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TCI

CAS 104-24-5

4-Phenylazobenzoyl Chloride TCI P0144

4-Phenylazobenzoyl Chloride TCI P0144

Chemical Identity

CAS No.
104-24-5
PubChem
CID 66910·SID 87574397
Formula
C13H9ClN2O
Molecular weight
244.67 g/mol
Purity
>98.0%(GC)(T)
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
4-phenyldiazenylbenzoyl chloride
SMILES
C1=CC=C(C=C1)N=NC2=CC=C(C=C2)C(=O)Cl
InChIKey
RYMHZBAYPLCCAC-UHFFFAOYSA-N
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4-Phenylazobenzoyl Chloride from TCI is an acyl chloride derived from 4-(phenylazo)benzoic acid. This reagent combines the high reactivity of an acyl chloride group with a strongly coloured azobenzene chromophore. In the laboratory it is used mainly as an acylating reagent to attach the phenylazobenzoyl unit to alcohols, amines and phenols. This serves two main purposes: analytical derivatization, such as adding a coloured label, and building photoresponsive materials based on azobenzene.

Researchers choose this reagent because it reacts quickly with nucleophiles and does not need any extra coupling reagent, which keeps reaction setups simple. The ester or amide products carry an azo chromophore that absorbs strongly in the visible and UV regions. This makes chromatographic detection much more sensitive. It is especially useful for compounds that have no chromophore of their own, such as aliphatic alcohols, sugars or simple amines. The azobenzene unit also keeps its ability to isomerize under light after it has been attached to the target molecule.

In Indonesia, this reagent is useful for analytical chemistry laboratories that develop derivatization-based HPLC methods. It also suits carbohydrate and lipid research groups that need to detect analytes with weak UV absorption. Materials science researchers who make photoresponsive polymers or dendrimers can use it to bring azobenzene units into their structures. University research laboratories, institutional research centres and industrial R&D teams working in these fields will find it a practical building block for their work.

  • Pre-column derivatization for HPLC: the reagent attaches a strongly absorbing azo chromophore to analytes that lack one, which greatly improves UV and visible detection sensitivity.
  • Coloured labelling of alcohols and phenols: the acyl chloride group reacts quickly with hydroxyl groups to form stable esters that carry a strong, easily detected colour.
  • Acylation of amines to form amides: it reacts directly with primary and secondary amines without extra coupling reagents, which makes it a convenient way to add the phenylazobenzoyl unit.
  • Derivatization of sugars and lipids: carbohydrates and many lipids have no useful chromophore, so labelling them with this reagent makes them easier to detect and quantify by chromatography.
  • Synthesis of photoresponsive polymers and dendrimers: the attached azobenzene unit can still isomerize under light, so it can be used to build materials whose properties change with light.

Brand TCI (product code P0144)
CAS number 104-24-5
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes see the available pack options on the product page
Physical form refer to the manufacturer's product documentation
Storage keep tightly closed in a cool, dry place, protected from moisture

As an acyl chloride, this reagent reacts with water and atmospheric moisture, which degrades it and releases hydrogen chloride. Keep it in its original tightly sealed container in a cool, dry, well-ventilated place, away from water, alcohols, amines, bases and oxidizers. Close the container quickly after each use, and consider storing it under an inert atmosphere or in a desiccator. Handle it in a fume hood while wearing chemical-resistant gloves, safety goggles and a lab coat. Avoid breathing in its dust or vapours, and avoid contact with skin and eyes. Always check the manufacturer's Safety Data Sheet for full hazard, storage and disposal information.

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