| Identification | More | [Name]
5-Bromo-2-hydroxybenzyl alcohol | [CAS]
2316-64-5 | [Synonyms]
2-HYDROXYMETHYL-4-BROMOPHENOL
4-BROMO-2-HYDROXYMETHYLPHENOL
5-BROMO-2-HYDROXYBENZYL ALCOHOL
5-BROMOSALICYL ALCOHOL
5-BROMOSALIGENIN
BROMOSALIGENIN
RARECHEM AL BD 0040
5-BROMO-2-HYDROXYBENZYL ALCOHOL, 98+%
5-BROMO-2-HYDROXYBENZYL ALCOHOL 98%
5-Bromosalicyl alcohol, Bromosaligenin | [EINECS(EC#)]
219-026-0 | [Molecular Formula]
C7H7BrO2 | [MDL Number]
MFCD00004618 | [Molecular Weight]
203.03 | [MOL File]
2316-64-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light brown crystalline powder or flakes | [Melting point ]
110-112 °C (lit.) | [Boiling point ]
281.8±10.0 °C(Predicted) | [density ]
1.5178 (rough estimate) | [refractive index ]
1.4620 (estimate) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
water: soluble0.7% at 25°C(lit.) | [form ]
Crystalline Powder or Flakes | [pka]
9.36±0.18(Predicted) | [color ]
White to light brown | [Water Solubility ]
water: soluble 0.7% at25°C(lit.)
olive oil: soluble 4.8%(lit.)
alcohol: freely soluble(lit.)
benzene: moderately soluble(lit.)
chloroform: moderately soluble(lit.)
diethyl ether: freely soluble(lit.)
ethyl acetate: freely soluble(lit.)
hot water: soluble(lit.) | [BRN ]
509726 | [InChIKey]
KNKRHSVKIORZQB-UHFFFAOYSA-N | [CAS DataBase Reference]
2316-64-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29081990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light brown crystalline powder or flakes | [Uses]
5-Bromo-2-hydroxybenzyl alcohol was used in the synthesis of:
- 7-bromo-2,3-diphenyl-5H-imidazo[2,1-b][1,3]benzoxazine
- 6-bromo-2-octyl-4H-1,3,2-benzodioxaphosphorin 2-oxide
- 4-bromo-2-(5-iodo-1H-indol-3-ylmethyl)- phenol
| [Synthesis]
The general procedure for the synthesis of 5-bromo-2-hydroxybenzenemethanol from 5-bromosalicylaldehyde was as follows: according to the improved synthetic method reported in the literature, 5-bromo-2-hydroxybenzenecarboxaldehyde (10.1 g, 50 mmol) was first dissolved in 250 mL of ethanol at 0 °C. Subsequently, NaBH4 (1.88 g, 50 mmol) was added to the stirring solution in batches (0.3 g each). The reaction mixture was stirred continuously for 18 hours at room temperature. Upon completion of the reaction, ethanol was evaporated under reduced pressure conditions (102 mbar) and the light yellow solid obtained was dissolved in 200 mL of saturated aqueous NH4Cl solution. The crude product was extracted by ether (three times, 80 mL each). The combined organic phases were washed with brine (three times, 20 mL each) and dried with MgSO4 for 2 hours. After drying, the MgSO4 was removed by filtration and the excess solvent was evaporated under reduced pressure (102 mbar). The product was purified by fast chromatography on a silica gel column with hexane/ethyl acetate (8:2, v/v) as eluent. Eventually, evaporation of the solvent gave a colorless solid product (8.52 g, 84% yield). | [References]
[1] Tetrahedron Asymmetry, 2011, vol. 22, # 13, p. 1395 - 1399
[2] Journal of Chemical Research - Part S, 2003, # 6, p. 335 - 339
[3] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2003, vol. 58, # 12, p. 1220 - 1226
[4] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 2, p. 307 - 315
[5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2005, vol. 60, # 4, p. 453 - 457 |
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