyl group enhances electronic delocalization, and the combination of polar functional groups contributes to solubility in organic solvents and potential interactions with biological targets. The synthesis of this compound typically involves esterification of 3,4-diaminobenzoic acid to form the ethyl ester, followed by guanylation of the 3-amino group to introduce the aminoiminomethyl functionality. The mononitrate is then obtained through selective nitration under controlled conditions, ensuring that only one nitrogen atom in the guanidine-type group is converted to the nitrate while preserving the ester and aromatic framework. Reaction conditions are carefully optimized to prevent over-nitration, hydrolysis of the ester, or degradation of the aromatic ring. In medicinal chemistry, compounds bearing aminoiminomethyl and nitrate functionalities are explored for cardiovascular, vasodilatory, and enzyme-modulating properties. The guanidine-like group can interact with acidic residues in enzyme active sites, while the nitrate ester has the potential to release nitric oxide under physiological conditions, which can modulate blood flow and signaling pathways. The ethyl ester improves lipophilicity, aiding in cellular uptake, while the methyl substituent can influence steric orientation and pharmacokinetic properties. Beyond biological applications, 3-[(Aminoiminomethyl)amino]-4-methylbenzoic acid ethyl ester mononitrate is valuable as a synthetic intermediate. The reactive guanidine and nitrate groups allow further functionalization through acylation, alkylation, or nucleophilic substitution, and the ester can be hydrolyzed or transformed into amides or other derivatives. This versatility enables the construction of derivative libraries, heterocyclic analogs, or nitric oxide–donating compounds for research purposes. Overall, 3-[(Aminoiminomethyl)amino]-4-methylbenzoic acid ethyl ester mononitrate is a multifunctional aromatic ester featuring a guanidine-type aminoiminomethyl group and a nitrate ester. Its combination of hydrogen-bonding, electrophilic, and lipophilic properties makes it a versatile intermediate for medicinal chemistry, synthetic organic chemistry, and the development of bioactive compounds with potential nitric oxide–related activity. Note: Non-ASCII characters in this text include “α” and “–”, which are already represented in ASCII-compatible form.

References

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