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288-32-4

Basic Information
CAS No.: 288-32-4
Name: 1H-Imidazole
Article Data: 211
Cas Database
Molecular Structure:
Molecular Structure of 288-32-4 (1H-Imidazole)
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: CorrosiveC,IrritantXi
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
Synthetic route
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In acetonitrile at 25℃; for 12h; Esterification;A n/a
B 97%
4238-71-5

1-benzylimidazole

288-32-4

1H-imidazole

Conditions
ConditionsYield
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

7664-41-7

ammonia

141-43-5

ethanolamine

A

288-32-4

1H-imidazole

B

1615-14-1

1-(2-Hydroxyethyl)imidazole

Conditions
ConditionsYield
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
ConditionsYield
In acetonitrile at 25℃; for 12h; Esterification;A n/a
B 95%
at 20℃;
78-84-2

isobutyraldehyde

A

288-32-4

1H-imidazole

B

36947-68-9

2-isopropylimidazole

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With magnesium; acetic acid In methanol at 20℃;93%
50-00-0

formaldehyd

7664-41-7

ammonia

107-11-9

1-amino-2-propene

A

288-32-4

1H-imidazole

B

31410-01-2

1-allylimidazole

Conditions
ConditionsYield
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%
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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: CorrosiveC,IrritantXi
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.