6-BROMO-2,3-DIFLUOROBENZALDEHYDE
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6-BROMO-2,3-DIFLUOROBENZALDEHYDE
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CAS No:
360576-04-1
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Formula:
C7H3BrF2O
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Chemical Name:
6-BROMO-2,3-DIFLUOROBENZALDEHYDE
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Synonyms:
6-BROMO-2,3-DIFLUOROBENZALDEHYDE;Benzaldehyde, 6-broMo-2,3-difluoro-
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CAS No:
Safety Information
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|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 6 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
6-BROMO-2,3-DIFLUOROBENZALDEHYDE Use and Manufacturing
Dissolve aryl bromide (1.0 [EQ)] in dry THF (0.2 M) and cool the reaction to-78 °C under nitrogen. Add LDA (2.0 M in THF, 1.1 eq. ) dropwise over 15 minutes. Stir for 20 minutes after addition complete. Add DMF (1.2 eq. ) and stir [AT-78 °C] for 15 minutes. Add glacial acetic acid (4.0 [EQ)] followed immediately by water [(12X] acetic acid volume) and [WARM] the reaction to room temperature. Separate the phases and extract the aqueous phase with ethyl acetate twice. Wash the combined organic layers with dilute aqueous HC1, water and brine. Dry with sodium sulfate, filter and concentrate. Purify the resulting residue on silica gel, eluting with 0 to 5percent ethyl acetate in hexanes.; PREPARATION 16 6-Bromo-2, 3-difluoro-benzaldehyde (83percent) Yellow [OIL.APOS;H] NMR [(CDC13) OL O.] 31 (t, [J= 1.] 4 Hz, 1H), 7.45 (ddd, J= 9.0, 4.1, 1.9 Hz, [1H), ] 7.29 (td, [J=] 9.2, 8.0 Hz, [1H).]4-Bromo-l, 2-difluorobenzene (5.00 g, 25.9 mmol) was dissolved in tetrahydrofuran (100 mL) and cooled to -78 °C. Lithium diisopropyl amide (1.8 M in tetrahydrofuran, 15.8 mL, 28.5 mmol) was added. After stirring at -78 °C for 30 min, N, N-dimethylformamide (2.28 g, 31.1 mmol) was added. After stirring at -78 °C for an additional 15 min, acetic acid (6 mL) and water (100 mL) was added and the mixture was warmed to RT. After extraction with ethyl acetate, the organic phase was washed with 1 M hydrochloride acid solution and brine, and dried over magnesium sulfate. Concentration in vacuo afforded the title compound (2.59 g, 52percent of theory). GC-MS (Method 2G): R4-Bromo-1, 2-difluorobenzene (5.00 g, 25.9 mmol) was dissolved in tetrahydrofuran (100 mL) and cooled to -78° C. Lithium diisopropyl amide (1.8 M in tetrahydrofuran, 15.8 mL, 28.5 mmol) was added.
Computed Properties
Molecular Weight:221.00
XLogP3:2.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:219.93353
Monoisotopic Mass:219.93353
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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6-BROMO-2,3-DIFLUOROBENZALDEHYDE
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