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[ CAS No. 89909-51-3 ]

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2D
Chemical Structure| 89909-51-3
Chemical Structure| 89909-51-3
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Product Details of [ 89909-51-3 ]

CAS No. :89909-51-3MDL No. :MFCD08234561
Formula : C7H8BrNO Boiling Point : 294.2±35.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :202.05Pubchem ID :44718432
Synonyms :

Computed Properties of [ 89909-51-3 ]

TPSA : 32.9 H-Bond Acceptor Count : 1
XLogP3 : 2 H-Bond Donor Count : 1
SP3 : 0.29 Rotatable Bond Count : 1

Safety of [ 89909-51-3 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89909-51-3 ]

  • Upstream synthesis route of [ 89909-51-3 ]
  • Downstream synthetic route of [ 89909-51-3 ]

[ 89909-51-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 2199-58-8 ]
  • [ 89909-51-3 ]
YieldReaction ConditionsOperation in experiment
92% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethaneHeating / reflux General procedure 6: To a suspension or solution of the starting pyrrole (1 eq. ) in CC14 is added NBS (1.05 eq. ) followed by benzoyl-peroxide (0.025 eq. ) under argon. The mixture is then heated to reflux and the reaction is followed by LC/MS. The crude mixture is then allowed to come to room temperature and cooled in an ice bath. A precipitate forms which is filtered and purified by flash chromatography. If no precipitation occurs the solvent is removed under reduced pressure and the crude is purified by flash chromatography. Preparation 23: 4-Bromo-3, 5-dimethyl-lH-pyrrole-2-carbaldehyde The general procedure 6 was followed using 3, 5-dimethyl-lH-pyrrole-2-carbaldehyde (8 g, 65 mmoles), NBS (12.16 g, 68.3 mmoles) and benzoyl-peroxide (394 mg, 1.63 mmole) in CC14 (300 mL). After purification 11.9 g of 4-bromo-3, 5-dimethyl-lH-pyrrole-2-carbaldehyde were obtained as a dark solid (92percent yield). 1H NMR (DMSO-d6) 8 12.06 (br, lH), 9.50 (s, lH), 2.22 (s, 3H), 2.19 (s, 3H).
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 17, p. 5412 - 5414
[2] Patent: WO2005/58309, 2005, A1, . Location in patent: Page/Page column 62
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 18, p. 7286 - 7309
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