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[ CAS No. 80500-27-2 ] {[proInfo.proName]}

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Chemical Structure| 80500-27-2
Chemical Structure| 80500-27-2
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Product Details of [ 80500-27-2 ]

CAS No. :80500-27-2 MDL No. :MFCD00191550
Formula : C7H8BNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :OASVXBRTNVFKFS-UHFFFAOYSA-N
M.W : 180.95 Pubchem ID :2773515
Synonyms :
Chemical Name :(4-Methyl-3-nitrophenyl)boronic acid

Safety of [ 80500-27-2 ]

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

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   1~16

  • 1
  • [ 5720-05-8 ]
  • [ 80500-27-2 ]
  • 2
  • [ 80500-27-2 ]
  • [ 22237-12-3 ]
  • 3
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  • [ 80500-28-3 ]
  • 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 ]
  • 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 ]
  • 7
  • [ 3622-23-9 ]
  • [ 80500-27-2 ]
  • 6-chloro-2-(4-methyl-3-nitrophenyl)benzo[d]thiazole [ No CAS ]
  • 8
  • [ 108-86-1 ]
  • [ 80500-27-2 ]
  • [ 80726-54-1 ]
YieldReaction ConditionsOperation 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.
  • 9
  • [ 80500-27-2 ]
  • acetic acid-(5-dihydroxyboranyl-2-methyl-anilide) [ No CAS ]
  • 10
  • [ 80500-27-2 ]
  • benzoic acid-(5-dihydroxyboranyl-2-methyl-anilide) [ No CAS ]
  • 11
  • [ 4294-57-9 ]
  • [ 80500-27-2 ]
  • 12
  • [ 4595-59-9 ]
  • [ 80500-27-2 ]
  • [ 333792-86-2 ]
YieldReaction ConditionsOperation 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).
  • 13
  • [ 4926-28-7 ]
  • [ 14221-01-3 ]
  • [ 80500-27-2 ]
  • [ 67-63-0 ]
  • [ 289470-05-9 ]
YieldReaction ConditionsOperation 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)
  • 14
  • [ 14221-01-3 ]
  • [ 89488-29-9 ]
  • [ 80500-27-2 ]
  • [ 289470-02-6 ]
YieldReaction ConditionsOperation 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)
  • 15
  • [ 14221-01-3 ]
  • [ 2042-37-7 ]
  • [ 80500-27-2 ]
  • [ 497-19-8 ]
  • 4-methyl-3-nitrobiphenyl-2-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation 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%.
  • 16
  • [ 1003034-18-1 ]
  • [ 80500-27-2 ]
  • [ 1003034-78-3 ]
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