2-(bromomethyl)naphthalene

• ChemBase ID: 88856
• Molecular Formular: C11H9Br
• Molecular Mass: 221.09316
• Monoisotopic Mass: 219.98876229
• SMILES: BrCc1cc2c(cc1)cccc2
• Canonical SMILES: BrCc1ccc2c(c1)cccc2
• InChI: InChI=1S/C11H9Br/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-7H,8H2
• InChIKey: RUHJZSZTSCSTCC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(bromomethyl)naphthalene
• IUPAC Traditional name: (2-naphthyl)bromomethane
• Synonyms: 2-(Bromomethyl)naphthalene 96%; 2-(Bromomethyl)naphthalene; 2-Naphthylmethyl bromide; 2-(bromomethyl)naphthalene; 2-(溴甲基)萘

Database IDs

• CAS Number: 939-26-4
• EC Number: 213-359-5
• MDL Number: MFCD00004123
• Beilstein Number: 636546
• PubChem SID: 162075754; 24850556; 24848601
• PubChem CID: 70320

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.73546
• LogD (pH = 7.4): 3.73546
• Log P: 3.73546
• Molar Refractivity: 55.3586 cm^3
• Polarizability: 22.21318 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 51-54 °C(lit.); 51-55°C; 52-54°C; 52-55 °C; 53 - 54°C
• Boiling Point: 213 °C/100 mmHg(lit.); 213°C/100mm; 213°C/100mm
• Flash Point: >110°C; >110°C(230°F); 110 °C; 230 °F
• Hydrophobicity(logP): 4.098

Safety Information

• Storage Warning: Corrosive/Lachrymatory/Keep Cold/Moisture Sensitive/Store under Argon
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34; 34-43
• Safety Statements: 20-26-36/37/39-45; 26-28-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H317; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC); 95%; 96%; 98%
• Grade: technical
• Linear Formula: C10H7CH2Br

DETAILS

Sigma Aldrich - 143677

Packaging
5, 25, 100 g in glass bottle

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).