59514-19-1|6-Bromo-9-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one| Ambeed

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CAS No. :	59514-19-1
Formula :	C₁₃H₁₂BrNO
M.W :	278.14
SMILES Code :	O=C1C(N(C)C2=C3C=C(Br)C=C2)=C3CCC1
MDL No. :	MFCD00459405

Yield	Reaction Conditions	Operation in experiment
82%		To a solution of <strong>[59514-18-0]6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one</strong> (200 mg, 0.76 mmol) inacetone (10 mL), sodium hydride (60% dispersed in oil, 91 mg, 2.28 mmol) was added at 0 C.After it was stirred for 15 minutes, methyl iodide (0.14 mL, 2.28 mmol) was added. The reaction mixture was stirred for 2 hours. The reaction mixture was diluted with ethyl acetate, and it was washed with water followed by brine. The organic layer was dried over sodium sulfate, and it was concentrated under reduced pressure. The residue was purified on an ISCOchromatograph (0-10% ethyl acetate/hexane) to give the product as a white solid (174 mg, 82%); ?H NIVIR (300 IVIHz) (CDC13) 7.78 (d, J= 2Hz, 1H), 7.46 (dd, J 9 Hz, J 2 Hz), 7.25-7.22 (m, 1H), 4.05 (s, 3H), 2.97 (t, J= 6Hz, 2H), 2.65 (t, J= 6 Hz, 2H), 2.23-2.17 (m, 2H).
63%		A solution of 6-bromo-2,3,4,9-tetrahydro-1 H-carbazol-1 -one (396 mg, 1.5 mmol) in anhydrous acetone (10 ml) was cooled to 0C and sodium hydride (7.5 mmol) was added. The mixture was stirred at room temperature for 30 minutes, then methyl iodide (1.065 g, 7.5 mmol) was added. After 4 hours of further stirring, the mixture was diluted with water (20 ml) and extracted with ethyl acetate (3 x 20 ml). The combined organic layers were dried over sodium sulfate and the solvents evaporated. Purification was accomplished by silica gel chromatography with dichloromethane/ethyl acetate (3:1 ), followed by recrystallisation from ethyl acetate to yield 6-bromo-9-methyl-2,3,4,9-tetrahydro-1 H-carbazol-1 -one as a pale brown solid (260 mg, 0.94 mmol, 63% yield). 1H-NMR (500 MHz, CDCI3): delta (ppm) = 7.78 (dd, J = 1.9, 0.5, 1 H), 7.45 (dd, J = 8.9, 1.9, 1 H), 7.22 (dd, J = 8.9, 0.5, 1 H), 4.04 (s, 3H), 2.96 (t, J = 6.1 , 2H), 2.65 (t, J = 6.5, 2H), 2.25 - 2.17 (mf J = 6.3, 2H). MS (El): m/z 278 [M+*]; MS (CI): m/z 279 [M+ + H].

Precautionary Statements-General
Code	Phrase
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Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P285	In case of inadequate ventilation wear respiratory protection.
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Response
Code	Phrase
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P320
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P321
P322
P330	Rinse mouth.
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
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Disposal
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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
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H225	Highly flammable liquid and vapour
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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
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 59514-19-1

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CAS No.: 59514-19-1

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