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Thermo Scientific™
4-Bromoveratrole, 97%
CAS: 2859-78-1 | C8H9BrO2 | 217.062 g/mol
化学物質識別子
CAS2859-78-1
IUPAC Name4-bromo-1,2-dimethoxybenzene
Molecular FormulaC8H9BrO2
InChI KeyKBTMGSMZIKLAHN-UHFFFAOYSA-N
SMILESCOC1=CC=C(Br)C=C1OC
さらに表示
仕様
スペックシート
スペックシートAssay (GC)≥96.0%
Refractive Index1.5705-1.5755 @ 20?C
Appearance (Color)Clear colorless to yellow
FormLiquid
Identification (FTIR)Conforms
4-Bromo-1,2-dimethoxybenzene is a metabolite of bromobenzene, with a catechol moiety in the substructure. It also has use as a redox shuttle additive, essentially a component in lithium batteries that consumes excess current during overcharge. And also used in the synthesis of the isoquinoline alkaloid (-)-mesembrine.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
4-Bromo-1,2-dimethoxybenzene is a metabolite of bromobenzene, with a catechol moiety in the substructure. It also has use as a redox shuttle additive, essentially a component in lithium batteries that consumes excess current during overcharge. And also used in the synthesis of the isoquinoline alkaloid (-)-mesembrine.
Solubility
Soluble in benzene, ether, toluene.
Notes
Store away from strong oxidizing agents. Keep container tightly closed. Store in cool, dry conditions in well sealed containers.
4-Bromo-1,2-dimethoxybenzene is a metabolite of bromobenzene, with a catechol moiety in the substructure. It also has use as a redox shuttle additive, essentially a component in lithium batteries that consumes excess current during overcharge. And also used in the synthesis of the isoquinoline alkaloid (-)-mesembrine.
Solubility
Soluble in benzene, ether, toluene.
Notes
Store away from strong oxidizing agents. Keep container tightly closed. Store in cool, dry conditions in well sealed containers.
RUO – Research Use Only
General References:
- Han Yu Xin.; Edward R. Biehl. Reaction of various nucleophiles with 2-bromo-p-xylene and 4-bromoveratrole via aryne reaction. J. Org. Chem. 1983, 48, (23), 4397-4399.
- Timothy K. Beng.; Robert E. Gawley. Application of Catalytic Dynamic Resolution of N-Boc-2-lithiopiperidine to the Asymmetric Synthesis of 2-Aryl and 2-Vinyl Piperidines. Org. Lett. 1983, 13, (3), 394-397.
- 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).