[ CAS No. 4023-81-8 ]

Name: 4023-81-8|1-(4-Bromophenyl)butane-1,3-dione|98%
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Quality Control of [ 4023-81-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 4023-81-8 ]

CAS No. :	4023-81-8	MDL No. :	MFCD04619579
Formula :	C₁₀H₉BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GIKXMINIUUFRFD-UHFFFAOYSA-N
M.W :	241.08	Pubchem ID :	432653
Synonyms :

Safety of [ 4023-81-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4023-81-8 ]

* 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 [ 4023-81-8 ]

[ 4023-81-8 ] Synthesis Path-Downstream 1~69

1
[ 4023-81-8 ]
[ 145353-53-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate; In methanol; for 2h;Reflux;	Add a 100 ml round bottom flask to the magnet and add 1-p-bromophenylbutane-1,3-dione inward. (4.82g, 20mmol, 1.0eq) And hydrazine hydrate (1.1g, 20mmol, 1.0eq), then add methanol 50 ml, heated under reflux for 2 h, extracted with ethyl acetate Silica gel column chromatography to give 3-methyl-5-p-bromophenyl 1-hydropyrazole;

Reference： [1]Justus Liebigs Annalen der Chemie,1927,vol. 458,p. 209
[2]Patent: CN108203408,2018,A .Location in patent: Paragraph 0027

2
[ 99-90-1 ]
[ 141-78-6 ]
[ 4023-81-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; at 20℃;Cooling with ice;	Add a 100 ml round bottom flask to the magnetizer and add sodium hydride inward. (0.88 g, 22 mmol, purity 60%, 1.1 eq), then 50 ml of ethyl acetate was added under ice bath. Slowly adding p-bromoacetophenone (3.98g, 20mmol, 1.0eq), after 30min in ice bath, react at room temperature for more than 10h, TLC plate was monitored and the reaction was completed and quenched with 10% ammonium chloride. Extraction with ethyl acetate, spin-drying solvent, silica gel column chromatography to give 1-p-bromophenylbutane-1,3-dione.
	With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 12h;Inert atmosphere;	General procedure: In a 100 ml round bottom flask, substituted acetophenone (30 mmol,1 equiv) and NaH (33 mmol, 1.1 equiv) was dissolved in THF at 0 C. Thecorresponding acid ethyl ester was added and the mixture was stirred at0 C for 30 min. Then, the reaction was stirred at room temperature for12 h. After the reaction was quenched with saturated NH4Cl (50 ml) andextracted with EtOAc (2 × 100 ml), the combined organic layers werewashed with brine (50 ml), dried over Na2SO4, concentrated undervacuum and purified by column chromatography on silica gel to affordthe corresponding product 2.

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 4179 - 4188
[2]Advanced Synthesis and Catalysis,2021,vol. 363,p. 3240 - 3244
[3]Justus Liebigs Annalen der Chemie,1927,vol. 458,p. 209
[4]Journal of the Chemical Society. Perkin transactions II,1993,p. 1067 - 1071
[5]Journal of Medicinal Chemistry,2007,vol. 50,p. 1958 - 1972
[6]Angewandte Chemie - International Edition,2009,vol. 48,p. 6052 - 6054
Angewandte Chemie,2009,vol. 121,p. 6168 - 6170
[7]Journal of Organic Chemistry,2011,vol. 76,p. 332 - 334
[8]European Journal of Organic Chemistry,2015,vol. 2015,p. 320 - 324
[9]Patent: CN108203408,2018,A .Location in patent: Paragraph 0027
[10]Chemical Communications,2018,vol. 54,p. 9513 - 9516
[11]Organic Letters,2019,vol. 21,p. 6736 - 6740
[12]Chemistry - An Asian Journal,2019,vol. 14,p. 4563 - 4567
[13]Bioorganic and Medicinal Chemistry,2021,vol. 46

3
[ 4023-81-8 ]
[ 13494-47-8 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 9513 - 9516
[2]Chemische Berichte,1966,vol. 99,p. 3128 - 3147
[3]Journal of Organic Chemistry,2009,vol. 74,p. 903 - 905

4
[ 7357-70-2 ]
[ 4023-81-8 ]
[ 109273-53-2 ]
[ 94639-15-3 ]

Reference： [1]Pharmazie,1986,vol. 41,p. 827 - 830
[2]Pharmazie,1991,vol. 46,p. 51 - 52

5
[ 4023-81-8 ]
[ 98078-02-5 ]
[ 98078-33-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 229 - 234

6
[ 4023-81-8 ]
[ 98078-37-6 ]
[ 98078-29-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 229 - 234

7
[ 4023-81-8 ]
[ 95081-19-9 ]
(6-Bromo-3-methyl-4H-benzo[1,4]thiazin-2-yl)-(4-bromo-phenyl)-methanone [ No CAS ]

Reference： [1]Pharmazie,1991,vol. 46,p. 602 - 602

8
[ 4023-81-8 ]
[ 98078-35-4 ]
[ 98078-21-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 229 - 234

9
[ 4023-81-8 ]
[ 98078-36-5 ]
[ 98078-25-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 229 - 234

10
[ 4023-81-8 ]
[ 102252-93-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 2085 - 2091
[2]Organic Letters,2014,vol. 16,p. 5410 - 5413

11
[ 4023-81-8 ]
[ 137-07-5 ]
[ 124453-66-3 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 82 - 88

12
[ 4023-81-8 ]
[ 107-91-5 ]
[ 109273-56-5 ]
[ 109273-58-7 ]

Reference： [1]Pharmazie,1986,vol. 41,p. 827 - 830
[2]Journal of Chemical Research, Miniprint,1991,p. 783 - 792

13
[ 4023-81-8 ]
[ 93168-99-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In dichloromethane; at 20℃; for 0.5h;	General procedure: To a solution of 1,3-diketones 1a-g (1.0 mmol) in DCM (10 mL) was added NBS (0.177 g, 1.0 mmol) and mixture was allowed to stir at rt for 30 min. Subsequently, 2-aminopyridine 2 (0.094 g, 1.0 mmol) was added and reaction mixture was maintained at rt with stirring. The reaction was monitored with TLC. On completion of reaction (4 h), excess DCM was distilled off in vacuo and the residue was washed with aq NaHCO3 and extracted with DCM. Organic layers were combined, dried over anhyd. Na2SO4 and excess solvent was distilled off. The residual mass was recrystallized from ethanol and 7a-g was obtained in 71-81% yield.

Reference： [1]Annales Pharmaceutiques Francaises,1995,vol. 53,p. 261 - 271
[2]Tetrahedron,2016,vol. 72,p. 3832 - 3838
[3]Organic and Biomolecular Chemistry,2022,vol. 20,p. 584 - 595

14
[ 99-90-1 ]
CH₃-COOR (2a-c,f) [ No CAS ]
[ 4023-81-8 ]

Reference： [1]Synthesis,1991,p. 195 - 198

15
[ 4023-81-8 ]
[ 1441-85-6 ]
1-(3-hydroxybenzo[b]selenophen-2-yl)ethanone [ No CAS ]
(4-bromo-phenyl)-(3-hydroxy-benzo[b]selenophen-2-yl)-methanone [ No CAS ]
2-acetyl-2-(4-bromo-benzoyl)-benzo[b]selenophen-3-one [ No CAS ]

Reference： [1]Chemistry Letters,2001,p. 826 - 827

16
[ 4023-81-8 ]
[ 3306-62-5 ]
[ 862420-62-0 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 7294 - 7303

17
[ 74-85-1 ]
[ 4023-81-8 ]
[ 53498-48-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine;palladium diacetate; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at -196 - 100℃; under 15514.9 Torr; for 12.3333h;Product distribution / selectivity;	Example 1 Synthesis of 4-vinylbenzoylacetone: Dimethyl formamide (30 mL), palladium acetate (0.022 g, 0.1 mmol), tri-o-tolyl phosphine (0.060 g, 0.2 mmol), triethylamine (9.1 g, 90 mmol), 4-bromobenzoylacetone (2.41 g, 10 mmol) were added to a 100 mL Parr high pressure reactor with an inner glass liner. The solution was degassed with nitrogen for 10 minutes before the reactor was cooled to -196 C. and ethylene (1.7 g, 61 mmol) was condensed for 20 minutes. The reactor was allowed to warm to room temperature before heating to 100 C. in an oil bath. The pressure was bled off until 300 psi was achieved and the reaction was allowed to proceed for 12 hours. The reaction vessel was cooled to room temperature, the extra pressure bled, and the contents dissolved in water (50 mL) and ether (50 mL). The aqueous phase was made acidic by addition of concentrated hydrochloric acid followed by extraction with ether (2*50 mL). The combined organic phase was rinsed with saturated sodium chloride solution, and the organic phase was dried over magnesium sulfate overnight. The solution was filtered, the solvent was removed by vacuum, and the residue dissolved in chloroform (3 mL). The product was isolated by column chromatography from silica gel (Selecto, mesh size 63-200) with chloroform as eluent. The first band collected resulted in a yellow powder (1.03 g, 55% yield) upon solvent removal. 1H-NMR (200 MHz, 25 C., CDCl3): δ 16.12 (s, 1 H), 7.83 (d, 2 H), 7.45 (d, 2 H), 6.70 (dd, 1 H), 6.17 (s, 1 H), 5.82 (d, 1 H), 5.35 (d, 1 H), 2.20 (s, 3 H).

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 9036 - 9039
[2]Patent: US2006/69288,2006,A1 .Location in patent: Page/Page column 7

18
[ 6048-21-1 ]
[ 67-64-1 ]
[ 4023-81-8 ]