O-(2,4-dinitrophenyl)hydroxylamine

한글명:O-(2,4-dinitrophenyl)hydroxylamine

카스 번호17508-17-7

상품명:O-(2,4-dinitrophenyl)hydroxylamine

CBNumberCB3922714

분자식C6H5N3O5

포뮬러 무게199.12

MOL 파일17508-17-7.mol

화학적 성질

녹는점	112.5°C
끓는 점	336.62°C (rough estimate)
밀도	1.6937 (rough estimate)
굴절률	1.6910 (estimate)
저장 조건	2-8°C(protect from light)
용해도	DMSO(적게), 메탄올(약간)에 용해됨
물리적 상태	고체
물리적 상태	단단한 모양
산도 계수 (pKa)	-1.07±0.70(Predicted)
색상	노란색

위험 및 안전 성명

위험 카페고리 넘버

22-36/37/38

안전지침서

TSCA

HS 번호

29221990

NFPA 704:

	0
2		2

그림문자(GHS)

O-(2,4-dinitrophenyl)hydroxylamine 화학적 특성, 용도, 생산

화학적 성질
Light yellow solid
용도
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.
제조 방법
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%.

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