2-METHOXY-5-NITROBENZYL BROMIDE Chemical Properties

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. 

under inert gas (nitrogen or Argon) at 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

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

RTECS 

XS7966500

F 

19-21

HazardClass 

8

PackingGroup 

III

MSDS

• Language:English Provider:SigmaAldrich

2-METHOXY-5-NITROBENZYL BROMIDE Usage And Synthesis

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

2-METHOXY-5-NITROBENZYL BROMIDE(3913-23-3)Related Product Information

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