Description

Methyl 3-amino-5-phenylthiophene-2-carboxylate (CAS No. 100063-22-7) is a high-purity organic compound with the molecular formula C₁₂H₁₁NO₂S. This thiophene derivative features a phenyl substituent at the 5-position and an amino group at the 3-position, making it a versatile intermediate for pharmaceutical and materials science research. Its methyl ester functionality enhances solubility in organic solvents, facilitating reactions such as amidation, hydrolysis, or further functionalization. With a molecular weight of 233.29 g/mol, this compound is supplied as a crystalline solid, rigorously tested for purity via HPLC, NMR, and mass spectrometry. Ideal for heterocyclic chemistry, drug discovery, and ligand synthesis, it is packaged under inert conditions to ensure stability and longevity.

Properties

• CAS Number: 100063-22-7
• Complexity: 253
• IUPAC Name: methyl 3-amino-5-phenyl-thiophene-2-carboxylate
• InChI: InChI=1S/C12H11NO2S/c1-15-12(14)11-9(13)7-10(16-11)8-5-3-2-4-6-8/h2-7H,13H2,1H3
• InChI Key: QESSCNMSOLRYBO-UHFFFAOYSA-N
• Exact Mass: 233.05104977
• Molecular Formula: C12H11NO2S
• Molecular Weight: 233.29
• SMILES: COC(=O)C1=C(C=C(S1)C2=CC=CC=C2)N
• Topological: 80.6
• Monoisotopic Mass: 233.05104977
• Synonyms: methyl 3-amino-5-phenylthiophene-2-carboxylate, 100063-22-7, DTXSID70351450, DTXCID00302516, 640-912-1, 2-Thiophenecarboxylic acid, 3-amino-5-phenyl-, methyl ester, MFCD00068161, CHEMBL207663, methyl 3-amino-5-(4-phenyl)thiophene-2-carboxylate, F2146-0037, 3-amino-5-phenyl-thiophene-2-carboxylic acid methyl ester, Maybridge1_003977, 3-Amino-2-(methoxycarbonyl)-5-phenylthiophene, SCHEMBL431794, HMS552M17, SMSSF-0017291, BDBM50186643, methyl 3-amino-5-phenyl-2-thenoate, SBB005525, STL083744, AKOS000280583, CCG-141719, CS-W012927, FS-1462, AC-15465, SY018616, methyl-3-amino-5-phenylthiophene-carboxylate, ST50407197, EN300-384296, methyl-3-amino-5-phenylthiophene-2-carboxylate, [4-Amino-5-(methoxycarbonyl)thien-2-yl]benzene, methyl-3-amino-5-phenyl-thiophene-2-carboxylate, Z56792521, Methyl 3-amino-5-phenylthiophene-2-carboxylate, AldrichCPR

Application

Methyl 3-amino-5-phenylthiophene-2-carboxylate serves as a key building block in medicinal chemistry for the synthesis of bioactive thiophene scaffolds. Researchers utilize it in the development of kinase inhibitors, antimicrobial agents, and CNS-targeted compounds due to its rigid aromatic core. Its reactive amino group enables conjugation with carboxylic acids or electrophiles, while the ester allows for late-stage diversification. This compound is also employed in materials science for constructing π-conjugated systems in organic electronics.

Safety and Hazards

GHS Hazard Statements

• H302 (28.6%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (14.3%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (28.6%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (28.6%)
• Acute Tox. 4 (14.3%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (28.6%)
• STOT SE 3 (100%)

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