2-Methylanisole

HCID 33637
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
578-58-5
Standard SMILES
COc1ccccc1C
InChIKey
DTFKRVXLBCAIOZ-UHFFFAOYSA-N
Molecular formula
C8H10O
Average molar mass
122.16 g/mol
Monoisotopic mass
122.07316494

Names & identifiers

Preferred name
2-Methylanisole
IUPAC
1-methoxy-2-methylbenzene
English name
2-Methylanisole
Molecular formula
C8H10O
Molecular weight
122.16

Names & synonyms

2-Methylanisole1-Methoxy-2-methylbenzene578-58-5o-Methylanisole2-Methoxytolueneo-Methoxytolueneo-Cresol methyl etherBENZENE, 1-METHOXY-2-METHYL-o-Cresyl methyl etherMethyl o-tolyl etherAnisole, o-methyl-2-Methylmethoxybenzene
Show more names
FEMA 26802-Methylanisolo-Methylanisol
Methyl o-cresyl etherFEMA No. 268009G73SL17KNSC-6253DTXSID9060368CHEBI:141702RefChem:88252DTXCID3042261

Database identifiers

CAS
578-58-5
PubChem CID
33637
DTXSID
DTXSID9060368
ChEBI
CHEBI:141702
UNII
09G73SL17K
EC Number
209-426-3
Nikkaji
J7.427F

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
9.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
9

Experimental & physicochemical properties

LogP2.74
Density0.983-0.986 (15.5 °C)
Solubility · 2 items

Insoluble in water, soluble in oils

soluble (in ethanol)

Boiling Point · 2 items

170.00 to 172.00 °C. @ 760.00 mm Hg

172 °C

Melting Point-34.1 °C
Vapor Pressure1.5 [mmHg]

Physicochemical properties

Melting point
-34.1 °C · -34.1°C
Boiling point
170 · 170-172 °C (lit.)
Density
0.985 g/mL · 0.985 g/mL at 25 °C (lit.)
vapor pressure
2 hPa · 2hPa at 25℃
FLAVIS Number
4.014 · 04.014 | 1-Methoxy-2-methylbenzene
refractive index
20 · n20/D 1.516(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 0.8% (11 of 1453) of reports.

Warning

H226 (10.7%): Flammable liquid and vapor [Warning Flammable liquids]；H302 (88.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P317, P303+P361+P353, P330, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1453 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 11 of 1453 reports by companies.；There are 4 notifications provided by 1442 of 1453 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 4 items

Chemical: Benzene, 1-methoxy-2-methyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Cease Manufacture Update: 25-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20341

Benzene, 1-methoxy-2-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummarySafe when used as a flavoring agent in food; [JECFA] May cause irritation; [Alfa Aesar MSDS] See Anisole.
Peroxide Forming Chemical · 4 items

o-Methyl anisole

D*: Other compounds that may form peroxides

No amount of peroxides were found in new commerically available containers

Removal of Peroxides from Ethers with Cerous Hydroxide

Hazard Classes and CategoriesFlam. Liq. 3 (10.7%)；Acute Tox. 4 (88.6%)

Toxicology

Adverse EffectsNeurotoxin - Acute solvent syndrome

Regulatory information

Regulatory Information · 4 items

Chemical: Benzene, 1-methoxy-2-methyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Cease Manufacture Update: 25-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20341

Benzene, 1-methoxy-2-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
ridadr
UN 1993 3/PG 3
hs_code
29093090
risk_code
10

Chemistry & industry

Pharmacology

Cellular LocationsMembrane

Uses & manufacturing

UsesUsed as flavoring agent or adjuvant; [FDA]
Use Classification · 5 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing InformationBenzene, 1-methoxy-2-methyl-: ACTIVE
Applications · 3 items

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.

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.

Preparation methods · 1 item

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.

Upstream & downstream products

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
Additional notes · 1 item

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.

Related reactions

47 records
New reaction record

Compound notes

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