3228-03-3

Basic information

• Product Name: 5-ISOPROPYL-3-METHYLPHENOL
• Synonyms: 3-Methyl-5-(1-methylethyl)phenol;3-isopropyl-5-methyl-phenol;3-methyl-5-(1-methylethyl)-pheno;3-METHYL-5-ISOPROPYL PHENOL;5-ISOPROPYL-3-METHYLPHENOL;5-isopropyl-m-cresol;5-ISOPROPYL-3-METHYLPHENOL 98%
• CAS NO: 3228-03-3
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: 221-762-2
• Product Categories: Phenols;Organic Building Blocks;Oxygen Compounds
• Mol File: 3228-03-3.mol

Chemical Properties

• Melting Point: 49-51 °C(lit.)
• Boiling Point: 241°C
• Flash Point: >230 °F
• Appearance: /
• Density: 0.9688 (estimate)
• Vapor Pressure: 0.0229mmHg at 25°C
• Refractive Index: 1.5106 (estimate)
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.14±0.10(Predicted)
• CAS DataBase Reference: 5-ISOPROPYL-3-METHYLPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ISOPROPYL-3-METHYLPHENOL(3228-03-3)
• EPA Substance Registry System: 5-ISOPROPYL-3-METHYLPHENOL(3228-03-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: 1759
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3228-03-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Isopropyl-3-methylphenol is used as an antimicrobial agent for its ability to inhibit the growth of Mycobacterium tuberculosis, a bacterium responsible for tuberculosis. Its action as an inhibitor of the chorismate mutase enzyme plays a crucial role in disrupting the bacterial cell wall synthesis, thus providing a potential therapeutic approach against tuberculosis.
Used in Food Industry:
5-Isopropyl-3-methylphenol, as a component of oregano oil, is used as a natural preservative and flavor enhancer in the food industry. Its antimicrobial properties help extend the shelf life of various food products by inhibiting the growth of spoilage-causing microorganisms.
Used in Cosmetics Industry:
In the cosmetics industry, 5-Isopropyl-3-methylphenol is used as an anti-inflammatory and antimicrobial agent. Its incorporation into skincare and personal care products can help reduce inflammation, fight acne-causing bacteria, and provide a pleasant, natural scent.
Used in Agriculture:
5-Isopropyl-3-methylphenol can be used in the agricultural sector as a natural pesticide. Its antimicrobial properties make it effective against various pests and pathogens that can damage crops, promoting healthier plant growth and increased yield.
Used in Aromatherapy:
As a component of oregano oil, 5-Isopropyl-3-methylphenol is used in aromatherapy for its potential therapeutic effects. Its anti-inflammatory and antimicrobial properties may help with respiratory issues, muscle pain, and stress relief when inhaled or applied topically.

InChI:InChI=1/C10H14O/c1-7(2)9-4-8(3)5-10(11)6-9/h4-7,11H,1-3H3

Upstream product

• 28587-71-5 3-methyl-5-(1-methylethyl)-2-cyclohexen-1-one 
• 19177-04-9 1-isopropoxy-3-methylbenzene 
• 75-29-6 isopropyl chloride 
• 108-39-4 3-methyl-phenol 
• 67-63-0 isopropyl alcohol 
• 41005-11-2 4-isopropyl-hepta-1,6-diyn-4-ol 
• 55322-01-5 2-methyl-3-prop-2-ynyl-hex-5-yn-2-ol 
• 7544-54-9 3-isopropyl-5-methylaniline 
• 89-83-8 thymol 
• 24545-81-1 3-thujen-2-one 
• 7446-70-0 aluminium trichloride 
• 107-06-2 1,2-dichloro-ethane 
• 3228-02-2 3-Methyl-4-isopropylphenol 
• 7726-95-6 bromine 

Downstream Products

• 91687-79-5 2,4,6-tribromo-3-isopropyl-5-methyl-phenol 
• 17479-65-1 2-Hydroxy-4-isopropyl-6-methyl-benzoesaeure 
• 94675-14-6 phenyl-carbamic acid-(3-isopropyl-5-methyl-phenyl ester) 
• 60249-32-3 3-methyl-5-isopropylphenyl-N-n-propylcarbamate 
• 56532-12-8 Ethyl-carbamic acid 3-isopropyl-5-methyl-phenyl ester 
• 60309-33-3 Butyl-carbamic acid 3-isopropyl-5-methyl-phenyl ester 
• 59010-46-7 4-(2-Hydroxy-4-methylphenyl)-4-oxobutanoic Acid 
• 96358-75-7 4-(2-Hydroxy-4-isopropyl-6-methyl-phenyl)-4-oxo-butyric acid 
• 121194-58-9 m-thymyl propionate 
• 38253-04-2 3-Isopropyl-5-methylpicrinsaeure 
• 51202-03-0 2,4,6-Trichloro-3-isopropyl-5-methyl-phenol 
• 51202-04-1 2,4,4,6-Tetrachloro-3-isopropyl-5-methyl-cyclohexa-2,5-dienone 
• 700370-86-1 (2R,4S)-4-(3-Isopropyl-5-methyl-phenoxy)-pentan-2-ol 
• 845622-65-3 4-iodo-3-isopropyl-5-methylphenol acetate 

Relevant articles and documents

Method of preparing 3-isopropyl-5-cresol and carvacrol with 3-carene

The invention discloses a method of preparing 3-isopropyl-5-cresol and carvacrol with 3-carene. The method comprises the following steps that 3-carene is reacted with oxygen at a room temperature to produce a product I under the catalysis of CrO3-Al2O3, wherein the product I is prepared from the main components including 5-carone, 2-carone and 4-carone with the selectivity ratio being about 10.8 to 3.5 to 1.0; the product I is distilled to recover 3-carene, wherein the recovery rate is larger than 80 percent, and the recovery purity is larger than 94 percent; the residual components are converted to a product II at 230 DEG C under catalysis of a 13X type molecular sieve, and reduced pressure distillation is performed on the product II to obtain a mixed phenol product with the purity largerthan 96 percent, wherein the product II is prepared from the main components including 3-isopropyl-5-cresol and carvacrol, the raw material conversion rate is 100 percent, the total selectivity of phenolic products can reach 98 percent, and the selectivity ratio of the two phenolic products is about 2.2 to 1.0; and column chromatography isolation is performed on the product II to obtain 3-isopropyl-5-cresol and carvacrol with the purities larger than 97 percent respectively.

Selective alkylation of m-cresol with isopropyl alcohol under solvent-free conditions

The outcome of the solvent free alkylation of m-cresol with isopropyl alcohol over strong acid resin catalyst has been investigated under microwave irradiation as well as conventional heating. The various reaction parameters like catalyst amount, mole rat

Improving carbon retention in biomass conversion by alkylation of phenolics with small oxygenates

Alkylation of phenolics with alcohols is an efficient way to retain carbon from small oxygenates in the liquid products of pyrolysis bio-oil. In this contribution, we have investigated the alkylation of m-cresol with several alkylating agents over H-Beta zeolite. The alkylation activity follows the sequence 2-propanol > propylene > 1-propanol. In all cases, propylene is the actual alkylation agent since the alcohols dehydrate at a faster rate than the rate of alkylation. A two-stage process is proposed to convert fractions of bio-oil rich in small aldehydes and ketones together with phenolics. In the first stage, aldehydes and ketones are selectively hydrogenated to alcohols. In the second stage, the resulting alcohols alkylate the phenolic compounds and get incorporated into the upgraded liquid. To illustrate this concept, two consecutive catalyst beds have been used. The first bed contains a metal catalyst for the selective hydrogenation. Among several catalysts investigated, Cu/SiO2 and Pt-Fe/SiO2 were found to exhibit good selectivity to hydrogenate the aldehyde and ketone, respectively, while preserving the aromatic ring of the phenolic compound. The second bed contains an H-Beta zeolite for the alkylation stage.

ALKYLATION OF HYDROXYARENES WITH OLEFINS, ALCOHOLS AND ETHERS IN IONIC LIQUIDS

Hydroxyarenes are alkylated using an ionic liquid catalyst system with olefins, alcohols, or ethers as alkylating agents. The ionic liquid catalyst system comprises chloroindate (III) anions. The reactions may be conducted at moderate temperatures and pressures to yield commercially relevant alkylated hydroxyarene compounds.

2DCOR-GC: An application of the generalized two-dimensional correlation analysis as a route to optimization of continuous flow supercritical fluid reactions

A new approach for optimization and monitoring of continuous reactions has been developed using 2D correlation methods for the analysis of GC data (2DCOR-GC). 2DCOR-GC maps are obtained following perturbation of the system that allow the effect of changing reaction parameters such as time, temperature, pressure, or concentration to be both monitored and sequenced with regard to changes in the raw GC data. In this paper, we describe the application of the 2DCOR-GC technique to monitoring the reverse water-gas shift reaction in scCO2. 2DCOR-GC is combined with FT-IR data to validate the methodology. We also report the application of 2DCOR-GC to probe the mechanism of the alkylation of m-cresol with isopropyl alcohol in scCO2 using Nafion SAC-13 as the catalyst. These results identify coeluting peaks that could easily be missed without exhaustive method development.

Alkylation of phenol and m-cresol over zeolites

The alkylation of phenols and phenol derivatives such as m-cresol are important reactions in a sequence of syntheses for the production of many important fine chemicals. Specifically it is of great importance to develop catalysts and processes, which are able to selectively produce one or other particular isomer or derivative. This paper presents results of an investigation into the alkylation of phenol and m-cresol, respectively, using methanol in the former case and propene in the latter. The catalysts of choice were H-ZSM-5 and H-MCM-22. In the case of phenol methylation it was found that controlling diffusivity by increasing crystal size was most conducive to the formation of p-cresol. H-MCM-22 showed a high selectivity to p-cresol. In the case of m-cresol propylation the selectivity over H-ZSM-5 to thymol was greater than 90% at conversions of around 50%, and 80% at conversions of around 85%. This high selectivity to thymol was considerably greater than reported in previous papers. In both systems mild reaction temperature and pressure conditions were desirable so as to minimize the formation of oligomeric products of methanol (via dimethyl ether) and propene, which could cause deactivation of the zeolite.

A fluorescence detection scheme for capillary electrophoresis of N- methylcarbamates with on-column thermal decomposition and derivatization

This paper describes a fluorescence detection method for N- methylcarbamate (NMC) pesticides in micellar electrokinetic chromatography (MEKC) separation. Fulfillment of the fluorescence detection hinged on the discovery that quaternary ammonium surfactants (particularly cetyltrimethylammonium bromide, CTAB), besides serving as hydrophobic pseudophases in MEKC, are also capable of catalyzing the thermal decomposition of NMCs to liberate methylamine. Thus, a multifunctional MEKC medium consisting of borate buffer, CTAB, and derivatizing components (o- phthaldialdehyde/2-mercaptoethanol) was formulated, which allowed first normal MEKC separation, subsequent thermal decomposition, and finally in situ derivatization of NMCs. With careful optimization of the operation conditions, fluorescence detection of 10 NMC compounds was achieved, with column efficiencies typically higher than 50 000 and detection limits better than 0.5 ppm. The present work represents an unprecedented effort in capillary electrophoresis (CE), in which an intact capillary was consecutively utilized as chambers for separation, decomposition, derivatization, and detection, without involving any interfacing features. The success in the implementation of such a detection system resulted in strikingly simple instrumentation as compared with the traditional postcolumn fluorescence determination of NMCs by reversed-phase HPLC. Similar protocols should be workable in the determination of a wide range of pesticides and pharmaceuticals in CE formats.

Process for the production of N-methylcarbamates

Process for the production of N-methylcarbamates: STR1 (wherein RO- is the radical of a substituted phenol or of a naphthol), wherein: in a first reaction step methylamine and diphenyl carbonate are reacted with each other, operating in the liquid phase and as a continuous process, in order to form phenol and phenyl-N-methylurethane; in a second reaction step phenyl-N-methylurethane, within the related reaction mixture outcoming from the first step, is thermally continuously decomposed, to yield a gaseous stream containing methyl isocyanate, from which the components different than methyl isocyanate are condensed off; in a third step the methyl isocyanate stream, outcoming from the second step, after an optional preliminary condensation, is continuously fed and contacted with a solution of a substituted phenol or of a naphthol in an inert organic solvent, containing a basic catalyst, to form N-methylcarbamate (I); N-methylcarbamate (I) is finally recovered from the reaction mixture outcoming from the third step.

Photochemical Transformationos of Protonated Phenols. A One-Step Synthesis of Umbellulone from Thymol

UV irradiation of thymol (7) at 254 or 300 nm in trifluoromethanesulfonic acid affords ten products, eight of which have been isolated and characterized.Four competitive processes are suggested to be operating in the formation of the photoproducts: (i) regioselective type A rearrangement leading to umbellulone (8, about 10percent, (ii) formal C2->C3 migration by type A rearrangement and ring opening which affords the principal products, 3-isopropyl-5-methylphenol (12, 17percent), (iii) intermolecular transalkylation leading to diisopropylphenols 13-15 (17percent), and (iv) formation ofpiperitenone (10, 5percent) initiated by hydrogen abstraction.A mechanism for the formation of 10 is proposed.Both para- and ortho-protonated 7 are suggested to be involved in product formation.