4-BROMOCATECHOL Chemical Properties

Melting point:

87 °C

Boiling point:

280.5±20.0 °C(Predicted)

Density 

1.844±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO

form 

Solid

pka

8.84±0.10(Predicted)

color 

Brown

Stability:

Light Sensitive

InChI

InChI=1S/C6H5BrO2/c7-4-1-2-5(8)6(9)3-4/h1-3,8-9H

InChIKey

AQVKHRQMAUJBBP-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(Br)C=C1O

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-24/25

HS Code 

29081990

4-BROMOCATECHOL Usage And Synthesis

Chemical Properties

Grey powder

Uses

A type of human dopamine sulfotransferase, belonging to the catechol family of molecules.

Definition

ChEBI: 4-Bromocatechol is a member of catechols.

Synthesis

GENERAL METHODS: Catechol (1 mmol) was dissolved in acetonitrile (5 mL) and a magnetic stirrer was added to form a magnetically stirred solution. Subsequently, OXBTEATB (0.233 g, 0.5 mmol) was added to the solution and the reaction was stirred at room temperature for the reaction time referred to in Table 1.The reaction progress was monitored by thin layer chromatography (TLC) with an eluent ratio of hexane/ethyl acetate (5:1). Upon completion of the reaction, OXBTEATB was removed by filtration, and the filtrate was transferred to a partition funnel and extracted sequentially with water (15 mL) and dichloromethane (20 mL). The organic layer was collected and dried with anhydrous Na2SO4 and subsequently concentrated in a rotary evaporator to remove solvent. The crude product was purified by silica gel column chromatography, the eluent being a solvent mixture of hexane and ethyl acetate. To regenerate the reagents, the resulting white solid was treated with liquid bromine. The structures of all products were confirmed by determination of melting points or 1H NMR spectra and comparison with data reported in the literature [29a-29e].

References

[1] Synthetic Communications, 2007, vol. 37, # 2, p. 323 - 328
[2] Organic letters, 2002, vol. 4, # 22, p. 3975 - 3978
[3] Molecules, 2014, vol. 19, # 3, p. 3401 - 3416
[4] Patent: US4791139, 1988, A
[5] Letters in Organic Chemistry, 2018, vol. 15, # 8, p. 682 - 687

4-BROMOCATECHOL(17345-77-6)Related Product Information

• 4-Bromo-1,2-benzenediamine
• 4-bromo-1,2-diethoxybenzene
• 4-Bromo-1-(methoxymethoxy)-2-(trifluoromethoxy)benzene
• 4-Bromo-1,2-bis(1-methylethoxy)benzene
• 2-BROMO-4,5-DIMETHOXYCINNAMIC ACID
• TETRABROMOCATECHOL
• 1-Bromo-3,4,5-trimethoxybenzene
• 2-BROMO-4,5-METHYLENEDIOXYCINNAMIC ACID
• 2-Bromo-4,5-dimethoxyphenylacetonitrile
• DL-6'-BROMOLAUDANOSIN
• 4,5-DIBROMOVERATROLE
• 6-Bromoveratraldehyde
• 5-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE
• 2-BROMO-4,5-DIMETHOXYPHENYLACETIC ACID
• 6-BROMO-1,4-BENZODIOXANE
• 3-BROMOBENZENE-1,2-DIOL
• 4,5-Dibromo-1,2-benzenediol
• 2-BROMO-1,3,2-BENZODIOXABOROLE