528-75-6|2,4-Dinitrobenzaldehyde| Ambeed

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Quality Control of [ 528-75-6 ] Purity: 98% SDS Specification

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Product Details of [ 528-75-6 ]

CAS No. :	528-75-6
Formula :	C₇H₄N₂O₅
M.W :	196.12
SMILES Code :	O=CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O
MDL No. :	MFCD00013376
InChI Key :	ZILXIZUBLXVYPI-UHFFFAOYSA-N
Pubchem ID :	68250

Safety of [ 528-75-6 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H228-H301+H311+H331-H315-H319
Precautionary Statements:	P240-P210-P241-P280-P370+P378-P501-P261-P270-P271-P264-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
Class:	4.1(6.1)
UN#:	2926
Packing Group:	Ⅱ

Application In Synthesis of [ 528-75-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 528-75-6 ]
Downstream synthetic route of [ 528-75-6 ]

[ 528-75-6 ] Synthesis Path-Upstream 1~1

1
[ 528-75-6 ]
[ 109466-84-4 ]

Yield	Reaction Conditions	Operation in experiment
98 %Chromat.	With hydrogen In methanol at 100℃; for 6 h; Autoclave	General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15molpercent Co/C–N–X catalyst, 100 L n-hexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC–MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm × 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).

References: [1] Chemische Berichte, 1904, vol. 37, p. 1873.
[2] Recueil des Travaux Chimiques des Pays-Bas, 1920, vol. 39, p. 581.
[3] Journal of Molecular Catalysis A: Chemical, 2016, vol. 420, p. 56 - 65.

[ 528-75-6 ] Synthesis Path-Downstream 1~15

1
[ 528-75-6 ]
[ 109466-84-4 ]

Yield	Reaction Conditions	Operation in experiment
98%Chromat.	With hydrogen; In methanol; at 100.0℃; under 7500.75 Torr; for 6.0h;Autoclave;	General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15mol% Co/C-N-X catalyst, 100 L n-hexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC-MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm × 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).

References: [1]Chemische Berichte,1904,vol. 37,p. 1873.
[2]Recueil des Travaux Chimiques des Pays-Bas,1920,vol. 39,p. 581.
[3]Journal of Molecular Catalysis A: Chemical,2016,vol. 420,p. 56 - 65.

2
[ 528-75-6 ]
[ 98276-57-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; In ethyl acetate; at 30℃; under 750.075 Torr; for 18.0h;Schlenk technique;Catalytic behavior;	General procedure: The substrate (0.5 mmol), NiPd/MIL-101 catalyst (0.023g, Pd 0.2 mol%), and ethyl acetate (4 mL) were added to a Schlenk tube, and the mixture was vigorously stirred with an affixed hydrogenation balloon at room temperature. Following the reaction, the solid catalyst was removed from the solution by filtration and washed with ethyl acetate. The product yields were determined by gas chromatography-mass spectrometry (GC/MS, Shimadzu GCMS- QP5050A) with a 0.25 mm × 30 mDB-WAX capillary column. Parameters were as follows: initialoven temperature, 100 C, 1 min; ramp, 20 C/min; final temperature, 280 C; final time, 5 min.

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 3365 - 3369.
[2]Chinese Journal of Chemistry,2010,vol. 28,p. 1547 - 1552.
[3]Organic Process Research and Development,2001,vol. 5,p. 539 - 541.
[4]Cuihua Xuebao/Chinese Journal of Catalysis,2016,vol. 37,p. 91 - 97.

3
[ 528-75-6 ]
iron(II) sulfate [ No CAS ]
CaCO₃ [ No CAS ]
[ 109466-84-4 ]

References: [1]Chemische Berichte,1904,vol. 37,p. 1873.

4
[ 528-75-6 ]
TiCl₃ [ No CAS ]
[ 109466-84-4 ]

References: [1]Chemische Berichte,1904,vol. 37,p. 1873.

5
2,3-dinitrobenzaldehyde [ No CAS ]
[ 528-75-6 ]
[ 98276-57-4 ]

Yield	Reaction Conditions	Operation in experiment
71%	With nitrogen; In water; acetic acid; ethyl acetate;	Method 1 2,4-Diaminobenzaldehyde To a nitrogen purged 5 liter 4-neck flask fitted with a condenser, mechanical stirrer, addition funnel, and temperature probe, was added 325 mesh iron dust, which can be obtained from Aldrich, Milwaukee, Wis. (220 g, 3.9 mol, 8 equiv), water (800 mL), and glacial acetic acid (5 mL). Over the next hour, some frothing occurred and the temperature rose to 28 C. In a separate container, 2,4-dinitrobenzaldehyde (97 g, 0.49 mol, 1 equiv) was dissolved in 1:1 glacial acetic acid/ethyl acetate (800 mL). 2,4-Dinitrobenzaldehyde can be purchased from Aldrich, Milwaukee, Wis. About 5 mL of the 2,4-dinitrobenzaldehyde solution was added dropwise to the iron mixture, which led to a dissipation of the frothing. The reaction mixture was warmed to 35 C. with a steam bath. Without further heating, the remaining dinitrobenzaldehyde solution was added at such a rate as to maintain the temperature below 50 C. The addition was completed after 6 hours. The reaction mixture was diluted with water (1 L) and diatomaceous earth (BNL Fine Chemicals and Reagents, Meriden, Conn.) was added (100 g). The reaction mixture was stirred an additional 3 hours at which point the temperature had dropped to 25 C. The solids were removed by filtration. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3400 mL). The extracts were then used to wash the solids from the initial filtration. The organic layers were combined and washed with water (400 mL) and saturated aqueous NaHCO3 (3400 mL). The combined organic layers were dried over MgSO4 and Darco G-60 (activated charcoal; BNL Fine Chemicals and Reagents, Meriden, Conn.) (10 g). After filtration to remove the drying agents, the organic layers were concentrated in vacuo to a slurry and diluted with 1 L of hexanes. The precipitated solids were collected by suction filtration and dried in air to give 2,4-diaminobenzaldehyde (48 g, 71%) as a light yellow solid. 1H NMR (acetone-d6) delta5.48 (brs, 2H), 5.94 (d, 1H, J=1.9 Hz), 6.08 (dd, 1H, J=2.0, 8.6 Hz), 6.75 (br s, 2H), 7.20 (d, 1H, J=8.6 Hz), 9.51 (s, 1H).
71%	With nitrogen; In water; acetic acid; ethyl acetate;	2,4-Diaminobenzaldehyde To a nitrogen purged 5 liter 4-neck flask fitted with a condenser, mechanical stirrer, addition funnel, and temperature probe, was added 325 mesh iron dust, which can be obtained from Aldrich, Milwaukee, Wis. (220 g, 3.9 mol, 8 equiv), water (800 mL), and glacial acetic acid (5 mL). Over the next hour, some frothing occurred and the temperature rose to 28 C. In a separate container, 2,4-dinitrobenzaldehyde (97 g, 0.49 mol, 1 equiv) was dissolved in 1:1 glacial acetic acid/ethyl acetate (800 mL). 2,4-Dinitrobenzaldehyde can be purchased from Aldrich, Milwaukee, Wis. About 5 mL of the 2,4-dinitrobenzaldehyde solution was added dropwise to the iron mixture, which led to a dissipation of the frothing. The reaction mixture was warmed to 35 C with a steam bath. Without further heating, the remaining dinitrobenzaldehyde solution was added at such a rate as to maintain the temperature below 50 C. The addition was completed after 6 hours. The reaction mixture was diluted with water (1 L) and diatomaceous earth (BNL Fine Chemicals and Reagents, Meriden, Conn.) was added (100 g). The reaction mixture was stirred an additional 3 hours at which point the temperature had dropped to 25 C. The solids were removed by filtration. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3400 mL). The extracts were then used to wash the solids from the initial filtration. The organic layers were combined and washed with water (400 mL) and saturated aqueous NaHCO3 (3400 mL). The combined organic layers were dried over MgSO4 and Darco G-60 (activated charcoal; BNL Fine Chemicals and Reagents, Meriden, Conn.) (10 g). After filtration to remove the drying agents, the organic layers were concentrated in vacuo to a slurry and diluted with 1 L of hexanes. The precipitated solids were collected by suction filtration and dried in air to give 2,4-diaminobenzaldehyde (48 g, 71%) as a light yellow solid. 1H NMR (acetone-d6) delta5.48 (br s, 2H), 5.94 (d, 1H, J=1.9 Hz), 6.08 (dd, 1H, J=2.0, 8.6 Hz), 6.75 (br s, 2H), 7.20 (d, 1H, J=8.6 Hz), 9.51 (s, 1H).

References: [1]Patent: US2002/42516,2002,A1 .
[2]Patent: US6369075,2002,B1 .

6
[ 103-82-2 ]
[ 599-67-7 ]
[ 528-75-6 ]
[ 60-12-8 ]
[ 106-47-8 ]
[ 126-30-7 ]
[ 613-45-6 ]
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[ 102-20-5 ]
[ 1620217-69-7 ]
[ 354538-08-2 ]