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100-66-3 - Anisole, 99% - Methoxybenzene - Methyl phenyl ether - A12997 - Alfa Aesar

A12997 Anisole, 99%

CAS Number
100-66-3
Synonyms
Methoxybenzene
Methyl phenyl ether

Size Price ($) Quantity Availability
500g 36.67
2500g 118.45
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Anisole, 99%

MDL
MFCD00008354
EINECS
202-876-1

Chemical Properties

Formula
C7H8O
Formula Weight
108.14
Melting point
-37°
Boiling Point
153-154°
Flash Point
43°(109°F)
Density
0.994
Refractive Index
1.5170
Solubility
Miscible with methanol and acetone. Immiscible with water.

Applications

Anisole is widely used as a solvent for the synthesis of various organic compounds, anethole, nonylphenol isomer 4-(3',6'-dimethyl-3-heptyl)phenol, perfumes, insect pheromones and pharmaceuticals. It finds application in the preparation of inorganic complexes and materials such as tin-core/tin oxide nanoparticles.

Notes

Keep away from sources of ignition. Incompatible with strong oxidizing agents.

Literature 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).

Lee, W-S.; Kumar, A.; Wang, Z.; Bhan, A. Chemical Titration and Transient Kinetic Studies of Site Requirements in Mo2C-Catalyzed Vapor Phase Anisole Hydrodeoxygenation. ACS Cata. 2015, 5 (7), 4104-4114.

Peters, J. E.; Carpenter, J. R.; David, D. C. Anisole and Guaiacol Hydrodeoxygenation Reaction Pathways over Selected Catalysts. Energy Fuels 2015, 29 (2), 906-916.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H332-H315-H319-H335-H303

Flammable liquid and vapour. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May be harmful if swallowed.

Precautionary Statements: P210-P261-P280-P240-P303+P361+P353-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,669
Beilstein
506892
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2909.30
TSCA
Yes
RTECS
BZ8050000

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