2-(Bromomethyl)naphthalene

• Catalog No.: B24568
• CAS Number: 939-26-4
• M. F.: C11H9Br
• M. W.: 221.09316
• Purity: 96%

SYNONYMS

• Title: 2-(溴甲基)萘
• IUPAC name: 2-(bromomethyl)naphthalene
• IUPAC Traditional name: (2-naphthyl)bromomethane
• Synonyms: 2-Naphthylmethyl bromide

DATABASE IDS

• Beilstein Number: 636546
• CAS Number: 939-26-4
• EC Number: 213-359-5
• MDL Number: MFCD00004123

PROPERTIES

• Purity: 96%
• Boiling Point: 213°C/100mm
• Flash Point: >110°C(230°F)
• Melting Point: 51-55°C
• GHS Hazard statements: H314-H318
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Risk Statements: 34
• Safety Statements: 20-26-36/37/39-45
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: II

REFERENCES

• Primary or secondary OH groups can be protected as 2-naphthylmethyl (NAP) ethers, e.g. with NaH in DMF. The NAP ether is stable to dilute aqueous HCl or NaOH, but is cleanly hydrogenolyzed with Pd/C; preferential cleavage in the presence of a benzyl ether can be achieved in high yield: J. Org. Chem., 63, 4172 (1998). NAP protection has been utilized in carbohydrate synthesis where stability to 4% TFA in CHCl₃, hot 80% AcOH, SnCl₂/AgOTf, or HCl/EtOH were demonstrated, conditions under which the 4-methoxybenzyl (PMB) group is cleaved; both NAP and PMB groups are efficiently cleaved with DDQ: Tetrahedron Lett., 41, 169 (2000).
• NAP protection of amino groups and other N functions has also been reported. Cleavage was effected under mild condtions with DDQ: Synlett, 2065 (2003).