904886-25-5|8-Bromoquinoline-2-carbaldehyde| Ambeed

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Quality Control of [ 904886-25-5 ] Purity: 95% SDS Specification

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Product Details of [ 904886-25-5 ]

CAS No. :	904886-25-5
Formula :	C₁₀H₆BrNO
M.W :	236.06
SMILES Code :	O=CC1=NC2=C(Br)C=CC=C2C=C1
MDL No. :	MFCD06824177
InChI Key :	AFDUIUOATSXDFH-UHFFFAOYSA-N
Pubchem ID :	36688019

Safety of [ 904886-25-5 ]

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

Application In Synthesis of [ 904886-25-5 ]

* 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.

Downstream synthetic route of [ 904886-25-5 ]

[ 904886-25-5 ] Synthesis Path-Downstream 1~35

1
[ 1165569-11-8 ]
[ 904886-25-5 ]

References: [1]Tetrahedron,2009,vol. 65,p. 4410 - 4417.

2
[ 111-95-5 ]
[ 904886-25-5 ]
[ 1252796-40-9 ]

References: [1]Chemical Communications,2010,vol. 46,p. 6554 - 6556.

3
[ 904886-25-5 ]
[ 1539-42-0 ]
[ 1252796-44-3 ]

References: [1]Chemical Communications,2010,vol. 46,p. 6554 - 6556.

4
[ 904886-25-5 ]
[ 119260-53-6 ]
[ 1252796-42-1 ]

References: [1]Chemical Communications,2010,vol. 46,p. 6554 - 6556.

5
[ 61047-43-6 ]
[ 904886-25-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With selenium(IV) oxide; In 1,4-dioxane; at 100℃;	In a round bottom flask, add 8-bromo-2-methylquinoline (1.110g, 5mmol), selenium dioxide (1.110g, 10mmol), 30ml dioxane, and heat to 100C. TLC monitor the reaction until All raw materials react. After the reaction was cooled to room temperature, the organic phase was filtered and concentrated to obtain a crude product. The product was purified using column chromatography. Obtained 1.006 g of 8-bromo-2-quinolinecarboxaldehyde with a yield of 85%
3.1 g	With selenium(IV) oxide; In 1,4-dioxane; at 60℃;	To a suspension of selenium dioxide (2.5 g, 23.0 mmol) in dioxane (15 mL) at 60 C was added a solution of 8-bromo-2-methylquinoline (3 g, 13.5 mmol) in dioxane (15 mL). Resulted mixture turned dark brown after 30 min at 60 C. The heating continued until reagents were consumed. The mixture was cooled down to rt, filtered and concentrated in vacuo. The cream solid was used without additional purification(3.1 g).
	With selenium(IV) oxide; In 1,4-dioxane; water;Reflux;	General procedure: A solution of the quinaldine (1.0 equiv.) and selenium dioxide (1.7 equiv.) in dioxane/water was heated under reflux monitored by thin-layer chromatography (TLC). The solid formed was filtered and washed with dichloromethane (2 × 2 mL). The filtrates were combined and the solvent removed under reduced pressure and the resulting oily residue was purified by column chromatography in dichloromethane.

With selenium(IV) oxide; In 1,4-dioxane;Inert atmosphere; Reflux;

Add 1.1 molar equivalent of crotonaldehyde to the hydrochloric acid solution of 2-bromoaniline, Reflux overnight at 100C, add 1 molar equivalent of zinc chloride to the aqueous phase obtained after adding ether at room temperature, The obtained yellow solid was washed once with isopropanol and hydrochloric acid, Add water and ammonia water in a volume ratio of 3:1, stir, add ether, and remove the organic phase to obtain 8-bromo-2-methylquinoline. Under nitrogen atmosphere, 8-bromo-2-methylquinoline and 1 molar equivalent of selenium dioxide were refluxed overnight in dioxane, the reaction solution was suction filtered at room temperature, and the filtrate was concentrated to obtain 8-Bromo-2quinolinecarboxaldehyde. Under a nitrogen atmosphere, dissolve the substituted aniline in toluene, add 1-1.5 molar equivalents of trimethylaluminum at room temperature, reflux for 4-6 hours, add the toluene solution of 8-bromo-2quinolinecarboxaldehyde, and reflux for 8- 12 hours; A 5% NaOH aqueous solution was added, the organic phase was dried, and after the organic solvent was removed under reduced pressure, a small amount of methanol solvent was added to obtain a yellow solid, that is, the imine intermediate. Under a nitrogen atmosphere, differently substituted imine intermediates and 1 molar equivalent of differently substituted mercaptans were coupled to synthesize ligands under palladium catalysis. Under nitrogen atmosphere, weigh the ligand (0.429g, 1.1mmol), Add 20mL of dry dichloromethane to dissolve, weigh [CrCl3(THF)3] (0.371g, 1mmol), add 20mL of dry dichloromethane, introduce the ligand solution into the latter, stir for 12 hours to obtain a green suspension liquid. Concentrate to 5-10 mL, add 5 mL of dry ether, filter, and then add 5 mL of dry ether to wash once, filter to obtain 0.46 g of green powder Cr1 compound, with a yield of 85%.

References: [1]Angewandte Chemie - International Edition,2022,vol. 61.
Angew. Chem.,2022,vol. 134.
[2]Angewandte Chemie - International Edition,2019,vol. 58,p. 16831 - 16834.
Angew. Chem.,2019,vol. 131,p. 16987 - 16990,4.
[3]Chemical Communications,2010,vol. 46,p. 6554 - 6556.
[4]Patent: CN112608336,2021,A .Location in patent: Paragraph 0045-0047.
[5]Patent: WO2013/5057,2013,A1 .Location in patent: Page/Page column 97.
[6]Journal of the Brazilian Chemical Society,2015,vol. 26,p. 1265 - 1273.
[7]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5021 - 5028.
[8]Chinese Journal of Chemistry,2021,vol. 39,p. 621 - 626.
[9]Patent: CN113666964,2021,A .Location in patent: Paragraph 0017-0018.

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[ 904886-25-5 ]
[ 1417632-07-5 ]