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5-Methoxy-2-nitrobenzaldehyde

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CAS:20357-24-8
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  • 2025-09-25
  • CAS:20357-24-8
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5-Methoxy-2-nitrobenzaldehyde Basic information
Product Name:5-Methoxy-2-nitrobenzaldehyde
Synonyms:5-METHOXY-2-NITROBENZALDEHYDE;2-NITRO-5-METHOXYBENZALDEHYDE;2-Formyl-4-methoxynitrobenzene, 3-Formyl-4-nitroanisole;Benzaldehyde, 5-methoxy-2-nitro-;m-Anisaldehyde, 6-nitro-;N-(3-bromo-7-fluoro-9H-fluoren-2-yl)acetamide;5-Methoxy-2-nitrobenzaldehyde ISO 9001:2015 REACH
CAS:20357-24-8
MF:C8H7NO4
MW:181.15
EINECS:
Product Categories:
Mol File:20357-24-8.mol
5-Methoxy-2-nitrobenzaldehyde Structure
5-Methoxy-2-nitrobenzaldehyde Chemical Properties
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
InChIInChI=1S/C8H7NO4/c1-13-7-2-3-8(9(11)12)6(4-7)5-10/h2-5H,1H3
InChIKeyBNTDDWPHSMILHQ-UHFFFAOYSA-N
SMILESC(=O)C1=CC(OC)=CC=C1[N+]([O-])=O
CAS DataBase Reference20357-24-8(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
WGK Germany WGK 3
HS Code 2912490090
Storage Class11 - Combustible Solids
MSDS Information
5-Methoxy-2-nitrobenzaldehyde Usage And Synthesis
Uses5-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
5-Hydroxy-2-nitrobenzaldehyde

42454-06-8

Iodomethane

74-88-4

5-Methoxy-2-nitrobenzaldehyde

20357-24-8

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
Tag:5-Methoxy-2-nitrobenzaldehyde(20357-24-8) Related Product Information
3,5-Dimethoxybenzaldehyde 2,6-Dimethoxybenzaldehyde 4-Nitrobenzaldehyde p-Anisaldehyde 2-Bromo-5-methoxybenzaldehyde Veratraldehyde (Trifluoromethoxy)benzene 3-Methoxybenzaldehyde o-Anisaldehyde 4-Nitrobenzoic acid 3-(METHOXYMETHOXY)BENZALDEHYDE 5-METHOXYTHIOPHENE-2-CARBOXYLIC ACID 5-METHOXY-2-METHYL-BENZOIC ACID METHYL ESTER 5-Methoxy-2-(trifluoroMethyl)benzaldehyde Nitrobenzene ETHYL 4,5-DIMETHOXY-2-NITROBENZOATE 6-Nitroveratraldehyde Methyl 2-nitro-3,4,5-trimethoxybenzoate