90151-40-9|4-Amino-3-methoxybenzaldehyde| Ambeed

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CAS No. :	90151-40-9
Formula :	C₈H₉NO₂
M.W :	151.16
SMILES Code :	O=CC1=CC=C(N)C(OC)=C1

Yield	Reaction Conditions	Operation in experiment
66%	With n-Butyl nitrite; copper(I) bromide; In acetonitrile; at 20℃; for 12h;	3C. 4-Bromo-3-methoxy-benzaldehydeA mixture of 4-amino-3-methoxy-benzaldehyde (4.5 g, 29.8 mmol), n-butyl nitrite (4.6 g, 35.8 mmol) and copper bromide (6.83 g, 47.7 mmol) in MeCN (45 mL) was stirred atroom temperature for 12 hours. The reaction mixture was diluted with EtOAc (100 mL), washed with water (200 mL), dried (Na2SO4) and evaporated under reduced pressure to leave a residue which was purified by column chromatography on neutral silica gel (60-120 mesh) using 0-70percent EtOAc/hexanes as the eluentto give the title compound (4.2 g, 66percent).
	With n-Butyl nitrite; copper(I) bromide; In acetonitrile; at 20℃;	A solution of the product of example 82b (38.3 g) in acetonitrile (600 ml) was added dropwise to a mixture of n-butyl nitrite (43.1 ml) and copper(I) bromide (63.6 g) in acetonitrile (1300 ml). After stirring for 18 h at room temperature, the reaction mixture <n="102"/>was diluted with ethyl acetate and washed with an aqueous HCl solution (1 N). The organic layer was separated and washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel in heptane/ethyl acetate [1 :1 (v/v)]. Yield: 27.4 g. LC/MS-ESI: [M+H]+ = 215.1 / 217.0.
	With n-Butyl nitrite; copper(I) bromide; In nitriobenzene; acetonitrile; at 20℃; for 18h;	A solution of the product of example Ib (38.3 g) in acetonitrile (600 ml) was added drop wise to a mixture of n-butyl nitrite (43.1 ml) and copper(I) bromide (63.6 g) in acetonitrile (1.3 1). After stirring for 18 h at room temperature, the reaction mixture was diluted with ethyl acetate and washed with an aqueous HCl solution (1 N). The organic layer was separated and washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel in heptane/ethyl acetate [1 :1 (v/v)].Yield: 27.4 g. LC/MS-ESI: [M+H]+ = 215.1 / 217.0; 1H-NMR (CDCl3): delta 3.98 (s, 3H, OMe), 7.32, 7.4, 7.75 (m, 3H, ArH), 9.95 (s, IH, CHO).

	With n-Butyl nitrite; copper(I) bromide; In acetonitrile; at 20℃; for 18h;	(c). 4-Bromo-3-methoxy-benzaldehyde A solution of the product of example 1b (38.3 g) in acetonitrile (600 ml) was added drop wise to a mixture of n-butyl nitrite (43.1 ml) and copper(I) bromide (63.6 g) in acetonitrile (1.3 l). After stirring for 18 h at room temperature, the reaction mixture was diluted with ethyl acetate and washed with an aqueous HCl solution (1 N). The organic layer was separated and washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel in heptane/ethyl acetate [1:1 (v/v)]. Yield: 27.4 g. LC/MS-ESI: [M+H]+=215.1/217.0; 1H-NMR (CDCl3): delta 3.98 (s, 3H, OMe), 7.32, 7.4, 7.75 (m, 3H, ArH), 9.95 (s, 1H, CHO).
27.4 g	With n-Butyl nitrite; copper(I) bromide; In acetonitrile; at 20℃; for 18h;	(c) . 4-Bromo-3-methoxy-benzaldehyde A solution of the product of example 42b (38.3 g) in acetonitrile (600 ml) was added dropwise to a mixture of n-butyl nitrite (43.1 ml) and copper(l) bromide (63.6 g) in acetonitrile (1300 ml). After stirring for 18 h at room temperature, the reaction mixture was diluted with ethyl acetate and washed with an aqueous 1 M HCI solution. The organic layer was separated and washed with brine, dried (MgS04), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel in heptane/ethyl acetate [1 :1 (v/v)]. Yield: 27.4 g. MS (ESI) m/z: 215,217 (M+H)+.

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CAS No.: 90151-40-9

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CAS No.: 90151-40-9

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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
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H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed