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
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
Safety
- HS Code
- 2916310090
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.
N-Bromosuccinimide Price
- Product number
- B685115
- Product name
- 2-Bromomethyl-6-nitrobenzoicAcidMethylEster
- Packaging
- 1g
- Price
- $215
- Updated
- 2021/12/16
- Product number
- Y6595
- Product name
- 2-(Bromomethyl)-6-nitro-benzoicacidmethylester
- Packaging
- 100mg
- Price
- $155
- Updated
- 2021/12/16
- Product number
- 119547
- Product name
- Methyl 2-(bromomethyl)-6-nitrobenzoate
- Purity
- 95+%
- Packaging
- 250mg
- Price
- $308
- Updated
- 2021/12/16
- Product number
- 55000
- Product name
- 2-Bromomethyl-6-nitrobenzoicAcidMethylEster
- Packaging
- 250mg
- Price
- $625
- Updated
- 2021/12/16
- 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
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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