2,4-ジニトロフェノール (約20%水湿潤品) 化学特性,用途語,生産方法
化学的特性
light yellow crystal powder
使用
2,4-Dinitrophenol (DNP) can be used:
- As a reactant for catalytic reduction reactions.
- To activate carboxylic acids by converting them into dinitrophenyl (DNP) esters.
- To prepare the corresponding ester via acylation reaction using isobutyric anhydride catalyzed by hafnium triflate.
- As an effective cocatalyst to accelerate the activity and enantioselectivity of primary amine organocatalyst derived from natural primary amino acids for direct asymmetric aldol reaction.
- As an alternative activator to tetrazoles in the reaction of phosphoroamidites with nucleosides.
調製方法
2,4-Dinitrochlorobenzene is hydrolyzed by heating with 6 % aqueous sodium hydroxide at 95 – 100 ℃ for 4 h. The product 2,4-Dinitrophenol is precipitated by addition of acid, filtered off, and washed to remove acid and also a small quantity of the more soluble 2,6-isomer. The yield is 95 %.
一般的な説明
Solid yellow crystals. Explosive when dry or with less than 15% water. The primary hazard is from blast of an instantaneous explosion and not flying projectiles and fragments. slightly soluble in water and soluble in ether and solutions of sodium or potassium hydroxide.
空気と水の反応
Highly flammable. Slightly soluble in water.
反応プロフィール
2,4-Dinitrophenol may explode if subjected to heat or flame. may explode if allowed to dry out. Forms explosive salts with alkalis and ammonia. Incompatible with heavy metals and their compounds. Also incompatible with strong oxidizing agents, strong bases and reducing agents. Reacts with combustibles.
健康ハザード
2,4-Dinitrophenol is a severely acute toxicant, exhibiting high toxicity in animals by all routes of administration. It can be absorbed through the intact skin. The toxic effects are heavy sweating, nausea, vomiting, collapse, and death. Ingestion of 1 g of solid can be fatal to humans. A 30-minute exposure to its vapors at a concentration of 300 mg/m
3 was lethal to dogs (NIOSH 1986). Chronic effects include polyneuropathy, weight loss, cataracts, and dermatitis.
LD50 value, oral (rats): 30 mg/kg.
火災危険
Combustible. May explode if subjected to heat or flame. POISONOUS GAS IS PRODUCED WHEN HEATED. Vapors are toxic. Can detonate or explode when heated under confinement.
安全性プロファイル
A deadly human poison
by ingestion. An experimental poison by
ingestion, inhalation, intravenous,
intraperitoneal, subcutaneous, and
intramuscular routes. Moderately toxic by
skin contact. Experimental teratogenic and
reproductive effects. Human systemic
effects: body temperature increase, change
in heart rate, coma. A skin irritant. Mutation
data reported. Phytotoxic. A pesticide. An
explosive. Forms explosive salts with alkalies
and ammonia. When heated to
decomposition it emits toxic fumes of NOx.
See also NITRO COMPOUNDS of
AROMATIC HYDROCARBONS.
発がん性
No teratogenic effects have been reported
in limited developmental toxicity studies in
rodents. Decreased fetal body weight and
crown-rump length were noted in rats and
mice after parenteral administration.
2,4-DNP was not genotoxic in most in
vivo and in vitro studies.
An ACGIH threshold limit value (TLV)
has not been established for 2,4-DNP.
代謝経路
The bacterial strain RB1, which is isolated by
enrichment cultivation with 2,4-dinitrophenol, degrades
this phenol into two aliphatic acids. One metabolite
results from the release of the 2-nitro group as nitrile,
with the production of aliphatic nitro compound,
3-nitroadipate. Then, the 3-nitro group is released
from this metabolite as nitrile. The other metabolite is
4,6-dinitrohexanoic acid possessing two nitro groups
from 2,4-dinitrophenol.
合成方法
ニトロフェノールを混酸と反応させると生成。別に2,6-ジニトロフェノールが生成。
純化方法
Crystallise it from *benzene, EtOH, EtOH/H2O or H2O acidified with dilute HCl, dry it, then recrystallise it from CCl4. Dry it in an oven and store it in a vacuum desiccator over CaSO4. The benzoate has m 132o (from EtOH). [Beilstein 6 IV 1369.]
2,4-ジニトロフェノール (約20%水湿潤品) 上流と下流の製品情報
原材料
準備製品