645-13-6

Basic information

• Product Name: 4'-Isopropylacetophenone
• Synonyms: 1-[4-(1-methylethyl)phenyl]ethan-1-one;4'-ISOPROPYLACETOPHENONE;4-ISOPROPYLACETOPHENONE;(4-ISO-PROPYLPHENYL)ETHANONE;LABOTEST-BB LT00261439;FEMA 2927;P-ISOPROPYLACETOPHENONE;1-(4-Isopropylphenyl)ethanone
• CAS NO: 645-13-6
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.23
• EINECS: 211-433-1
• Product Categories: Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 645-13-6.mol
• Article Data: 33

Chemical Properties

• Melting Point: 254 C
• Boiling Point: 119-120 °C (10 mmHg)
• Flash Point: 238°C
• Appearance: clear almost colorless to yellow liquid
• Density: 0,97 g/cm3
• Vapor Pressure: 0.0171mmHg at 25°C
• Refractive Index: 1.522-1.524
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Methanol (Sparingly)
• Water Solubility: Soluble in alcohol. Insoluble in water.
• BRN: 2205694
• CAS DataBase Reference: 4'-Isopropylacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Isopropylacetophenone(645-13-6)
• EPA Substance Registry System: 4'-Isopropylacetophenone(645-13-6)

Safety Data

• Hazard Codes: Xi,F,Xn
• Statements: 10-36/37/38-52-43-22
• Safety Statements: 24/25-36-26-36/37
• RIDADR: 1224
• WGK Germany: WGK 3 highly water endangering
• TSCA: Yes
• PackingGroup: III
• Hazardous Substances Data: 645-13-6(Hazardous Substances Data)

Usage

Description

4'-Isopropylacetophenone, also known as p-Isopropylacetophenone, is an organic compound with a chemical structure derived from acetophenone, featuring an isopropyl group attached to the 4' position. It has a spicy, woody, herbaceous odor reminiscent of orris and basil, along with a warm, spicy flavor. 4'-Isopropylacetophenone can be synthesized through various methods, such as condensing cymene with acetyl chloride in the presence of AlCl3 or from benzol, acetyl chloride, and isopropyl chloride via Friedel Crafts. It is a clear, almost colorless to yellow liquid.

Uses

Used in Perfumery and Flavor Industry:
4'-Isopropylacetophenone is used as a perfuming agent and flavoring agent due to its pleasant odor and warm, spicy flavor. It adds a unique and desirable scent to various products in these industries.
Used in the Synthesis of Indenes:
4'-Isopropylacetophenone serves as a precursor in the one-step synthesis of indenes using a heterogeneous catalyst. This application is particularly relevant in the chemical and pharmaceutical industries, where indenes are valuable intermediates for the production of various compounds.
Occurrence:
4'-Isopropylacetophenone has been reported to be found in the essential oil of lavandin, starfruit, and dried bonito, indicating its natural presence in certain plants and food products.

Preparation

By condensing cymene with acetyl chloride in the presence of AlCl3; also from benzol, acetyl chloride and isopropyl chloride via Friedel–Craft

InChI:InChI=1/C11H14O/c1-8(2)10-4-6-11(7-5-10)9(3)12/h4-8H,1-3H3

Upstream product

• 98-82-8 Isopropylbenzene 
• 108-24-7 acetic anhydride 
• 99-62-7 1,3-diisopropylbenzene 
• 75-36-5 acetyl chloride 
• 18620-03-6 4-isopropylphenylmagnesium bromide 
• 75-05-8 acetonitrile 
• 100-18-5 1,4-bis(1-methylethyl)benzene 
• 4218-48-8 1-ethyl-4-isopropylbenzene 
• 106353-53-1 1-(4-Isopropyl-phenyl)-3,3-di-morpholin-4-yl-propenone 
• 2055-40-5 4-isopropylstyrene 
• 2089-31-8 1-(4-isopropylphenyl)ethan-1-one oxime 
• 7446-70-0 aluminium trichloride 
• 107-06-2 1,2-dichloro-ethane 
• 75-09-2 dichloromethane 

Downstream Products

• 84921-99-3 3t-[2]furyl-1-(4-isopropyl-phenyl)-propenone 
• 1688-53-5 1-(4-isopropyl-phenyl)-3-morpholino-propan-1-one; hydrochloride 
• 1030-52-0 1-(4-isopropyl-phenyl)-3-piperidino-propan-1-one; hydrochloride 
• 107621-06-7 3-hydroxy-1-(4-isopropyl-phenyl)-3,4,4-trimethyl-pentan-1-one 
• 54549-72-3 1-(4-(2-hydroxypropan-2-yl)phenyl)ethan-1-one 
• 4218-48-8 1-ethyl-4-isopropylbenzene 
• 1475-10-1 1-(4-isopropylphenyl)ethanol 
• 3445-42-9 α,α-dimethyl-p-isopropylbenzyl alcohol 
• 1634-63-5 1-(4-isopropyl-3-nitrophenyl)ethan-1-one 
• 32122-03-5 2-(4-isopropyl-phenyl)-3-methyl-butan-2-ol 
• 2089-31-8 1-(4-isopropylphenyl)ethan-1-one oxime 
• 100059-60-7 2-(4-isopropyl-phenyl)-2-oxo-ethanesulfonic acid 
• 713132-14-0 dichloro-acetic acid-(4-isopropyl-phenacylamide) 
• 438531-43-2 6-bromo-2-(4-isopropyl-phenyl)-quinoline-4-carboxylic acid 

Relevant articles and documents

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Site-Specific Oxidation of (sp3)C-C(sp3)/H Bonds by NaNO2/HCl

A site-specific oxidation of (sp3)C-C(sp3) and (sp3)C-H bonds in aryl alkanes by the use of NaNO2/HCl was explored. The method is chemical-oxidant-free, transition-metal-free, uses water as the solvent, and proceeds under mild conditions, making it valuable and attractive to synthetic organic chemistry.

Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands

Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.