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MilliporeSigma

548030

Sigma-Aldrich

3-Bromo-4-methylpyridine

96%

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About This Item

Fórmula empírica (notación de Hill):
C6H6BrN
Número de CAS:
Peso molecular:
172.02
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

96%

refractive index

n20/D 1.56 (lit.)

bp

199-200 °C (lit.)

density

1.549 g/mL at 25 °C (lit.)

SMILES string

Cc1ccncc1Br

InChI

1S/C6H6BrN/c1-5-2-3-8-4-6(5)7/h2-4H,1H3

InChI key

GSQZOLXWFQQJHJ-UHFFFAOYSA-N

Application

3-Bromo-4-methylpyridine may be used as a building block in the preparation of:
  • substituted 4-(2,2-diphenylethyl)pyridine-N-oxides for use as potent phosphodiesterase type 4 (PDE4) inhibitors
  • benzodiazepine site ligands bearing tricyclic pyridone moiety for human GABAA receptor
  • a novel isomer of ascididemin
  • 3-bromopyridine-4-carbonitrile

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

174.9 °F - closed cup

flash_point_c

79.4 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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James Crawforth et al.
Bioorganic & medicinal chemistry letters, 14(7), 1679-1682 (2004-03-18)
A series of tricyclic pyridones has been evaluated as benzodiazepine site ligands with functional selectivity for the alpha(3) over the alpha(1) containing subtype of the human GABA(A) receptor ion channel. This investigation led to the identification of a high affinity
Richard Frenette et al.
Bioorganic & medicinal chemistry letters, 12(20), 3009-3013 (2002-09-25)
A detailed SAR study directed toward the optimization of pharmacokinetic parameters for analogues of L-791,943 is reported. The introduction of a soft metabolic site on this structure permitted the identification of L-826,141 as a potent phosphodiesterase type 4 (PDE4) inhibitor
Condensed heteroaromatic ring systems. XV. Synthesis of pyranopyridinones from halopyridinecarbonitriles.
Sakamoto T, et al.
Chemical & Pharmaceutical Bulletin, 36(5), 1890-1894 (1988)
Ida Nymann Petersen et al.
Chemical communications (Cambridge, England), 48(72), 9092-9094 (2012-08-07)
A new and convergent synthesis of ascididemin is presented. Using an anionic cascade ring closure as the key step, this natural product is obtained in 45% overall yield in just 6 steps starting from 2'-fluoroacetophenone. This new approach was extended

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