80500-27-2|(4-Methyl-3-nitrophenyl)boronic acid| Ambeed

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Quality Control of [ 80500-27-2 ] Purity: 98% SDS Specification

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Product Details of [ 80500-27-2 ]

CAS No. :	80500-27-2
Formula :	C₇H₈BNO₄
M.W :	180.95
SMILES Code :	CC1=C(C=C(C=C1)B(O)O)[N+]([O-])=O
MDL No. :	MFCD00191550
InChI Key :	OASVXBRTNVFKFS-UHFFFAOYSA-N
Pubchem ID :	2773515

Safety of [ 80500-27-2 ]

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

Application In Synthesis of [ 80500-27-2 ]

* 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 [ 80500-27-2 ]

[ 80500-27-2 ] Synthesis Path-Downstream 1~35

1
[ 5720-05-8 ]
[ 80500-27-2 ]

References: [1]Journal of the American Chemical Society,1932,vol. 54,p. 4415,4418.

2
[ 80500-27-2 ]
[ 22237-12-3 ]

References: [1]Green Chemistry,2020,vol. 22,p. 1301 - 1307.
[2]Journal of the American Chemical Society,1932,vol. 54,p. 4415,4418.

3
[ 80500-27-2 ]
[ 80500-28-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3416 - 3419.
[2]Arkiv foer Kemi,1957,vol. 10,p. 497,503.

4
[ 80500-27-2 ]
[ 98-88-4 ]
[ 79482-00-1 ]

References: [1]Russian Chemical Bulletin,1997,vol. 46,p. 1631 - 1632.
[2]Tetrahedron Letters,1999,vol. 40,p. 3057 - 3060.
[3]Russian Chemical Bulletin,2004,vol. 53,p. 364 - 369.

5
[ 80500-27-2 ]
Merrifield resin-CH₂O(CH₂)4S-CH₂C₆H₄-C(O)OEt-4 [ No CAS ]
4-(4-methyl-3-nitro-benzyl)-benzoic acid [ No CAS ]

References: [1]Angewandte Chemie - International Edition in English,2000,vol. 39,p. X1679-1683.

6
[ 80500-27-2 ]
Merrifield resin-CH₂O(CH₂)4S-CH₂C₆H₄-Me-4 [ No CAS ]
1-Methyl-4-(4-methyl-benzyl)-2-nitro-benzene [ No CAS ]

References: [1]Angewandte Chemie - International Edition in English,2000,vol. 39,p. X1679-1683.

7
[ 3622-23-9 ]
[ 80500-27-2 ]
6-chloro-2-(4-methyl-3-nitrophenyl)benzo[d]thiazole [ No CAS ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 3091 - 3094.

8
[ 108-86-1 ]
[ 80500-27-2 ]
[ 80726-54-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 80℃; for 4h;	[0387] (a) Preparation of 1-methyl-2-nitro-4-phenylbenzene. Bromobenzene (Aldrich) (3.3 mL, 29.6 mmol), 3-nitro-4-methylbenzene boronic acid (Avocado) (5.11 g, 28.3 mmol), and 2M Na2CO3 (63 mL, 126.0 mmol) were dissolved in 100 mL of toluene/15 mL of EtOH. Pd(PPh3)4 (2.04 g, 1.8 mmol) was added and the mixture was stirred at 80 C. for 4 h. The reaction was cooled to RT, and partitioned between EtOAc:H2O. The aqueous layer was extracted with EtOAc (3×). The combined EtOAc layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The crude solid was purified by flash chromatography on silica gel using 98:2 Hexane:EtOAc to afford a light orange solid.

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 6574 - 6595.
[2]RSC Advances,2021,vol. 11,p. 37684 - 37699.
[3]Patent: US2003/229068,2003,A1 .Location in patent: Page 31.

9
[ 80500-27-2 ]
acetic acid-(5-dihydroxyboranyl-2-methyl-anilide) [ No CAS ]

References: [1]Journal of the American Chemical Society,1932,vol. 54,p. 4415,4418.

10
[ 80500-27-2 ]
benzoic acid-(5-dihydroxyboranyl-2-methyl-anilide) [ No CAS ]

References: [1]Journal of the American Chemical Society,1932,vol. 54,p. 4415,4418.

11
[ 4294-57-9 ]
[ 80500-27-2 ]

References: [1]Journal of the American Chemical Society,1932,vol. 54,p. 4415,4418.

12
[ 4595-59-9 ]
[ 80500-27-2 ]
[ 333792-86-2 ]

Yield	Reaction Conditions	Operation in experiment
84.2%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃; for 24h;	To a suspension of 5-bromopyrimidine (1.59 g), 4-methyl-3-nitrophenylboronic acid (2.35 g) and tetrakis(triphenylphosphine)-palladium (578 mg) in 1,2-dimethoxyethane (20 ml) was added an aqueous solution of sodium carbonate (2M, 13 ml) followed by stirring at 80 C. for 24 hours.. The mixture was diluted with dichloromethane and washed with water and brine.. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure.. The residue was triturated with methanol.. The resulting precipitated was collected by filtration, washed with methanol and diisopropyl ether and dried to give 5-(4-methyl-3-nitrophenyl)-pyrimidine (918 mg, 84.2%).NMR (CDCl3, δ): 2.56 (3H, s), 7.68 (1H, d, J=8.0 Hz), 8.10 (1H, dd, J=8.0 Hz, 1.8 Hz), 8.42 (1H, d. J=1.8 Hz), 9.23 (3H, s) APCI-Mass m/z: 216 (M+1).

References: [1]Patent: US6770667,2004,B1 .Location in patent: Page column 11.

13
[ 4926-28-7 ]
[ 14221-01-3 ]
[ 80500-27-2 ]
[ 67-63-0 ]
[ 289470-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In 1,2-dimethoxyethane;	Preparation 75 To a suspension of 2-bromo-4-methylpyridine (5.16 g), 4-methyl-3-nitrophenylboronic acid (7.06 g) and tetrakis(triphenylphosphine)-palladium (1.73 g) in 1,2-dimethoxyethane (100 ml) was added 2M aqueous solution of sodium carbonate (39 ml). The mixture was stirred at 80 C. for 12 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. 2-Propanol was added to the residue. The precipitate was collected by filtration and dried under reduced pressure to give 4-(4-methylpyridin-2-yl)-2-nitrotoluene (4.54 g). 1H-NMR (CDCl3): δ2.44(3H,s), 2.65(3H,s), 7.11(1H,d,J=4.3 Hz), 7.43(1H,d,J=8.0 Hz), 7.58(1H,s), 8.17(1H,dd,J=8.0 Hz,1.9 Hz), 8.55(1H,d,J=5.0 Hz), 8.58(1H,d,J=1.9 Hz)

References: [1]Patent: US6521643,2003,B1 .

14
[ 14221-01-3 ]
[ 89488-29-9 ]
[ 80500-27-2 ]
[ 289470-02-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In methanol; 1,2-dimethoxyethane;	Preparation 72 To a suspension of 2-bromo-4-methoxypyridine (2.5 g), 4-methyl-3-nitrophenylboronic acid (3.37 g) and tetrakis(triphenylphosphine)-palladium (768 mg) in 1,2-dimethoxyethane (100 ml) was added 2M aqueous solution of sodium carbonate (18.6 ml). The mixture was stirred at 80 C. for 7 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. Methanol was added to the residue. The precipitate was collected by filtration and dried under reduced pressure to give 4-(4-methoxypyridin-2-yl)-2-nitrotoluene (3.09 g). 1H-NMR (CDCl3): δ2.65(3H,s), 3.93(3H,s), 6.82(1H,dd,J=5.7 Hz,2.4 Hz), 7.25(1H,d,J=2.7 Hz), 7.43(1H,d,J=8.0 Hz), 8.14(1H,dd,J=8.0 Hz,2.0 Hz), 8.53(1H,d,J=5.8 Hz), 8.58(1H,d,J=2.0 Hz)

References: [1]Patent: US6521643,2003,B1 .

15
[ 14221-01-3 ]
[ 2042-37-7 ]
[ 80500-27-2 ]
[ 497-19-8 ]
4-methyl-3-nitrobiphenyl-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	Example 6 4-Methyl-3-nitro-phenyl boronic acid (obtained as described in J.A.C.S., 1932, 54 , 4415) (3.0g) was added to a solution of 2-bromobenzonitrile (2.73 g) and tetrakis(triphenylphosphine)palladium(O) (0.525 g) in a mixture of 2M aqueous sodium carbonate (15 ml) and toluene (38 ml). The mixture was heated at 100C for 16 hours, then allowed to cool. The mixture was extracted with ethyl acetate and the extracts washed with saturated sodium chloride solution and dried. The solvent was removed by evaporation and the resultant light brown solid recrystallized from ethyl acetate to give 4--methyl-3--nitrobiphenyl-2-carbonitrile as a solid (3.13 g), m.p. 155-156C; NMR(CDCl3): 2.68(s, 3H), 7.44-7.86(complex m, 6H), 8.14(d, 1H); microanalysis, found: C, 70.3; H, 4.0; N, 11.8%; C14H10N2O2 requires: C, 70.6; H, 4.2; N, 11.8%.

References: [1]Patent: EP470795,1992,A1 .

16
[ 1003034-18-1 ]
[ 80500-27-2 ]
[ 1003034-78-3 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 9140 - 9143.

17
[ 5720-05-8 ]
[ 7697-37-2 ]
[ 80500-27-2 ]

References: [1]Journal of the American Chemical Society,1932,vol. 54,p. 4415 - 4424.
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: B: B-Verb.13, 4.7.2.5, page 209 - 219.

18
[ 36437-19-1 ]
[ 80500-27-2 ]
[ 1248589-25-4 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 5005 - 5008.

19
[ 1269408-12-9 ]
[ 80500-27-2 ]
C₂₈H₃₃N₅O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 140℃; for 0.25h;Microwave irradiation;	PdCl2(dppf) (0.01 - 0.1 equiv.) was added to a mixture of 1 , 1 -dimethylethyl (2S)-2-([(3 S)-I -(4-bromo-2-cyanophenyl)-3 -pyrrolidinyl] amino } carbonyl)- 1 - pyrrolidinecarboxylate (1 equiv.), an appropriate boronic acid (1.05 equiv.), and K2CO3 (3 equiv.) in 1,4-dioxane and water in a microwave vial. The vial was capped and the reaction mixture was heated in a microwave reactor at 140 0C (high absorbance) for 15 min. The reactions were transferred into 20 mL vials, and the 1,4-dioxane was blown off using nitrogen at 55 0C. Water and CH2Cl2 were added to the reaction mixture. The mixture was transferred to a hydrophobic frit and the layers were separated. The aqueous layer was extracted with CH2Cl2. The solvent was evaporated using nitrogen at 50 0C, the residue was dissolved in 1.0 mL DMSO and purified by reverse phase HPLC to afford the desired compound VI.

References: [1]Patent: WO2011/25799,2011,A1 .Location in patent: Page/Page column 156-157; 160.

20
[ 1318261-52-7 ]
[ 80500-27-2 ]
[ 1318261-66-3 ]

References: [1]Organic Letters,2011,vol. 13,p. 4236 - 4239.

21
[ 22037-28-1 ]
[ 80500-27-2 ]
[ 1303573-60-5 ]