咪唑

咪唑用途

【用途一】
用作有机合成原料及中间体，用于制取药物及杀虫剂
【用途二】
用作分析试剂，也用于有机合成
【用途三】
咪唑是农药抑霉唑、咪鲜胺等杀菌剂的中间体，也是医药抗真菌药双氯苯咪唑、益康唑、酮康唑、克霉唑的中间体。
【用途四】
咪唑类主要用作环氧树脂的固化剂，在日本占咪唑类消费量的一半以下，其用量为环氧树脂的0.5%-10%咪唑类化合物可用作抗真菌药、抗霉剂、低血糖治疗药、人造血浆等，还可用作治疗、人造血浆等，还可用作治疗滴虫病及火鸡黑头病的药物。咪唑类抗真菌药双氯苯咪唑、益康唑、酮康唑、克霉唑的生产中，咪唑是主要原料之一。由咪唑和2,4,ω-三氯苯乙酮为主要原料可制得果实杀菌剂伊迈唑。将2,4,ω-三氯苯乙酮加入无水甲醇中，加热回流，滴加溴素。待溶液颜色逐渐消失后冷却至0℃，加入咪唑，激烈搅拌3h。然后减压蒸去甲醇。剩余液倒入水中，用二氯甲烷萃取，萃取液回收二氯甲烷后加入稀硝酸成盐，用水重结晶后再用氨水处理得到2',4'-二氯-2-咪唑苯乙酮。再进一步用硼氢化钠还原成相应的醇，最后在氢氧化钠和二甲基甲酰胺存在下，用烯丙基氯基化而制得伊迈唑（Enilconazde，也称恩康唑）。伊迈唑与双氯苯咪唑（咪康唑）的结构和生产方法有一些共同之处。双氯苯咪唑是广谱护真菌药物，伊迈唑也是抗真菌药，但广泛用作水果的防腐剂（也称Imazalil）。

咪唑名称

[ CAS 号 ]:
288-32-4

[ 中文名 ]:
咪唑

[ 英文名 ]:
Imidazole

[中文别名 ]:

[英文别名 ]:

IMD
1,3-Diaza-2,4-cyclopentadiene,Glyoxaline
GLYOXALIN
LMIDAZOLE
glioksal
1,3-diaza-2,4-cyclopentadiene
Imidazol
Miazole
1,3-imidazole
Imidazoie

咪唑生物活性

[ 描述 ]:

Imidazole是一种平面五元环, 是一种高极性化合物, 已被广泛用作腐蚀抑制剂

[ 相关类别 ]:

信号通路 >> 其他 >> 其他

生化试剂

研究领域 >> 其他

[相关活性小分子]

咪唑物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
257.0±9.0 °C at 760 mmHg

[ 熔点 ]:
88-91 °C(lit.)

[ 分子式 ]:
C₃H₄N₂

[ 分子量 ]:
68.077

[ 闪点 ]:
145.0±0.0 °C

[ 精确质量 ]:
68.037445

[ PSA ]:
28.68000

[ LogP ]:
-0.16

[ 外观性状 ]:
白色至黄色晶体或粉末,带有一种胺的气味

[ 蒸汽压 ]:
0.0±0.5 mmHg at 25°C

[ 折射率 ]:
1.528

[ 储存条件 ]:
2-8°C

[ 稳定性 ]:
Stable. Incompatible with acids, strong oxidizing agents. Protect from moisture.

[ 水溶解性 ]:
633 g/L (20 ºC)

咪唑MSDS

详细MSDS(安全技术说明书)

咪唑毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI3325000

CHEMICAL NAME :: Imidazole

CAS REGISTRY NUMBER :: 288-32-4

BEILSTEIN REFERENCE NO. :: 0103853

LAST UPDATED :: 199710

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C3-H4-N2

MOLECULAR WEIGHT :: 68.09

WISWESSER LINE NOTATION :: T5M CNJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 220 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 626 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 880 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 817 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 475 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 28 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 125 mg/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Behavioral - rigidity (including catalepsy) Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 760 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 150 mg/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - impotence

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Human Cells - not otherwise specified

DOSE/DURATION :: 1 mmol/L

REFERENCE :: JIDEAE Journal of Investigative Dermatology. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1938- Volume(issue)/page/year: 65,400,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - M1601 No. of Facilities: 158 (estimated) No. of Industries: 3 No. of Occupations: 5 No. of Employees: 1401 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - M1601 No. of Facilities: 313 (estimated) No. of Industries: 3 No. of Occupations: 4 No. of Employees: 3009 (estimated) No. of Female Employees: 2411 (estimated)

咪唑安全信息

[ 符号 ]:

GHS05, GHS07, GHS08

[ 信号词 ]:
Danger

[ 危害声明 ]:
H302-H314-H360D

[ 警示性声明 ]:
P201-P260-P280-P303 + P361 + P353-P305 + P351 + P338-P308 + P313

[ 个人防护装备 ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ 危害码 (欧洲) ]:
C:Corrosive

[ 风险声明 (欧洲) ]:
R22;R34;R63

[ 安全声明 (欧洲) ]:
S26-S36/37/39-S45-S22-S36

[ 危险品运输编码 ]:
UN 2923 8/PG 3

[ WGK德国 ]:
1

[ RTECS号 ]:
NI3325000

[ 包装等级 ]:
III

[ 危险类别 ]:
8

[ 海关编码 ]:
2933990090

咪唑合成路线

详细合成路线

咪唑上下游产品

咪唑上游产品

咪唑下游产品

咪唑制备

由乙二醛经环合；中和而得。将乙二醛、甲醛、硫酸铵投入反应锅，搅拌加热至85-88℃，保温4h。冷至50-60℃，用石灰水中和至pH为10以上。加热至85-90℃，排氨1h以上，稍冷，过滤，滤饼用热水洗涤，合并洗；滤液，减压浓缩至无水蒸出时，继续减压蒸馏至低沸物全部蒸完，收集105-160℃（0.133-0.267kPa）馏分，得咪唑。收率约45%。

另一种制法是使邻苯二胺与甲酸环合生成苯骈咪唑，再经双氧水反应开环为4,5-二羟基咪唑，最后脱羧制得咪唑。4,5-二羟基咪唑也可由d-酒石酸经硝化、环合而得。4,5-二羧基咪唑的脱羧制取咪唑的工艺过程如下：将4,5-二羟基咪唑与氧化铜混合，加热至100-280℃，放出大量二氧化碳气体，收集馏出液即得粗品，用苯重结晶得成品，收率76%。

3.咪唑的化学合成路线有乙二醛合成法、腈类合成法、酒石酸法、邻苯二胺与甲酸环合法、溴乙醛法等。

（1）工业乙二醛合成法　将乙二醛、甲醛、硫酸铵投入反应釜，搅拌加热至85～88℃，保温4h。然后冷却至50～60℃，用石灰水中和至pH值10以上，再加热至85～90℃，排氨1h以上。稍冷后，过滤，滤饼用热水洗涤，合并洗、滤液，加入到蒸馏装置中，先减压浓缩至无水蒸出，再继续减压蒸馏至低沸物全部蒸完，然后收集105～160℃/133.3～266.7Pa馏分，得咪唑。收率约45%。每吨产品消耗乙二醛4172kg，甲醛（37%）2344kg，硫酸铵（99%）3826kg，石灰2571kg。反应式如下：

该法由于收率和产品质量不尽如人意，文献报道了一些改进方法，如采用异丙醚萃取的方法、用乌洛托品代替甲醛的合成方法、用氨水代替硫酸铵的合成方法、用草酸铵代替硫酸铵的合成方法等。如用草酸铵代替硫酸铵可使收率提高到65%。

4.邻苯二胺与甲酸环合法　将邻苯二胺与甲酸环合生成苯并咪唑，再经双氧水反应开环为4,5-二羧基咪唑，最后脱羧制得咪唑

5.溴乙醛法　用醋酸乙烯酯与溴加成，再用乙醇处理，生成溴代乙醛，再与溴化氢、乙醇作用生成缩醛。缩醛在乙二醇及浓盐酸作用下生成环状缩醛，用过量甲酰胺与缩醛在不断通入氨气情况下反应，生成咪唑，产率为50%。

咪唑海关

[ 海关编码 ]: 2933290090

[ 中文概述 ]:
2933290090. 其他结构含非稠合咪唑环的化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

咪唑文献

A small molecule targeting ALK1 prevents Notch cooperativity and inhibits functional angiogenesis.

Angiogenesis 18(2) , 209-17, (2015)

Activin receptor-like kinase 1 (ALK1, encoded by the gene ACVRL1) is a type I BMP/TGF-β receptor that mediates signalling in endothelial cells via phosphorylation of SMAD1/5/8. During angiogenesis, sp...

Pro-apoptotic and pro-autophagic effects of the Aurora kinase A inhibitor alisertib (MLN8237) on human osteosarcoma U-2 OS and MG-63 cells through the activation of mitochondria-mediated pathway and inhibition of p38 MAPK/PI3K/Akt/mTOR signaling pathway.

Drug Des. Devel. Ther. 9 , 1555-84, (2015)

Osteosarcoma (OS) is the most common malignant bone tumor occurring mostly in children and adolescents between 10 and 20 years of age with poor response to current therapeutics. Alisertib (ALS, MLN823...

Analysis of cytochrome P450 CYP119 ligand-dependent conformational dynamics by two-dimensional NMR and X-ray crystallography.

J. Biol. Chem. 290(16) , 10000-17, (2015)

Defining the conformational states of cytochrome P450 active sites is critical for the design of agents that minimize drug-drug interactions, the development of isoform-specific P450 inhibitors, and t...

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咪唑