ChemicalBook Product Catalog Organic Chemistry Hydrocarbons and derivatives Hydrocarbon nitrification 4-HYDROXY-3-NITROPHENYLACETIC ACID

4-HYDROXY-3-NITROPHENYLACETIC ACID

Product Name4-HYDROXY-3-NITROPHENYLACETIC ACID
CAS10463-20-4
MFC8H7NO5
MW197.14
EINECS233-948-0
MOL File10463-20-4.mol

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)

Safety Information

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

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

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

156-38-7

10463-20-4

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

Chemical Properties

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MSDS

Usage And Synthesis

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