O-(2,4-dinitrophenyl)hydroxylamine
- Product Name
- O-(2,4-dinitrophenyl)hydroxylamine
- CAS No.
- 17508-17-7
- Chemical Name
- O-(2,4-dinitrophenyl)hydroxylamine
- Synonyms
- 2,4-Dinitrophenylhydroxylamine;NSC 148499;2,4-NitrophenoxyaMine;2,4-DinitrophenoxyaMine;4-dinitrophenyl)hydroxylamine;1-aMinooxy-2,4-dinitro-benzene;O-(2,4-dinitrophenyl)hydroxylamine;HydroxylaMine,O-(2,4-dinitrophenyl)-;O-(2,4-Dinitrophenyl)hydroxylamine,98%;TIANFUCHEM--17508-17-7---O-(2,4-dinitrophenyl)hydroxylamine
- CBNumber
- CB3922714
- Molecular Formula
- C6H5N3O5
- Formula Weight
- 199.12
- MOL File
- 17508-17-7.mol
O-(2,4-dinitrophenyl)hydroxylamine Property
- Melting point:
- 112.5°C
- Boiling point:
- 336.62°C (rough estimate)
- Density
- 1.6937 (rough estimate)
- refractive index
- 1.6910 (estimate)
- storage temp.
- 2-8°C(protect from light)
- solubility
- DMSO (Sparingly), Methanol (Slightly)
- form
- solid
- pka
- -1.07±0.70(Predicted)
- color
- yellow
- InChI
- InChI=1S/C6H5N3O5/c7-14-6-2-1-4(8(10)11)3-5(6)9(12)13/h1-3H,7H2
- InChIKey
- YLACRFYIUQZNIV-UHFFFAOYSA-N
- SMILES
- NOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O
Safety
- Risk Statements
- 22-36/37/38
- Safety Statements
- 26
- TSCA
- No
- HS Code
- 29221990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- D5103
- Product name
- O-(2,4-Dinitrophenyl)hydroxylamine
- Packaging
- 1G
- Price
- $81
- Updated
- 2025/07/31
- Product number
- D5103
- Product name
- O-(2,4-Dinitrophenyl)hydroxylamine
- Packaging
- 5G
- Price
- $282
- Updated
- 2025/07/31
- Product number
- D479985
- Product name
- O-(2,4-Dinitrophenyl)hydroxylamine
- Packaging
- 5g
- Price
- $110
- Updated
- 2021/12/16
- Product number
- FD22435
- Product name
- O-(2,4-Dinitrophenyl)hydroxylamine
- Packaging
- 5G
- Price
- $150
- Updated
- 2021/12/16
- Product number
- FD22435
- Product name
- O-(2,4-Dinitrophenyl)hydroxylamine
- Packaging
- 10g
- Price
- $200
- Updated
- 2021/12/16
O-(2,4-dinitrophenyl)hydroxylamine Chemical Properties,Usage,Production
Chemical Properties
Light yellow solid
Uses
Efficient agent for metal-free amination of arylboronic acids leading to primary anilines. Reagents used in Rhodium-catalyzed aziridines formation.
Uses
O-(2,4-Dinitrophenyl)hydroxylamine is a rapid active-site-directed inhibitor of D-amino acid oxidase; modification results in specific incorporation of an amine group into an accessible nucleophilic r esidue with concomitant release of 2,4-dinitrophenol.
Preparation
To a stirred solution of 13.3 gm (0.1 mole) of t-butyl JV-hydroxycar-bamate and 5.6 gm (0.1 mole) of potassium hydroxide in 200 ml of absolute ethanol is added 20.2 gm (0.1 mole) of 2,4-dinitrochlorobenzene. The resultant deep red solution is stirred at room temperature for 1 hr; then enough glacial acetic acid is added dropwise to produce a light yellow solution. The solution is poured into 1.5 liters of cold water. The yellow oil which separates is gradually converted to crystals. The solid ?-butyl JV-(2,4-dinitrophenoxy)carbamate is separated, dried, and recrystallized from an ethyl acetate-hexane mixture to afford 16.4 gm (53%), m.p. 74-75°C. To 15 ml of trifluoroacetic acid is added 4 gm (0.0133 mole) of the i-butyl J/V-(2,4-dinitrophenoxy)carbamate. After the evolution of carbon dioxide has subsided, the solution is poured into 100 ml of ice water. The resultant oily layer crystallizes on standing to afford 2.5 gm (95%), m.p. 112°C (from ethanol).
Recently it was discovered that the alkylation of ethyl JV-hydroxy-carbamate under alkaline conditions, particularly in a DMF medium at 60°C in the presence of sodium bicarbonate, leads to the ultimate formation of O-alkylated hydroxylamines. On the other hand, at 80-85°C, the direct alkylation without the presence of a base ultimately leads to N-alkylhydrox-ylamines (see Table I) [59]. The reaction of ethylazidoformate with an alcohol, while perhaps hazardous, may have some merit (Eqs. 31-33). The overall yield, based on ethyl chloroformate, is said to be on the order of 60%.
Synthesis
60506-35-6
17508-17-7
General procedure for the synthesis of 2,4-dinitrophenylhydroxylamine from 2-(2,4-dinitrophenoxy)-isoindole-1,3-dione: first, compound 1-2 2-(2,4-nitrophenoxy)isoindoline-1,3-dione 17.74 g (53.88 mmol) was prepared, and then the hydrazine monohydrate was dissolved in 350 mL of dichloromethane under the protection of argon. 7.6 g (157.33 mmol) of hydrazine monohydrate was added and the reaction was stirred for 4 hours. After completion of the reaction, the reaction mixture was poured into stirred 1N HCl and the resulting solid was filtered. The solid was washed with acetonitrile (MeCN) and the filtrate was extracted with methylene chloride (MC), the organic layers were combined and dried with anhydrous magnesium sulfate (MgSO4) to give 10.50 g of the target compound 1-2 (98% yield).
References
[1] Patent: KR101551895, 2015, B1. Location in patent: Paragraph 0171-0172; 0180-0181
[2] Patent: KR2015/74833, 2015, A. Location in patent: Paragraph 0134-0135; 0138-0139; 0191; 0194-0195
[3] Patent: KR2015/74793, 2015, A. Location in patent: Paragraph 0093-0094; 0097-0098
[4] Organic Letters, 2017, vol. 19, # 8, p. 1994 - 1997
[5] Patent: WO2009/146358, 2009, A1. Location in patent: Page/Page column 87-88
O-(2,4-dinitrophenyl)hydroxylamine Preparation Products And Raw materials
Raw materials
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View Lastest Price from O-(2,4-dinitrophenyl)hydroxylamine manufacturers
- Product
- O-(2,4-dinitrophenyl)hydroxylamine 17508-17-7
- Price
- US $1.10/g
- Min. Order
- 1g
- Purity
- 99.0% min
- Supply Ability
- 100 tons min
- Release date
- 2025-09-24
- Product
- O-(2,4-dinitrophenyl)hydroxylamine 17508-17-7
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 98.0%
- Supply Ability
- 5000KGS
- Release date
- 2024-11-10
- Product
- O-(2,4-dinitrophenyl)hydroxylamine 17508-17-7
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-10