| Identification | Back Directory | [Name]
2-Bromo-7-hydroxynaphthalene | [CAS]
116230-30-9 | [Synonyms]
7-Bromo-2-naphthol
BroMonaphthalen-2-ol
7-Bromo-2-naphthol 99%
7-BROMONAPHTHALEN-2-OL
7-Bromo-2-Naphthalenol
7-Bromo-2-naphthol >
2-Naphthalenol,7-broMo-
7-Bromonaphthalene-2-ol
7-Bromo-2-naphthol, >=98%
2-Bromo-7-hydroxynaphthaL
2-Bromo-7-hydroxyphthalene
2-Bomo-7-Hydroxynaphthalene
2-BROMO-7-HYDROXYNAPHTHALENE
2-hydroxy-7-BROMONAPHTHALENE
2-Bromo-7-hydroxynaphthalene FP160407
2-Bromo-7-hydroxynaphthalene ISO 9001：2015 REACH | [EINECS(EC#)]
628-835-1 | [Molecular Formula]
C10H7BrO | [MDL Number]
MFCD00277644 | [MOL File]
116230-30-9.mol | [Molecular Weight]
223.07 |
| Chemical Properties | Back Directory | [Melting point ]
133-138 °C | [Boiling point ]
353.8±15.0 °C(Predicted) | [density ]
1.614±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
powder to crystal | [pka]
9.17±0.40(Predicted) | [color ]
White to Light yellow | [InChI]
InChI=1S/C10H7BrO/c11-9-3-1-7-2-4-10(12)6-8(7)5-9/h1-6,12H | [InChIKey]
VWSBGGRCEQOTNU-UHFFFAOYSA-N | [SMILES]
C1=C2C(C=CC(Br)=C2)=CC=C1O | [CAS DataBase Reference]
116230-30-9 |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Synthesis]
The general procedure for the synthesis of 7-bromo-2-naphthol from 2,7-dihydroxynaphthalene was as follows:
1. Preparation of 2-bromo-7-methoxynaphthalene: Triphenylphosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were added to a 1 L flask under nitrogen protection and the mixture was cooled to 10 °C. Bromine (17.6 mL, 0.342 mol) was added slowly and dropwise over 10 min. After removing the cooling bath, 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added and rinsed with 350 mL of acetonitrile. The resulting yellow-brown mixture was heated to reflux for 3 hours. Subsequently, the acetonitrile was removed by distillation under reduced pressure, taking about 2 hours to give an off-white solid.
2. Preparation of 7-bromo-2-naphthol: The above solid was heated to 280°C within 30 minutes to form a black liquid. The liquid was continued to be heated to 310°C within 20 minutes and maintained at this temperature for 15 minutes until gas release ceased. After the black mixture was cooled to room temperature, 34.5 g of the intermediate title compound was obtained by chromatographic separation as an off-white solid with HPLC purity of 87% (43% yield). | [References]
[1] Journal of the American Chemical Society, 2008, vol. 130, # 13, p. 4541 - 4552
[2] Dyes and Pigments, 2014, vol. 107, p. 174 - 181
[3] Patent: WO2015/121785, 2015, A1. Location in patent: Page/Page column 32; 33
[4] Helvetica Chimica Acta, 1999, vol. 82, # 7, p. 981 - 1004
[5] Chemical Communications, 2012, vol. 48, # 5, p. 750 - 752 |
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