57356-28-2|5-Nitro-2,3-dihydrobenzo[b][1,4]dioxine| Ambeed

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CAS No. :	57356-28-2
Formula :	C₈H₇NO₄
M.W :	181.15
SMILES Code :	O=[N+](C1=C2C(OCCO2)=CC=C1)[O-]
MDL No. :	MFCD09414744

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H319-H317
Precautionary Statements:	P305+P351+P338-P280

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 2h;	Ste B: 5-nitro-2,3-dihydrobenzo[b][1 ,4]dioxineTo a solution of 3-nitrobenzene-1 ,2-diol (11 g , 0.071 mol) in Lambda/,Nu -dimethylformamide (500 mL) was added potassium carbonate (29 g ,0.0.213 mol) followed by 1 ,2-dibromoethane (14.7 g, 0.078 mol). The mixture was heated at 110 C for 2 hours. After cooled to room temperature, the mixture was poured into water and then extracted with ether. The organic phases were combined and dried over anhydrous sodium sulfate, filtrated and concentrated to give a crude product, which was purified by silica gel column chromatography (petroleum ether/ethyl acetate 20/1 ) to afford the product 5-nitro-2,3-dihydrobenzo[to][1 ,4]dioxine (8 g, yield 62 %). 1 H NMR (400 MHz, CDCI3) delta ppm 7.48-7.50 (dd, 1 H, J = 1 .6 Hz, 8.4 Hz), 7.09-7.12 (dd, 1 H, J = 1.6 Hz, 8.4 Hz), 6.88-6.92 (t, 1 H, J = 8.4 Hz), 4.40-4.42 (m, 2H), 4.34-4.36 (m, 2H).
	With potassium carbonate; In i-Amyl alcohol; for 15h;Heating / reflux;	A mixture of compound 16A (1.10 g, 7.1 mol), 1 ,2-dibromoethane (9.33 g, 49.7 mmol) and anhydrous potassium carbonate (2.94 g, 21.3 mmol) in isoamyl alcohol (100 mL) was heated to reflux and allowed to stir at this temperature for 7 hours. Additional 1 ,2-dibromoethane (6.57 g, 35.0 mmol) and anhydrous potassium carbonate (4.84 g, 35.0 mmol) were added to the reaction mixture and reaction was stirred at reflux for 8 additional hours, then cooled to room temperature. The isoamyl alcohol was removed in vacuo and the liquid residue obtained was decanted into water, extracted with dichlorometha?e and the dichloromethane solution was concentrated in vacuo. The resulting residue was purified using flash column chromatography on silica gel (20% ethyl acetate-hexanes) to provide compound 16B as pale-yellow solid. HPLC-MS tR = 1.57 min (UV254 nm); mass calculated for formula C8H7NO4 181.0. observed LCMS m/z 182.1 (M+H).

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃;	Step C / intermediate B3: 2,3-dihydrobenzo[/5][1 ,4]dioxin-5-amineA suspension of 5-nitro-2,3-dihydrobenzo[£»][1 ,4]dioxine (8 g, 0.044 mol) and palladium on carbon (10 %, 2 g) in methanol (250 mL) was stirred vigorously under an atmosphere of hydrogen overnight at room temperature. The mixture was filtered through a pad of Celite and then concentrated to give the crude product, which was purified by silica gel column chromatography (petroleum ether/ethyl acetate 9/1 ) to afford the product 2,3-dihydrobenzo[b][1 ,4]dioxin-5-amine (6.5 g, yield 97 %). 1H NMR (400 MHz, CDCI3) δ ppm 8.61-8.65 (t, 1 H, J = 8.0 Hz), 6.30-6.33 (dt, 2H, J ~ 1 .2 Hz, 2.4 Hz), 4.22-4.27 (m, 4H), 3.75 (s, 2H).
	With ammonium formate;palladium on charcoal; In methanol;	EXAMPLE 13 2,3-Dihydro-1,4-benzodioxin-5-amine Ammonium formate (3.40 g, 0.054 mol) and 10% palladium on charcoal (1.44 g) were added to a stirred solution of the product of example 12 (2.45 g, 0.0135 mol) in methanol (15 ml). After the considerable effervescence had ceased, the mixture was filtered, evaporated in vacuo and triturated with acetonitrile. The residue was purified by chromatography (silica; ether) to give the product (1.51 g).

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CAS No.: 57356-28-2

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CAS No.: 57356-28-2

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Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In toluene;	EXAMPLE 12 5-Nitro-2,3-dihydro-1,4-benzodioxin 1,2-Dibromoethane (12.0 g, 0.064 mol), potassium carbonate (17.6 g, 0.127 mol) and tetra-n-butyl ammonium bromide (1.37 g, 0.0043 mol) were added to a stirred solution of <strong>[6665-98-1]3-<strong>[6665-98-1]nitrocatechol</strong></strong> (6.59 g, 0.043 mol) in toluene (210 ml). The solution was heated at reflux with azeotropic removal of water for 23 h, cooled to room temperature, washed with 2N. sodium hydroxide solution (150 ml), dried (Na2 SO4), and evaporated in vacuo to give an orange oil. Purification by column chromatography (silica; ether) gave the product (2.55 g), m.p. 55-59 C.
	With potassium carbonate; In toluene;	EXAMPLE 1 5-Nitro-2,3-dihydro-1,4-benzodioxin 1,2-Dibromoethane (12.0 g, 0.064 mol), potassium carbonate (17.6 g, 0.127 mol) and tetra-n-butyl ammonium bromide (1.37 g, 0.0043 mol) were added to a stirred solution of <strong>[6665-98-1]3-<strong>[6665-98-1]nitrocatechol</strong></strong> (6.59 g, 0.043 mol) in toluene (210 ml). The solution was heated at reflux with azeotropic removal of water for 23 h, cooled to room temperature, washed with 2N sodium hydroxide solution (150 ml), dried (Na2 SO4) and evaporated in vacuo to give an orange oil. Purification by column chromatography (silica; ether) gave the product (2.55 g) m.p. 55-59 C.

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
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.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
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.
P243	Take precautionary measures against static discharge.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
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P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
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P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
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Response
Code	Phrase
P301	IF SWALLOWED:
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P312	Call a POISON CENTER or doctor/physician if you feel unwell.
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P320
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P321
P322
P330	Rinse mouth.
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P337	If eye irritation persists:
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P342	If experiencing respiratory symptoms:
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
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P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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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P411
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P413
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P422
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P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
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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
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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