2-Methylanisole

2-Methylanisole Basic information
Product Name:2-Methylanisole
Synonyms:1-methoxy-2-methyl-benzen;2-Methylanisol;2-Methylmethoxybenzene;Anisole, o-methyl-;Methyl o-cresyl ether;Methyl o-methylphenyl ether;o-Cresyl methyl ether;o-Methoxytoluene
CAS:578-58-5
MF:C8H10O
MW:122.16
EINECS:209-426-3
Product Categories:Ethers;Organic Building Blocks;Oxygen Compounds;Alphabetical Listings;Flavors and Fragrances;M-N;Anisoles, Alkyloxy Compounds & Phenylacetates;578-58-5
Mol File:578-58-5.mol
2-Methylanisole Structure
2-Methylanisole Chemical Properties
Melting point -34.1°C
Boiling point 170-172 °C (lit.)
density 0.985 g/mL at 25 °C (lit.)
vapor pressure 2hPa at 25℃
FEMA 2680 | O-METHYLANISOLE
refractive index n20/D 1.516(lit.)
Fp 125 °F
storage temp. Sealed in dry,Room Temperature
solubility Chloroform, Ethyl Acetate (Slightly)
form Liquid
color Clear colorless to light yellow
Specific Gravity0.985
Odorat 1.00 % in dipropylene glycol. sweet nutty floral earthy walnut
Odor Typenaphthyl
Odor Threshold0.0029ppm
Water Solubility immiscible
JECFA Number1242
BRN 1857415
LogP3 at 25℃
CAS DataBase Reference578-58-5(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, 1-methoxy-2-methyl-(578-58-5)
EPA Substance Registry SystemBenzene, 1-methoxy-2-methyl- (578-58-5)
Safety Information
Hazard Codes F
Risk Statements 10
Safety Statements 16
RIDADR UN 1993 3/PG 3
WGK Germany 3
Hazard Note Flammable
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29093090
MSDS Information
ProviderLanguage
1-Methoxy-2-methylbenzene English
SigmaAldrich English
ACROS English
ALFA English
2-Methylanisole Usage And Synthesis
Chemical Propertieso-Methylanisole has a pungent, warm, floral odor with earthy, walnut undertones. It has a sweet, fruity, nut-like flavor at low levels.
Physical propertiesclear colorless to light yellow liquid. soluble in alcohol and ether, insoluble in water.
OccurrenceReported found in starfruit, mastic gum oil and rooibus tea (Aspalathus linearis).
UsesThe catalytic system of disubstituted aromatics was optimized for the 2-methylanisole reduction by a proper choice of the amine/Rh ratio which should be high enough to stabilize very small colloidal rhodium particles and low enough to avoid deactivation. The total synthesis of (±)-heliannuol D and its epimer has been completed in 9 steps and 12% overall yield from 2-methylanisole. The thermal activation of 2-methylanisole (60°C) by the Ir (III) complex TpMe2Ir (C6H5) 2 (N2)(1; TpMe2= hydrotris (3, 5-dimethylpyrazolyl) borate) yielded a mixture of hydride complexes. The total synthesis of the phenolic sesquiterpene mutisianthol has been accomplished in 12 steps from the readily available 2-methylanisole. The catalytic system was optimized for the 2-methylanisole reduction by a proper choice of the amine/Rh ratio which should be high enough to stabilize very small colloidal rhodium particles and low enough to avoid deactivation.
DefinitionChEBI: 2-methylanisole is a monomethoxybenzene that is o-cresol in which phenolic hydroxy group has been converted to the corresponding methyl ether. A 'green' solvent (b.p. 171°C) and food flavour ingredient, it is found in mastic oils, virgin olive oils and frankincense. It has a role as a polar aprotic solvent and a flavouring agent. It is a monomethoxybenzene, a volatile organic compound and a member of toluenes. It derives from an o-cresol.
Preparation2-Methylanisole is synthesized by methylation of o-cresol using dimethylsulfate in caustic soda at 40°C.
synthesis of 2-methylanisole: Make sodium hydroxide into a 20% solution, stir and mix with o-cresol, cool to below 10°C, and slowly add dimethyl sulfate dropwise. After the addition was completed, the temperature was raised to 40 °C for 20 min, and then reacted with 100 °C for 12 h. Then the reactant was washed with water until neutral, water was removed, distilled, and the fraction at 171°C was collected to obtain the finished product of 2-methylanisole.
Aroma threshold valuesDetection: 600 ppb. Aroma characteristics at 1.0%: naphthyl, camphoreous, phenolic and woody with a salicylate nuance.
Taste threshold valuesTaste characteristics at 5.0 ppm: camphoreous, earthy, woody and alicylate with minty, spicy nuances.
General Description2-Methylanisole is found in mastic oils, virgin olive oils and frankincense. It is a monomethoxybenzene and acts as an intermediate for the preparation of compounds with methylhydroquinone core.
Flammability and ExplosibilityFlammable
2,3,5-TRIMETHYLANISOLE 2,3-DIFLUORO-4-METHYLANISOLE Tiglic aldehyde 4-(2-Bromoallyl)-2-methylanisole 2,2-Bis(4-hydroxy-3-methylphenyl)propane 2-tert-butyl-4-methylanisole 3-tert-butyl-5-methylanisole Methoxy 2-ETHYL-4-METHYLANISOLE (-)-2-[METHYLAMINO]-1-PHENYLPROPANE 2-NITRO-4-METHYLSULFONYLTOLUENE 2,5-dibromo-3-methylanisole tert-butyl-4-methylanisole Methoxymethyldiphenylamine 5-FLUORO-2-METHYLANISOLE 2-tert-butyl-5-methylanisole 4-tert-butyl-3-methylanisole 4-(Trifluoromethyl)anisole

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