58472-36-9|7-Fluoro-2-hydroxynaphthalene-1,4-dione| Ambeed

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CAS No. :	58472-36-9
Formula :	C₁₀H₅FO₃
M.W :	192.14
SMILES Code :	O=C1C(O)=CC(C2=C1C=C(F)C=C2)=O
MDL No. :	MFCD14706170

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
92%		[00192] To a solution of KOu (547 mg, 4.873 mmol) in anhydrous i-BuOH (7.6 mL) which had previously been saturated with 02 (bubbled for 10 min) was added a solution of 7-fluoro- 1-tetralone 1 (100 mg, 0.609 mmol) in anhydrous i-BuOH (2.4 mL), and the resulting red reaction mixture was stirred at ambient temperature for 30 min under 02 atmosphere. Then, the reaction mixture was cooled down to 0 °C and acidified with 3M HCl until the pH of the mixture became 1-2. The volatiles were removed in vacuo, and the crude material was extracted with CH2C12. Combined organic layers were dried over anhydrous sodium sulfate then filtered and concentrated under vacuo to afford 7-fluoro-2-hydroxynaphthalene-l,4- dione 2 as a yellow solid (108 mg, 92percent yield).
14.2%	With N-benzyl-N,N,N-triethylammonium chloride; oxygen; potassium carbonate; potassium hydroxide; In 1,4-dioxane; for 72h;	In dioxane (40 mL), 7-fluoro-1- tetralone (0.556 g, 3.37 mmol), KOH (0.992 g, 17.7 mmol), K2C03 (2.3 15 g, 16.8 mmol), Re2(C0)10 (0.116 g, 1.78 mmol), and benzyltriethylammonium chloride (cat) were stirred for 72 hours under bubbling oxygen. The reaction solution was acidified with concentrated HC1. The product was extracted from the reaction solution with ethyl acetate and dried with Mg504. Any volatile solvents were removed in vacuo. The crude product was triturated with 5 mL ether and 2 mL hexane to result in a brown-orange solid (0.092 g, 14.2percent). ?HNMR (Acetone-d6) oe 11.8 (bs, 1H), 8.11 (dd, 1H, J= 8.80, 5.2 Hz), 7.73 (dd, 1H, J= 8.8, 2.4 Hz), 7.63 (td, 1H, J= 8.8, 2.4Hz), 6.25 (s, 1H); ?3CNMR (Acetone-d6): 184.95, 182.05, [168.12, 165.60, d, Jc-F = 253.6 Hzl, 134.52, 134.44, [130.79, 130.76, d, Jc-F 3.0 Hzl, [130.61, 130.51, d, Jc-F 10.1 Hzl, [122.90, 122.68, d, JF=22.1 Hzl, [113.90, 113.67, d, Jc-F 23.1 Hzl, 112.31; Rf= 0.31 (10:1 EtOAc:MeOH); mp = >190°C (dec.); MS (ES+): 193.0.

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Disposal
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CAS No.: 58472-36-9

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CAS No.: 58472-36-9

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[ 58472-36-9 ] Synthesis Path-Downstream 1~1

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed