シアノ酢酸 エチル 化學(xué)特性,用途語,生産方法
外観
無色～うすい黃色, 澄明の液體
溶解性
水に難溶。エタノール, エーテルと混和。エタノール及びジエチルエーテルに極めて溶けやすく、水に溶けにくい。
解説
シアノ酢酸エチル,無色の液體．融點(diǎn)－22 ℃，沸點(diǎn)206 ℃．エタノール，エーテル，アルカリ水溶液に可溶，水に不溶．有機(jī)化合物，醫(yī)薬品，染料の合成原料として用いられる．
森北出版「化學(xué)辭典（第2版）
製造
シアノ酢酸エチル,シアノ酢酸をエチルエステル化することにより得られる．
説明
Ethyl cyanoacetate is the ethyl ester of cyanoacetic acid. Ethyl cyanoacetate hydrolizes rapidly under neutral and alkaline conditions to cyanoacetic acid and ethanol (and so it does under most physiological and environmental conditions), while in acid pH the half life is considerably longer.
Knoevenagel condensation of ethyl cyanoacetate with aldehyde is reported. Microwave enhanced Knoevenegal condensation reaction of ethyl cyanoacetate with an aldehyde, P2O5, piperidine and chlorobenzene is reported.
化學(xué)的特性
Ethyl cyanoacetate is a colorless to straw colored liquid with a mild pleasant odor
使用
Reagent used in labelled pyrimidine and purine synthesis. Ethyl cyanoacetate is an ester. It may be used in the synthesis of ethyl glyoxylate.It was used to investigate the Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites.
製造方法
Ethyl cyanoacetate can be prepared by the action of sodium or potassium cyanide on ethyl chloroacetate, and by the action of sodium cyanide on sodium chloroacetate, followed by esterification.
一般的な説明
A colorless liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. Flash point 210°F. May be toxic by ingestion. Used to make other chemicals.
空気と水の反応
Slightly soluble in water.
反応プロフィール
Ethyl cyanoacetate is both a nitrile and an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.
危険性
Toxic by ingestion and inhalation.
健康ハザード
TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
火災(zāi)危険
Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
安全性プロファイル
oison by ingestion.
Moderately toxic by intraperitoneal and
subcutaneous routes. Combustible when
exposed to heat or flame; can react with
oxidzing materials. Wdl react with water or
steam to produce toxic and flammable
vapors. To fight fire, use CO2, dry chemical.
When heated to decomposition or on
contact with acid or acid fumes it emits
highly toxic fumes of CN-. See also
NITRILES.
職業(yè)ばく露
A nitrile used to manufacture dyes,
pharmaceuticals, and other chemicals.
輸送方法
UN3276 Nitriles, liquid, toxic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required, Potential Inhalation Hazard (Special
Provision 5).
純化方法
Shake the ester several times with aqueous 10% Na2CO3, wash it well with water, dry with Na2SO4 and fractionally distil it. [Beilstein 2 IV 1889.]
不和合性
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides, and reducing agents.
Nitriles may polymerize in the presence of metals and
some metal compounds. They are incompatible with acids;
mixing nitriles with strong oxidizing acids can lead to
extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and
epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both
aqueous acid and base to give carboxylic acids (or salts of
carboxylic acids). These reactions generate heat. Peroxides
convert nitriles to amides. Nitriles can react vigorously
with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have
low aqueous solubility. They are also insoluble in aqueous
acids. Reacts with moisture, water, and steam, forming
toxic fumes.
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 with EPA regulations governing storage, transportation, treatment, and waste disposal.
參考文獻(xiàn)
[1] Wohlfarth, C. “Viscosity of ethyl cyanoacetate.” 1900. 0.、
[2] A. C. Cope, E. M. Hancock. “Ethyl (1‐Ethylpropylidene)cyanoacetate.” Organic Syntheses 38 1 (2003): 46–46.
[3] Ismailov, V.M. et al. “SYNTHESIS BASED ON ETHYL CYANOACETATE.” Kimya probleml?ri 86 1 (2023): 0.
[4] T.R. Kasturi, A. Srinivasan. “A revised structure for the condensation product of 2-carbethoxycyclopentanone and ethyl cyanoacetate.” Tetrahedron 22 8 (1966): Pages 2575-2580.
[5] Akram Ranjbar Derranji, Mohammad Anary-Abbasinejad. “An efficient synthesis of 4,5-disubstituted 1,2,3-triazoles by three-component reaction between sodium azide, ethyl cyanoacetate or malonitrile and arylglyoxals.” Synthetic Communications 54 6 (2024): Pages 471-477.
シアノ酢酸 エチル 上流と下流の製品情報(bào)
原材料
準(zhǔn)備製品
4-メトキシメチル-6-メチル-2-オキソ-1,2-ジヒドロ-3-ピリジンカルボニトリル
ETHYL 2-CYANO-3-METHYL-2-PENTENOATE
2-アミノ-4,5,6,7-テトラヒドロベンゾ[b]チオフェン-3-カルボン酸エチル
トリアムテレン
2-(4,6-diamino-1,3,5-triazin-2-yl)acetic acid
アロプリノール
2-アミノ-4-(トリフルオロメチル)ベンゾニトリル
3-メチル-4-シアノ-5-アミノチオフェン-2-カルボン酸エチル
2-メチル-2-エチルこはく酸
Disperse Yellow S-3GL
6-AMINO-2-METHYLTHIO-3-METHYLURACIL
1,2,3,5-テトラヒドロ-8-チア-5,7-ジアザ-シクロペンタ[A]インデン-4-オン
2-アミノ-4,6-ジメチルピリジン-3-カルボオキサミド
6-アミノウラシル (4-)
2-CHLORO-4-METHYLQUINOLINE-3-CARBONITRILE
2-アミノ-4,5-ジメチル-3-チオフェンカルボン酸エチル
6-AMINO-2-MERCAPTO-PYRIMIDIN-4-OL
Ethyl α-cyanoacrylate instantaneous adhesive
2-アミノ-6-メチル-4,5,6,7-テトラヒドロ-1-ベンゾチオフェン-3-カルボン酸エチル
4-アミノ-5-カルボエトキシ-2-エチルメルカプトピリミジン
3-アミノ-2,2-ジメチル-1-プロパノール
2-AMINO-5-ISOPROPYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER
2-アミノ-4-エチル-5-メチルチオフェン-3-カルボン酸エチル
ETHYL(Z)-2-CYANO-3-ETHOXY-2-PROPENOATE
アミロリド·塩酸塩
3-アミノ-5-メチルピラゾール-4-カルボン酸エチル
6-アミノ-1-メチルピリミジン-2,4(1H,3H)-ジオン
2-FORMAMIDINO-2-PHENYLDIAZOACETAMIDE HYDROCHLORIDE
1-Cyclohexyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile ,97%
2,5,6-トリアミノピリミジン-4-オール
2-クロロ-4-(メトキシメチル)-5-ニトロ-6-メチルピリジン-3-カルボニトリル
4-アミノ-6-ヒドロキシ-2-メルカプトピリミジン水和物
ETHYL 5-AMINO-1-PYRIDIN-2-YL-1H-PYRAZOLE-4-CARBOXYLATE
グアニン硫酸塩二水和物
ダカルバジン
2-アミノ-5,6-ジヒドロ-4H-シクロペンタ[B]チオフェン-3-カルボン酸エチルエステル
6-アミノ-1-メチル-5-ニトロソウラシル
6-AMINO-3-METHYLURACIL
3-エトキシ-3-イミノプロピオン酸エチル
5,6-ジアミノ-1-メチルウラシル