104-24-5

Basic information

• Product Name: 4-PHENYLAZOBENZOYL CHLORIDE
• Synonyms: 4-(phenylazo)-benzoylchlorid;4-Phenylazobenzoylchloride,98%;4-PHENYLAZOBENZOYL CHLORIDE 97+%;4-Phenylazobenzoic acid chloride;Azobenzene-4-carbonyl Chloride Azoyl Chloride;AZOYL CHLORIDE;AZOBENZENE-4-CARBONYL CHLORIDE;AZOBENZENE-4-CARBOXYLIC ACID CHLORIDE
• CAS NO: 104-24-5
• Molecular Formula: C₁₃H₉ClN₂O
• Molecular Weight: 244.68
• EINECS: 203-188-4
• Product Categories: Azo/Diazo Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 104-24-5.mol

Chemical Properties

• Melting Point: 94-97 °C(lit.)
• Boiling Point: 382.6 °C at 760 mmHg
• Flash Point: 148.2 °C
• Appearance: orange-red crystalline powder
• Density: 1.3023 (rough estimate)
• Vapor Pressure: 4.66E-06mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• CAS DataBase Reference: 4-PHENYLAZOBENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHENYLAZOBENZOYL CHLORIDE(104-24-5)
• EPA Substance Registry System: 4-PHENYLAZOBENZOYL CHLORIDE(104-24-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 104-24-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Phenylazobenzoyl chloride is used as a key intermediate in the synthesis of polyacetylene derivatives. Its azo group facilitates the formation of conjugated systems in the resulting polymers, which are known for their unique electronic, optical, and structural properties.
Used in Polymer Science:
In the field of polymer science, 4-Phenylazobenzoyl chloride is utilized as a monomer for the preparation of conjugated polymers. These polymers have potential applications in various areas, such as organic electronics, optoelectronics, and materials science, due to their tunable properties and functionalities.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 4-Phenylazobenzoyl chloride may also find applications in the pharmaceutical industry as a building block for the synthesis of drug molecules. Its unique structure and reactivity can be exploited to create novel compounds with potential therapeutic properties.
Used in Dye and Pigment Industry:
Given its vibrant orange-red color, 4-Phenylazobenzoyl chloride could be used as a dye or pigment in various industries, such as textiles, plastics, and coatings. Its intense color and stability may make it a valuable component in the formulation of colored products.

Purification Methods

Crystallise the acid chloride from pet ether (b 60-80o). [Beilstein 16 III 224.]

InChI:InChI=1/C13H9ClN2O/c14-13(17)10-6-8-12(9-7-10)16-15-11-4-2-1-3-5-11/h1-9H/b16-15+

Upstream product

• 1562-93-2 4-(2-phenyldiazen-1-yl)benzoic acid 
• 150-13-0 4-amino-benzoic acid 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 92061-10-4 2-diazo-1-(4-phenylazo-phenyl)-ethanone 
• 41681-72-5 (E)-(4-(phenyldiazenyl)phenyl)(piperidin-1-yl)methanone 
• 109502-55-8 4-(4-phenylazo-benzoyl)-morpholine 
• 50696-24-7 9-(4-Phenylazo-benzoyloxy)-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-⁽⁶⁾-yl)-nonatetraen-(1.3t.5t.7t) 
• 114999-61-0 4-phenylazo-benzoic acid biphenyl-2-yl ester 
• 13107-85-2 N-(4-phenylazo-benzoyl)-glycine 
• 102840-84-6 4-phenylazo-benzoic acid methylamide 
• 119479-29-7 methyl 4-(phenyldiazenyl)benzoate 
• 101869-10-7 4-phenylazo-benzoic acid-(1-vinyl-but-3-ynyl ester) 
• 103046-89-5 4-phenylazo-benzoic acid-(4,8-dimethyl-nona-3t,7-dienyl ester) 

Relevant articles and documents

Light-triggered reversible "one-to-two" morphological transition in a "latent double-amphiphilic" linear-hyperbranched supramolecular block copolymer

This study reports a new category of stimuli-responsive morphological transitions, i.e., from one morphology (e.g., vesicles) to another two different ones (e.g., nanosheets and nanofibers), by investigating the light-responsive self-assembly behaviour of a "latent double-amphiphilic" linear-hyperbranched supramolecular block copolymer.

Azobenzene abamectin derivative and preparation method and application thereof

The invention relates to an azobenzene abamectin derivative and preparation and application thereof. Specifically, the invention discloses a compound with a formula (I) or an optical isomer, a cis-trans-isomer or an agricultural pharmacologically acceptable salt thereof, and a preparation method thereof. The invention further discloses an agricultural composition containing the compound and application of the agricultural composition. The derivative has high killing activity on agricultural pests, mites and the like, and can be used for preventing and treating the pests.

Azologization of serotonin 5-HT3 receptor antagonists

The serotonin 5-hydroxytryptamine 3 receptor (5-HT3R) plays a unique role within the seven classes of the serotonin receptor family, as it represents the only ionotropic receptor, while the other six members are G protein-coupled receptors (GPCRs). The 5-HT3 receptor is related to chemo-/radiotherapy provoked emesis and dysfunction leads to neurodevelopmental disorders and psychopathologies. Since the development of the first serotonin receptor antagonist in the early 1990s, the range of highly selective and potent drugs expanded based on various chemical structures. Nevertheless, on-off-targeting of a pharmacophore’s activity with high spatiotemporal resolution as provided by photopharmacology remains an unsolved challenge bearing additionally the opportunity for detailed receptor examination. In the presented work, we summarize the synthesis, photochromic properties and in vitro characterization of azobenzene-based photochromic derivatives of published 5-HT3R antagonists. Despite reported proof of principle of direct azologization, only one of the investigated derivatives showed antagonistic activity lacking isomer specificity.