2-bromohydroquinone

2-bromohydroquinone Structure
2-bromohydroquinone structure
Common Name 2-bromohydroquinone
CAS Number 583-69-7 Molecular Weight 189.007
Density 1.8±0.1 g/cm3 Boiling Point 278.3±20.0 °C at 760 mmHg
Molecular Formula C6H5BrO2 Melting Point 112-116 °C(lit.)
MSDS Chinese USA Flash Point 122.1±21.8 °C
Symbol GHS07
GHS07
Signal Word Warning

Dihydroxylated mercapturic acid metabolites of bromobenzene.

Chem. Res. Toxicol. 5(4) , 561-7, (1992)

Bromobenzene is metabolized to electrophilic epoxides and quinones which covalently bind to protein sulfur nucleophiles, yet no quinone-derived mercapturic acid metabolites of bromobenzene have been reported. To search for them, phenobarbital-induced Sprague-...

Inhibition of respiration in rabbit proximal tubules by bromophenols and 2-bromohydroquinone.

Adv. Exp. Med. Biol. 197 , 911-7, (1986)

Cellular toxicity of bromobenzene and bromobenzene metabolites to rabbit proximal tubules: the role and mechanism of 2-bromohydroquinone.

J. Pharmacol. Exp. Ther. 237(2) , 456-61, (1986)

An in vitro model using a suspension of rabbit renal proximal tubules was developed to investigate the mechanism of nephrotoxicity of bromobenzene. Using oxygen consumption, glutathione concentrations and retention of lactate dehydrogenase activity as markers...

Synthesis and nephrotoxicity of 6-bromo-2,5-dihydroxy-thiophenol.

Mol. Pharmacol. 34(1) , 15-22, (1988)

The formation of potentially reactive thiols has been postulated to play a role in the nephrotoxicity caused by a number of glutathione and/or cysteine conjugates. However, the inherent reactivity of such compounds has precluded both their identification in b...

2-Bromohydroquinone-induced toxicity to rabbit renal proximal tubules: evidence against oxidative stress.

Toxicol. Appl. Pharmacol. 99(1) , 11-8, (1989)

2-Bromohydroquinone (BHQ) plays an important role in bromobenzene-induced nephrotoxicity and is a model toxic hydroquinone. Since BHQ has a quinone nucleus and various quinones have been shown to produce cytotoxicity via oxidative stress, the goal of this stu...

Co-oxidation of 2-bromohydroquinone by renal prostaglandin synthase. Modulation of prostaglandin synthesis by 2-bromohydroquinone and glutathione.

Drug Metab. Dispos. 15(6) , 801-7, (1987)

Homogenates from rat renal papillae, a rich source of the prostaglandin (PG) H synthase system (PHS), metabolized [14C]2-bromohydroquinone, in the presence of arachidonic acid, to products which are covalently bound to protein. The co-oxidation of 2-bromohydr...

Developmental toxicity of bromohydroquinone (BHQ) and BHQ-glutathione conjugates in vivo and in whole embryo culture.

Toxicol. Appl. Pharmacol. 120(1) , 1-7, (1993)

Glutathione conjugates of 2-bromohydroquinone (GSyl-BHQ) cause renal proximal tubular necrosis that is dependent upon the activity of gamma-glutamyl transferase (GGT). GGT is present in embryonic yolk sac and its activity increases with gestational age, sugge...

Mechanism of pH amelioration of 2-bromohydroquinone-induced toxicity to rabbit renal proximal tubules.

J. Pharmacol. Exp. Ther. 256(3) , 917-21, (1991)

The basis of extracellular acidosis amelioration of 2-bromohydroquinone (BHQ)-induced renal proximal tubular cell death was determined by comparing the metabolism, uptake and mitochondrial effects of BHQ (0.2 mM) and bromoquinone (BQ) (0.05 mM) on isolated ra...

Differential uptake of isomeric 2-bromohydroquinone-glutathione conjugates into kidney slices.

Biochem. Biophys. Res. Commun. 152(1) , 223-30, (1988)

2-Bromo-(diglutathion-Syl)hydroquinone (2-Br-[diGSyl]HQ) is a more potent nephrotoxicant than any of three mono-substituted isomers. The reason for this differential toxicity is unknown. We now report that the rate of uptake of 2-Br-(diGSyl)HQ, 2-Br-3-(GSyl)H...

2-Bromohydroquinone: structures, vibrational assignments and RHF, B- and B3-based density functional calculations.

Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 69(3) , 926-32, (2008)

Vibrational spectral measurements, namely, infrared (4000-400 cm(-1)) and Raman (3500-50 cm(-1)) spectra have been made for 2-Bromohydroquinone. Optimized geometrical structures, harmonic vibrational frequencies and intensities have been computed by the ab in...