Description

Ethyl 4-amino-3-bromobenzoate (CAS No. 7149-03-3) is a high-purity organic compound with the molecular formula C₉H₁₀BrNO₂. This benzoate derivative features an ethyl ester group and a strategically positioned bromine and amino substituent on the aromatic ring, making it a valuable intermediate in synthetic organic chemistry. Its well-defined structure (ethyl 4-amino-3-bromobenzoate by IUPAC nomenclature) ensures consistent reactivity for cross-coupling reactions, amidation, or further functionalization. Available in >98% purity (HPLC), this compound is supplied as a crystalline solid with strict quality control to meet research standards. Synonyms include DTXSID20287598 and DTXCID60238746.

Properties

• CAS Number: 7149-03-3
• Complexity: 186
• IUPAC Name: ethyl 4-amino-3-bromo-benzoate
• InChI: InChI=1S/C9H10BrNO2/c1-2-13-9(12)6-3-4-8(11)7(10)5-6/h3-5H,2,11H2,1H3
• InChI Key: NOGUJGZZMMKQOZ-UHFFFAOYSA-N
• Exact Mass: 242.98949
• Molecular Formula: C9H10BrNO2
• Molecular Weight: 244.08
• SMILES: CCOC(=O)C1=CC(=C(C=C1)N)Br
• Topological: 52.3
• Monoisotopic Mass: 242.98949
• Synonyms: ethyl 4-amino-3-bromobenzoate, DTXSID20287598, DTXCID60238746, 848-802-7, 7149-03-3, 4-Amino-3-bromo-benzoic acid ethyl ester, MFCD03407825, ethyl 4-azanyl-3-bromanyl-benzoate, Ethyl4-Amino-3-bromobenzoate, Benzoic acid, 4-amino-3-bromo-, ethyl ester, NSC51689, ethyl 4-amino-3-brombenzoate, SCHEMBL3523526, NOGUJGZZMMKQOZ-UHFFFAOYSA-N, BCP06353, AB1417, NSC-51689, SBB067770, AKOS001453791, CS-W004210, DS-2751, SB38425, SY022571, DB-074437, DB-316196, EN300-30554, Z300089520, H4E

Application

Ethyl 4-amino-3-bromobenzoate serves as a versatile building block in pharmaceutical and materials science research. Its bromo and amino groups enable participation in Buchwald-Hartwig aminations or Suzuki-Miyaura couplings for drug candidate synthesis. The ester moiety allows hydrolysis to carboxylic acids or conversion to amides, facilitating scaffold diversification. Researchers also utilize it in designing liquid crystals or agrochemical intermediates due to its planar aromatic core with polarized substituents.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• 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, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

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

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