3,4-DIHYDROXY-6-NITROBENZALDEHYDE
- CAS No.
- 73635-75-3
- Chemical Name:
- 3,4-DIHYDROXY-6-NITROBENZALDEHYDE
- Synonyms
- 6-NITROPROTOCATECUALDEHYDE;6-NITROPROTOCATECHUALDEHYDE;3,4-DIHYDROXY-6-NITROBENZALDEHYDE;4,5-DIHYDROXY-2-NITROBENZALDEHYDE;2-nitro-4,5-dihydroxybenzaldehyde;Benzaldehyde, 4,5-dihydroxy-2-nitro-
- CBNumber:
- CB7210116
- Molecular Formula:
- C7H5NO5
- Molecular Weight:
- 183.12
- MDL Number:
- MFCD00016645
- MOL File:
- Mol file
| Product description | Number | Pack Size | Price |
| 4,5-Dihydroxy-2-nitrobenzaldehyde | D453970 | 5g | $690 |
| 3,4-Dihydroxy-6-nitrobenzaldehyde | FD67691 | 25g | $625 |
| 3,4-Dihydroxy-6-nitrobenzaldehyde | FD67691 | 1g | $50 |
| 3,4-Dihydroxy-6-nitrobenzaldehyde | FD67691 | 2g | $84 |
| 3,4-Dihydroxy-6-nitrobenzaldehyde | FD67691 | 5G | $175 |
| Melting point | 202-205°C |
|---|---|
| Boiling point | 417.0±45.0 °C(Predicted) |
| Density | 1.667±0.06 g/cm3(Predicted) |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| solubility | DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) |
| form | Solid |
| pka | 6.01±0.24(Predicted) |
| color | Dark Yellow to Very Dark Brown |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302-H315-H319-H332-H335 |
| Precautionary statements | P261-P280-P305+P351+P338 |
| Hazard Codes | Xi |
| Risk Statements | 36/37/38-43 |
| Safety Statements | 26-36-36/37 |
| Hazard Note | Irritant |
3,4-DIHYDROXY-6-NITROBENZALDEHYDE price
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| TRC | D453970 | 4,5-Dihydroxy-2-nitrobenzaldehyde | 73635-75-3 | 5g | $690 | 2021-12-16 | Buy |
| Biosynth Carbosynth | FD67691 | 3,4-Dihydroxy-6-nitrobenzaldehyde | 73635-75-3 | 25g | $625 | 2021-12-16 | Buy |
| Biosynth Carbosynth | FD67691 | 3,4-Dihydroxy-6-nitrobenzaldehyde | 73635-75-3 | 1g | $50 | 2021-12-16 | Buy |
| Biosynth Carbosynth | FD67691 | 3,4-Dihydroxy-6-nitrobenzaldehyde | 73635-75-3 | 2g | $84 | 2021-12-16 | Buy |
| Biosynth Carbosynth | FD67691 | 3,4-Dihydroxy-6-nitrobenzaldehyde | 73635-75-3 | 5G | $175 | 2021-12-16 | Buy |
3,4-DIHYDROXY-6-NITROBENZALDEHYDE Chemical Properties,Uses,Production
Uses
4,5-Dihydroxy-2-nitrobenzaldehyde is used as a reagent in the synthesis of 5,6-diacetoxyindole which is a stable eumelanin precursor. 4,5-Dihydroxy-2-nitrobenzaldehyde is also used in the preparation of 6-aminoisoproterenol which is an impurity of the non-selective beta-adrenergic agonist, Isoproterenol (I874200, HCl).
Synthesis
73635-74-2
73635-75-3
An aluminum chloride solution was prepared by dissolving pure aluminum chloride (11 g, 82.4 mmol) in anhydrous 1,2-dichloroethane (25 mL) under argon protection and cooling to -5°C. Subsequently, Compound 1 (5 g, 25.6 mmol) was dissolved in anhydrous 1,2-dichloroethane (20 mL) and slowly added dropwise to the above aluminum chloride solution, keeping the temperature between -5°C and 5°C. The reaction was stirred continuously for 2 hours until the complete disappearance of compound 1 was confirmed by TLC detection. Upon completion of the reaction, the mixture was poured into 48% hydrobromic acid (60 mL) and stirred for 48 hours at room temperature (~20°C) until the intermediate chloromethyl ether disappeared (TLC monitoring). The reaction mixture was diluted with water (60 mL) and extracted with ethyl acetate (3 x 50 mL), the organic phases were combined and dried with magnesium sulfate. After evaporation of the solvent, the residue was treated with hot hexane. The crude product was further treated with hot dichloromethane (50 mL) to afford 4,5-dihydroxy-2-nitrobenzaldehyde (4.3 g, 90% yield). The product was recrystallized by water (100 mL) to afford chromatographically pure yellow crystals (1.79 g) with a melting point of 202-203 °C and an Rf value of 0.25 (acetone-hexane, 1:2).1H NMR (CDCl3) data: δ 7.21 (s, 1H, C6-H), 7.50 (s, 1H, C3-H), 10.14 (s, 1H, CHO) , 10.85 (s, 2H, 2×OH). 4,5-Dihydroxy-2-nitrobenzaldehyde (0.5 g, 2.7 mmol) was dissolved in DMF and anhydrous finely powdered potassium carbonate (0.94 g, 6.8 mmol) and n-bromobutane (1.1 g, 8.1 mmol) were added. The mixture was stirred under argon protection and protected from light, and the mixture was heated at 60 °C for 15 hours. After completion of the reaction, it was diluted with water and extracted with ether (3 x 50 mL). The organic phases were combined, dried with magnesium sulfate and the solvent was evaporated. The residue was recrystallized by ether to give chromatographically pure compound 5 (0.66 g, 83% yield) as a crystalline powder with a melting point of 80-85 °C and an Rf value of 0.62 (acetone-hexane, 1:2). Elemental analysis measured values (%): C, 61.04; H, 7.20; N, 5.71. molecular formula C15H21NO5 calculated values (%): C, 61.00; H, 7.17; N, 4.74. 1H NMR (CDCl3) data: δ 0.98-1.03 (m, 6H, 2 × CH3), 1.47-1.58 (m, 4H, 2 × CH2), 1.82-1.91 (m, 4H, 2 × CH2), 4.13-4.16 (m, 4H, 2 × CH2), 7.38 (s, 1H, C6-H), 7.58 (s, 1H, C3-H), 10.43 (s, 1H, CHO).
References
[1] Journal of Organic Chemistry, 1980, vol. 45, # 14, p. 2750 - 2753
[2] Synthetic Communications, 1985, vol. 15, # 4, p. 321 - 330
[3] Journal of Organic Chemistry, 1985, vol. 50, # 26, p. 5873 - 5875
[4] Patent: US4595765, 1986, A
[5] Russian Chemical Bulletin, 2016, vol. 65, # 2, p. 507 - 512
3,4-DIHYDROXY-6-NITROBENZALDEHYDE Preparation Products And Raw materials
3,4-DIHYDROXY-6-NITROBENZALDEHYDE Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Capot Chemical Co.,Ltd. | +86-（0）57185586718; +8613336195806 | sales@capot.com | China | 29735 | 60 |
| Dayang Chem (Hangzhou) Co.,Ltd. | +86-0571-88938639 +8617705817739 | info@dycnchem.com | China | 52846 | 58 |
| Hefei TNJ Chemical Industry Co.,Ltd. | +86-0551-65418684 +8618949823763 | sales@tnjchem.com | China | 25356 | 58 |
| Coresyn Pharmatech Co., Ltd. | +86-571-86626709 +86-18157142896 | cbc@coresyn.com | China | 9984 | 58 |
| GIHI CHEMICALS CO.,LIMITED | +86-571-86217390; +8618058761490 | info@gihichemicals.com | China | 49958 | 58 |
| Shanghai Acmec Biochemical Technology Co., Ltd. | +86-18621343501; +undefined18621343501 | product@acmec-e.com | China | 33325 | 58 |
| Aladdin Scientific | tp@aladdinsci.com | United States | 52923 | 58 | |
| SHANGHAI KEAN TECHNOLOGY CO., LTD. | +8613817748580 | cooperation@kean-chem.com | China | 40066 | 58 |
| Amadis Chemical Company Limited | 571-89925085 | sales@amadischem.com | China | 131957 | 58 |
| Shanghai Sinch Parmaceuticals Tech. Co. Ltd. | +86-21-54098501 | sales@sinch.com.cn | China | 11598 | 64 |
