Anisole

• Catalog No.: A12997
• CAS Number: 100-66-3
• M. F.: C7H8O
• M. W.: 108.13782
• Purity: 99%

SYNONYMS

• Title: 苯甲醚
• IUPAC name: anisole
• IUPAC Traditional name: anisole
• Synonyms: Methyl phenyl ether; Methoxybenzene

DATABASE IDS

• Beilstein Number: 506892
• CAS Number: 100-66-3
• MDL Number: MFCD00008354
• Merck Index: 14669
• EC Number: 202-876-1

PROPERTIES

• Purity: 99%
• Boiling Point: 153-154°C
• Density: 0.994
• Flash Point: 43°C(109°F)
• Melting Point: -37°C
• Refractive Index: 1.5170
• GHS Hazard statements: H226-H332-H315-H319-H335-H303
• European Hazard Symbols: X
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 10-20-36/37/38
• RTECS: BZ8050000
• Safety Statements: 9-23-26-36/37-60
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2222
• Packing Group: III

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).