5-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE
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5-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE
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CAS No:
5034-74-2
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Formula:
C8H7BrO3
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Chemical Name:
5-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE
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Synonyms:
5-BROMO-2-VANILLIN;5-BROMO-O-VANILLIN;BUTTPARK15333-74;OTAVA-BBBB7018802005;5-BROMO-3-METHOXYSALICYLALDEHYDE;3-Methoxy-5-bromosalicylaldehyde;5-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE;Benzaldehyde,5-bromo-2-hydroxy-3-methoxy-;5-Bromo-2-hydroxy-3-methoxybenzaldehyde,98%;5-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE98%
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CAS No:
5-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE Basic Attributes
231.045
229.957855
95683
DTXSID10294271
2913000090
Characteristics
46.5
2.1
brown powder
1.7±0.1 g/cm3
125-127 °C(lit.)
277.2°C at 760 mmHg
121.4±25.9 °C
1.623
Safety Information
NONH for all modes of transport
3
R36/37/38
S26-S37/39
Xi
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 43 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE Use and Manufacturing
To a solution of o-vanillin (11; 4.0 g, 0.026 mol) in AcOH (80 mL) at 0°C was added NaOAc (2.37 g, 0.029 mol), followed by the dropwise additionof Br2 (1.49 mL, 0.029 mol). The solution was stirred at r.t. for30 min. H2O (100 mL) was added and the aqueous mixture extractedwith CH2Cl2 (3 × 80 mL). The combined organic extracts were washedwith H2O (100 mL) and brine (50 mL), dried (MgSO4) and the solventwas removed in vacuo. The crude product was purified by flash chromatography(19:1 hexanes–EtOAc) to yield the title compound 26(6.0 g, 98percent) as a yellow solid; mp 119–123 °C (Lit.19 mp 122–124 °C).1H NMR (400 MHz, CDCl3/TMS): δ = 3.92 (3 H, s, OCH3), 7.18 (1 H, d, J = 2.4 Hz, 4-H), 7.31 (1 H, d, J = 2.4 Hz, 6-H), 9.86 (1 H, s, CHO), 11.00(1 H, s, OH).13C NMR (100 MHz, CDCl3): δ = 56.3 (OCH3), 111.1 (C-5), 120.8 (C-6), 121.3 (C-1), 126.1 (C-4), 149.3 (C-2), 150.9 (C-3), 195.4 (CHO).The 1H NMR and 13C NMR data were in agreement with literature values.19To a well stirred mixture of o-vanillin (20 g, 130 mmol) in dichloroethane (75 mL), liquid bromine (23.2 g, 140 mmol) was added over a period of 0.5 h, at room temperature. The reaction was completed in 1 h (monitored by TLC). Ice cold water (50 mL) was added to the reaction mixture. The organic layer was separated and washed with water. It was dried over anhydrous NaTo a suspension of o-vanillin 21 (1.0 g, 6.6 mmol) and silica (1.0 g) in wet CCl[0928] The solution of 2-hydroxy-3-methoxybenzaldeliyde (10.0 g, 65.79 mmole) in acetic acid (50 mL) was cooled to 0 °C (ice bath). Bromine (12.55 g, 78.95 mmole) was added dropwise to above solution, which was allowed to stir for 2 hours. The reaction was warmed to room temperature and diluted with water (100 mL). A light brown precipitate was formed. The solid was filtered and washed with water (50 mL). The filtrate was dried on high vacuum to give a light brown solid (12.2 g, 80.0percent) : GCMS M/Z 231. 0 (M+). HNMR (CDC13/400 MHz) 10.97 (s, 1H), 9.82 (s, 1H), 7.29 (s, 1H), 7.15 (s, 1H), 3.89 (m, 3H).
Computed Properties
Molecular Weight:231.04
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:229.95786
Monoisotopic Mass:229.95786
Topological Polar Surface Area:46.5
Heavy Atom Count:12
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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