74663-48-2

Basic information

• Product Name: 2-Isopropyl-6-propylphenol (Propofol Impurity O)
• Synonyms: 2-(1-Methylethyl)-6-propylphenol;2-Isopropyl-6-propylphenol (Propofol Impurity O);Propofol Impurity O;2-Isopropyl-6-propylphenol;Brn 4383251;Phenol, 2-isopropyl-6-propyl-;2-(1-Methylethyl)-6-propyl;Propofol EP Impurity O
• CAS NO: 74663-48-2
• Molecular Formula: C₁₂H₁₈O
• Molecular Weight: 178.27
• Product Categories: Chemical Impurities;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 74663-48-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 254.537 °C at 760 mmHg
• Flash Point: 115.315 °C
• Appearance: /
• Density: 0.952 g/cm³
• Vapor Pressure: 0.0107mmHg at 25°C
• Refractive Index: 1.515
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 11.00±0.10(Predicted)
• CAS DataBase Reference: 2-Isopropyl-6-propylphenol (Propofol Impurity O)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Isopropyl-6-propylphenol (Propofol Impurity O)(74663-48-2)
• EPA Substance Registry System: 2-Isopropyl-6-propylphenol (Propofol Impurity O)(74663-48-2)

Safety Data

• Hazardous Substances Data: 74663-48-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 74663-48-2 differently. You can refer to the following data:
1. Propofol impurity O
2. 2-Isopropyl-6-propylphenol (Propofol EP Impurity O).

InChI:InChI=1/C12H18O/c1-4-6-10-7-5-8-11(9(2)3)12(10)13/h5,7-9,13H,4,6H2,1-3H3

Synthetic route

Conditions	Yield
With hydrogen In ethanol at 25℃; under 760 Torr;	95%
With hydrogen; palladium on activated charcoal In ethanol at 25℃; under 760 Torr; for 0.25h; Yield given;
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 12h;	6 g

→ 2-(1-methylethyl)-6-propylphenol (74663-48-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1 N aq. NaOH, benzyltri-n-butylammonium bromide / CH2Cl2 / 2 h / Ambient temperature 2: 1.5 h / 250 °C 3: H2 / 10percent Pd/C / ethanol / 0.25 h / 25 °C / 760 Torr View Scheme
Multi-step reaction with 5 steps 1.1: sodium hydroxide / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 1.17 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: sodium carbonate / tetrahydrofuran / 0.25 h / Inert atmosphere 3.2: 16 h / 50 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / methanol / 7 h / 20 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 16 h View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 8 h / 80 °C 2: N,N-diethylaniline / 1.33 h / 220 °C / Inert atmosphere 3: palladium on activated charcoal; hydrogen / methanol / 12 h / 20 °C View Scheme

Upstream product

• 71-23-8 propan-1-ol 
• 622-85-5 propoxybenzene 
• 3354-56-1 2-allyl-6-isopropylphenol 
• 108-95-2 phenol 
• 88-69-7 2-(1-methylethyl)phenol 
• 106-95-6 allyl bromide 
• 74931-59-2 1-isopropyl-2-methoxymethyloxybenzene 
• 1510867-00-1 2-isopropyl-6-(prop-1-enyl)phenol 
• 942-58-5 1-(1-methylethyl)-2-(2-propen-1-yloxy)benzene 

Downstream Products

• 342892-39-1 allyl 2-isopropyl-6-n-propylphenyl ether 
• 74663-61-9 2-isopropyl-4-allyl-6-n-propylphenol 
• 74663-56-2 2-isopropyl-4,6-di-n-propylphenol 

Relevant articles and documents

USE OF A GABAA RECEPTOR ALLOSTERIC ENHANCER IN MEDICINE

An application of a GABAA receptor allosteric enhancer in medicine. Specifically provided is use of the GABAA receptor allosteric enhancer shown in formula (I) in preparation of drugs for sedatives, hypnosis, treatment or prevention of anxiety, depression, insomnia, nausea, vomiting, migraine, schizophrenia, convulsions, and

Commercial manufacturing of propofol: Simplifying the isolation process and control on related substances

A commercially viable manufacturing process for propofol (1) is described. The process avoids acid-base neutralization events during isolation of intermediate, 2,6-di-isopropylbenzoic acid (3) and crude propofol, and thus simplifies the synthesis on industrial scale to a considerable extent. Syntheses of five impurities/related substances (USP and EP) are also described.

Synthesis, Biological Evaluation, and Preliminary Structure-Activity Considerations of a Series of Alkylphenols as Intravenous Anesthetic Agents

Following our discovery of the intravenous (iv) anesthetic activity of 2,6-diethylphenol in mice, a series of alkylphenols was examined in this species and the most active analogues were further evaluated in rabbits.The synthesis of compounds which were not commercially available was accomplished by adaptations of standard ortho-alkylation procedures for phenols.Structure-activity relationships were found to be complex, but, in general, potency and kinetics appeared to be a function of both the lipophilic character and the degree of steric hindrance exerted by ortho substituents.The most interesting compounds were found in the 2,6-dialkyl series, and the greatest potency was associated with 2,6-di-sec-alkyl substitution.In particular, 2,6-diisopropylphenol (ICI 35868) emerged as a candidate for further development and has subsequently been shown to be an effective iv anesthetic agent in man.