4-bromo-1,2-dimethoxybenzene

• ChemBase ID: 6551
• Molecular Formular: C8H9BrO2
• Molecular Mass: 217.05986
• Monoisotopic Mass: 215.97859153
• SMILES: c1(ccc(cc1OC)Br)OC
• Canonical SMILES: COc1cc(Br)ccc1OC
• InChI: InChI=1S/C8H9BrO2/c1-10-7-4-3-6(9)5-8(7)11-2/h3-5H,1-2H3
• InChIKey: KBTMGSMZIKLAHN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-bromo-1,2-dimethoxybenzene
• IUPAC Traditional name: 4-bromo-1,2-dimethoxybenzene
• Synonyms: 3,4-Dimethoxybromobenzene; 4-BROMOVERATROLE; 4-Bromo-1,2-dimethoxybenzene; 4-Bromoveratrole; 1-Bromo-3,4-dimethoxybenzene; 1-Bromo-3,4-dimethoxybenzene; 4-Bromoveratrole; 4-Bromo-1,2-dimethoxybenzene; 4-溴藜芦醚; 4-溴-1,2-二甲氧基苯; 4-溴黎芦醚

Database IDs

• CAS Number: 2859-78-1
• EC Number: 220-677-8
• MDL Number: MFCD00008381
• Beilstein Number: 2046884
• PubChem SID: 160969858; 24891940
• PubChem CID: 76114

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.426656
• LogD (pH = 7.4): 2.426656
• Log P: 2.426656
• Molar Refractivity: 46.6072 cm^3
• Polarizability: 18.215975 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 124-126°C/9mm; 255-256 °C(lit.); 255-256°C
• Flash Point: 109 °C; 109°C(228°F); 228.2 °F
• Density: 1.509 g/mL at 25 °C(lit.); 1.510; 1.702
• Refractive Index: 1.5730; n20/D 1.573; n20/D 1.573(lit.)
• Hydrophobicity(logP): 2.734

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: true; 是
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: ≥95.0% (GC); 95%; 97%; 98%
• Grade: purum
• Linear Formula: BrC6H3-1,2-(OCH3)2

DETAILS

MP Biomedicals - 05208775

MP Biomedicals Rare Chemical collection

Sigma Aldrich - B83355

Packaging
25, 100 g in glass bottle

REFERENCES

• In the presence of sodamide, displacement by nucleophiles, e.g. anions of secondary amines or nitriles, occurs by an ortho-metallation-benzyne mechanism. The incoming nucleophile adds regioselectively such that the resulting anion is ortho-stabilized by methoxyl: J. Org. Chem., 48, 4397 (1983):
  
• The derived Grignard reagent has been used in the synthesis of the isoquinoline alkaloid (-)-mesembrine: J. Org. Chem., 60, 6785 (1995).