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腈类化合物

腈类化合物是重要的化工原料,广泛应用于制造药物、合成纤维及塑料,还用于电镀、钢的淬火以及选矿等领域。氢氰酸及其盐类主要用于电镀业与采矿业(提取金银),同时也用作各种树脂和合成腈类化合物的制备,甚至在仓库和船舱中进行烟熏灭鼠。

丙烯腈和甲基丙烯腈等是合成纤维、合成橡胶及塑料的重要原料。值得注意的是,某些植物果实和核仁,如苦杏仁、枇杷仁、桃仁、木薯和白果等含有氰化物。过量摄入这些物质,特别是对儿童而言,可能导致中毒甚至死亡。

不同种类的动物对氰和腈类化合物的敏感性差异显著:狗和豚鼠最为敏感,其次是小鼠和兔,而大鼠则相对不敏感。人类对其的敏感度介于两者之间。

在调香行业中,有机腈类化合物因其强烈的香气被广泛使用,具有如下的通式:R—CN 或 R—O—CN。

腈类化合物以其强烈且类似于醛类的香气著称,但更尖锐和强烈。它们最重要的特性是在弱碱性介质中(例如肥皂、洗涤剂等产品)表现出良好的稳定性。因此,在这类产品中用相应的腈类代替醛类可以提高香精的稳定性。

无机氰化氢是一种极其毒性的物质,相比之下,大多数有机腈类化合物不具备毒性或刺激性,即使是苯乙腈也仅具有轻微的刺激作用。

乙腈,又称甲基氰,是一种无色液体,带有芳香气味,沸点为81.6℃。主要用于有机合成和药物、香料制造等领域,属于中等毒物类别。小鼠口服LD50值在200~453.2 mg/kg之间,吸入2小时的LC50值为3,860~9,651 mg/m³。

乙腈皮下注射后,血浆中的SCN-含量会在两小时内增加,并在7小时达到高峰。小鼠实验显示无明显蓄积作用,人类嗅觉阈值为67.2 mg/m³。短期暴露于840 mg/m³的浓度下会引发鼻咽部刺激症状;超过该浓度则可能导致恶心、呕吐、胸痛、腹痛及血管变化等症状,并曾有职业中毒案例报道。

中文名称 英文名称 CAS号 化学式 结构式图片
(5-甲氧基-2-吡啶基)乙腈 2-(5-methoxy-2-pyridinyl)acetonitrile 204067-34-5 C8H8N2O
(5-甲氧基-2-吡啶基)乙腈
(4-氯苯基)[2-氯-4-(羟基亚胺)-5-甲基环己-2,5-二烯-1-亚基]乙腈 4-chloro-α-(2-chloro-4-hydroxyimino-5-methyl-2,5-cyclohexadien-1-ylidene)phenylacetonitrile 844-24-6 C15H10Cl2N2O
(4-氯苯基)[2-氯-4-(羟基亚胺)-5-甲基环己-2,5-二烯-1-亚基]乙腈
(3aS-顺式)-3a,8a-二氢-8H-茚并[1,2-d]恶唑-2-乙腈 2-((3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazol-2-yl)acetonitrile 175166-50-4 C12H10N2O
(3aS-顺式)-3a,8a-二氢-8H-茚并[1,2-d]恶唑-2-乙腈
(3,5-二氟苯基)(羟基)乙腈 3,5-difluoromandelonitrile 132741-32-3 C8H5F2NO
(3,5-二氟苯基)(羟基)乙腈
(2-氟苯基)-氧代乙腈 2-fluorobenzoyl cyanide 80277-41-4 C8H4FNO
(2-氟苯基)-氧代乙腈
(2-乙氧基苯氧基)乙腈 (2-ethoxyphenoxy)methyl cyanide 6781-16-4 C10H11NO2
(2-乙氧基苯氧基)乙腈
(1R,2S)-2-羟基环己烷-1-腈 (1R,2S)-2-hydroxycyclohexane-1-carbonitrile 125356-62-9 C7H11NO
(1R,2S)-2-羟基环己烷-1-腈
(1-甲基-1H-咪唑-4-基)乙腈 (1-methyl-1<i>H</i>-imidazol-4-yl)-acetonitrile 41065-00-3 C6H7N3
(1-甲基-1H-咪唑-4-基)乙腈
—— (S)-3-(4-bromophenyl)-3-hydroxypropanenitrile 877876-70-5 C9H8BrNO
(S)-3-(4-bromophenyl)-3-hydroxypropanenitrile
—— 4-acetyl-3-fluorobenzonitrile 1352144-78-5 C9H6FNO
4-acetyl-3-fluorobenzonitrile
—— 5-iodo-2-(methylthio)benzonitrile 1161499-58-6 C8H6INS
5-iodo-2-(methylthio)benzonitrile
—— 2-chloro-3-fluoro-4-iodobenzonitrile 1114547-55-5 C7H2ClFIN
2-chloro-3-fluoro-4-iodobenzonitrile
—— (1<i>H</i>-pyrazol-4-yl)-acetonitrile 1195672-98-0 C5H5N3
(1<i>H</i>-pyrazol-4-yl)-acetonitrile
—— (R)-3-(4-bromophenyl)-3-hydroxypropanenitrile 877876-61-4 C9H8BrNO
(R)-3-(4-bromophenyl)-3-hydroxypropanenitrile
—— 3-(2-bromoethoxy)benzonitrile 210963-61-4 C9H8BrNO
3-(2-bromoethoxy)benzonitrile
—— tricarbonyl-tris(acetonitrile)tungsten(0) 16800-47-8 C9H9N3O3W
tricarbonyl-tris(acetonitrile)tungsten(0)
—— 2-(bromomethyl)acrylonitrile 17200-53-2 C4H4BrN
2-(bromomethyl)acrylonitrile
—— 2-(hydroxymethyl)-acrylonitrile 23873-54-3 C4H5NO
2-(hydroxymethyl)-acrylonitrile
—— rac-Leucinnitril 65451-12-9 C6H12N2
rac-Leucinnitril
—— TRANS-4-(4'-N-BUTYLCYCLOHEXYL)-BENZONITRILE 61204-00-0 C17H23N
TRANS-4-(4'-N-BUTYLCYCLOHEXYL)-BENZONITRILE
—— (4-Chlorophenyl)[2-chloro-4-(hydroxyimino)-5-methylcyclohexa-2,5-dien-1-ylidene]acetonitrile 844-24-6 C15H10Cl2N2O
(4-Chlorophenyl)[2-chloro-4-(hydroxyimino)-5-methylcyclohexa-2,5-dien-1-ylidene]acetonitrile
—— 1-((Benzyloxy)methyl)cyclopropane-1-carbonitrile 1387565-90-3 C12H13NO
1-((Benzyloxy)methyl)cyclopropane-1-carbonitrile
—— 3-Brom-4-nitro-benzylcyanid 124840-60-4 C8H5BrN2O2
3-Brom-4-nitro-benzylcyanid
—— 6-(4-bromophenyl)naphthalene-2-carbonitrile 1228267-66-0 C17H10BrN
6-(4-bromophenyl)naphthalene-2-carbonitrile
—— 3-(2-methoxy-6-methyl-pyridin-3-yl)-3-oxo-propionitrile 1375637-50-5 C10H10N2O2
3-(2-methoxy-6-methyl-pyridin-3-yl)-3-oxo-propionitrile
—— 3-(4-hydroxy-3-methylphenyl)propanenitrile 22516-99-0 C10H11NO
3-(4-hydroxy-3-methylphenyl)propanenitrile
—— 2-hydroxy-4-methoxyphenylacetonitrile 32884-26-7 C9H9NO2
2-hydroxy-4-methoxyphenylacetonitrile
—— 2-(trans-4-aminocyclohexyl)acetonitrile 1266328-42-0 C8H14N2
2-(trans-4-aminocyclohexyl)acetonitrile
—— CYCLOHEXANE-1,4-DICARBONITRILE 6550-85-2 C8H10N2
CYCLOHEXANE-1,4-DICARBONITRILE
—— 5-bromo-1,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 450841-30-2 C8H7BrN2O
5-bromo-1,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
—— 2-amino-5-tert-butylbenzonitrile 874814-72-9 C11H14N2
2-amino-5-tert-butylbenzonitrile
—— 2-(7-chloro-4-oxo-3,4-dihydroquinazolin-2(1H)-ylidene)-3-(2,4-dichlorophenyl)-3-oxopropanenitrile 1370554-01-0 C17H8Cl3N3O2
2-(7-chloro-4-oxo-3,4-dihydroquinazolin-2(1H)-ylidene)-3-(2,4-dichlorophenyl)-3-oxopropanenitrile
—— 3-Chlor-2-methyl-acrylonitril 10329-37-0 C4H4ClN
3-Chlor-2-methyl-acrylonitril
—— 2-cyano-4-nitro-N-methylaniline 85020-87-7 C8H7N3O2
2-cyano-4-nitro-N-methylaniline
—— 4-(difluoromethyl)benzonitrile 55805-10-2 C8H5F2N
4-(difluoromethyl)benzonitrile
—— 2-(6-bromopyridin-2-yl)-2-methylpropanenitrile 1093879-76-5 C9H9BrN2
2-(6-bromopyridin-2-yl)-2-methylpropanenitrile
—— 1,3,5-tri(3,4-dicyanophenoxy)benzene 444717-57-1 C30H12N6O3
1,3,5-tri(3,4-dicyanophenoxy)benzene
—— 1,2,3,4,5,6-hexakis(2-cyanoethoxy)hexane 2465-92-1 C24H32N6O6
1,2,3,4,5,6-hexakis(2-cyanoethoxy)hexane
—— 1,2,3,4,5,6-Hexakis-(2-cyan-ethoxy)-hexan 2465-92-1 C24H32N6O6
1,2,3,4,5,6-Hexakis-(2-cyan-ethoxy)-hexan
—— 2-(cyanomethyl)cyclohexanone 42185-27-3 C8H11NO
2-(cyanomethyl)cyclohexanone
—— 4-(2-hydroxypropan-2-yl)benzonitrile 77802-22-3 C10H11NO
4-(2-hydroxypropan-2-yl)benzonitrile
—— (S)-3-hydroxy-3-phenylpropanenitrile 132203-26-0 C9H9NO
(S)-3-hydroxy-3-phenylpropanenitrile
—— lanoconazole 126509-69-1 C14H10ClN3S2
lanoconazole
—— 1,3-dicyano-4,6-dimethylbenzene 17309-31-8 C10H8N2
1,3-dicyano-4,6-dimethylbenzene
—— 2,2,6,6-tetrakis(2-cyanoethyl)cyclohexanone 5883-05-6 C18H22N4O
2,2,6,6-tetrakis(2-cyanoethyl)cyclohexanone