4132-48-3

Basic information

• Product Name: 4-Isopropylanisole
• Synonyms: 2-(4'-METHOXYPHENYL)PROPANE;4-ISOPROPYLANISOLE;4-METHOXYCUMENE;P-ISOPROPYLANISOLE;2-(p-Methoxyphenyl)propane;Anisole, p-isopropyl-;Benzene, 1-methoxy-4-(1-methylethyl)-;p-Methoxycumene
• CAS NO: 4132-48-3
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: 223-952-0
• Product Categories: Aromatic Ethers;Anisoles, Alkyloxy Compounds & Phenylacetates
• Mol File: 4132-48-3.mol
• Article Data: 73

Chemical Properties

• Melting Point: 60-61 °C
• Boiling Point: 210 °C(lit.)
• Flash Point: 183 °F
• Appearance: /
• Density: 0.935 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.25E-14mmHg at 25°C
• Refractive Index: n20/D 1.504(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• BRN: 2080269
• CAS DataBase Reference: 4-Isopropylanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isopropylanisole(4132-48-3)
• EPA Substance Registry System: 4-Isopropylanisole(4132-48-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: S24/25:Avoid contact with skin and eyes.
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 4132-48-3(Hazardous Substances Data)

Usage

General Description

4-Isopropylanisole, also known as isoamylphenol, is a chemical compound with the molecular formula C9H12O. It is a colorless liquid with a sweet, floral odor and is commonly used as a flavoring and fragrance agent in the food and beverage industry. 4-Isopropylanisole is also found in essential oils such as clove oil and is known for its antimicrobial and antioxidant properties. It is often used in the production of perfumes, soaps, and cosmetics, as well as in the pharmaceutical and chemical industries. Additionally, 4-Isopropylanisole is a key ingredient in the manufacturing of various household products and is used in the production of plastics and rubber.

InChI:InChI=1/C17H15N3O3S3/c1-23-15-8-4-13(5-9-15)11-25-17-19-18-16(26-17)24-10-12-2-6-14(7-3-12)20(21)22/h2-9H,10-11H2,1H3

Upstream product

• 1712-69-2 1-isopropenyl-4-methoxybenzene 
• 33868-91-6 3-(4-methoxyphenyl)glutaric acid 
• 71-23-8 propan-1-ol 
• 100-66-3 methoxybenzene 
• 187737-37-7 propene 
• 2307-69-9 toluene-4-sulfonic acid isopropyl ester 
• 67-63-0 isopropyl alcohol 
• 99-89-8 4-Isopropylphenol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 32454-14-1 2-(4-methoxyphenyl)-2-methylpropanal 
• 7428-99-1 2-(4-methoxyphenyl)propan-2-ol 
• 613-31-0 9,10-dihydroanthracene 
• 2944-47-0 o-isopropylanisole 

Downstream Products

• 32445-98-0 2,3-bis(4-methoxyphenyl)-2,3-dimethylbutane 
• 99-89-8 4-Isopropylphenol 
• 5259-66-5 isopropyl-4 cyclohexene-3 one-1 
• 99180-72-0 1-methoxy-4-(1'-methylethyl)cyclohexa-1,4-diene 
• 1200-06-2 4-methoxyphenyl acetate 
• 2158-59-0 cryptone 
• 127092-00-6 4-methoxybicumene 
• 127092-01-7 4-methoxy-4'-methylbicumene 
• 129970-59-8 4-methoxy-4'-cyanobicumene 
• 130379-05-4 4-methoxy-4'-(trifluoromethyl)bicumene 
• 5432-85-9 4-isopropyl-cyclohexanone 
• 100-02-7 4-nitro-phenol 
• 100-17-4 para-methoxynitrobenzene 
• 1576-10-9 4-isopropyl-2-nitrophenol 

Relevant articles and documents

Nickel-Catalyzed Negishi-Type Arylation of Trialkylsulfonium Salts

Negishi-type arylation of trialkylsulfonium salts with arylzinc reagents has been accomplished under nickel catalysis. The use of cyclohexanethiol as an additional ligand was found to be particularly important to promote C-S cleavage. The present reaction accommodates one-pot arylation of dialkyl sulfides by combining with S -methylation with MeOTf. Mechanistic experiments suggest that C-S cleavage would proceed via single-electron transfer (SET) to generate the most stable carbon-centered radical and that the thiolate ligand would promote the C-S cleavage and radical recombination step.

Efficient Pd-Catalyzed Direct Coupling of Aryl Chlorides with Alkyllithium Reagents

Organolithium compounds are amongst the most important organometallic reagents and frequently used in difficult metallation reactions. However, their direct use in the formation of C?C bonds is less established. Although remarkable advances in the coupling of aryllithium compounds have been achieved, Csp2?Csp3 coupling reactions are very limited. Herein, we report the first general protocol for the coupling or aryl chlorides with alkyllithium reagents. Palladium catalysts based on ylide-substituted phosphines (YPhos) were found to be excellently suited for this transformation giving high selectivities at room temperature with a variety of aryl chlorides without the need for an additional transmetallation reagent. This is demonstrated in gram-scale synthesis including building blocks for materials chemistry and pharmaceutical industry. Furthermore, the direct coupling of aryllithiums as well as Grignard reagents with aryl chlorides was also easily accomplished at room temperature.

Water and Sodium Chloride: Essential Ingredients for Robust and Fast Pd-Catalysed Cross-Coupling Reactions between Organolithium Reagents and (Hetero)aryl Halides

Direct palladium-catalysed cross-couplings between organolithium reagents and (hetero)aryl halides (Br, Cl) proceed fast, cleanly and selectively at room temperature in air, with water as the only reaction medium and in the presence of NaCl as a cheap additive. Under optimised reaction conditions, a water-accelerated catalysis is responsible for furnishing C(sp3)–C(sp2), C(sp2)–C(sp2), and C(sp)–C(sp2) cross-coupled products, in competition with protonolysis, within a reaction time of 20 s, in yields of up to 99 %, and in the absence of undesired dehalogenated/homocoupling side products even when challenging secondary organolithiums serve as the starting material. It is worth noting that the proposed protocol is scalable and the catalyst and water can easily and successfully be recycled up to 10 times, with an E-factor as low as 7.35.