| Identification | More | [Name]
4-HYDROXY-3-NITROPHENYLACETIC ACID | [CAS]
10463-20-4 | [Synonyms]
2-(4-HYDROXY-3-NITROPHENYL)ACETIC ACID
3-NITRO-4-HYDROXYPHENYLACETIC ACID
4-HYDROXY-3-NITROPHENYLACETIC ACID
TIMTEC-BB SBB007785
Benzeneacetic acid, 4-hydroxy-3-nitro-
4-Hydroxy-3-nitrophenylacetic acid 98%
4-Hydroxy-3-nitrobenzeneacetic acid | [EINECS(EC#)]
233-948-0 | [Molecular Formula]
C8H7NO5 | [MDL Number]
MFCD00007122 | [Molecular Weight]
197.14 | [MOL File]
10463-20-4.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow crystalline powder | [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. ]
−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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
T | [HazardClass ]
IRRITANT | [HS Code ]
29182900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow crystalline powder | [Uses]
4-Hydroxy-3-nitrophenylacetic acid was used in the synthesis of 4-hydroxy-3-nitrophenylacetyl caproic acid. | [Uses]
A metabolite of Nitrotyrosine (N597000), which is excreted in the urine. | [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 |
|
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J & K SCIENTIFIC LTD.
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https://www.jkchemical.com |
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Alfa Aesar
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400-6106006 |
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http://chemicals.thermofisher.cn |
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Energy Chemical
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400-0056266 |
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www.energy-chemical.com |
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Cool Pharm, Ltd
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www.coolpharm.com |
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