| Identification | More | [Name]
5-Methoxy-2-nitrobenzaldehyde | [CAS]
20357-24-8 | [Synonyms]
2-NITRO-5-METHOXYBENZALDEHYDE
5-METHOXY-2-NITROBENZALDEHYDE | [Molecular Formula]
C8H7NO4 | [MDL Number]
MFCD00456498 | [Molecular Weight]
181.15 | [MOL File]
20357-24-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
83 °C | [Boiling point ]
354.7±27.0 °C(Predicted) | [density ]
1.322±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
crystalline solid | [color ]
Yellow | [InChI]
InChI=1S/C8H7NO4/c1-13-7-2-3-8(9(11)12)6(4-7)5-10/h2-5H,1H3 | [InChIKey]
BNTDDWPHSMILHQ-UHFFFAOYSA-N | [SMILES]
C(=O)C1=CC(OC)=CC=C1[N+]([O-])=O | [CAS DataBase Reference]
20357-24-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
5-Methoxy-2-nitrobenzaldehyde is a starting material used to synthesize a novel class of cis-locked combretastatins named combretabenzodiazepines which shows cytotoxic and antitubulin activity. | [Synthesis]
Step 1. Synthesis of 5-methoxy-2-nitrobenzaldehyde: 5-hydroxy-2-nitrobenzaldehyde (1 eq.), iodomethane (1.1 eq.) and potassium carbonate (1 eq.) were dissolved in DMF at room temperature and the reaction was stirred for 16 hours. Upon completion of the reaction, the reaction mixture was concentrated and subsequently partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated to give 5-methoxy-2-nitrobenzaldehyde in quantitative yield. Mass spectrometry analysis showed the molecular ion peak [M+H]+ = 182. | [References]
[1] Patent: US2005/85482, 2005, A1. Location in patent: Page/Page column 13; 17
[2] Patent: WO2010/51031, 2010, A1. Location in patent: Page/Page column 45
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1678 - 1681
[4] Patent: CN107522766, 2017, A. Location in patent: Paragraph 0136; 0137; 0138
[5] Chemical Communications, 2011, vol. 47, # 42, p. 11683 - 11685 |
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