Methyl 2-bromomethyl-3-nitrobenzoate Chemical Properties

Melting point:

72-74°

Boiling point:

370.9±32.0 °C(Predicted)

Density 

1.624±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

soluble in Methanol

form 

Solid

color 

White to Light yellow

InChI

InChI=1S/C9H8BrNO4/c1-15-9(12)6-3-2-4-8(11(13)14)7(6)5-10/h2-4H,5H2,1H3

InChIKey

FCGIVHSBEKGQMZ-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=CC([N+]([O-])=O)=C1CBr

Safety Information

RIDADR 

UN 3261 8/PG III

HazardClass 

IRRITANT

HazardClass 

8

PackingGroup 

III

HS Code 

2916310090

Methyl 2-bromomethyl-3-nitrobenzoate Usage And Synthesis

Description

Methyl 2-bromomethyl-3-nitrobenzoate is a white or light yellow solid under normal temperature and pressure. It is insoluble in water but soluble in alcoholic organic solvents. It is an organic ester derivative that can be used as an organic synthesis intermediate and a raw material for pharmaceutical chemical synthesis. It is a crucial synthesis intermediate for the drug molecule lenalidomide. Lenalidomide is an antineoplastic drug. The ester group and benzyl bromide unit in the Methyl 2-bromomethyl-3-nitrobenzoate structure are easily convertible functional groups. Its structure contains a strong electron-attracting nitro group and an easily leaving bromine atom. The nitro group is a strong electron-withdrawing group that can increase the reactivity of molecules through conjugation effects and electron attraction. Due to these properties, it has wide applications in organic synthesis transformations. 

Chemical Properties

Pale Yellow Solid

Uses

Methyl 2-bromomethyl-3-nitrobenzoate is an organic ester derivative that can be used as an organic synthesis intermediate and a raw material for pharmaceutical chemical synthesis. It is a crucial synthesis intermediate for the drug molecule lenalidomide.

Synthesis

Step a) Synthesis of methyl 2-(bromomethyl)-3-nitrobenzoate: 21 g (109 mmol) of methyl 2-methyl-3-nitrobenzoate was dissolved in 300 mL of carbon tetrachloride, heated to reflux with continuous stirring. Subsequently, 23 g (130 mmol, 1.2 eq.) of N-bromosuccinimide and 1.8 g (11 mmol, 0.1 eq.) of 2,2'-azobis-2-methylpropanenitrile were sequentially added to the reaction system. Maintaining reflux conditions, the reaction mixture was stirred overnight. After completion of the reaction, it was cooled to room temperature, the reaction mixture was diluted with dichloromethane and washed with water several times. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. Yield: 31 g (quantitative). The product was analyzed by high performance liquid chromatography (HPLC, Method 12) with a retention time (Rt) of 4.33 min; the mass spectrum (ESI positive ion mode) showed m/z = 273 [M + H]+; 1H-NMR (300 MHz, DMSO-d6) data were as follows: δ= 8.16 (d, 1H), 8.11 (d, 1H), 7.74 (t, 1H), and 5.03 (s, 2H), 3.92 (s, 3H).

References

[1] Patent: US2010/10060, 2010, A1. Location in patent: Page/Page column 19
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 81 - 85
[3] Patent: WO2015/57043, 2015, A1. Location in patent: Paragraph 0017
[4] Chemistry of Heterocyclic Compounds, 2015, vol. 51, # 2, p. 133 - 138
[5] Khim. Geterotsikl. Soedin., 2015, vol. 51, # 2, p. 133 - 138,6

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