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Methyl 5-bromo-2-nitrobenzoate

  • CAS No. 883554-93-6

  • Cat. No. CS-0150869
  • Molecule weight260.04
  • Purity≥98%
  • MDL No.MFCD00092886

*For research and further manufacturing use only, not for direct human use.

Methyl 5-bromo-2-nitrobenzoate|CS-0150869

Structure of 883554-93-6

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General Information

  • CAS No. 883554-93-6
  • Cat. No. CS-0150869
  • Purity ≥98%
  • MDL No. MFCD00092886
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrNO₄
  • Molecular Weight 260.04
  • Synonym(s) Methyl 2-nitro-5-broMobenzoate
  • SMILES COC(=O)C1=C(C=CC(=C1)Br)[N+](=O)[O-]

Description

Methyl 5-bromo-2-nitrobenzoate features a bromine substituent at the meta position relative to the ester group and a nitro group at the ortho position, creating a highly electron-deficient aromatic ring. This combination enables selective cross-coupling reactions under palladium catalysis, while the methyl ester serves as a stable handle for downstream functionalization. The compound exhibits excellent bench stability and compatibility with standard synthetic protocols in medicinal chemistry and materials science applications.

Application

Methyl 5-bromo-2-nitrobenzoate serves as a versatile building block for C–H functionalization and cross-coupling reactions, enabling efficient access to substituted aromatic scaffolds. The ortho-nitro and bromo groups provide complementary reactivity for sequential transformations, including Suzuki-Miyaura coupling and nitro reduction, with excellent chemoselectivity. Bench-stable and readily purified by flash chromatography, it facilitates streamlined synthesis of complex heterocycles and pharmaceutical intermediates.

Safety Information

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GHS Pictogram :
GHS No : GHS02,GHS07
Signal Word : Danger
UN#: 1325
Class : 4.1
Packing Group : Ⅲ
Hazard Statements : H225-H261-H302+H312+H332-H315-H319
Precautionary Statements : P210-P223-P231+P232-P233-P240-P241-P242-P243-P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P370+P378-P402+P404-P501

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Computational Chemistry Data

  • TPSA   69.44
  • LogP   2.1439
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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