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[ CAS No. 626-55-1 ]

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2D
Chemical Structure| 626-55-1
Chemical Structure| 626-55-1
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Product Details of [ 626-55-1 ]

CAS No. :626-55-1MDL No. :MFCD00006373
Formula : C5H4BrN Boiling Point : 168.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :158.00Pubchem ID :12286
Synonyms :

Computed Properties of [ 626-55-1 ]

TPSA : 12.9 H-Bond Acceptor Count : 1
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 626-55-1 ]

Signal Word:DangerClass:3
Precautionary Statements:P261-P305+P351+P338UN#:1993
Hazard Statements:H225-H302-H315-H319-H335Packing Group:
GHS Pictogram:

Application In Synthesis of [ 626-55-1 ]

  • Upstream synthesis route of [ 626-55-1 ]
  • Downstream synthetic route of [ 626-55-1 ]

[ 626-55-1 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 626-55-1 ]
  • [ 139585-50-5 ]
  • [ 1003-09-4 ]
  • [ 581-46-4 ]
  • [ 1762-41-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 6, p. 1768 - 1773
  • 2
  • [ 626-55-1 ]
  • [ 1120-90-7 ]
YieldReaction ConditionsOperation in experiment
98% With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 18 h; Inert atmosphere; Schlenk technique Aromatic Finkelstein Reaction; General ProcedureThe reaction was carried out under argon using standard Schlenktechniques due to the moisture and oxygen sensitivity of the copper(I) iodide. A two-neck pear-shaped flask equipped with a refluxcondenser was charged with the (het)aryl bromide starting material,NaI (2 equiv per bromine to exchange), and CuI (5 molpercent per bromineto exchange). N,N′-Dimethylethylenediamine (L1) or N,N′-dimethyl-1,2-cyclohexanediamine (L2) (10 molpercent per bromine toexchange) and anhydrous 1,4-dioxane (0.5 mL per 1 mmol NaI)were added. The resulting suspension was heated to 110 °C for 18h. After cooling to r.t., the mixture was poured into aq 25percent NH3 solution.The blue solution was diluted to a doubled volume with H2Oand was extracted three times with CH2Cl2. In the case of the 2,2′-bipyridines, the combined organic phases were additionally washedwith aq EDTA solution. Otherwise, the combined organic phaseswere solely washed with brine and dried with MgSO4. The solventwas removed under reduced pressure to give the desired product inpure form. If needed, the crude product can be purified by columnchromatography or recrystallization.
Reference: [1] Synthesis (Germany), 2014, vol. 46, # 8, p. 1085 - 1090
[2] Tetrahedron Letters, 1999, vol. 40, # 23, p. 4339 - 4342
[3] Tetrahedron, 2000, vol. 56, # 10, p. 1349 - 1360
[4] Chemistry - A European Journal, 2010, vol. 16, # 41, p. 12425 - 12433
[5] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1731 - 1737
  • 3
  • [ 626-55-1 ]
  • [ 110-86-1 ]
  • [ 1120-90-7 ]
Reference: [1] Synthesis, 2009, # 22, p. 3823 - 3827
  • 4
  • [ 626-55-1 ]
  • [ 10201-71-5 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 1147,1148
  • 5
  • [ 626-55-1 ]
  • [ 4595-59-9 ]
  • [ 497-19-8 ]
  • [ 109-94-4 ]
  • [ 10070-92-5 ]
YieldReaction ConditionsOperation in experiment
35% With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane; water 1)
Preparation of pyrimidine-5-carbaldehyde
A solution of 5-bromo-pyrimidine (5 g, 31.4 mmol, 1.0 eq.) in anhydrous THF (300 mL) was placed under an argon atmosphere in a three-necked round bottom flask equipped with a low-temperature thermometer.
The mixture was cooled to -100°C in a EtOH/N2(1) bath.
To the solution of 5-bromopyridine was added a solution of n-BuLi in hexane (20 mL, 1.6 M, 32.5 mmol, 1.0 eq.).
The resulting mixture was stirred for 20 minutes at 100°C and the organolithium that formed was trapped with a solution of ethyl formate (2.7 mL, 33.5 mmol, 1.1 eq.) in THF (10 mL).
The reaction was stirred for another 20 minutes at 100°C and quenched with a solution of hydrochloric acid in ether (17 mL, 2M, 34 mmol).
Then, the cold bath was removed and the mixture stirred at room temperature for 1 hour.
The solution was concentrated under reduced pressure, and then treated with water and saturated aqueous sodium carbonate (10 mL).
The mixture was extracted with dichloromethane and the organic layer was dried over MgSO4.
The solvent was removed under reduced pressure and the residue purified by silica gel flash-column chromatography (eluent: CH2Cl2/AcOEt, 60:40 to 50:50) to afford pyrimidine-5-carbaldehyde as beige crystals (1.2 g, 35percent).
Reference: [1] Patent: EP2266562, 2010, A1,
  • 6
  • [ 626-55-1 ]
  • [ 626-05-1 ]
  • [ 106047-28-3 ]
Reference: [1] Synlett, 2002, # 6, p. 1008 - 1010
[2] Synthesis, 2009, # 22, p. 3823 - 3827
  • 7
  • [ 626-55-1 ]
  • [ 1014631-89-0 ]
Reference: [1] Patent: US2011/118290, 2011, A1,
[2] Patent: US2012/95023, 2012, A1,
  • 8
  • [ 626-55-1 ]
  • [ 1062368-71-1 ]
  • [ 1062368-70-0 ]
Reference: [1] Patent: WO2011/15343, 2011, A1,
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