anisole

• ChemBase ID: 125871
• Molecular Formular: C7H8O
• Molecular Mass: 108.13782
• Monoisotopic Mass: 108.05751488
• SMILES: COc1ccccc1
• Canonical SMILES: COc1ccccc1
• InChI: InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
• InChIKey: RDOXTESZEPMUJZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: anisole
• IUPAC Traditional name: anisole
• Synonyms: Anisole; anisole; phenoxymethane; phenyl methyl ether; Anisole; Methoxybenzene; Methyl phenyl ether; 甲基苯基醚; 甲氧基苯; 苯甲醚

Database IDs

• CAS Number: 100-66-3
• EC Number: 202-876-1
• MDL Number: MFCD00008354
• Beilstein Number: 506892
• Merck Index: 14669
• PubChem SID: 24857849; 24847529; 24900857; 162220216; 24890264; 24846694
• PubChem CID: 7519
• CHEBI ID: 16579
• CHEMBL: 278024
• Chemspider ID: 7238
• FEMA ID: 2097
• KEGG ID: C01403
• Unique Ingredient Identifier: B3W693GAZH
• Wikipedia Title: Anisole
• Council of Europe Number: 2056
• Flavis Number: 4.032

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.8155745
• LogD (pH = 7.4): 1.8155745
• Log P: 1.8155745
• Molar Refractivity: 32.5212 cm^3
• Polarizability: 12.858547 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: colorless liquid
• Melting Point: -37 °C(lit.); -37°C; -37°C
• Boiling Point: 153-154°C; 154 °C(lit.); 154°C
• Flash Point: 109 °F; 109.4 °F; 123.8 °F; 43 °C; 43°C(109°F); 51 °C
• Auto Ignition Point: 887 °F
• Density: 0.994; 0.995 g cm^-3; 0.995 g/mL at 25 °C(lit.)
• Refractive Index: 1.5170; n20/D 1.516(lit.); n20/D 1.517; n20/D 1.518
• Vapor Pressure: 10 mmHg ( 42.2 °C)
• Vapor Density: 3.7 (vs air)
• Organoleptic: alcohol; butter; cheese; ethereal

Safety Information

• RTECS: BZ8050000
• European Hazard Symbols: X
• UN Number: 2222; UN2222
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10; 10-20-36/37/38
• Safety Statements: 9-23-26-36/37-60
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319; H226-H332-H315-H319-H335-H303
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2222 3/PG 3
• Regulation Compliance: FCC

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥99%; ≥99.0% (GC); ≥99.9% (GC); 99%; 99.7%
• Grade: analytical standard; anhydrous; Kosher; NI; purum; ReagentPlus®
• Evaporation Residue: <0.0003%
• Impurities: <0.002% water; <0.005% water(100 mL pkg)
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: CH3OC6H5

DETAILS

Sigma Aldrich - 296295

Packaging
1, 2 L in Sure/Seal™
100 mL in Sure/Seal™

Sigma Aldrich - 123226

Packaging
1, 4 L in glass bottle
100 mL in glass bottle
20 L in steel drum
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• The rate of ortho-lithiation of anisole is accelerated dramatically in the presence of TMEDA, effective also in sub-stoichiometric amounts: Tetrahedron Lett., 35, 385 (1994). For discussion of the mechanism of ortho-lithiation, see: J. Org. Chem., 62, 3024 (1997). Although direct dilithiation with n-BuLi/TMEDA was unsuccessful, a sequence involving monolithiation, silylation and further lithiation at the 6-position gave the 2,6-disilyl derivative in 72% yield: J. Org. Chem., 49, 4657 (1984).
• Widely used as a carbocation scavenger in the deblocking of, e.g. N-Boc or N-Cbz (Z) peptides with acidic reagents. Addition of anisole removes t-butyl or benzyl cations from the reaction mixture; see, e.g.: J. Chem. Soc., Chem. Commun., 922 (1976); Chem. Pharm. Bull., 25, 2929 (1977); Chem. Ber., 101, 3649 (1968).