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CAS No.: | 576-26-1 |
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Name: | 2,6-Dimethylphenol |
Article Data: | 249 |
Molecular Structure: | |
Formula: | C8H10O |
Molecular Weight: | 122.167 |
Synonyms: | 2,6-Xylenol(8CI);1-Hydroxy-2,6-dimethylbenzene;NSC 2123; |
EINECS: | 209-400-1 |
Density: | 1.15 g/cm3 |
Melting Point: | 43-45 °C(lit.) |
Boiling Point: | 201.1 °C at 760 mmHg |
Flash Point: | 78.3 °C |
Solubility: | 10 g/L (20 °C) in water |
Appearance: | Colorless to off-white crystalline olid |
Hazard Symbols: | T, N |
Risk Codes: | 24/25-34-51/53 |
Safety: | 26-36/37/39-45-61 |
Transport Information: | UN 2261 6.1/PG 2 |
PSA: | 20.23000 |
LogP: | 2.00900 |
2.6-dimethylphenol
Conditions | Yield |
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With sodium methylate In methanol; dichloromethane at 20℃; for 3h; | 98% |
With hydrogenchloride In 1,4-dioxane for 3h; Product distribution; Heating; deprotection; | 91% |
In 2,2,2-trifluoroethanol at 100℃; for 1h; Microwave irradiation; | 96 %Spectr. |
Conditions | Yield |
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aluminum oxide; nickel(II) sulphate In various solvent(s) at 305℃; Product distribution; fixed, quartz powder bed tubular reactor; gaseous phase in N2 flow; varied: temperature 280 to 330 deg C; N2 flow; quartz powder/catalyst ratio; residence time; substrates other alkylated phenols too; | A 97.5% B n/a |
Conditions | Yield |
---|---|
97% |
2,6-bis-<(dimethyamino)methyl>phenol
2.6-dimethylphenol
Conditions | Yield |
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With hydrogen; nickel-titanium-aluminum In various solvent(s) at 160℃; for 3h; | 96.2% |
With hydrogen; nickel-titanium-aluminum In various solvent(s) at 160℃; for 3h; Product distribution; Rate constant; Thermodynamic data; other temperatures; other concentrations of title compound; | 96.2% |
Conditions | Yield |
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With diethyl dibromomalonate at 100℃; for 48h; Dehydrogenation; | 96% |
at 330 - 335℃; Leiten ueber Palladium/Kohle; |
Conditions | Yield |
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With cesiumhydroxide monohydrate; bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II); 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole In tetrahydrofuran at 24℃; for 20h; Inert atmosphere; | 96% |
With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 8h; | 94% |
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; tris-(dibenzylideneacetone)dipalladium(0); cesiumhydroxide monohydrate In tetrahydrofuran at 24℃; Inert atmosphere; Glovebox; Sealed tube; | 92% |
Stage #1: 2,6-dimethyl-1-chlorobenzene With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole In 1,4-dioxane; water at 100℃; for 20h; Inert atmosphere; Stage #2: With hydrogenchloride In 1,4-dioxane; water at 20℃; Inert atmosphere; | 90% |
2,6-dimethylbenzene boronic acid
2.6-dimethylphenol
Conditions | Yield |
---|---|
With water; caesium carbonate; hydrazine hydrate at 80℃; for 12h; | 96% |
With water; 3-chloro-benzenecarboperoxoic acid In ethanol at 20℃; for 6h; | 94% |
With 2,5-dimethylfuran; zinc(II) phthalocyanine; oxygen; citric acid In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h; Irradiation; Sealed tube; Schlenk technique; | 93% |
Conditions | Yield |
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With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique; | 95% |
Ni(CH2C(CH3)2C6H5)OC6H3(CH3)2(((CH3)2CH)2P(CH2)2P(CH(CH3)2)2)
A
2.6-dimethylphenol
Ni(CH2C(CH3)2C6H4)(((CH3)2CH)2P(CH2)2P(CH(CH3)2)2)
Conditions | Yield |
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In tetrahydrofuran (N2); stirring a soln. of nickel complex in THF at room temp. for 12 h; evapn., extn. with Et2O, filtration, concn., addn. of petroleum ether, cooling to -30°C; elem. anal.; | A n/a B 94% |
2.6-dimethylphenol
Conditions | Yield |
---|---|
With Oxone; water In acetone at 20℃; for 0.0333333h; | 94% |
The IUPAC name of 2,6-Dimethylphenol is 2,6-dimethylphenol. With the CAS registry number 576-26-1, it is also named as 1-Hydroxy-2,6-dimethylbenzene. The product's categories are aromatic phenols; phenoles and thiophenoles. It is colorless to off-white crystalline solid with a sweet tarry odor. And this chemical is soluble in alcohol, ether, chloroform, benzene and alkali solution, very slightly soluble in cold water. In addition, it is stable, very flammable, and incompatible with oxidizing agents, acid chlorides, acid anhydrides, steel, copper, copper alloys, bases, acid chlorides. Furthermore, 2,6-Dimethylphenol should be stored away from extreme heat and away from strong oxidizing agents.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.40; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.4; (4)ACD/LogD (pH 7.4): 2.4; (5)ACD/BCF (pH 5.5): 39.41; (6)ACD/BCF (pH 7.4): 39.39; (7)ACD/KOC (pH 5.5): 482.78; (8)ACD/KOC (pH 7.4): 482.51; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.54; (13)Molar Refractivity: 37.78 cm3; (14)Molar Volume: 120.4 cm3; (15)Polarizability: 14.97×10-24 cm3; (16)Surface Tension: 37.2 dyne/cm; (17)Enthalpy of Vaporization: 45.51 kJ/mol; (18)Vapour Pressure: 0.221 mmHg at 25°C; (19)Tautomer Count: 2; (20)Exact Mass: 122.073165; (21)MonoIsotopic Mass: 122.073165; (22)Topological Polar Surface Area: 20.2; (23)Heavy Atom Count: 9; (24)Complexity: 80.6.
Preparation 2,6-Dimethylphenol: Using phenol or orthocresol as raw material, then they have a gas phase catalytic reaction with methanol. Through distillation and purification, we can obtain the product and its purity is over 99%.
Uses of 2,6-Dimethylphenol: It is an intermediate for the manufacture of polyphenylene oxide and modified phenolic resins and phosphate esters. And it is also used in the production of hydraulic fluids, in halogenation and aminolysis reactions.
When you are using this chemical, please be cautious about it as the following:
It is toxic in contact with skin and if swallowed. And it is also toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
1. Smiles: c1(c(cccc1C)C)O;
2. InChI: InChI=1/C8H10O/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3.
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mammal (species unspecified) | LC | inhalation | > 270mg/m3 (270mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(4), Pg. 43, 1976. | |
mouse | LD50 | intraperitoneal | 150mg/kg (150mg/kg) | National Technical Information Service. Vol. AD691-490, | |
mouse | LD50 | intravenous | 80mg/kg (80mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: SLEEP | Journal of Medicinal Chemistry. Vol. 23, Pg. 1350, 1980. |
mouse | LD50 | oral | 450mg/kg (450mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(4), Pg. 43, 1976. |
mouse | LD50 | skin | 920mg/kg (920mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(2), Pg. 58, 1974. | |
rabbit | LD50 | oral | 700mg/kg (700mg/kg) | BEHAVIORAL: ATAXIA BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Hygiene and Sanitation Vol. 33(7-9), Pg. 329, 1968. |
rabbit | LD50 | skin | 1gm/kg (1000mg/kg) | Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. Vol. 6, Pg. 1, 1967. | |
rat | LD50 | oral | 296mg/kg (296mg/kg) | Gigiena Truda i Professional'naya Patologiya v Estonskoi SSR. Labor Hygiene and Occupational Pathology in the Estonian SSR. Vol. 8, Pg. 145, 1972. | |
rat | LD50 | skin | 2325mg/kg (2325mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(4), Pg. 43, 1976. |