837392-54-8|2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole| Ambeed

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CAS No. :	837392-54-8
Formula :	C₁₅H₂₀BNO₂
M.W :	257.14
SMILES Code :	CC1(C)C(C)(C)OB(C2=CC3=C(NC(C)=C3)C=C2)O1
MDL No. :	MFCD13181964
InChI Key :	GTGXBZPFDNAVMM-UHFFFAOYSA-N
Pubchem ID :	18450648

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
49%		Methyl-6-(tetramethyl-l ,3,2-dioxaborolan-2-yl)-7H-indoleTo a solution of 6-bromo-2-methyl-7H-indole (2.0 g, 9.52 mmol) in dry tetrahydrofuran (100 mL) was added sodium hydride (381 mg, 9.53 mmol ) with ice-cooling. After stirring for about 30 min , a solution of n-BuLi (15 mL, 2.5 M solution in hexane) was added dropwise with stirring at -78°C under nitrogen. It was warmed slowly to -40°C during 45 min and stirred at this temperature for another 30 min. The mixture was cooled again below -78°C followed by dropwise addition of 4,4,5, 5-tetramethyl-2-(propan-2-yloxy)- 1 ,3,2- dioxaborolane (3.54 g, 19.03 mmol). After warming to room temperature, the mixture was quenched with NH4CI (aq) and extracted with ethyl acetate (3 x 80 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the residue, which was purified by silica gel columnchromatography (2percent ethyl acetate in petroleum ether) to afford 2-methyl-6-(tetramethyl- l,3,2-dioxaborolan-2-yl)-7H-indole (1.2 g, 49percent).'H-NMR (300 MHz, CDCI3): delta 8.06 (s, 1Eta), 7.91(s, 1Eta), 7.58 - 7.60 (t, 7 = 7.5 Hz, 1H), 7.31 (d, J = 8.1 Hz, 1H), 6.24 (s, 1H), 2.46 (s, 3H), 1.39 (s, 12H)
38%		Step 2. 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole To a solution of <strong>[1075-34-9]5-bromo-2-methyl-1H-indole</strong> (3.0 g, 14.35 mmol) in dry tetrahydrofuran (20 ml) was added sodium hydride (900 mg, 22.5 mmol) with ice-cooling. After stifling for about 30 min, a solution of t-BuLi (27.5 ml, 1.3 M solution in hexane) was added dropwise with stifling at -78° C. under an inert atmosphere of nitrogen. The reaction mixture was warmed slowly to -40° C. over 45 min and stirred at this temperature for another 30 min. The mixture was cooled again below -78° C., followed by the addition of 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane (5.3 g, 28.49 mmol) dropwise. After warming to room temperature, the mixture was quenched with NH4Cl solution (100 ml) and extracted with ethyl acetate (3.x.100 ml). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the residue, which was purified by a silica gel column (2percent ethyl acetate in petroleum ether) to afford 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (1.4 g, 38percent). 1H NMR (300 MHz, CDCl3): delta 8.06 (s, 1H), 7.91 (s, 1H), 7.58-7.60 (t, J=7.5 Hz, 1H), 7.31 (d, J=8.1 Hz, 1H), 6.24 (s, 1H), 2.46 (s, 3H), 1.39 (s, 12H).

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P222	Do not allow contact with air.
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P230	Keep wetted
P231	Handle under inert gas.
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P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
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P263	Avoid contact during pregnancy/while nursing.
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P270	Do not eat, drink or smoke when using this product.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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Code	Phrase
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P320
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P321
P322
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P342	If experiencing respiratory symptoms:
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P378
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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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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
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:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
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
Code	Phrase
P501	Dispose of contents/container to ...
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CAS No.: 837392-54-8

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CAS No.: 837392-54-8

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[ 837392-54-8 ] Synthesis Path-Downstream 1~3

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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