ChemicalBook > CAS DataBase List > METHYL 2-BROMOMETHYL-6-NITRO-BENZOATE

METHYL 2-BROMOMETHYL-6-NITRO-BENZOATE

Product Name
METHYL 2-BROMOMETHYL-6-NITRO-BENZOATE
CAS No.
61940-21-4
Chemical Name
METHYL 2-BROMOMETHYL-6-NITRO-BENZOATE
Synonyms
-6-nitrobenzoate;Lenalidomide Impurity 18;Lenalidomide Impurity 107;METHYL 2-BROMOMETHYL-6-NITRO-BENZOATE;Methyl 2-(bromomethyl)-6-nitrobenzoaite;Methyl 2-(bromomethyl)-6-nitrobenzoate 98%;Methyl 2-(bromomethyl)-6-nitrobenzoate 98%;Methyl 2-(bromomethyl)-6-nitrobenzoate 98%;2-BroMoMethyl-6-nitrobenzoic Acid Methyl Ester;Benzoic acid, 2-(bromomethyl)-6-nitro-, methyl ester
CBNumber
CB6114178
Molecular Formula
C9H8BrNO4
Formula Weight
274.07
MOL File
61940-21-4.mol
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METHYL 2-BROMOMETHYL-6-NITRO-BENZOATE Property

Melting point:
84-86°C
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Solid
color 
Light Yellow
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Safety

HS Code 
2916310090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

TRC
Product number
B685115
Product name
2-Bromomethyl-6-nitrobenzoicAcidMethylEster
Packaging
1g
Price
$215
Updated
2021/12/16
AK Scientific
Product number
Y6595
Product name
2-(Bromomethyl)-6-nitro-benzoicacidmethylester
Packaging
100mg
Price
$155
Updated
2021/12/16
Matrix Scientific
Product number
119547
Product name
Methyl 2-(bromomethyl)-6-nitrobenzoate
Purity
95+%
Packaging
250mg
Price
$308
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
55000
Product name
2-Bromomethyl-6-nitrobenzoicAcidMethylEster
Packaging
250mg
Price
$625
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
HCH0029864
Product name
BENZOIC ACID, 2-(BROMOMETHYL)-6-NITRO-, METHYL ESTER
Purity
95.00%
Packaging
1G
Price
$789.6
Updated
2021/12/16
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METHYL 2-BROMOMETHYL-6-NITRO-BENZOATE Chemical Properties,Usage,Production

Uses

2-Bromomethyl-6-nitrobenzoic Acid Methyl Ester is a potential cyclooxygenase inhibitor derived from thalidomide (T338850), an immunomodulatory agent used primarily in combination with dexamethasone to treat multiple myeloma.

Synthesis

61940-22-5

61940-21-4

Example 2 Preparation of methyl 2-bromomethyl-6-nitrobenzoate: under nitrogen protection, methyl 2-methyl-6-nitrobenzoate (200.0 g, 1.02 moles), 1,3-dibromo-5,5-dimethylacetonitrile (DBH, 162.0 g, 0.57 moles), and methyl acetate (1.20 L) were added to a 3L three-neck flask, and the reaction temperature was maintained at 20 to 25°C. After refluxing the reaction mixture for 0.5-1 h, a solution of 2,2'-azobisisobutyronitrile (AIBN, 8.6 g, 52 mmol) dissolved in 100 mL of methyl acetate was added dropwise over 15-30 min. The reaction was continued at reflux for 6.5-8 hours until the residue of methyl 2-methyl-6-nitrobenzoate was less than 5-10%. Upon completion of the reaction, it was cooled to 15-18 °C and maintained for 50-60 min. The solid was collected by filtration and washed with cold methyl acetate (2 x 100 mL, 5-10 °C) until the amount of methyl 2-bromomethyl-6-nitrobenzoate in the solid was less than 3%. Heptane (1.00 L) was added to the filtrate and the organic phase was subsequently washed with 2% brine (2 x 500 mL) and deionized water (1-2 x 500 mL) until the percentage area of unreacted 5,5-dimethylglycolide urea was less than 0.5% by HPLC detection (210 nm). After removing about 1.80-1.90 L of methyl acetate by concentration under reduced pressure, methyl tert-butyl ether (MTBE, 300 mL) was added. The mixture was refluxed at 65-70 °C for 10-15 min and subsequently cooled to 50-55 °C over 0.5-1 h. 500 mg of methyl 2-bromomethyl-6-nitrobenzoate was added as a crystal seed. The suspension was cooled to 20-25 °C and kept for 2-3 hours. The product was collected by filtration, washed with cold heptane and MTBE (1:2 v/v, 2 x 100 mL, 5-10 °C), and dried at 20-25 °C, 100-120 torr under vacuum to constant weight. Using 200.0 g of methyl 2-methyl-6-nitrobenzoate as raw material, 185.2 g of methyl 2-bromomethyl-6-nitrobenzoate was obtained in 66% yield. The purity of the product was >98% (HPLC area percentage) and the moisture content was <0.1% (Karl Fisher titration).

References

[1] Patent: US2011/251395, 2011, A1. Location in patent: Page/Page column 15
[2] Chemical and Pharmaceutical Bulletin, 2003, vol. 51, # 9, p. 1098 - 1102
[3] Patent: US2011/87033, 2011, A1. Location in patent: Page/Page column 10-11
[4] Patent: WO2015/175773, 2015, A1. Location in patent: Paragraph 0117
[5] Patent: US9272035, 2016, B2. Location in patent: Page/Page column 28-29

METHYL 2-BROMOMETHYL-6-NITRO-BENZOATE Preparation Products And Raw materials

Raw materials

Preparation Products

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61940-21-4, METHYL 2-BROMOMETHYL-6-NITRO-BENZOATERelated Search:


  • METHYL 2-BROMOMETHYL-6-NITRO-BENZOATE
  • Benzoic acid, 2-(bromomethyl)-6-nitro-, methyl ester
  • 2-BroMoMethyl-6-nitrobenzoic Acid Methyl Ester
  • -6-nitrobenzoate
  • Lenalidomide Impurity 18
  • Methyl 2-(bromomethyl)-6-nitrobenzoaite
  • Methyl 2-(bromomethyl)-6-nitrobenzoate 98%
  • Lenalidomide Impurity 107
  • Methyl 2-(bromomethyl)-6-nitrobenzoate 98%
  • Methyl 2-(bromomethyl)-6-nitrobenzoate 98%
  • 61940-21-4