4-Bromo-1,8-naphthalic anhydride
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4-Bromo-1,8-naphthalic anhydride
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CAS No:
81-86-7
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Formula:
C12H5BrO3
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Chemical Name:
4-Bromo-1,8-naphthalic anhydride
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Synonyms:
1H,3H-Naphtho[1,8-cd]pyran-1,3-dione,6-bromo-;Naphthalic anhydride,4-bromo-;6-Bromo-1H,3H-naphtho[1,8-cd]pyran-1,3-dione;4-Bromonaphthalic anhydride;4-Bromo-1,8-naphthalenedicarboxylic anhydride;4-Bromo-1,8-naphthalic acid anhydride;4-Bromo-1,8-naphthalic anhydride;4-Bromonaphthalene-1,8-dicarboxylic acid anhydride;4-Bromo-1,8-naphthoic anhydride;4-Bromo-1,8-naphtalic anhydride;8-Bromo-3-oxatricyclo[7.3.1.0 5,13]trideca-1(13),5,7,9,11-pentaene-2,4-dione;6-Bromobenzo[de]isochromene-1,3-dione;4-Bromo-1,8-naphthalene anhydride
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CAS No:
Characteristics
43.4
3.2
White to yellow solid
1.8±0.1 g/cm3
215 °C
467.2ºC at 760 mmHg
236.3±24.0 °C
1.733
6.66E-09mmHg at 25°C
Safety Information
NONH for all modes of transport
3
R36/37/38
S26-S37/39
Xi:Irritant;
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 50 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
4-Bromo-1,8-naphthalic anhydride Use and Manufacturing
To a solution of acenaphthene (2.31 g, 15.0 mmol) and acetic acid (60 ml), sodium dichromate (11.17 g, 40.0 mmol) was added with stirring at room temperature. The suspensionwas heated to 75 °C for 8 h. After the completion of reaction, cold water was added to the reaction mixture to get solid, filtered and washed with water. Off white product of 1, 8-naphthalic anhydride (2) (2.6 g, 80percent, m.p. 266-268 °C) was obtained. To a cooled solution of 1, 8-naphthalic anhydride(1.98 g, 10.0 mmol) in KOH (2.8 g in 12ml water), bromine was charged with dropping funnel. The reaction mixture was heated to 60 °C for 6 h and then acidified with HCl solution. Solid was separated out, filtered to get crude product. The solid residue was heated with 5percent NaOH solution, filtered and neutralized with HCl solution. Again filtered and washed with cold water, dried to get yellow powder of 4-bromo-1, 8-naphthalic anhydride (3) (2.05 g, 82percent, m.p.117-119 °C). 4-Bromo-1, 8-naphthalic anhydride (2.00 g, 5.0 mmol) and o-phenylenediamine (0.618 g, 5.0 mmol) in THF was refluxed for 6 h. After the completion of reaction (TLC), cooled the reaction mixture to get crude solid, filtered and washed with THF to afford pure 3-bromo-benzo[de]benzo[4, 5]imidazo[2, 1-a]isoquinolin-7-one (4). Brown powder (2.51 g, 63percent) m.p. 190-192 °C. 1, 8-Naphthalic anhydride (10mmol, 1.98g) was dissolved in a 4M 18 KOH solution (12mL) under vigorous stirring. The reaction mixture was cooled in an ice-bath and 15 bromine (1mmol, 6.3mL) was slowly added. Subsequently, the mixture was heated to 65°C and stirred for 12h. When the reaction was complete, the reaction mixture was cooled in an ice-bath and 14 sulfuric acid (10mL) was slowly added. The resulting solution was allowed to reflux for 1h. Cool to room temperature and add crystals. The 19 crystals were recovered by vacuum filtration and recrystallized from methanol. The product was further purified by column chromatography (adsorbent: silica gel, eluent: ethyl acetate/hexane (1:5)).Yield: 64.2percent;
1H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-bromo-: ACTIVE
Computed Properties
Molecular Weight:277.07
XLogP3:3.2
Hydrogen Bond Acceptor Count:3
Exact Mass:275.94221
Monoisotopic Mass:275.94221
Topological Polar Surface Area:43.4
Heavy Atom Count:16
Complexity:341
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-Bromo-1,8-naphthalic anhydride
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