Cas no 885953-51-5 (tert-butyl N-(2-methyl-6-nitrophenyl)carbamate)

Tert-butyl N-(2-methyl-6-nitrophenyl)carbamate is a protected aniline derivative commonly employed in organic synthesis and pharmaceutical intermediates. The tert-butyloxycarbonyl (Boc) group provides stability under basic conditions while allowing selective deprotection under acidic conditions, making it valuable for multi-step syntheses. The nitro and methyl substituents on the aromatic ring enhance its reactivity in subsequent transformations, such as reductions or cross-coupling reactions. This compound is particularly useful in the preparation of complex molecules, including agrochemicals and active pharmaceutical ingredients (APIs), due to its controlled reactivity and compatibility with diverse reaction conditions. Its crystalline nature also facilitates purification and handling.
tert-butyl N-(2-methyl-6-nitrophenyl)carbamate structure
885953-51-5 structure
Product Name:tert-butyl N-(2-methyl-6-nitrophenyl)carbamate
CAS No:885953-51-5
MF:C12H16N2O4
MW:252.266443252563
CID:5980925
PubChem ID:4401586
Update Time:2025-06-22

tert-butyl N-(2-methyl-6-nitrophenyl)carbamate Chemical and Physical Properties

Names and Identifiers

    • Carbamic acid, N-(2-methyl-6-nitrophenyl)-, 1,1-dimethylethyl ester
    • tert-Butyl (2-methyl-6-nitrophenyl)carbamate
    • tert-butyl N-(2-methyl-6-nitrophenyl)carbamate
    • EN300-12450834
    • 1,1-Dimethylethyl N-(2-methyl-6-nitrophenyl)carbamate
    • DTXSID601214525
    • 885953-51-5
    • Inchi: 1S/C12H16N2O4/c1-8-6-5-7-9(14(16)17)10(8)13-11(15)18-12(2,3)4/h5-7H,1-4H3,(H,13,15)
    • InChI Key: JMBIADRKSRAOSP-UHFFFAOYSA-N
    • SMILES: C(OC(C)(C)C)(=O)NC1=C([N+]([O-])=O)C=CC=C1C

Computed Properties

  • Exact Mass: 252.11100700g/mol
  • Monoisotopic Mass: 252.11100700g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 3
  • Complexity: 319
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2
  • Topological Polar Surface Area: 84.2?2

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Additional information on tert-butyl N-(2-methyl-6-nitrophenyl)carbamate

tert-butyl N-(2-methyl-6-nitrophenyl)carbamate: A Comprehensive Overview

tert-butyl N-(2-methyl-6-nitrophenyl)carbamate (CAS No. 885953-51-5) is a versatile organic compound that has garnered significant attention in the fields of chemistry and materials science. This compound, characterized by its unique structure, plays a pivotal role in various chemical reactions and applications. Recent advancements in synthetic methodologies have further enhanced its utility, making it a valuable asset in modern chemical research.

The molecular structure of tert-butyl N-(2-methyl-6-nitrophenyl)carbamate is defined by the presence of a tert-butyl group attached to a carbamate functional group, which is further connected to a 2-methyl-6-nitrophenyl moiety. This combination of functional groups imparts the compound with distinctive chemical properties, including high stability and reactivity under specific conditions. The tert-butyl group contributes to the compound's steric bulk, while the carbamate functionality facilitates various nucleophilic substitutions and condensation reactions.

Recent studies have highlighted the potential of tert-butyl N-(2-methyl-6-nitrophenyl)carbamate as an intermediate in the synthesis of advanced materials. For instance, researchers have explored its role in the preparation of polyurethanes and other polymer-based systems. The nitrophenyl group within the molecule has been shown to enhance the thermal stability and mechanical properties of these materials, making them suitable for high-performance applications.

In addition to its role in polymer chemistry, tert-butyl N-(2-methyl-6-nitrophenyl)carbamate has found applications in pharmaceutical research. Its ability to undergo selective transformations has made it a valuable precursor in the synthesis of bioactive compounds. For example, recent investigations have demonstrated its utility in the preparation of antiviral agents and anticancer drugs. The methyl substituent on the phenyl ring has been shown to influence the bioavailability and pharmacokinetics of these compounds, making them more effective in therapeutic settings.

The synthesis of tert-butyl N-(2-methyl-6-nitrophenyl)carbamate involves a multi-step process that combines principles from organic synthesis and catalysis. Key steps include the formation of intermediates through nucleophilic aromatic substitution and subsequent functionalization to introduce the carbamate group. The use of transition metal catalysts has significantly improved the efficiency and selectivity of these reactions, enabling large-scale production.

From an environmental perspective, the ecological impact of tert-butyl N-(2-methyl-6-nitrophenyl)carbamate has been carefully evaluated. Studies indicate that it exhibits low toxicity to aquatic organisms under standard testing conditions. However, its degradation pathways remain an area of active research, particularly in relation to its potential use in agricultural applications.

In conclusion, tert-butyl N-(2-methyl-6-nitrophenyl)carbamate (CAS No. 885953-51-5) stands as a testament to the ingenuity of modern chemical research. Its diverse applications across multiple disciplines underscore its importance as a key intermediate in contemporary chemical synthesis. As research continues to uncover new possibilities for this compound, its role in advancing science and technology is expected to grow further.

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