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TCI

CAS 122-28-1

3'-Nitroacetanilide TCI N0106

3'-Nitroacetanilide TCI N0106

Chemical Identity

CAS No.
122-28-1
PubChem
CID 31206·SID 87573495
Formula
C8H8N2O3
Molecular weight
180.16 g/mol
Purity
>98.0%(GC)
Reference databases
ChemSpider·ECHA
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
N-(3-nitrophenyl)acetamide
SMILES
CC(=O)NC1=CC(=CC=C1)[N+](=O)[O-]
InChIKey
KFTYNYHJHKCRKU-UHFFFAOYSA-N
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TCI N0106 3'-Nitroacetanilide is an acetanilide derivative bearing a nitro group at the meta position of the benzene ring, and it stands as one of the classic aromatic building blocks in synthetic organic chemistry. The compound serves as an important intermediate on the route to a wide range of substituted aniline derivatives, because the acetamide group acts as a temporary amine protecting group while the nitro group can be reduced to an amine at a later stage. In the laboratory, this material is used both for multi-step synthesis work and as teaching material for aromatic substitution reactions.

The characteristic that makes this compound a preferred choice is its clearly defined substitution pattern at the meta position, so that users obtain a single isomer without having to carry out the separation of nitration product mixtures themselves. Supplied as a crystalline solid, the material is easy to weigh, straightforward to purify by recrystallization, and suitable for long-term storage. The electron-withdrawing nitro group lowers the reactivity of the ring toward further electrophilic substitution while at the same time providing a reliable transformation point through reduction, and the acetamide group can be hydrolyzed under either acidic or basic conditions to liberate the aromatic amine.

In Indonesian laboratories, 3'-nitroacetanilide is typically found in university organic chemistry teaching laboratories, in research groups working on the preparation of substituted aniline derivatives, and in synthesis laboratories that build target molecules through multi-step routes. Its role as a well-defined single isomer makes it convenient for practical work where reproducibility matters, and its crystalline nature suits laboratories that handle materials in modest quantities and store reagents on the shelf between experiments.

  • Intermediate toward substituted aniline derivatives: the nitro group provides a dependable point for reduction to an aromatic amine, giving access to meta-substituted anilines in a controlled sequence.
  • Multi-step organic synthesis: the acetamide group protects the amine function during intermediate steps and can later be hydrolyzed under acidic or basic conditions to release the free aromatic amine.
  • Teaching material for aromatic substitution reactions: the defined meta substitution pattern makes it a clear illustration of directing effects, allowing students to relate structure to observed regiochemistry.
  • Recrystallization practice and purification exercises: as a crystalline solid it dissolves and recrystallizes predictably, which suits laboratory training in purification technique and in assessing crystal quality.
  • Reference building block for synthetic route development: because it is supplied as a single isomer, researchers avoid the separation of nitration mixtures and can focus on the downstream transformation being studied.

Brand TCI
CAS number 122-28-1
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes available in standard laboratory pack sizes as listed on the product page
Physical form crystalline solid
Storage store in a closed container in a cool, dry place away from light

Store 3'-nitroacetanilide in its original tightly closed container, kept in a cool, dry place away from direct sunlight and from sources of heat or ignition. Amber glass or the manufacturer's supplied packaging is suitable, and containers should be resealed promptly after weighing to limit moisture uptake. Handle the solid in a fume hood or a well-ventilated area to avoid inhaling dust, and wear a laboratory coat, safety glasses, and chemical-resistant gloves. Use a clean spatula for each transfer to prevent cross-contamination, keep the material separated from strong oxidizing and reducing agents, and consult the supplier's safety data sheet before first use and before disposal of residues.

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