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Imidazole

chemical properties Physical characteristics Main application Preparation method Chemical properties Uses Production method

CAS No. 288-32-4
Chemical Name: Imidazole
Synonyms: IMD;Imutex;Miazole;Imidazol;glioksal;IMINAZOLE;IMIDAZOLE;GLYOXALIN;Imidazoie;LMIDAZOLE
CBNumber: CB6460617
Molecular Formula: C3H4N2
Formula Weight: 68.08
MOL File: 288-32-4.mol
Imidazole Property
Melting point : 88-91 °C(lit.)
Boiling point : 256 °C(lit.)
density : 1.01 g/mL at 20 °C
vapor pressure : <1 mm Hg ( 20 °C)
refractive index : 1.4801
Fp : 293 °F
storage temp. : 2-8°C
solubility : H2O: 0.1 M at 20 °C, clear, colorless
form : crystalline
pka: 6.953(at 25℃)
color : white
PH: 9.5-11.0 (25℃, 50mg/mL in H2O)
Water Solubility : 633 g/L (20 ºC)
Sensitive : Hygroscopic
Merck : 14,4912
BRN : 103853
Stability:: Stable. Incompatible with acids, strong oxidizing agents. Protect from moisture.
CAS DataBase Reference: 288-32-4(CAS DataBase Reference)
NIST Chemistry Reference: 1H-Imidazole(288-32-4)
EPA Substance Registry System: 1H-Imidazole(288-32-4)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes : C,Xi,T
Risk Statements : 36/38-63-34-22-20/21/22-61
Safety Statements : 26-36/37/39-45-22-36-27-53
RIDADR : UN 2923 8/PG 3
WGK Germany : 1
RTECS : NI3325000
TSCA : Yes
HazardClass : 8
PackingGroup : III
HS Code : 29332990
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H301 Toxic if swalloed Acute toxicity,oral Category 3 Danger P264, P270, P301+P310, P321, P330,P405, P501
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H314 Causes severe skin burns and eye damage Skin corrosion/irritation Category 1A, B, C Danger P260,P264, P280, P301+P330+ P331,P303+P361+P353, P363, P304+P340,P310, P321, P305+ P351+P338, P405,P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H318 Causes serious eye damage Serious eye damage/eye irritation Category 1 Danger P280, P305+P351+P338, P310
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H360 May damage fertility or the unborn child Reproductive toxicity Category 1A, 1B Danger
H361 Suspected of damaging fertility or the unborn child Reproductive toxicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H371 May cause damage to organs Specific target organ toxicity, single exposure Category 2 Warning P260, P264, P270, P309+P311, P405,P501
Precautionary statements:
P201 Obtain special instructions before use.
P202 Do not handle until all safety precautions have been read and understood.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P310 Immediately call a POISON CENTER or doctor/physician.
P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303+P361+P353 IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P308+P313 IF exposed or concerned: Get medical advice/attention.
P405 Store locked up.
P501 Dispose of contents/container to..…

Imidazole Chemical Properties,Usage,Production

chemical properties
Imidazole is between the two nitrogen atoms of five membered heterocyclic compounds containing. The unshared electron pair of 1-bit nitrogen atom in imidazole ring participates in the cyclic conjugation, reduces the electron density of the nitrogen atom, and makes hydrogen of the nitrogen atom easily leave in the form of hydrogen. Therefore imidazole has weak acidity, and can form salt with strong base.
The unshared electron pair of 3-bit nitrogen atom in imidazole ring doesn’t participates in the cyclic conjugation, while it occupies the sp2 hybridized orbital, can accept protons, and form salt with strong acid. Alkaline of imidazole is slightly stronger than pyrazole and pyridine.
There is tautomerism in the imidazole ring. The hydrogen on the 1-bit nitrogen atom can be transferred to the 3-atom, therefore, imidazole derivatives with same substituent respectively on 4-bit and 5-bit are tautomers.
Imidazole is stable to acid, and has antioxidant activity. Imidazole derivatives are widely found in nature, such as histamine, histidine and benzimidazole, etc.
There are some interesting reagents in acyl imidazole compounds. For example, 1-acetyl imidazole is a stable acylating agent, after reaction with pyrrole, it becomes 1-acetyl pyrrole. Furthermore, in general, 1-acetyl imidazole can get ketones and aldehydes using Grignard reagent and reducing agent. Reaction of N, N-carbonyldimidazole and carboxyl will get useful reagent acyl imidazole. The relationship between imidazole and natural compounds is very close. For example, pyrimidine ring turns into purine derivatives after condensation. In addition to being like 6-amino purine and guanine the nucleic acid bases, it also exists in the organisms of uric acid, caffeine and theophylline. The catalytic action of imidazole, such as accelerated enzyme hydrolysis, still under study. As the cause of allergic skin, its toxicity is similar todiamine. Rat oral LD501880mg/kg.
Physical characteristics
In nature, there are only imidazole derivatives and no free imidazole. The precipitation from benzene is a colorless crystalline prism, with scents of ammonia. Relative molecular mass 68.08. Relative density 1.0303(101/4℃) . Melting point 89~91℃,boiling point 257℃,165℃~168℃(2.67×103Pa) and 138.2℃(1.60×103Pa). Flash point 145℃. Refractive index 1.4801(101℃). Viscosity 2.696mPa·s(100℃). Slightly soluble in benzene, petroleum ether, soluble in ether, acetone, chloroform and pyridine, easily soluble in water (at normal temperature 70) and ethanol. It appears weak alkaline. As the-NH-bond on 1 bite and-N= bond on 3 bit forms hydrogen bond, the boiling point is quite high; when 1 bit hydrogen is substituted, hydrogen bond cannot be formed, hence the boiling point decreases. As to thermal stability, it rarely dissolves under 250℃ (decomposition temperature is 590℃). It is also very stable to reducing agent and oxidant, but can form stable salt with inorganic acid. Owning some certain aromatic properties, also could get halogenation, nitration, sulfonation and hydroxymethylation in the presence of catalyst. Can be coupled with the heavy nitrogen salt in 2 bit. In addition, due to the =NH (1 bit) connected to the two double bonds, with some of the "acid", it can be replaced by metal to get salt. In addition, 3 bit nitrogen ions have coordination effect on metal ions, which can form chelate compounds. Although it is difficult to restore, but can be combined with the proton to generate cation type with resonance structure, and get of a stable form. Tautomers of imidazole ring are very easy to change, so it is hard to tell isomers on 4 bit or 5 bit.
The above information is edited by the Chemicalbook He Liao Pu.
Main application
Imidazole can be used as epoxy curing agent, improve the mechanical properties such as bending, stretching and compression etc., improve the electrical properties of the insulation, and improve performance of chemical resistance properties, which is widely used in computers and electrical appliances;
Used as an anti-rust agent for copper in printed circuit boards and integrated circuits;
Used as pharmaceutical raw materials for manufacturing anti-fungal drugs, antifungal agents, drug for treatment of hypoglycemia, artificial plasma, trichomonad drug, bronchial asthma drug, macula agent, etc.;
Used as pesticide raw material for synergist, insecticides and fungicides of boric acid agent;
In addition, imidazole is also used as raw material of urea-formaldehyde resin curing agent, photographic medicine, adhesive, coating, vulcanizer, antistatic agent, etc.; intermediate for organic synthesis.
Preparation method
With glyoxal as raw material, reactive in formaldehyde and ammonium sulfate (or ammonia) in 85~90℃, and get imidazole sulfate and then neutralized with calcium hydroxide to get imidazole crude product. Filtering, water washing, combining filtrate and washings, decompression evaporation concentration and crystallization, then it’s done. If using ammonia directly, then there should be no sulfate processing steps and it can be prepared at once. Either with ammonium sulfate or ammonia, the yield is relatively low, approximately 45%.
With o-phenylenediamine and formic acid as raw material, via cyclization to benzimidazole, and then through oxidation in the sulfuric acid solution to generate dicarbonyl imidazole; later in the effect of copper oxidation, via decarboxylation from 100 to 150℃ to get crude; And then in benzene solution recrystallization to get imidazole finished products.
With d-tartrate acid as raw material, in sulfuric acid, nitric acid was used to carry out nitrification, and get 2, 3-dinitro tartrate acid; and then in the formaldehyde and ammonia reaction, to get dicarboxylic imidazole; finally decarboxylation to get it.
Chemical properties
Colorless prismatic crystals, weakly alkaline. Easily soluble in water, ethanol, ethyl ether, chloroform and pyridine, slightly soluble in benzene, insoluble in petroleum ether.
Uses
1.Used as intermediate of bactericide for imazalil, prochloraz, etc., and that of pharmaceutical anti-fungal drug, econazole, ketoconazole, and clotrimazole as well.
2.Used as organic synthetic materials and intermediates for the preparation of drugs and pesticides.
3.Used as analytical reagent, as well as in organic synthesis.
4.Imidazole is mainly used as curing agent for epoxy resin. In Japan the imidazole accounts for less than half of the consumption. For imidazole compounds whose dosage is 0.5 to 10 percent of epoxy resin, it can be used in antifungal drug, ant mildew agent, hypoglycemic drug, artificial plasma, etc., also can be used in medicines to cure trichomoniasis and turkey blackhead. Imidazole is also one of the main raw material during production of imidazole antifungal miconazole, econazole, clotrimazole and ketoconazole. By imidazole and 2, 4, ω-trichloroacetophenon as the main raw material, it can get fruit fungicide enilconazde. Add 2, 4, ω-trichloroacetophenon into absolute methanol, with heating reflux, adding bromine. Wait until the solution color gradually disappeared, cooling to 0℃, and then intensely mixing it for 3h. And the vacuum distillation of methanol. Put the remaining liquid into the water, to extract it with dichloromethane. After the extract recovered with dichloromethane, add dilute nitric acid to get salt; recrystallization with water and then treated with ammonia to get 2', 4'-dichloro-2-imidazole acetophenone. Furthermore use sodium borohydride reduction into the corresponding alcohols, and then in the presence of sodium hydroxide and dimethyl formamide, use allyl chloride based to get enilconazde (also known as enilconazole). the after adding dilute nitric acid salt and water after recrystallization using ammonia water treatment of 2,2 ', 4'-dichloro 2-methyl imidazole phenyl ethyl ketone. It has something in common of the structure and production methods between enilconazde and miconazole. Miconazole is a broad-spectrum antifungal agent, and enilconazde is also antifungal agent, which is widely used in imazalil.
5.Agrochemical intermediates, bactericide intermediates, triazole fungicide.
Production method
1.It can be made via cyclization and neutralization by glyoxal. Put glyoxal, formaldehyde and ammonium sulfate into reaction pot, stir and heat up to 85-85℃ with heat preservation 4h. Cool it to 50-60℃, with limewater neutralization to pH for more than 10. Heat up to 85-90℃, ammonia excretion for more than 1h, cool it slightly, filter and filter cake washing with hot water; Combined wash, filtrate, and vacuum concentration until anhydrous steamed out; continue to vacuum distillation until low boiling substances all steamed out, collect 105-160℃ (0.133-0.267kPa) fractions and then imidazole is done. The yield is about 45%. Another method is to make cyclization of o-diaminobenzene and formic acid to get benzimidazole, followed by 4, 5-dyhydroxy imidazole via reaction and open-loop of hydrogen peroxide, and finally get imidazole via decarboxylation. 4, 5-dyhydroxy imidazole also can be made by d-tartrate through nitration and cyclization. The process of getting imidazole via decarboxylation of 4, 5-dyhydroxy imidazole is as below: mix 4, 5-dyhydroxy imidazole with copper oxide, heat up to 100-280℃, emit lots of carbon dioxide gas, then the collected distillate is crude product, and at last recrystallize it with benzene to get the product, and the yield is 76%.
2.The production method is to put glyoxal, formaldehyde and ammonium sulfate into reaction pot, stir and heat up to 85-85℃ with heat preservation 4h. Cool it to 50-60℃, with limewater neutralization to pH for more than 10. Heat up to 85-90℃, ammonia excretion for more than 1h, cool it slightly, filter and filter cake washing with hot water; Combined wash, filtrate, and vacuum concentration until anhydrous steamed out; continue to vacuum distillation until low boiling substances all steamed out, collect 105~160℃/133~266Pa fractions and then imidazole is done.
With o-phenylenediamine as raw material, put it into formic acid, stir and heat up, heat preservation at 95~98℃ for 2h, cool it to 50~60℃, adjust PH value to 10 with 10%NaOH; When it reaches room temperature, with filtering, washing and drying to get benzimidazole. Put benzimidazole into concentrated sulfuric acid, heat up to 100℃, and slowly drop in H2O2. Reaction while stirring under 140~150℃ for 1h, cooling to 40℃, water dilution, precipitation, crystallization, filtration, washing, drying, and then 4, 5-dyhydroxy imidazole is done. Mix 4, 5-dyhydroxy imidazole with copper oxide, heat up to 100-280℃, emit lots of carbon dioxide gas, then the collected distillate is white block crude product, and at last recrystallize it with benzene to get the fine imidazole.
Chemical Properties
White to off white crystals
Uses
Excellent for buffers in the range of pH 6.2-7.8
Uses
Imidazole is a versatile heterocycle used in the preparation of various biologically active compounds such as the amino acid histidine and is present in many antifungal medication. It is also used ext ensively as a corrosion inhibitor on transition metals such as copper.
Uses
Used as a buffer reagent in the pH range 6.2-7.8
Definition
ChEBI: An imidazole tautomer which has the migrating hydrogen at position 1.
Imidazole Preparation Products And Raw materials
Raw materials
4,5-Imidazoledicarboxylic acid Glyoxal Ammonium hydroxide Benzimidazole Potassium hydroxide Hydrogen peroxide Formaldehyde Cupric oxide Ammonium chloride Hydrochloric acid o-Phenylenediamine
Preparation Products
2-(1H-IMIDAZOL-1-YL)BENZOIC ACID 2,6-Dihydroxypurine Imidazole-2-carboxaldehyde beta-Methyl vinyl phosphate (MAP) Miconazole nitrate 2-Bromo-4-nitroimidazole imidazol-2-ylamine sulphate 1-Methylimidazole 4-(IMIDAZOL-1-YL)PHENOL Orazamide 6-FLUORO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBONITRILE 1-(1-2-HYDROXYPHENYL)ETHENYL)-1H-IMIDAZOLE 1-Boc-3-(Amino)azetidine 1-[4-(BROMOMETHYL)PHENYL]-1H-PYRAZOLE 5-Bromoindazole N-(3-Aminopropyl)-imidazole 4-Chloroimidazole 1-Phenylimidazole TRIFLUMIZOLE 1-[(4-Methylphenyl)sulfonyl]-1H-imidazole 6-FLUORO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBOXYLIC ACID Imazalil Oxiconazole nitrate 1-BENZYL-2-IMIDAZOLECARBOXYLIC ACID 2-CYANOPYRIDINE-4-CARBOXALDEHYDE 4-(1H-IMIDAZOL-1-YL)BENZOIC ACID Clotrimazole Detergent,industrial chloroalcohol type homogeneous strongly basic anion exchange membrane 4-(HYDROXYMETHYL)PICOLINITRILE (S)-4-BOC-MORPHOLINE-3-CARBOXYLIC ACID 1-METHYL-5-NITROIMIDAZOLE Climbazole 4-(1H-Imidazol-1-yl)benzaldehyde 4-Nitroimidazole Sisthsne Ketoconazole 2-Imidazol-1-ylethanamine Econazole 5-(AMINOMETHYL)-1-METHYLPYRROLIDIN-2-ONE
Imidazole Suppliers      Global( 473)Suppliers     
Supplier Tel Fax Email Country ProdList Advantage
Capot Chemical Co.,Ltd. +86 (0)571-855 867 18
+86 (0)571-858 647 95 sales@capotchem.com China 19953 60
Shenzhen Sendi Biotechnology Co.Ltd. 0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3230 55
Shanghai Rolead Chemical Technology Co., Ltd. 021-69992230 / 69992220
021-69992237 roleadchem@163.com China 4641 50
Shanghai Macklin Biochemical Co.,Ltd. 15221275939
021-51821727 shenlinxing@macklin.cn China 13254 55
SHANGHAI BANGCHENG CHEMICAL Co.,Ltd. 021-52696680
021-69106780 bangchem1@163.com China 8323 60
Shanghai Pengsuo Biochemical Technology Co., Ltd. 021-59118555
021-59119222 pengsuochem@163.com China 3683 55
Shenzhen Vtolo Chemicals Co., Ltd. 13534282526
+86 0755 2767-0086-806 yolanda@vtolo.com China 232 55
Shanghai Kangman Biological Technology Co., Ltd. 18800375331
021-50908862 kangmansales@163.com China 7642 55
Shanghai Aladdin Bio-Chem Technology Co.,LTD 021-20337333/400-620-6333
021-50323701 sale@aladdin-e.com China 25125 65
Aikon International Limited 025-66061683,18551800669//qq:2850281404
cfding@aikonchem.com China 10222 58
 
288-32-4(Imidazole)Related Search:
1-[(3,4-DICHLOROBENZYL)OXY]-1H-IMIDAZOLE 1-(3-CARBOXY-PHENYL)-2-(2-FLUORO-PHENYL)-5-METHYL-1H-IMIDAZOLE-4-CARBOXYLIC ACID ETHYL ESTER 2-Butyl-4-chloro-5-formylimidazole 1,3-BIS(3-CHLOROBENZYL)-1H-IMIDAZOLE-2,4,5(3H)-TRIONE Candesartan 1-[(3-METHOXYBENZYL)OXY]-1H-IMIDAZOLE 1-[(3-CHLOROBENZYL)OXY]-3-(3-FLUOROBENZYL)-1H-IMIDAZOLE-2,4,5(3H)-TRIONE 1-(3-FLUOROPHENYL)IMIDAZOLE-2-THIONE 1-(3,4-DICHLOROBENZYL)-3-[(2,4-DICHLOROBENZYL)OXY]-1H-IMIDAZOLE-2,4,5(3H)-TRIONE 1,3-DIMETHYL-4-[(4-METHYLPHENYL)SULFONYL]-1,3-DIHYDRO-2H-IMIDAZOLE-2-THIONE 1-(3,4-DIMETHOXYBENZYL)-1H-IMIDAZOLE-2,4,5(3H)-TRIONE 1-(3-CHLOROBENZYL)-1H-IMIDAZOLE-2,4,5(3H)-TRIONE 2-nitro-1H-imidazole 4,5-Dicyanoimidazole 4,5-DIPHENYL-2-IMIDAZOLETHIOL 1,1'-Carbonyldiimidazole Imidazole Levamisole hydrochloride
1,3-Dia-zole,Miazole 1H-Imidazol Formamidine, N,N'-vinylene- glioksal IMD Imidazol Imidazolin Imutex Methanimidamide, N,N'-1,2-ethenediyl- methanimidamide,N,N’-1,2-ethenediyl- Miazole n,n’-vinylene-formamidin Pyrro(b)monazole USAF ek-4733 usafek-4733 Reagents for Oligosaccharide Synthesis 1,3-DIAZA-2,4-CYCLOPENTADIENE 1,3-DIAZOLE Biological Buffers Biochemicals BioChemika Ultra Analytical Chromatography Product Catalog BioChemical Biochemicals and Reagents Analytical Reagents Amino Acids and Peptides 1H-IMIDAZOLE 288-32-4 AKOS BBS-00004265 LABOTEST-BB LTBB001344 IMIDAZOLE BUFFER IMINAZOLE IMIDAZOLE GLYOXALIN GLYOXALINE GLYOXALINE BUFFER N,N'-VINYLENEFORMAMIDINE Peptide Analysis and Characterization Optimization Reagents Reagents Reagents and Products for use with HIS-Select Purification and Detection Puriss p.a. Proteomics and Protein Expression Protein Analysis Protein Expression Solvents, Buffers and Reagents for Luminescence X-Ray Crystallography Luminescent Compounds/Detection Molecular Biology Reagents Molecular Biology DNA & RNA Purification Crystallization and Renaturation Screening Kit Components General Use HIS-Select® HIS Select Supporting Products and Reagents Imidazole Glyoxaline Imidazole, ULTROL Grade
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