4-Bromo-2-methoxyphenol

4-Bromo-2-methoxyphenol Property

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

pka

9.40±0.18(Predicted)

form 

Low Melting Solid or Crystalline Solid

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29095000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-Bromo-2-methoxyphenol Chemical Properties,Usage,Production

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

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