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Methyl 2-(5-bromo-2-nitrophenyl)acetate

  • CAS No. 189748-25-2

  • Cat. No. CS-0150711
  • Purity≥98%
  • MDL No.MFCD11977366

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

Methyl 2-(5-bromo-2-nitrophenyl)acetate|CS-0150711

Structure of 189748-25-2

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General Information

  • CAS No. 189748-25-2
  • Cat. No. CS-0150711
  • Purity ≥98%
  • MDL No. MFCD11977366
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈BrNO₄
  • Molecular Weight 274.07
  • Synonym(s) BENZENEACETIC ACID, 5-BROMO-2-NITRO-, METHYL ESTER
  • SMILES COC(=O)CC1=CC(=CC=C1[N+](=O)[O-])Br

Description

Methyl 2-(5-bromo-2-nitrophenyl)acetate features a brominated nitroaryl core with a pendant ester group, enabling direct incorporation into cross-coupling and functionalization cascades. The electron-deficient aromatic system enhances reactivity in palladium-mediated transformations, while the methyl ester serves as a handle for subsequent derivatization under mild conditions. This compound exhibits robust stability under standard bench handling protocols.

Application

Methyl 2-(5-bromo-2-nitrophenyl)acetate serves as a versatile building block for the synthesis of substituted heterocycles and bioactive intermediates. The molecule combines a bromo substituent for late-stage functionalization via cross-coupling and a nitro group amenable to reduction, enabling access to anilines or further derivatization. Its methyl ester functionality supports standard transformations including hydrolysis, amidation, and coupling reactions. Bench-stable and readily purified by recrystallization, it facilitates efficient integration into multi-step synthetic sequences common in medicinal chemistry and process development workflows.

Safety Information

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GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H311-H331
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361-P405-P501

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Computational Chemistry Data

  • TPSA   69.44
  • LogP   2.0728
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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