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548030

Sigma-Aldrich

3-Bromo-4-methylpyridine

96%

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About This Item

Empirical Formula (Hill Notation):
C6H6BrN
CAS Number:
3430-22-6
Molecular Weight:
172.02
MDL number:
MFCD00082592
UNSPSC Code:
12352100
PubChem Substance ID:
24879007
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.)

functional group

bromo

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[1]
  • benzodiazepine site ligands bearing tricyclic pyridone moiety for human GABAA receptor[2]
  • a novel isomer of ascididemin[3]
  • 3-bromopyridine-4-carbonitrile[4]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

174.9 °F - closed cup

Flash Point(C)

79.4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB3429
BCBT1604
BCBR8196V
BCBN2632V
BCBH3162V

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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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