4-HYDROXY-3-NITROPHENYLACETIC ACID manufacturers
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| | 4-HYDROXY-3-NITROPHENYLACETIC ACID Basic information |
| | 4-HYDROXY-3-NITROPHENYLACETIC ACID Chemical Properties |
| Melting point | 146-148 °C (lit.) | | Boiling point | 334.23°C (rough estimate) | | density | 1.5023 (rough estimate) | | refractive index | 1.5700 (estimate) | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | solubility | ethanol: soluble5%, clear, yellow to orange | | form | crystalline | | pka | 4.25±0.10(Predicted) | | color | yellow | | BRN | 2696044 | | InChI | 1S/C8H7NO5/c10-7-2-1-5(4-8(11)12)3-6(7)9(13)14/h1-3,10H,4H2,(H,11,12) | | InChIKey | QBHBHOSRLDPIHG-UHFFFAOYSA-N | | SMILES | OC(=O)Cc1ccc(O)c(c1)[N+]([O-])=O | | CAS DataBase Reference | 10463-20-4(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | TSCA | T | | HazardClass | IRRITANT | | HS Code | 29182900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 4-HYDROXY-3-NITROPHENYLACETIC ACID Usage And Synthesis |
| Chemical Properties | yellow crystalline powder | | Uses | A metabolite of Nitrotyrosine (N597000), which is excreted in the urine. | | Uses | 4-Hydroxy-3-nitrophenylacetic acid was used in the synthesis of 4-hydroxy-3-nitrophenylacetyl caproic acid. | | Definition | ChEBI: (4-hydroxy-3-nitrophenyl)acetic acid is a monocarboxylic acid that is acetic acid carrying a 2-hydroxy-3-nitrophenyl substituent at C-2. It has a role as a hapten. It is a conjugate acid of a (4-hydroxy-3-nitrophenyl)acetate. | | Synthesis Reference(s) | Journal of Medicinal Chemistry, 30, p. 1166, 1987 DOI: 10.1021/jm00390a009 | | General Description | 4-Hydroxy-3-nitrophenylacetic acid enhances the ice-nucleation activity of Xanthomonas campestris. | | Synthesis | General procedure for the synthesis of 4-hydroxy-3-nitrophenylacetic acid from p-hydroxyphenylacetic acid:
(a) Nitration reaction: fuming nitric acid (1.36 mL) was slowly added dropwise to a solution of 4-hydroxyphenylacetic acid (4.00 g, 26.3 mmol) in acetic acid (25 mL) under cooling in an ice bath. After the dropwise addition was completed, the reaction mixture was slowly warmed up to room temperature and reacted for 1 hour, during which time the solution gradually changed from yellow to brown color, accompanied by the formation of a precipitate. After completion of the reaction, the solid product was collected by filtration and recrystallized from ethyl acetate/hexane mixed solvent to obtain yellow needle-like crystals of 4-hydroxy-3-nitrophenylacetic acid (3.61 g, 70% yield). The structure of the product was confirmed by 1H-NMR: δ (CDCl3-d4/DMSO, 4:1) 3.50 (2H, s), 7.04 (1H, d, J = 9 Hz), 7.46 (1H, dd, J = 9, 3 Hz), 7.94 (1H, d, J = 3 Hz). | | References | [1] Synthetic Communications, 1985, vol. 15, # 12, p. 1075 - 1080
[2] Patent: US5229510, 1993, A
[3] Journal of Medicinal Chemistry, 1987, vol. 30, # 7, p. 1166 - 1176
[4] Patent: US9995679, 2018, B2. Location in patent: Page/Page column 52
[5] Patent: US5852191, 1998, A |
| | 4-HYDROXY-3-NITROPHENYLACETIC ACID Preparation Products And Raw materials |
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