| Identification | Back Directory | [Name]
Pyridine, 2-bromo-5-(bromomethyl)- (9CI) | [CAS]
101990-45-8 | [Synonyms]
2-Bromo-5-(bromomethyl)
2-Bromo-5-(bromomethyl)pyridine
6-Bromo-3-pyridylmethyl bromide
3-Pyridineacetonitrile, 6-bromo-
2-Bromo-5-(bromomethyl)pyridine 96%
Pyridine, 2-bromo-5-(bromomethyl)- (9CI) | [Molecular Formula]
C6H5Br2N | [MDL Number]
MFCD11656267 | [MOL File]
101990-45-8.mol | [Molecular Weight]
250.919 |
| Chemical Properties | Back Directory | [Melting point ]
60-65°C | [Boiling point ]
296.9±25.0 °C(Predicted) | [density ]
1.955 | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
Chloroform (Soluble), Methanol (Slightly) | [form ]
Solid | [pka]
-0.12±0.10(Predicted) | [color ]
White to Pale Yellow | [InChIKey]
CRRMIKBAPPOPNW-UHFFFAOYSA-N |
| Hazard Information | Back Directory | [Uses]
2-Bromo-5-(bromomethyl)pyridine is a useful research chemical compound used in the synthesis of methyleneimidazole substituted biaryls as inhibitors of human 17α-hydroxylase-17,20-lyase. | [Synthesis]
General procedure for the synthesis of 2-bromo-5-(bromomethyl)pyridine from 2-bromo-5-methylpyridine:
1. dissolve 12 g (70 mmol) of 2-bromo-5-methylpyridine in 100 mL of 1,2-dichloroethane.
2. 16 g (91 mmol) of N-bromosuccinimide and 0.40 g (2.4 mmol) of 2,2'-azobis(isobutyronitrile) were added to the above solution.
3. The reaction mixture was stirred at 85 °C for 15 min.
4. Upon completion of the reaction, water was added to the reaction mixture and the organic layer was separated.
5. The organic layer was dried with anhydrous magnesium sulfate and subsequently concentrated under vacuum.
6. The resulting residue was purified by silica gel column chromatography with an eluent ratio of solvent-free hexane:ethyl acetate = 10:1 to 9:1 (v/v).
7. The fraction containing the target compound was collected and concentrated in vacuo to give 15 g of 2-bromo-5-(bromomethyl)pyridine as white powder in 89% yield. 8.
8. The Rf value of the product was 0.63 (n-hexane:ethyl acetate=9:1, v/v).
9. Mass spectrum (CI, m/z): 250, 252, 254 (M++1). 10.
10. 1H-NMR spectrum (CDCl3, δ ppm): 4.42 (s, 2H), 7.49 (d, J=8.3 Hz, 1H), 7.61 (dd, J1=8.3 Hz, J2=2.7 Hz, 1H), 8.39 (d, J=2.7 Hz, 1H). | [References]
[1] Patent: EP1679308, 2006, A1. Location in patent: Page/Page column 35
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1992 - 2010
[3] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 1, p. 2 - 6
[4] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 8, p. 559 - 564
[5] Patent: WO2012/52540, 2012, A1. Location in patent: Page/Page column 47; 48-49 |
|
| Company Name: |
China Langchem Inc.
|
| Telephone: |
0086-21-58956006 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList19141/0_EN.htm |
| Company Name: |
SynAsst Chemical.
|
| Telephone: |
021-60343070 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList15848/0_EN.htm |
| Company Name: |
Cochemical Ltd.
|
| Telephone: |
029-86115547 17791676824 |
| Website: |
http://www.cochemical.com |
| Company Name: |
Sigma-Aldrich
|
| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
| Company Name: |
Struchem Co., Ltd.
|
| Telephone: |
0512-63009836 18994340901 |
| Website: |
http://www.beidapharma.com |
|