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5-Bromo-2-hydroxyisophthalaldehyde
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[ CAS No. 109517-99-9 ] {[proInfo.proName]}

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Chemical Structure| 109517-99-9
Chemical Structure| 109517-99-9
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CAS No. :109517-99-9 MDL No. :MFCD01142867
Formula : C8H5BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 229.03 Pubchem ID :-
Synonyms :

Safety of [ 109517-99-9 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 109517-99-9 ]

* 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 [ 109517-99-9 ]

[ 109517-99-9 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 3328-69-6 ]
  • [ 109517-99-9 ]
  • C24H23BrO6 [ No CAS ]
  • C24H22Br2O6 [ No CAS ]
Reference： [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 204 - 209
  • 2
  • [ 109517-99-9 ]
  • [ 20439-47-8 ]
  • [ 581100-41-6 ]
YieldReaction ConditionsOperation in experiment
72% In dichloromethane at 0 - 20℃; for 48h; 56 Example 56 [0349] Preparation of hexamer: N N N N Br w Br I OH Hp i N N Mu N N tNtN b Br Hexamer la-Br Br [0350] To 0.300 g (1R, 2R)- (-)-TRANS-1, 2-DIAMINOCYCLOHEXANE (2.63 mmol) in 5 mL CH2C12 at 0° C was added 0.600 g of 2, 6-diformyl-4-bromophenol (2.62 mmol) in 5 mL OF CH2C12. The yellow solution was allowed to warm to room temperature and stirred for 48 hours. The reaction solution was decanted, and added to 150 mL of methanol. After standing for 30 minutes, the yellow precipitate was collected, washed with methanol, and air-dried (0.580 g; 72% yield).
In dichloromethane at 20℃; for 24h; Inert atmosphere;
With air In dichloromethane at 20℃; for 24h; Inert atmosphere;
Reference： [1]Current Patent Assignee: COVALENT PARTNERS - WO2005/30711, 2005, A2 Location in patent: Page/Page column 130
[2]Petryk, Małgorzata; Troc, Anna; Gierczyk, Błazej; Danikiewicz, Witold; Kwit, Marcin [Chemistry - A European Journal, 2015, vol. 21, # 29, p. 10318 - 10321]
[3]Janiak, Agnieszka; Petryk, Małgorzata; Barbour, Leonard J.; Kwit, Marcin [Organic and Biomolecular Chemistry, 2015, vol. 14, # 2, p. 669 - 673]
  • 3
  • [ 112-41-4 ]
  • [ 109517-99-9 ]
  • [ 581100-11-0 ]
YieldReaction ConditionsOperation in experiment
51% With tetrabutylammomium bromide; sodium hydrogencarbonate; lithium chloride In N,N-dimethyl-formamide at 82℃; for 40.1667h; 3 2,6-Diformyl-4-(dodecen-1-yl)phenol 2,6-Diformyl-4-bromophenol (1.00 g, 4.37 mmol), 1-dodecene (4.8 mL, 21.7 mmol), 1.40 g tetrabutylammonium bromide (4.34 mmol), 0.50 g NaHCO3 (5.95 mmol), 1.00 g LiCl (23.6 mmol) and 0.100 g palladium diacetate (Pd(OAc)2) (0.45 mmol) were combined in 30 mL degassed anhydrous dimethylformamide (DMF). The mixture was sparged with argon for 10 min and then sealed in a pressure vial which was warmed to 82[deg.] C. and held for 40 h. The crude reaction mixture was partitioned between CH2Cl2 and 0.1 M HCl solution. The organic layer was washed with 0.1 M HCl (2*), brine (2*), and saturated aqueous NaHCO3 (2*), dried over MgSO4 and concentrated under reduced pressure. The dark yellow oil was purified by column chromatography on silica gel (25% hexanes in Et2O) to give 0.700 g (51%) of the title compound as primarily the Z isomer. [0124] <1>H NMR (400 MHz, CDCl3) [delta]11.50 (s, 1 H, OH), 10.21 (s, 2 H, CHO), 7.95 (s, 2 H, ArH), 6.38 (d, 1 H, vinyl), 6.25 (m, 1 H, vinyl), 2.21 (m, 2 H, allylic), 1.30-1.61 (m, 16 H, aliphatic), 0.95 (t, 3 H, J=7.0 Hz, CH3). [0125] MS (FAB): Calcd. for C20H27O3 315.20; found 315.35 [M-H].
Reference： [1]Current Patent Assignee: COVALENT PARTNERS - US2003/199688, 2003, A1 Location in patent: Page/Page column 29
  • 4
  • [ 109517-99-9 ]
  • [ 21436-03-3 ]
  • C42H45Br3N6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% In methanol; acetonitrile; at 20℃; for 24h; To a solution of (S,S)-(+)-1,2-diaminocyclohexane (0.38 g, 3.3 mmol) in CH3CN (160 ml) was added a solution of 2,6-diformyl-4-bromophenol (0.69 g, 3.0 mmol) in MeOH (60 ml). The mixture was stirred at room temperature for 24 h. The Schiff-base macrocycle separated as a yellow solid, was filtered, and recrystallized from CH2Cl2-CH3CN. (S,S,S,S,S,S)-1f: yellow prisms, mp 228-232 C. Yield 0.79 g (86%). [alpha]D = +192 (c 0.1, CH2Cl2). IR: 3411 cm-1 (OH), 1637 cm-1 (CN). 1H NMR (CDCl3) delta 14.14 (s, OH), 8.58 (s, HCN), 8.18 (s, HCN), 7.88 (s, Ar), 7.24 (s, Ar), 3.27-3.49 (m, N-CH), 1.46-2.01 (m, -CH2-), 1.11(d, J = 8 Hz, CH3). 13C NMR (CDCl3) delta 24.4, 31.1, 33.7, 73.0, 75.7, 118.5, 122.8, 126.1, 130.6, 140.1, 156.1, 159.3, 164.0. MS (ESI) m/z: found 923.33[M+H]+, calcd 923.11.
Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 205 - 208
  • 5
  • [ 4807-55-0 ]
  • [ 109517-99-9 ]
  • 5-bromo-2-hydroxy-3-[(Z)-(3-methyl-4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With sodium methylate; acetic acid at 90℃; for 0.333333h; Microwave irradiation; Synthesis of 17a-f: General procedure: To a 5 mL glass tube, sodium methoxide (1 mmol) was added to the mixture of 2,6-diformylphenols 15a-c (0.5 mmol) and rhodanines 9a,c (1.1 mmol) in acetic acid (2 mL). The reaction tube was placed inside the cavity of the microwave, operated at power 200-250 W. The tube was irradiated in the microwave oven for appropriate time and temperature (according to Table 3). The work-up and purification step was the same used for conventional thermal heating.
Reference： [1]Arafa, Wael A. A.; Shaker, Raafat M.; Rabeh, Saleh A. [Heterocycles, 2016, vol. 92, # 7, p. 1224 - 1243]
  • 6
  • [ 109517-99-9 ]
  • [ 66892-34-0 ]
  • (3E,3'E)-3,3'-((5-bromo-2-hydroxy-1,3-phenylene)bis(methanylylidene))bis(6-fluorochroman-4-one) [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With C8H17N2O(1+)*C2H3O2(1-) In water at 20℃; for 0.166667h; Sonication; Green chemistry;
Reference： [1]Arafa, Wael A. A. [Journal of Heterocyclic Chemistry, 2018, vol. 55, # 2, p. 456 - 464]
  • 7
  • [ 20582-55-2 ]
  • [ 109517-99-9 ]
  • C15H13NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydrogencarbonate; isobutyric Acid; copper(I) bromide; In toluene; at 110℃; for 16.0h; Weigh N2 (110g, 480.3mmol, 1.0eq), N3 (98.7g, 576.4mmol, 1.2eq), appropriate amount of Pd (dppf) Cl2 (0.5g), cuprous bromide (5.0g), potassium bicarbonate (10.0g), isobutyric acid (2.0g), and toluene (500ml) were added to a three-necked flask, and the temperature was raised to 110 C for 16 hours. After TLC monitored the reaction of the raw material N2, the temperature was lowered to room temperature. DCM (500ml) was rinsed, and the organic phase was dried and spin-dried to obtain a crude product. The crude product was purified by column purification (petroleum ether: ethyl acetate = 5: 1) to obtain pure A (107g), purity: 98.8%, yield 70%.
Reference： [1]Patent: CN110642804,2020,A .Location in patent: Paragraph 0024; 0025; 0027; 0030; 0032; 0035; 0037

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