methyl 3-nitro-4-bromomethylbenzoate

Product Name: methyl 3-nitro-4-bromomethylbenzoate
CAS No.: 88089-94-5
Chemical Name: methyl 3-nitro-4-bromomethylbenzoate
Synonyms: methyl 3-nitro-4-bromomethylbenzoate;Methyl 4-(bromomethyl)-3-nitrobenzoate;4-(bromomethyl)-3-nitrobenzoic acid methyl ester;Benzoic acid, 4-(bromomethyl)-3-nitro-, methyl ester
CBNumber: CB93037783
Molecular Formula: C9H8BrNO4
Formula Weight: 274.07
MOL File: 88089-94-5.mol

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methyl 3-nitro-4-bromomethylbenzoate Property

Boiling point:: 364.5±32.0 °C(Predicted)
Density: 1.624±0.06 g/cm3(Predicted)
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC

Product number: M293835
Product name: Methyl4-(Bromomethyl)-3-nitrobenzoate
Packaging: 500mg
Price: $175
Updated: 2021/12/16

Crysdot

Product number: CD12019665
Product name: Methyl4-(bromomethyl)-3-nitrobenzoate
Purity: 95+%
Packaging: 5g
Price: $462
Updated: 2021/12/16

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methyl 3-nitro-4-bromomethylbenzoate Chemical Properties,Usage,Production

Uses

methyl 4-(bromomethyl)-3-nitrobenzoate is a useful reactant used for the preparation of nitrobenzyl-substituted α-hydroxy esters, (hydroxy)oxindoles, and benzosultams.

Synthesis

7356-11-8

88089-94-5

General procedure for the synthesis of methyl 4-(bromomethyl)-3-nitrobenzoate from methyl 4-methyl-3-nitrobenzoate: in a 1000 mL round-bottomed flask, a nitrogen purge was performed first and an inert nitrogen atmosphere was maintained. Methyl 4-methyl-3-nitrobenzoate (10 g, 51.24 mmol, 1.00 eq.), N-bromosuccinimide (NBS, 9.13 g, 51.29 mmol, 1.00 eq.), benzoyl peroxide (BPO, 1.24 g, 5.12 mmol, 0.10 eq.), and carbon tetrachloride (400 mL) were added sequentially. The reaction mixture was stirred at 100 °C for 15 hours. After completion of the reaction, the crude product was purified by silica gel column chromatography with the eluent ethyl acetate/petroleum ether (gradient elution in the ratio of 0:1 to 1:9). Finally, 11.1 g of methyl 4-(bromomethyl)-3-nitrobenzoate was obtained in 79% yield, and the product was a yellow oil. The crude product obtained can be directly used in the next reaction without further purification.

References

[1] Patent: US2015/315198, 2015, A1. Location in patent: Paragraph 1365; 1366
[2] Patent: WO2005/66136, 2005, A1. Location in patent: Page/Page column 93
[3] Tetrahedron Letters, 2002, vol. 43, # 34, p. 5949 - 5952
[4] Patent: WO2013/131408, 2013, A1. Location in patent: Page/Page column 73
[5] Patent: US6348474, 2002, B1. Location in patent: Page column 87

methyl 3-nitro-4-bromomethylbenzoate Preparation Products And Raw materials

Raw materials

Preparation Products

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88089-94-5, methyl 3-nitro-4-bromomethylbenzoateRelated Search:

methyl 3-nitro-4-bromomethylbenzoate

Methyl 4-(bromomethyl)-3-nitrobenzoate

4-(bromomethyl)-3-nitrobenzoic acid methyl ester

Benzoic acid, 4-(bromomethyl)-3-nitro-, methyl ester

88089-94-5