ChemicalBook Product Catalog Organic Chemistry Alcohols,Phenols,Phenol alcohols Phenol derivatives 4-Bromo-2-methoxyphenol

4-Bromo-2-methoxyphenol

Product Name4-Bromo-2-methoxyphenol
CAS7368-78-7
MFC7H7BrO2
MW203.03
EINECS
MOL File7368-78-7.mol

Chemical Properties

Melting point	34-37 °C (lit.)
Boiling point	129-132°C 12mm
Density	1.585±0.06 g/cm3(Predicted)
Flash point	>230 °F
storage temp.	Inert atmosphere,Room Temperature
solubility	Chloroform, Methanol
form	Low Melting Solid or Crystalline Solid
pka	9.40±0.18(Predicted)
color	Colorless to white to pale brown
Water Solubility	Slightly soluble in water.
BRN	2045286
InChI	InChI=1S/C7H7BrO2/c1-10-7-4-5(8)2-3-6(7)9/h2-4,9H,1H3
InChIKey	WHSIIJQOEGXWSN-UHFFFAOYSA-N
SMILES	C1(O)=CC=C(Br)C=C1OC
CAS DataBase Reference	7368-78-7(CAS DataBase Reference)
NIST Chemistry Reference	4-Bromoguaiacol(7368-78-7)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
Hazard Note	Irritant
HS Code	29095000
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Uses

4-bromo-2-methoxyphenol is an important organic intermediate (building block) to synthetize substituted phenzyl products, and it can also be used for the synthesis of polyfunctionalized bicyclic systems.

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Uses

4-Bromo-2-methoxyphenol is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.A. Schoenberg; R. F. Heck. Palladium-catalyzed formylation of aryl, heterocyclic, and vinylic halides. J. Am. Chem. Soc. 1974, 96 (25), 7761-7764.Joel S. Freundlich; Howard E. Landis. An expeditious aqueous Suzuki-Miyaura method for the arylation of bromophenols. Tetrahedron Letters. 2006, 47(25), 4275-4279.

Synthesis

90-05-1

7368-78-7

General procedure for the synthesis of 4-bromo-2-methoxyphenol from guaiacol: NBu4Br3 (1.0 eq.) was dissolved in CH2Cl2 (ca. 5 mL/mmol NBu4Br3), which was immediately added to a CH2Cl2 solution (ca. 5 mL/mmol guaiacol) of guaiacol (1.0 eq.). The reaction mixture was stirred at 23 °C for 2 hours. Subsequently, the solvent was removed under reduced pressure (12 mbar, 40 °C). Water (5.0 mL) was added to the residue and the aqueous layer was extracted with Et2O (3 x 10 mL). The organic layer was separated and dried with MgSO4. The organic solvent was removed under reduced pressure (14 mbar, 40 °C) to give an oily residue, which was finally purified by silica gel column chromatography (SiO2, CH2Cl2).

References

[1] Synthetic Communications, 2007, vol. 37, # 2, p. 323 - 328
[2] Tetrahedron, 2014, vol. 71, # 1, p. 91 - 101
[3] Tetrahedron Letters, 1995, vol. 36, # 10, p. 1705 - 1708
[4] Synlett, 2012, vol. 23, # 7, p. 1082 - 1084
[5] Journal of the Serbian Chemical Society, 2011, vol. 76, # 5, p. 685 - 692

4-Bromo-2-methoxyphenol

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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