496-78-6

Basic information

• Product Name: 2,4,5-Trimethylphenol
• Synonyms: 1-Hydroxy-2,4,5-trimethylbenzene;2,4,5-Trimethylphenol; 5-Hydroxypseudocumene; NSC 38776; Pseudocumenol
• CAS NO: 496-78-6
• Molecular Formula: C₉H₁₂O
• Molecular Weight: 0
• EINECS: 207-832-5
• Mol File: 496-78-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 232°Cat760mmHg
• Flash Point: 102.3°C
• Appearance: /
• Density: 0.996g/cm³
• Vapor Pressure: 0.0398mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: 2,4,5-Trimethylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-Trimethylphenol(496-78-6)
• EPA Substance Registry System: 2,4,5-Trimethylphenol(496-78-6)

Safety Data

• Hazardous Substances Data: 496-78-6(Hazardous Substances Data)

Usage

General Description

2,4,5-Trimethylphenol, also known as Toluene-2,4,5-trimethanol or TMT, is a chemical compound with a molecular formula C9H12O. It is a colorless to light yellow liquid that is commonly used as a fragrance ingredient and as a chemical intermediate in the production of dyes, pharmaceuticals, and agricultural chemicals. TMT is also used as an antioxidant in rubber and as a stabilizer in plastics, as well as a corrosion inhibitor in lubricating oils and fuel additives. It has a strong, phenolic odor and is considered to be toxic when ingested or inhaled in large quantities, but is relatively low in toxicity when used in the concentrations typically found in consumer products.

InChI:InChI=1/C9H12O/c1-6-4-8(3)9(10)5-7(6)2/h4-5,10H,1-3H3

Synthetic route

4,5-dimethyl-2-hydroxybenzyl alcohol (10496-92-1) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
With 1% Pd/C; hydrogen In methanol	100%

2,4,5-Trimethyl-3-methylsulfanyl-phenol (89711-25-1) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
With nickel In methanol for 2h; Heating;	99%

1-methoxy-2,4,5-trimethylbenzene (21573-38-6) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
With water; hydrogen bromide; Aliquat 336 at 105℃; for 8h; Catalytic behavior;	75%

6-acetoxy-2,4,6-trimethyl-cyclohexa-2,4-dienone (4906-82-5) → 2,4,5-trimethylphenol (496-78-6) + Essigsaeure-(3-hydroxy-2,4,6-trimethylphenyl)ester (55977-89-4) + (RS)-6-exo-Acetoxy-3,5,6-trimethylbicyclo<3.1.0>hex-3-en-2-on + (RS)-4-Acetoxy-2,4,5-trimethylcyclohexa-2,5-dien-1-on

Conditions	Yield
With 2,2,2-trifluoroethanol for 2h; Ambient temperature; Irradiation; Further byproducts given;	A 2.2% B 1.6% C 45% D 27%

methanol (67-56-1) + 3,4-Dimethylphenol (95-65-8) → 3,4,5-trimethylphenol (527-54-8) + 2,4,5-trimethylphenol (496-78-6) + 2,3,4-trimethylphenol (526-85-2)

Conditions	Yield
Pd-containing mordenite at 350℃;	A 1% B 40% C 45%

2,4,4-Trimethyl-2,5-cyclohexadien-1-on (38441-63-3) + Trimethyl(methylthio)silane (3908-55-2) → 2,4,5-trimethylphenol (496-78-6) + C10H14S (1215002-19-9)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane for 168h; Reflux;	A 39% B 42%

2,4,4-Trimethyl-2,5-cyclohexadien-1-on (38441-63-3) + phenylthiotrimethylsilane (4551-15-9) → 2,4,5-trimethylphenol (496-78-6) + phenyl(2,4,5-trimethylphenyl)sulfane (1215002-21-3)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane for 168h; Reflux;	A 35% B 32%

1,2,4-Trimethylbenzene (95-63-6) → 2,4-dimethylbenzyl alcohol (16308-92-2) + Trimethylhydroquinone (700-13-0) + 2,4,5-trimethylphenol (496-78-6) + 2,5-dimethylbenzyl alcohol (53957-33-8)

Conditions	Yield
With glucose dehydrogenase; D-glucose; P450 BM3 R47S, Y51W mutant; NADPH; catalase; ascorbic acid In aq. phosphate buffer; dimethyl sulfoxide pH=7.5; Catalytic behavior; Enzymatic reaction;	A 31% B 12% C 34% D 12%

1,2,4-Trimethylbenzene (95-63-6) → 2,4-dimethylbenzyl alcohol (16308-92-2) + 3,4-dimethylbenzyl alcohol (6966-10-5) + 2,4,5-trimethylphenol (496-78-6) + 2,3,6-trimethylphenol (2416-94-6) + 2,3,5-trimethylphenol (697-82-5) + 2,5-dimethylbenzyl alcohol (53957-33-8)

Conditions	Yield
With glucose dehydrogenase; D-glucose; P450 BM3; NADPH; catalase; ascorbic acid In aq. phosphate buffer; dimethyl sulfoxide pH=7.5; Catalytic behavior; Enzymatic reaction;	A 27% B 5% C 34% D 9% E 8% F 14%

1,2,4-Trimethylbenzene (95-63-6) → 2,4-dimethylbenzyl alcohol (16308-92-2) + Trimethylhydroquinone (700-13-0) + 2,4,5-trimethylphenol (496-78-6) + 2,3,5-trimethylphenol (697-82-5) + 2,5-dimethylbenzyl alcohol (53957-33-8)

Conditions	Yield
With glucose dehydrogenase; D-glucose; P450 BM3 R47S, Y51W, I401M mutant; NADPH; catalase; ascorbic acid In aq. phosphate buffer; dimethyl sulfoxide pH=7.5; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;	A 17% B 32% C 31% D 7% E 7%

1,2,4-Trimethylbenzene (95-63-6) → 2,4-dimethylbenzyl alcohol (16308-92-2) + Trimethylhydroquinone (700-13-0) + 2,4,5-trimethylphenol (496-78-6) + 2,3,6-trimethylphenol (2416-94-6) + 2,3,5-trimethylphenol (697-82-5) + 2,5-dimethylbenzyl alcohol (53957-33-8)

Conditions	Yield
With glucose dehydrogenase; D-glucose; P450 BM3 R47S, Y51W, A330F, I401M mutant; NADPH; catalase; ascorbic acid In aq. phosphate buffer; dimethyl sulfoxide pH=7.5; Catalytic behavior; Enzymatic reaction;	A 25% B 23% C 28% D 5% E 8% F 9%

3,4-Dimethylphenol (95-65-8) + diiodomethane (75-11-6) → 2,4,5-trimethylphenol (496-78-6) + 2,3,4-trimethylphenol (526-85-2)

Conditions	Yield
With diethylzinc In toluene for 1.58333h; Inert atmosphere; Reflux;	A 3% B 2%

methyl magnesium iodide (917-64-6) + 2,5-Dimethyl-1,4-benzoquinone (137-18-8) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield

1-<(4-Hydroxy-3,6-dimethyl-phenyl)-methyl>-piperidin (68097-96-1) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
With 1,4-dioxane; copper oxide-chromium oxide at 165℃; under 73550.8 Torr; Hydrogenolyse;

4-formyl-2,5-dimethylphenol (85231-15-8) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
With hydrogenchloride; amalgamated zinc; toluene

2,4,5-trimethylaniline (137-17-7) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
Diazotization;
(i) NaNO2, H2SO4, (ii) H2O; Multistep reaction;

2,4,5-trimethylbenzenesulfonic acid (3453-84-7) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
With potassium hydroxide beim Verschmelzen;

1-methoxy-2,4,5-trimethylbenzene (21573-38-6) + pyridine hydrochloride (628-13-7) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield

nitroso-(2,4,5-trimethyl-phenyl)-amidosulfuric acid → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
With water

1,2,5-Trimethyl-cyclohexen-(2)-ol-(3)-on-(4) (90765-52-9) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
With phosphoric acid

3,4,6-trimethyl-2-cyclohexen-1-one (7474-10-4) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
palladium on barium sulfate In biphenyl

7-methoxy-4,6-dimethyl-3H-isobenzofuran-1-one (633337-82-3) + hydrogen iodide (10034-85-2) + red phosphorus → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield

trimer(ic) 4.5.7-trimethyl-coumarone → 4,5,7-trimethyl-benzofuran (1027417-43-1) + 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield

copper(II) sulfate (7758-99-8) + acetic acid (64-19-7) + (2,4,5-trimethyl-phenyl)-hydrazine (90565-17-6) → 1,2,4-Trimethylbenzene (95-63-6) + 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield

sodium salt of/the/ N-<2.4.5-trimethyl-phenyl>-hydrazine-N'-sulfonic acid → 2,4,5-trimethylphenol (496-78-6) + (2,4,5-trimethyl-phenyl)-hydrazine (90565-17-6)

Conditions	Yield
With hydrogenchloride

dichloromethane (75-09-2) + 1,2,4-Trimethylbenzene (95-63-6) + trifluoroacetyl peroxide (359-48-8) → 2,3,5-Trimethyl-1,4-benzoquinone (935-92-2) + 2,4,5-trimethylphenol (496-78-6) + 2,3,6-trimethylphenol (2416-94-6) + 4-hydroxy-2,4,5-trimethyl-cyclohexa-2,5-dienone (?)

Conditions	Yield

1,2,4-Trimethylbenzene (95-63-6) → Mesitol (527-60-6) + 2,4,5-trimethylphenol (496-78-6) + 2,3,6-trimethylphenol (2416-94-6) + 2,3,5-trimethylphenol (697-82-5) + ArCH2OH, ArCH2Ar',

Conditions	Yield
palladium diacetate; sodium persulfate In acetic acid at 115℃; for 3h; Product distribution; other oxidants: NaNO3, HPA-2, H2O2, AgNO3; other other reaction times and temperatures;

acidic 1.2.4-trimethyl-benzenediazonium sulfate-(5) → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
With sulfuric acid Sonnenlicht;

2,4,5-trimethylbenzenesulfonic acid (3453-84-7) + potash → 2,4,5-trimethylphenol (496-78-6)

Conditions	Yield
beim Schmelzen;

2,4,5-trimethylphenol (496-78-6) + bromoacetic acid methyl ester (96-32-2) → (2,4,5-Trimethyl-phenoxy)-acetic acid methyl ester (95450-50-3)

Conditions	Yield
With potassium carbonate In butanone for 5.5h; Heating;	100%

peracetic acid (79-21-0) + 2,4,5-trimethylphenol (496-78-6) → 2,3,5-trimethyl-1,6-benzoquinone (13038-87-4) + 1-acetoxy-2,4,5-trimethylbenzene (69305-42-6) + 1,4-dimethoxy-2,3,5-trimethyl-benzene (4537-09-1) + 1-methoxy-2,4,5-trimethylbenzene (21573-38-6) + 5-acetoxy-2,4-dihydroxy-2,4,5-trimethyl-3,6-lacto-1-hexanoic acid

Conditions	Yield
sulfuric acid at 50℃; for 0.5h; Mechanism; Thermodynamic data; effect of catalysts;	A n/a B 0.03% C 0.07% D 0.07% E 99.76%

2,4,5-trimethylphenol (496-78-6) → 5-acetoxy-2,4-dihydroxy-2,4,5-trimethyl-3,6-lacto-1-hexanoic acid

Conditions	Yield
With peracetic acid; sulfuric acid at 50℃; for 0.5h;	99.76%

2,4,5-trimethylphenol (496-78-6) + acetic acid (64-19-7) → 2,3,5-trimethyl-1,6-benzoquinone (13038-87-4) + 1-acetoxy-2,4,5-trimethylbenzene (69305-42-6) + 1-methoxy-2,4,5-trimethylbenzene (21573-38-6) + 4-acetoxy-2,3,5-trimethylphenol (36592-62-8) + 3-acetoxy-2,5-dihydroxy-5-carboxy-2,3,5-trimethylpentan-4-olide (109576-73-0)

Conditions	Yield
With peracetic acid at 50℃; for 0.25h; Product distribution; Kinetics; Thermodynamic data;	A 0.03% B 0.03% C 0.06% D 0.06% E 97.8%

2,4,5-trimethylphenol (496-78-6) + Diphenyliodonium fluoride → C15H16O

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane at 40℃;	90%

trifluoromethylsulfonic anhydride (358-23-6) + 2,4,5-trimethylphenol (496-78-6) → 2,3,5-trimethylphenyl trifluoromethanesulfonate

Conditions	Yield
In pyridine; dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	90%

2,4,5-trimethylphenol (496-78-6) + 7-(4-fluorophenyl)-7-hydroxyheptanoic acid (103187-28-6) → 7-(4-fluorophenyl)-7-(2-hydroxy-3,5,6-trimethylphenyl)heptanoic acid (121099-56-7)

Conditions	Yield
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 60℃; for 6h;	78%

2,4,5-trimethylphenol (496-78-6) → sodium[tertrakis(2,4,5-trimethylphenoxy)borate]

Conditions	Yield
Stage #1: With boric acid In toluene for 12h; Heating; Stage #2: 2,4,5-trimethylphenol With sodium In tetrahydrofuran at 20℃;	71%

sodium 2,4,5-trimethylphenolate (1040913-82-3) + 2,4,5-trimethylphenol (496-78-6) + boric acid (11113-50-1) → sodium[tertrakis(2,4,5-trimethylphenoxy)borate]

Conditions	Yield
In toluene phenol (excess) and acid heated for 2 h (Dean-Stark trape), volatiles removed (vac.), dissolved (THF), added dropwise to a soln. of Na compd. (THF), stirred for 1-12 h; ppt. filtered, washed (diethyl ether, pentane), dried (high vac.); elem.anal.;	71%

2,4,5-trimethylphenol (496-78-6) + 4-(2-oxoimidazolidin-1-yl)benzene-1-sulfonyl chloride → 2,4,5-trimethylphenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonate (1311945-68-2)

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 24h; Inert atmosphere;	69%

2,4,5-trimethylphenol (496-78-6) + ethyl 4-chloronicotinate (37831-62-2) → ethyl 4-(2,4,5-trimethylphenoxy)nicotinate (1415407-43-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3h;	69%

formaldehyd (50-00-0) + 2,4,5-trimethylphenol (496-78-6) → 2-hydroxymethyl-3,4,6-trimethylphenol

Conditions	Yield
With sodium hydroxide	59%
With extinguished lime; water; calcium carbonate at 50℃;

2,4,5-trimethylphenol (496-78-6) → 3,3',4,4',5,5'-hexamethyl-2,2'-biphenol (110932-47-3)

Conditions	Yield
With 4,4'-di-tert-butylbiphenyl; 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In 1,2-dichloro-ethane at 35℃; Solvent; Irradiation;	56%
With selenium(IV) oxide; acetic acid at 85℃;	39%
With trifluoroacetic acid at 30℃; Ionic liquid; Electrochemical reaction;	30%
With tetraethylammonium methyl sulfate In hexafluoropropan-2-ol at 50℃; Electrolysis;	22%

methanol (67-56-1) + 2,4,5-trimethylphenol (496-78-6) → 5-methoxy-2,3-dimethylbenzyl methyl ether

Conditions	Yield
With chlorine In dichloromethane -60 deg C -> room temperature;	53%

2,4,5-trimethylphenol (496-78-6) → C18H22O2Se

Conditions	Yield
With pyridine; selenium(IV) oxide at 55℃;	40%

2,4,5-trimethylphenol (496-78-6) + methyl iodide (74-88-4) → 1-methoxy-2,4,5-trimethylbenzene (21573-38-6)

Conditions	Yield
Stage #1: 2,4,5-trimethylphenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; Solvent;	32%

2-Chloro-N-(hydroxymethyl)acetamide (2832-19-1) + 2,4,5-trimethylphenol (496-78-6) → 2-Aminomethyl-3,4,6-trimethyl-phenol; hydrochloride (51571-06-3)

Conditions	Yield
With hydrogenchloride In ethanol for 0.5h; Heating;	22%

2,4,5-trimethylphenol (496-78-6) + 1,1,1-trichloro-2-methyl-2-propanol (57-15-8) → 2-(2,4,5-Trimethylphenoxy)isobutyric Acid (86550-00-7)

Conditions	Yield
With sodium hydroxide In acetone for 21h; temp. below 35 degC;	20%

Upstream product

• 137-17-7 2,4,5-trimethylaniline 
• 633337-82-3 7-methoxy-4,6-dimethyl-3H-isobenzofuran-1-one 
• 10034-85-2 hydrogen iodide 
• 7758-99-8 copper(II) sulfate 
• 64-19-7 acetic acid 
• 90565-17-6 (2,4,5-trimethyl-phenyl)-hydrazine 
• 95-65-8 3,4-Dimethylphenol 
• 75-11-6 diiodomethane 
• 95-63-6 1,2,4-Trimethylbenzene 
• 80-15-9 Cumene hydroperoxide 
• 21573-38-6 1-methoxy-2,4,5-trimethylbenzene 
• 38441-63-3 2,4,4-Trimethyl-2,5-cyclohexadien-1-on 
• 3908-55-2 Trimethyl(methylthio)silane 
• 4551-15-9 phenylthiotrimethylsilane 

Downstream Products

• 67548-70-3 2-(2,4,5-trimethyl-phenoxy)-ethanol 
• 132912-53-9 3,4,6-Trimethyl-2-piperidinomethyl-phenol 
• 325-75-7 (2-chloro-1,1,2-trifluoro-ethyl)-(2,4,5-trimethyl-phenyl)-ether 
• 2234-75-5 1,2,4-trimethylcyclohexane 
• 854714-26-4 2,4,5-Trimethyl-cyclohexanol 
• 13038-87-4 2,3,5-trimethyl-1,6-benzoquinone 
• 14353-72-1 4-hydroxy-2,4,5-trimethyl-2,5-cyclohexadien-1-one 
• 79755-29-6 3,4,6-trimethyl-2,4-dinitrocyclohexa-2,5-dienone 
• 58138-52-6 2-hydroxy-4,5-dimethylbenzoic acid 
• 854694-08-9 3,4,6,3',4',6'-hexamethyl-2,2'-sulfanediyl-di-phenol 
• 135839-05-3 4-nitro-benzoic acid-(3,4,5-trimethyl-phenyl ester) 
• 858836-18-7 3,4,6-trimethyl-2-(2-nitro-phenylsulfanyl)-phenol 
• 69305-42-6 2,4,5-trimethyl-1-acetoxybenzene 
• 26431-63-0 3-(2,4,5-Trimethyl-phenoxy)-butan-2-one 

Relevant articles and documents

Aromatics to diquinanes: An expeditious synthesis of tetramethylbicyclo[3. 3.0]octane framework of ptychanolide

An expeditious route to methyl-7-oxo-1,4,5,8-tetramethylbicyclo[3.3.0] octane-3-carboxylate from a simple aromatic precursor is described. Oxidative dearomatization of 2-hydroxymethyl-3,4,6-trimethylphenol into spiroepoxycyclohexa-2,4-dienone, its cycloaddition and triplet-sensitized 1,2-acyl shift, and stereochemical inversion are the key features of our methodology. Georg Thieme Verlag Stuttgart.

Volatiles from the hypoxylaceous fungi Hypoxylon griseobrunneum and Hypoxylon macrocarpum

The volatiles emitted by the ascomycetes Hypoxylon griseobrunneum and Hypoxylon macrocarpum (Hypoxylaceae, Xylariales) were collected by use of a closed-loop stripping apparatus (CLSA) and analysed by GC-MS. The main compound class of both species were polysubstituted benzene derivatives. Their structures could only be unambiguously determined by comparison to all isomers with different substitution patterns. The substitution pattern of the main compound from H. griseobrunneum, the new natural product 2,4,5-trimethylanisole, was explainable by a polyketide biosynthesis mechanism that was supported by a feeding experiment with (methyl-2H3)methionine.

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Cumene hydroperoxide (CHP) is widely used in chemical processes, mainly as an initiator for the polymerization of acrylonitrile-butadiene-styrene. It is a typical organic peroxide and an explosive substance. It is susceptible to thermal decomposition and is readily affected by contamination; moreover, it has high thermal sensitivity. The reactor tank, transit storage vessel, and pipeline used for manufacturing and transporting this substance are made of metal. Metal containers used in chemical processes can be damaged through aging, wear, erosion, and corrosion; furthermore, the containers might release metal ions. In a metal pipeline, CHP may cause incompatibility reactions because of catalyzed exothermic reactions. This paper discusses and elucidates the potential thermal hazard of a mixture of CHP and an incompatible material's metal ions. Differential scanning calorimetry (DSC) and thermal activity monitor III (TAM III) were employed to preliminarily explore and narrate the thermal hazard at the constant temperature environment. The substance was diluted and analyzed by using a gas chromatography spectrometer (GC) and gas chromatography/mass spectrometer (GC/MS) to determine the effect of thermal cracking and metal ions of CHP. The thermokinetic parameter values obtained from the experiments are discussed; the results can be used for designing an inherently safer process. As a result, the paper finds that the most hazards are in the reaction of CHP with Fe2+. When the metal release is exothermic in advance, the system temperature increases, even leading to uncontrollable levels, and the process may slip out of control.