| Identification | Back Directory | [Name]
3-BROMOBENZENE-1,2-DIOL | [CAS]
14381-51-2 | [Synonyms]
3-Bromopyrocatechol
3-Bromocatechol >
3-bromo-1,2-benzenediol
3-BROMOBENZENE-1,2-DIOL
1,2-Benzenediol, 3-bromo-
2,3-dihydroxy-broMobenzene
Phloroglucinol Impurity 30
1-Bromo-2,3-dihydroxybenzene
3-BROMOBENZENE-1,2-DIOL ISO 9001：2015 REACH | [Molecular Formula]
C6H5BrO2 | [MDL Number]
MFCD00869768 | [MOL File]
14381-51-2.mol | [Molecular Weight]
189.007 |
| Chemical Properties | Back Directory | [Melting point ]
40-41℃ | [Boiling point ]
243℃ | [density ]
1.844 | [Fp ]
101℃ | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Soluble in organic solvents. | [form ]
powder to crystal | [pka]
8.26±0.10(Predicted) | [color ]
White to Gray to Brown | [InChI]
InChI=1S/C6H5BrO2/c7-4-2-1-3-5(8)6(4)9/h1-3,8-9H | [InChIKey]
JPBDMIWPTFDFEU-UHFFFAOYSA-N | [SMILES]
C1(O)=CC=CC(Br)=C1O | [CAS DataBase Reference]
14381-51-2 |
| Hazard Information | Back Directory | [Chemical Properties]
Needle-like crystals | [Uses]
3-Bromocatechol, is used as a drug and agrochemicals intermediate, Pharmaceutical intermediate. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 69, p. 2241, 1947 DOI: 10.1021/ja01201a514 | [Synthesis]
The general procedure for the synthesis of 3-bromocatechol from 2-bromo-6-methoxyphenol was as follows: to an anhydrous dichloromethane (40 mL) solution of 2-bromo-6-methoxyphenol (8.00 g, 39.4 mmol) was slowly added boron tribromide (1 M in dichloromethane, 43.1 mmol, 43.0 mL) at -78 °C. The reaction mixture was stirred for 1 hour at room temperature, then poured into ice water and continued to stir for 30 minutes. Subsequently, extraction was performed with dichloromethane (3 x 30 mL). The organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated to give the target product 3-bromocatechol (6.90 g, 93% yield) as a brown oil. Thin layer chromatography (TLC) analysis showed an Rf value of 0.2 (unfolding agent: toluene/ethyl acetate = 9:1). The 1H NMR data of the product were as follows: δH 5.60 (1H, broad single peak, OH), 5.69 (1H, broad single peak, OH), 6.72 (1H, double peak, J=8.1 Hz), 6.87 (1H, double peak, J=1.5,8.1 Hz), 7.00 (1H, double peak, J=1.5,8.1 Hz); 13C NMR data: δC 109.5, 114.9, 121.9, 123.3, 140.3, 144.5.The 1H NMR spectra of the products were in agreement with the literature reports. | [References]
[1] Organic Letters, 2016, vol. 18, # 15, p. 3726 - 3729
[2] Tetrahedron, 2011, vol. 67, # 34, p. 6308 - 6315
[3] Tetrahedron Letters, 1995, vol. 36, # 36, p. 6413 - 6414 |
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