2450-26-2|2-硝基-3-甲氧基-4-羟基苯甲醛|4-HYDROXY-2-NITRO-M-ANISALDEHYDE|MFCD00017020-范德生物科技公司

2-硝基-3-甲氧基-4-羟基苯甲醛

NMR下载 COA and HPLC MSDS下载
names：
4-HYDROXY-2-NITRO-M-ANISALDEHYDE
CAS号：
2450-26-2
MDL Number： MFCD00017020
MF(分子式)： C8H7NO5 MW(分子量)： 197
EINECS: Reaxys Number:
Pubchem ID:96959 Brand:BIOFOUNT

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中文别名	2-硝基-3-甲氧基-4-羟基苯甲醛(2450-26-2)
英文别名	4-HYDROXY-2-NITRO-M-ANISALDEHYDE;4-Hydroxy-3-Methoxy-2-Nitrobenzaldehyde; 2450-26-2; 2-Nitrovanillin; Benzaldehyde, 4-Hydroxy-3-Methoxy-2-Nitro-; 4-Hydroxy-3-Methoxy-2-Nitro-Benzaldehyde;
CAS号	2450-26-2
SMILES	COC1=C(C=CC(=C1[N+](=O)[O-])C=O)O
Inchi	InChI=1S/C8H7NO5/c1-14-8-6(11)3-2-5(4-10)7(8)9(12)13/h2-4,11H,1H3
InchiKey	PHCNQUJHXJQLQR-UHFFFAOYSA-N
分子式 Formula	C8H7NO5
分子量 Molecular Weight	197
闪点 FP	No data available
熔点 Melting point	137-138 °C
沸点 Boiling point	387.8±42.0 °C
Polarizability极化度	No data available
密度 Density	1.456±0.06 g/cm3
蒸汽压 Vapor Pressure	No data available
溶解度Solubility
性状	solid power
储藏条件 Storage conditions	Store at room temp

2-硝基-3-甲氧基-4-羟基苯甲醛???????合成方法1：

Yield	Reaction Conditions	Operation in experiment
96.3%	With potassium carbonate In methanol at 20℃; for 2.00 h; Acidic aqueous solution	A mixture of 4-formyl-2-methoxy-3-nitrophenyl acetate 4.54g [(L9.] [OMMOL)] and potassium carbonate 5.24g (37.9mmol) in methanol [40ML] was stirred at room temperature for 2 hours. The reaction mixture was poured into [WATER,-ACIDIFIED] by 1N [HC1] solution and extracted into AcOEt. The organic layer was washed with brine, dried over [MGS04,] filtrated and the solvent was evaporated. The residue was washed with n-hexane to give the title compound 3. [60G] as white solid. Yield 96.3percent.
95%	Stage #1: With sodium hydroxide In water at 10 - 45℃; Stage #2: at 20 - 30℃; for 0.25 h;	24 g acetyl-2-nitrovanilline were suspended in 300 ml water at 10-30 The mixture was heated to 40 - 45 and 40 g NaOH 30percent (300 mmol, 3 equiv.) were added in 10-20 min. Stirring was continued for 30-45 min. The reaction was cooled to 25-30 and the pH was set to 2.0-2.5 by the addition of 10percent sulfuric acid. Stirring was continued for 15 min at 20-25 and the product was filtered off and washed with water (2 x 100 ml). The product was dried at 45-50 under reduced pres sure and 1 8.7 g 2- nitrovanilline were obtained a white to yellow solid in 95percent yield.
88%	Stage #1: at 20℃; for 16.00 h;	Step 2: Preparation of 4-hvdroxy-3-methoxy-2-nitrobenzaldehvde; A mixture of 4-formyl-2-methoxy-3-nitrophenyl acetate 438 g (1.8 mol) and potassium carbonate (506 g, 3.7 mol) in MeOH (4000 mL) was stirred at room temperature for 16 h. ="67">The reaction mixture was concentrated under reduced pressure to afford a viscous oil. This was dissolved in water, acidified using a solution of HCI (2 N) and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO₄) and filtered. The solvent was concentrated under reduced pressure to 1/3 volume and the resulting solids were filtered and air-dried to give the title compound (317 g, 88percent): ¹H NMR (DMSO-Cy₆) δ: 9.69 (1 H₁ s), 7.68 (1 H, d), 7.19 (1 H, d), 3.82 (3H, s).

产品说明	2-硝基-3-甲氧基-4-羟基苯甲醛(2450-26-2)作为中间体使用,2450-26-2溶解度,熔点见主页
Introduction	4-HYDROXY-2-NITRO-M-ANISALDEHYDE(2450-26-2)
Application1
Application2
Application3

合成方法2：

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: With sulfuric acid; nitric acid In dichloromethane; water at 0 - 5℃; for 12.00 h; Microwave irradiation; Large scale Stage #2: With potassium carbonate In methanol; dichloromethane at 30℃; for 3.00 h; Large scale Stage #3: With hydrogenchloride In dichloromethane; water at 30℃; for 0.25 h; Large scale	2-Nitrovanilin (2) was synthesized via a flow nitration of vanillin acetate (1 ) in a micro reactor. 3.94 kg of nitric acid (65 wpercent) were added to 5.87 kg of concentrated sulfuric acid at 0 (nitrating acid). 1 .5 kg of va nillin acetate were dissolved in 2.9 kg of dichloromethane (vanillin acetate solution). Both solutions reacted in a micro reactor with flow rates of app. 8.0 mL/min (nitrating acid) and app. 4.0 mL/min (vanillin acetate solution) at 5. The reaction mi xture was directly dosed into 8 kg of water at 3 . After 3h flow rates were increased to 10 mL/min (nitrating acid) and 5.0 mL/min (vanillin acetate solution). After additional 9 h the flow reaction was completed. The layers were separated at r.t., and the aqueous phase was extracted with 2 L of dichloromethane. The combined organic phases were washed with 2 L of saturated sodium bicarbonate, and then 0.8 L of water. The dichloromethane solution was concentrated in vacuum to app. 3 L, 3.9 L of methanol were added and app. the same volume was removed by distillation again. Additional 3.9 L of methanol were added, and the solution concentrated to a volume of app. 3.5 L. 1 .25 kg of methanol were added, followed by 2.26 kg of potassium carbonate. The mixture was stirred at 30 for 3h. 7.3 kg of dichl oromethane and 12.8 kg of aqueous hydrochloric acid (10 wpercent) were added at < 30 (pH 0.5 - 1 ). The mixture was stirred for 15 min, and the layers were separated. The organic layer was filtered, and the filter cake washed with 0.5 L of dichloromethane. The aqueous layer was extracted twice with 4.1 kg of dichloromethane. The combined organic layers were concentrated in vacuum to app. 4 L. 3.41 kg of toluene were added, and the mixture concentrated to a final volume of app. 4 L. The mixture was cooled to 0. After 90 min the suspension was filtered. T he collected solids were washed with cold toluene and dried to give 0.95 kg (62 percent). ¹ H-NMR (400 MHz, de-DMSO): δ = 3.84 (s, 3H), 7.23 (d, 1 H), 7.73 (d, 1 H), 9.74 (s, 1 H), 1 1 .82 (brs, 1 H).
Ca. 10 %Spectr.	Stage #1: With sulfuric acid; nitric acid In dichloromethane; water at 3 - 5℃; for 12.00 h; Flow reactor; Large scale Stage #2: at 30℃; for 3.00 h; Large scale	Example 1 : Step A1 : Preparation of 4-acetoxy-3-methoxy-2- nitrobenzaldehyde (2) 3.94 kg of nitric acid (65 wpercent) were added to 5.87 kg of concentrated sulfuric acid at 0°C (nitrating acid). 1 .5 kg of vanillin acetate were dissolved in 2.9 kg of dichloromethane (vanillin acetate solution). Both solutions reacted in a micro reactor with flow rates of app. 8.0 mL/min (nitrating acid) and app. 4.0 mL/min (vanillin acetate solution) at 5°C. The reaction mixture was directly dosed into 8 kg of water at 3°C. After 3h flow rates were increased to 10 mL/min (nitrating acid) and 5.0 mL/min (vanillin acetate solution). After additional 9 h the flow reaction was completed. The layers were separated at r.t., and the aqueous phase was extracted with 2 L of dichloromethane. The combined organic phases were washed with 2 L of saturated sodium bicarbonate, and then 0.8 L of water. The dichloromethane solution was concentrated in vacuum to app. 3 L, 3.9 L of methanol were added and app. the same volume was removed by distillation again. Additional 3.9 L of methanol were added, and the solution concentrated to a volume of app. 3.5 L. This solution of 4-acetoxy-3-methoxy-2- nitrobenzaldehyde (2) was directly used in the next step. Example 2 : Step A2 : Preparation of 4-hydroxy -3-methoxy-2- nitrobenzaldehyde (2-nitro-vanillin) (3) To the solution of 4-acetoxy-3-methoxy-2-nitrobenzaldehyde (2) prepared as described in example 1 (see above) 1 .25 kg of methanol were added, followed by 2.26 kg of potassium carbonate. The mixture was stirred at 30°C for 3h. 7.3 kg of dichloromethane and 12.8 kg of aqueous hydrochloric acid (10 wpercent) were added at < 30°C (pH 0.5 - 1 ). The mixture was stirred for 15 min, and the layers were separated. The organic layer was filtered, and the filter cake washed with 0.5 L of dichloromethane. The aqueous layer was extracted twice with 4.1 kg of dichloromethane. The combined organic layers were concentrated in vacuum to app. 4 L. 3.41 kg of toluene were added, and the mixture concentrated to a final volume of app. 4 L. The mixture was cooled to 0°C. After 90 min the suspension was filtered. The collected solids were washed with cold toluene and dried to give 0.95 kg (62 percent). ¹H-NMR (400 MHz, de-DMSO): δ =3.84 (s, 3H), 7.23 (d, 1 H), 7.73 (d, 1 H), 9.74 (s, 1 H), 1 1 .82 (brs, 1 H). NMR spectrum also contains signals of regioisomer 6-nitrovanillin (app. 10percent): δ = 3.95 (s, 3H), 7.37 (s, 1 H), 7.51 (s, 1 H), 10.16 (s, 1 H), 1 1 .1 1 (brs, 1 H).
7.6 g	Stage #1: at -10 - 0℃; for 3.00 h; Stage #2: for 0.25 h; Reflux	After fuming nitric acid (50 mL) was cooled at -20 ° C.,The acetate salt obtained above was added in small portions. Then,After stirring the mixture at -10 to 0 ° C. for 3 hours,Poured into ice cold water (~ 200 mL) and stirred for 10 minutes.The mixture was extracted with ethyl acetate, the combined organic layers were washed with brine,After drying with anhydrous Na 2 SO 4,Evaporation to dryness gave a crude product.The crude product obtained above was added to a 2 M KOH solution (200 mL)Reflux heating was carried out for 15 minutes.After cooling to room temperature, the reaction was stopped by slowly adding concentrated hydrochloric acid at 0 ° C.After filtering the solid matter, washing with cold water and vacuum drying,A mixture of Compound 1 as a brown solid and its regioisomer was obtained (7.6 g,

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[3] Patent: JP2018/8900, 2018, A. Location in patent: Paragraph 0081; 0082; 0084; 0085

警示图
危险性
危险性警示	No data available
安全声明	H317+H301
安全防护	P261, P264, P270, P272, P280, P301+
备注

Pictogram(s)
Signal	Danger
GHS Hazard Statements	H301 (97.5%): Toxic if swallowed [Danger Acute toxicity, oral] H317 (97.5%): May cause an allergic skin reaction [Warning Sensitization, Skin] Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Precautionary Statement Codes	P261, P264, P270, P272, P280, P301

First Total Synthesis of 9-Hydroxy-8H-pyrano[3,2-f]indol-2-one J. Heterocyclic Chem. 2015 10.1002/jhet.2251

(E)-4-[(3,5-Dimethyl-phen-yl)imino-meth-yl]-2-meth-oxy-3-nitro-phenol；Acta crystallographica. Section E, Structure reports online；PMID：22259502 2012-01-01

RSC Advances, 2017, vol. 7, # 82, p. 52180 - 52186

Patent: CN107074876, 2017, A. Location in patent: Paragraph 0309; 0310; 0313

Patent: JP5876570, 2016, B2. Location in patent: Paragraph 0407-0411

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