メチルクロロホルマート 化学特性,用途語,生産方法
外観
無色～わずかにうすい黄色, 澄明の液体
溶解性
水に微溶, エタノールに混和, エーテルに可溶。エタノール及びアセトンに極めて溶けやすく、水によって徐々に分解する。
用途
有機合成化学において、求核剤にメトキシカルボニル基を導入するのに用いられる。
使用上の注意
不活性ガス封入
化学的特性
Methyl chloroformate is a colorless liquid with an unpleasant, acrid odor. This is a highly corrosive and flammable material. Decomposed by hot water; stable to cold water. Soluble in methanol alcohol, ether, and benzene.
使用
Chloroformic Acid Methyl Ester is used in the synthesis of a new class of potent Cdk4 inhibitors in the treatment of cancer. Also used in the synthesis of Phorboxazole B.
主な応用
Methyl chloroformate (MCF) is generally used for the derivatization of functional groups such as carboxylic acids, amines, and phenols.
MCF can also be used:
To activate 3-acylpyridines for nucleophilic addition with alkynyltin reagents to form 2,3-disubstituted 1,2-dihydropyridines.
Chloroesterification of terminal alkynes to form β-chloro-α,β-unsaturated esters.
As an electrophilic reagent to mediate the reaction of pyridine with lithium dialkyl- or diarylcuprates to form 4-substituted 1,4-dihydropyridine derivatives.
To convert nitronates into methoxycarbonyl nitronates.
調製方法
Prepared from phosgene and methyl alcohol.
一般的な説明
A colorless liquid with a pungent odor. Flash point 54°F. Corrosive to metals and tissue. Vapors heavier than air. Very toxic by inhalation. Used to make other chemicals and insecticides.
空気と水の反応
Highly flammable. Gives off hydrochloric acid fumes in contact with moist air. Slightly soluble in water and decomposed by water to hydrochloric acid with evolution of heat.
反応プロフィール
Methyl chloroformate is incompatible with water, strong oxidizing agents, alcohols, bases (including amines). Decomposes slowly in water to yield methanol, HCl, and CO2; reaction can be hazardous if water is hot. Attacks many metals especially in humid atmosphere [Handling Chemicals Safely 1980. p. 476]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
危険性
Flammable, dangerous fire risk. Highly corrosive and irritant to skin and eyes.
健康ハザード
Methyl chloroformate is highly toxic upon inhalation and upon ingestion. A concentration of 1 mg/liter (190 ppm) has been lethal in 10 minutes. It is corrosive and irritating to skin.
火災危険
Methyl chloroformate is very dangerous when exposed to heat sources, sparks, flame, or oxidizers. Methyl chloroformate will react with water or steam to produce toxic and corrosive fumes. Vapors may travel to a source of ignition and flash back. Withdraw immediately in case of rising sound from venting safety device or any discoloration of tank due to fire. Toxic fumes of phosgene are produced when the material is heated to decomposition. Heat or steam should be avoided.
化学反応性
Reactivity with Water: Reacts slowly, evolving hydrogen chloride (hydrochloric acid). Reaction can be hazardous if water is hot; Reactivity with Common Materials: Corrodes rubber; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water, rinse with sodium bicarbonate or lime solution; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
安全性プロファイル
Poison by ingestion,
inhalation, and intraperitoneal routes.
Moderately toxic by skin contact. Human
systemic effects by inhalation: conjunctiva
irritation and respiratory effects. Corrosive
to skin, eyes, and mucous membranes. Very
dangerous fire hazard when exposed to heat
sources, sparks, flame, or oxidzers. Reacts
with water or steam to produce toxic and
corrosive fumes. When heated to
decomposition it emits toxic fumes of Cl-,
methyl chloroformate, and phosgene.
職業ばく露
Used in synthesis of pharmaceuticals;
herbicides, plastics and other organic chemicals; as a solvent in the photographic industry; as a chemical intermediate in the production of other chemicals. In WWI it was
used as military tear-producing warfare agent.
輸送方法
UN1238 Methyl chloroformate, Hazard class:
6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable
liquid, 8-Corrosive material Inhalation Hazard Zone A
不和合性
May form explosive mixture with air.
Violent reaction with alkali metals; ethers. Incompatible
with strong acids; strong bases; alcohols, oxidizers,
dimethylsulfoxide; dimethyl formamide. Contact with water
or moisture produces corrosive and poisonous hydrogen
chloride gas, methanol and carbon monoxide. Corrodes
metals in the presence of moisture. Attacks some plastics,
rubber and coatings.
廃棄物の処理
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations
governing storage, transportation, treatment, and waste
disposal
メチルクロロホルマート 上流と下流の製品情報
原材料
準備製品
シアノカルバミン酸メチル
オキシベンダゾール
3-(2-メトキシフェニル)-5-メトキシ-2-オキソ-2,3-ジヒドロ-1,3,4-オキサジアゾール
セファクロル一水和物
METHYL 3-THIOPHENECARBOXYLATE
PIPERAZINE-1,4-DICARBOXYLIC ACID TERT-BUTYL ESTER METHYL ESTER
カルバモイルホスホン酸エチルアンモニウム
カルバミン酸メチル
テニダプ
5-ブロモ-L-トリプトファン
アシュラム
METHYL THIOCYANOFORMATE
2-(メトキシカルボニルアミノ)-1H-ベンゾイミダゾール
(S)-5-メチル-α-アミノ-1H-インドール-3-プロピオン酸
3-ブロモチオフェン-2-カルボン酸メチル
炭酸アリルメチル
[1,2-フェニレンビス(イミノカルボノチオイル)]ビス(カルバミド酸)ジメチル
3,4-ジクロロカルバニル酸メチル
(3-メチルフェニル)カルバミド酸3-[(メトキシカルボニル)アミノ]フェニル
メベンダゾール
トロキサトン
炭酸 ジメチル
2,5-ジヒドロ-2,5-ジオキソ-1H-ピロール-1-カルボン酸メチル
2-メチル-4-(2,6,6-トリメチル-1-シクロヘキセニル)-2-ブテナール