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| CAS No.: | 288-32-4 |
|---|---|
| Name: | Imidazole |
| Article Data: | 211 |
| Molecular Structure: | |
|
|
|
| Formula: | C3H4N2 |
| Molecular Weight: | 68.0782 |
| Synonyms: | Methanimidamide, N,N-1,2-ethenediyl-;1H-Imidazole (9CI);1H-Imidazole, monohydrochloride;1,3-Diazole;1,3-Diaza-2,4-cyclopentadiene;Imidazol;Methanimidamide, N,N-1, 2-ethenediyl-;Formamidine, N,N-vinylene-;Him;IMD;Glyoxaline;1467-16-9;Glyoxalin;Iminazole;Imutex;imidazole chloride;Pyrro(b)monazole;Miazole;2-phenyl-4,5-dihydroxy metylimidazole; |
| EINECS: | 206-019-2 |
| Density: | 1.116 g/cm3 |
| Melting Point: | 88-91 °C(lit.) |
| Boiling Point: | 257 °C at 760 mmHg |
| Flash Point: | 145 °C |
| Solubility: | H2O: 0.1 M at 20 °C, clear, colorless |
| Appearance: | white to off white crystals |
| Hazard Symbols: |
 C, Xi
|
| Risk Codes: | 36/38-63-34-22-20/21/22 |
| Safety: | 26-36/37/39-45-22-36-27 |
| Transport Information: | UN 2923 8/PG 3 |
| PSA: | 28.68000 |
| LogP: | 0.40970 |
- 483366-12-7(2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine
- 361456-36-2METHYL (R)-(+)-ISOCYANATO-3-PHENYLPROPI&
- 5156-58-1N-(1-Benzyl-4-pipperidinyl)-N-phenylpropanamide HCl
- 81281-59-67-Benzylideneaminotheophylline
- 50288-62-5threo-Phenyl-2-piperidyl acetamide
- 82993-81-5D-threo-Ritalinic acid hydrochloride
- 47087-37-6Z-D-Glu-OMe
- 73441-42-6METHYL-5-CHLORO-2,2-DIMETHYLVALERATE
- 68439-39-4Poly(oxy-1,2-ethanediyl), alpha-(2-ethylhexyl)-omega-hydroxy-,
- 852475-26-4MC1568
- 18156-74-6
1-(Trimethylsilyl)imidazole
- 103-79-7
1-phenyl-acetone
A
- 288-32-4
1H-imidazole
B
- 43108-63-0
1-phenyl-2-trimethylsiloxy-1-propene
| Conditions | Yield |
|---|---|
| Ambient temperature; other silylazoles and carbonyl compounds; | A n/a B 100% |
- 49761-82-2
tert-butyl 1H-imidazole-1-carboxylate
- 288-32-4
1H-imidazole
| Conditions | Yield |
|---|---|
| With water at 100℃; for 0.166667h; | 99% |
| With silica gel In dichloromethane for 0.0333333h; Irradiation; | 98% |
| With water at 150℃; for 2h; Subcritical conditions; | 95% |
- 530-62-1
1,1'-carbonyldiimidazole
- 100-51-6
benzyl alcohol
A
- 288-32-4
1H-imidazole
B
- 22129-07-3
N-benzyloxycarbonylimidazole
| Conditions | Yield |
|---|---|
| In acetonitrile at 25℃; for 12h; Esterification; | A n/a B 97% |
| Conditions | Yield |
|---|---|
| With Na2K-SG(I) In 1,2-dimethoxyethane at 20℃; Inert atmosphere; | 96% |
| With triethylsilane; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 92% |
- 50-00-0
formaldehyd
- 131543-46-9
Glyoxal
- 7664-41-7
ammonia
- 141-43-5
ethanolamine
A
- 288-32-4
1H-imidazole
B
- 1615-14-1
1-(2-Hydroxyethyl)imidazole
| Conditions | Yield |
|---|---|
| Stage #1: formaldehyd; ammonia; ethanolamine In water at 25℃; for 1h; Stage #2: Glyoxal; ammonia at 25℃; for 1h; Product distribution / selectivity; | A 2% B 96% |
- 64-17-5
ethanol
- 530-62-1
1,1'-carbonyldiimidazole
A
- 288-32-4
1H-imidazole
B
- 19213-72-0
ethyl 1-imidazolecarboxylate
| Conditions | Yield |
|---|---|
| In acetonitrile at 25℃; for 12h; Esterification; | A n/a B 95% |
| at 20℃; |
| Conditions | Yield |
|---|---|
| Stage #1: isobutyraldehyde With ammonia In methanol; water at 25℃; for 1h; Stage #2: Glyoxal With ammonia In methanol; water at 25℃; for 2h; Product distribution / selectivity; | A 2 %Chromat. B 95% |
| With ammonia In water at 25℃; for 1h; Product distribution / selectivity; | A 23 %Chromat. B 56% |
- 124-68-5
2-Amino-2-methyl-1-propanol
- 530-62-1
1,1'-carbonyldiimidazole
A
- 288-32-4
1H-imidazole
B
- 26654-39-7
4,4-dimethyl-1,3-oxazolidin-2-one
| Conditions | Yield |
|---|---|
| In diethyl ether for 0.166667h; Ambient temperature; | A n/a B 94% |
- 24155-34-8
2-(1H-imidazol-1-yl)-1-phenylethanone
- 288-32-4
1H-imidazole
| Conditions | Yield |
|---|---|
| With magnesium; acetic acid In methanol at 20℃; | 93% |
- 50-00-0
formaldehyd
- 131543-46-9
Glyoxal
- 7664-41-7
ammonia
- 107-11-9
1-amino-2-propene
A
- 288-32-4
1H-imidazole
B
- 31410-01-2
1-allylimidazole
| Conditions | Yield |
|---|---|
| Stage #1: formaldehyd; ammonia; 1-amino-2-propene In water at 25℃; for 1h; Stage #2: Glyoxal; ammonia at 25℃; for 1h; | A 4% B 93% |
- 209995-38-02,4,5-Trifluorophenylacetic acid
- 151213-42-21H-Pyrrolo[3,4-b]pyridine,octahydro-, (4aR,7aR)-
- 63-91-2L-Phenylalanine
- 103577-45-3Lansoprazole
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- 97240-79-4Topiramate
- 1643-19-21-Butanaminium,N,N,N-tributyl-, bromide (1:1)
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- 104987-11-3Tacrolimus
- 141-53-7Sodium formate
- 8001-54-5Quaternary ammonium compounds, alkylbenzyldimethyl, chlorides
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- 402957-28-2Telaprevir
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Chemistry
Structure of Imidazole (CAS NO.288-32-4):
Molecular Formula: C3H4N2
Molecular Weight: 68.08 g/mol
Index of Refraction: 1.528
Density: 1.116 g/cm3
Flash Point: 145 °C
Enthalpy of Vaporization: 47.46 kJ/mol
Boiling Point: 257 °C at 760 mmHg
Vapour Pressure: 0.024 mmHg at 25 °C
Melting point: 88-91 °C(lit.)
Storage tempreture: 2-8 °C
Solubility: H2O: 0.1 M at 20 °C, clear, colorless
Appearance: White to off white crystals
IUPAC Name: 1H-Imidazole
Product Category of Imidazole (CAS NO.288-32-4): Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines ; Reagents for Oligosaccharide Synthesis ; Zone Refined Products ; Buffer
History
In 1858, Imidazole (CAS NO.288-32-4) was first synthesized by Heinrich Debus. But various imidazole derivatives had been discovered as early as the 1840s.
Production
The synthesis of Imidazole (CAS NO.288-32-4) is shown below, and you can use glyoxal and formaldehyde in ammonia to form imidazole. This synthesis, while producing relatively low yields, is still used for creating C-substituted imidazoles.
In one microwave modification the reactants are benzil, formaldehyde and ammonia in glacial acetic acid forming 2,4,5-triphenylimidazole (Lophine).
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| cat | LDLo | subcutaneous | 125mg/kg (125mg/kg) | BEHAVIORAL: FOOD INTAKE (ANIMAL) BEHAVIORAL: REGIDITY | Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 84, Pg. 155, 1918. |
| dog | LD50 | subcutaneous | 28mg/kg (28mg/kg) | Przeglad Epidemiologiczny. Vol. 67, Pg. 295, 1993. | |
| guinea pig | LD50 | oral | 760mg/kg (760mg/kg) | Przeglad Epidemiologiczny. Vol. 67, Pg. 295, 1993. | |
| mammal (species unspecified) | LD50 | oral | 1gm/kg (1000mg/kg) | Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 608, 1966. | |
| mouse | LD50 | intraperitoneal | 300mg/kg (300mg/kg) | National Technical Information Service. Vol. AD277-689, | |
| mouse | LD50 | intravenous | 475mg/kg (475mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 716, 1983. |
| mouse | LD50 | oral | 880mg/kg (880mg/kg) | German Offenlegungsschrift Patent Document. Vol. #3046325, | |
| mouse | LD50 | subcutaneous | 817mg/kg (817mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 119, Pg. 444, 1957. | |
| rat | LD50 | oral | 220mg/kg (220mg/kg) | Przeglad Epidemiologiczny. Vol. 67, Pg. 295, 1993. | |
| rat | LD50 | subcutaneous | 626mg/kg (626mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 119, Pg. 444, 1957. |
Safety Profile
Hazard Codes: 
C,
Xi
Risk Statements: 36/38-63-34-22-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R22:Harmful if swallowed.
R34:Causes burns.
R36/38:Irritating to eyes and skin.
R63:Possible risk of harm to the unborn child.
Safety Statements: 26-36/37/39-45-22-36-27
S22:Do not breathe dust.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S27:Take off immediately all contaminated clothing.
S36:Wear suitable protective clothing.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
Specification
Imidazole , its cas register number is 288-32-4. It also can be called 1,3-Diazole ; 1H-Imidazole ; and Glyoxaline . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, Imidazole (CAS NO.288-32-4) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, acids, acid chlorides, and you must not take it with incompatible materials, dust generation. And also prevent it to broken down into hazardous decomposition products: hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide, ammonia.