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2466-76-4

Basic Information
CAS No.: 2466-76-4
Name: 1-Acetylimidazole
Article Data: 76
Molecular Structure:
Molecular Structure of 2466-76-4 (1-Acetylimidazole)
Formula: C5H6N2O
Molecular Weight: 110.115
Synonyms: 1H-Imidazole,1-acetyl- (9CI);Imidazole, 1-acetyl- (6CI,8CI);1-Acetyl-1H-imidazole;Acetylimidazole;
EINECS: 219-577-7
Density: 1.146 g/cm3
Melting Point: 99-105 °C(lit.)
Boiling Point: 221.955 °C at 760 mmHg
Flash Point: 88.035 °C
Solubility: Hydrolyzes in water. Solubility in methanol (almost transparency).
Appearance: white to beige or light tan adhering crystals
Risk Codes: 36/37/38
Safety: 24/25
PSA: 34.89000
LogP: 0.54320
Synthetic route
288-32-4

1H-imidazole

108-24-7

acetic anhydride

2466-76-4

N-Acetylimidazole

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h; Inert atmosphere;98%
In tetrahydrofuran for 0.5h; Inert atmosphere;98%
Stage #1: 1H-imidazole; acetic anhydride In ethyl acetate at 20℃; for 9h; Inert atmosphere;
Stage #2: With potassium carbonate In ethyl acetate at 20℃; Inert atmosphere;
94%
288-32-4

1H-imidazole

75-36-5

acetyl chloride

2466-76-4

N-Acetylimidazole

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Inert atmosphere;96%
Stage #1: 1H-imidazole; acetyl chloride In tetrahydrofuran for 0.5h; Cooling with ice; Inert atmosphere;
Stage #2: With triethylamine In tetrahydrofuran at 0℃; for 12h; Inert atmosphere;
94.5%
With triethylamine In tetrahydrofuran at 0℃; for 12h;93%
75-36-5

acetyl chloride

18156-74-6

1-(Trimethylsilyl)imidazole

2466-76-4

N-Acetylimidazole

Conditions
ConditionsYield
96%
96503-18-3

Acetic acid 3-hydroperoxy-2,3-dimethyl-4-oxo-3,4-dihydro-naphthalen-1-yl ester

A

2466-76-4

N-Acetylimidazole

B

53948-58-6

1a,7a-dimethylnaphtho[2,3-b]oxirene-2,7(1aH,7aH)-dione

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In chloroform for 2h; Ambient temperature;A 89%
B 95%
288-32-4

1H-imidazole

2735-73-1

1,3-diacetyl-1,3-dihydro-benzoimidazol-2-one

2466-76-4

N-Acetylimidazole

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.333333h;80%
288-32-4

1H-imidazole

108-22-5

Isopropenyl acetate

2466-76-4

N-Acetylimidazole

Conditions
ConditionsYield
With sulfuric acid
288-32-4

1H-imidazole

30074-98-7

1-Acetyl-4(1H)-pyridinon

2466-76-4

N-Acetylimidazole

Conditions
ConditionsYield
In chloroform-d1 at 20℃;
288-32-4

1H-imidazole

18773-93-8

1-acetyl-1H-benzotriazole

A

2466-76-4

N-Acetylimidazole

B

95-14-7

1,2,3-Benzotriazole

Conditions
ConditionsYield
With imidazolium buffer pH 5.95 In water; water-d2 at 25℃; Rate constant;
288-32-4

1H-imidazole

15119-62-7

1-acetylsulfanyl-4-nitro-benzene

A

2466-76-4

N-Acetylimidazole

B

1849-36-1

para-nitrobenzenethiol

Conditions
ConditionsYield
In benzene at 25℃; Kinetics; Mechanism; Rate constant; other solvent;
97730-04-6

tert-butylphenylphosphinic imidazolidosulfuric anhydride

75-36-5

acetyl chloride

A

2466-76-4

N-Acetylimidazole

B

97730-06-8

tert-butylphenylphosphinic chlorosulfonic anhydride

Conditions
ConditionsYield
In diethyl ether; dichloromethane for 1h; Ambient temperature; Yield given;
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The 1-Acetylimidazole, with the CAS registry number 2466-76-4, is also known as 1-Acetylimidazole. It belongs to the product categories of Imidazoles; Acylation (GC Derivatizing Reagents); GC Derivatizing Reagents; Analytical Chemistry; Imidazoles Protein Modification; Reagents for Tyrosine Modification; Building Blocks; Heterocyclic Building Blocks; Specific Amino Acid Modification. Its EINECS registry number is 219-577-7. This chemical's molecular formula is C5H6N2O and molecular weight is 110.11. What's more, its IUPAC name is called 1-Imidazol-1-ylethanone. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 1-Acetylimidazole are: (1)ACD/LogP: -0.34; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.35; (4)ACD/LogD (pH 7.4): -0.34; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 15.37; (8)ACD/KOC (pH 7.4): 15.56; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 34.89 Å2; (13)Index of Refraction: 1.552; (14)Molar Refractivity: 30.711 cm3; (15)Molar Volume: 96.06 cm3; (16)Polarizability: 12.175×10-24cm3; (17)Surface Tension: 42.057 dyne/cm; (18)Density: 1.146 g/cm3; (19)Flash Point: 88.035 °C; (20)Enthalpy of Vaporization: 45.841 kJ/mol; (21)Boiling Point: 221.955 °C at 760 mmHg; (22)Vapour Pressure: 0.1040 mmHg at 25 °C.

Preparation of 1-Acetylimidazole: this chemical can be prepared by 1H-imidazole with acetyl chloride. This reaction needs solvent tetrahydrofuran at ambient temperature. The reaction time is 15 hours.

1-Acetylimidazole can be prepared by 1H-imidazole with acetyl chloride.

Uses of 1-Acetylimidazole: (1) it is used for biochemical research; (2) it is used to produce other chemicals. For example, it can react with fluorene to get 1-fluoren-2-yl-ethanone. The reaction occurs with reagent trifluoroacetic acid and other condition of heating for 5 hours. The yield is 89 %.

1-Acetylimidazole can react with fluorene to get 1-fluoren-2-yl-ethanone.

When you are dealing with this chemical, you should be very careful. This chemical is irritating to eyes, respiratory system and skin. Therefore, you should avoid contacting with skin and eyes.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(n1ccnc1)C
(2) InChI: InChI=1S/C5H6N2O/c1-5(8)7-3-2-6-4-7/h2-4H,1H3
(3) InChIKey: VIHYIVKEECZGOU-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intraperitoneal 250mg/kg (250mg/kg) IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASED IMMUNE RESPONSE Personal Communication from G.D. Stoner, Dept. of Community Medicine, School of Medicine, Univ. of California, La Jolla, CA 92037, May 25, 1975Vol. 27MAY1975,