| Identification | Back Directory | [Name]
2-BROMOMETHYL-4-NITRO-BENZOIC ACID METHYL ESTER | [CAS]
133446-99-8 | [Synonyms]
Lenalidomide Impurity 16
Methyl 2-(broMoMethyl)-4-nitrobenzoate
Methyl 2-(bromomethyl)-4-nitrobenzoate 99%
2-BROMOMETHYL-4-NITRO-BENZOIC ACID METHYL ESTER
Benzoic acid, 2-(bromomethyl)-4-nitro-, methyl ester | [Molecular Formula]
C9H8BrNO4 | [MDL Number]
MFCD11505948 | [MOL File]
133446-99-8.mol | [Molecular Weight]
274.07 |
| Chemical Properties | Back Directory | [Boiling point ]
398.4±37.0 °C(Predicted) | [density ]
1.624±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
solid | [color ]
Off-white | [InChI]
1S/C9H8BrNO4/c1-15-9(12)8-3-2-7(11(13)14)4-6(8)5-10/h2-4H,5H2,1H3 | [InChIKey]
PGNKFDOPHHNVNF-UHFFFAOYSA-N | [SMILES]
COC(=O)c1ccc(cc1CBr)[N+]([O-])=O |
| Hazard Information | Back Directory | [Uses]
Methyl 2-(Bromomethyl)-4-nitrobenzoate is used in the synthetic preparation of cyclic hydroxamic acid derivatives as histone deacetylase inhibitors with antitumor activity. | [Synthesis]
General procedure for the synthesis of methyl 2-(bromomethyl)-4-nitrobenzoate from methyl 2-methyl-4-nitrobenzoate: methyl 2-methyl-4-nitrobenzoate (20 g, 88.01 mmol) was dissolved in carbon tetrachloride (100 mL) in a 500 mL three-necked round-bottomed flask. Subsequently, N-bromosuccinimide (39.16 g, 220.03 mmol) and azobisisobutyronitrile (AIBN, 2.16 g, 13.20 mmol) were added, and the reaction mixture was heated to reflux for 20 hours. Upon completion of the reaction, the reaction was quenched with distilled water (500 mL) and extracted with dichloromethane (200 mL x 3). The organic layers were combined, washed with saturated brine solution and dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure and the crude product obtained was purified by silica gel column chromatography to afford pure methyl 2-(bromomethyl)-4-nitrobenzoate (19 g, 78.7% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 8.52 (s, 1H), 8.27-8.30 (dd, 1H), 8.07-8.10 (d, 1H), 5.10 (s, 2H), 3.94 (s, 3H). | [References]
[1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 22, p. 7625 - 7651
[2] Patent: WO2010/139953, 2010, A1. Location in patent: Page/Page column 32
[3] Patent: US2012/115862, 2012, A1. Location in patent: Page/Page column 34-35
[4] Patent: WO2016/81464, 2016, A1. Location in patent: Paragraph 00118
[5] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 3, p. 250 - 255 |
|
| Company Name: |
T&W GROUP
|
| Telephone: |
021-61551611 13296011611 |
| Website: |
www.trustwe.com/ |
| Company Name: |
Cool Pharm, Ltd
|
| Telephone: |
021-60455363 18019463053 |
| Website: |
www.coolpharm.com |
| Company Name: |
NovoChemy Ltd.
|
| Telephone: |
86-(0)21-31261262 373522135 |
| Website: |
www.novochemy.com |
|