| Identification | Back Directory | [Name]
2-METHOXY-5-NITROBENZYL BROMIDE | [CAS]
3913-23-3 | [Synonyms]
MNBB
KOSHLAND II
KOSHLANDREAGENTII
Koshland II reagent
koshlandreagentno.2
KOSHLAND'S REAGENT II
2-BROMOMETHYL-4-NITROANISOLE
2-(bromomethyl)-4-nitro-anisol
2-METHOXY-5-NITROBENZYL BROMIDE
2-Methoxy-5-nitrobenzyl bromide 97%
alpha-bromo-2-methoxy-6-nitro-toluen
2-Bromomethyl-1-methoxy-4-nitrobenzene
2-(bromomethyl)-1-methoxy-4-nitro-benzen
1-Methoxy-2-(bromomethyl)-4-nitrobenzene
Benzene, 2-(bromomethyl)-1-methoxy-4-nitro-
2-Bromomethyl-4-nitroanisole, Koshlands Reagent II | [EINECS(EC#)]
223-471-6 | [Molecular Formula]
C8H8BrNO3 | [MDL Number]
MFCD00007329 | [MOL File]
3913-23-3.mol | [Molecular Weight]
246.06 |
| Chemical Properties | Back Directory | [Melting point ]
76-78 °C(lit.)
| [Boiling point ]
348.7±27.0 °C(Predicted) | [density ]
1.589±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Inert atmosphere,2-8°C | [InChI]
InChI=1S/C8H8BrNO3/c1-13-8-3-2-7(10(11)12)4-6(8)5-9/h2-4H,5H2,1H3 | [InChIKey]
JRHMPHMGOGMNDU-UHFFFAOYSA-N | [SMILES]
C1(OC)=CC=C([N+]([O-])=O)C=C1CBr |
| Hazard Information | Back Directory | [Uses]
2-Methoxy-5-nitrobenzyl bromide was used to modify tryptophan residues of mouse interferon to enhance their activity. It was also used as reagent for sulfhydryl modification. | [General Description]
2-Methoxy-5-nitrobenzyl bromide is a potential mechanism-based inactivator of enzymes that perform O-dealkylations. | [Biochem/physiol Actions]
2-Methoxy-5-nitrobenzyl bromide inactivates cytochrome P-450 in male rat liver microsomes. | [Synthesis]
Example 8: Synthesis of Compound XIII-6; Step 1: Synthesis of 2-(bromomethyl)-1-methoxy-4-nitrobenzene (2); A mixture of 4-nitroanisole (1,1 g, 6.529 mmol), paraformaldehyde (0.218 g) and sodium bromide (0.8 g) in glacial acetic acid (1.3 mL) was heated to 85 °C. Sulfuric acid (0.8 mL) and glacial acetic acid (0.8 mL) were slowly added dropwise to the reaction mixture over a period of 5 hours. The reaction mixture was continued to be stirred at 85°C for 3 hours, followed by stirring at 28°C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ether, the ether layer was washed sequentially with 5% sodium bicarbonate solution and water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2-(bromomethyl)-1-methoxy-4-nitrobenzene (2,0.965 g, 60% yield).NMR (400 MHz, CDCl3): δ 8.30-8.22 (m, 2H), 7.00-6.95 (d, 1H), 4.55 (s, 2H), 4.05 (s, 3H). | [References]
[1] Patent: WO2011/140338, 2011, A1. Location in patent: Page/Page column 56-57
[2] Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1471 - 1475
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 527 - 532 |
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