N-Acetylimidazole

Base Information

• Chemical Name: N-Acetylimidazole
• CAS No.: 2466-76-4
• Molecular Formula: C5H6N2O
• Molecular Weight: 110.115
• Hs Code.: 29332900
• European Community (EC) Number: 219-577-7
• UNII: ZMP8X1Y11G
• DSSTox Substance ID: DTXSID8062440
• Nikkaji Number: J34.876G
• Wikidata: Q27102162
• Metabolomics Workbench ID: 50726
• ChEMBL ID: CHEMBL1592087
• Mol file: 2466-76-4.mol

Synonyms:acetylimidazole;N-acetylimidazole

Chemical Property of N-Acetylimidazole

Chemical Property:

• Appearance/Colour: white to beige or light tan adhering crystals
• Vapor Pressure: 0.104mmHg at 25°C
• Melting Point: 99-105 °C(lit.)
• Refractive Index: 1.552
• Boiling Point: 221.955 °C at 760 mmHg
• PKA: pKa 3.6(H2O,t = 25,I=0.2) (Uncertain)
• Flash Point: 88.035 °C
• PSA: 34.89000
• Density: 1.146 g/cm³
• LogP: 0.54320
• Storage Temp.: Store at 0
• Sensitive.: Moisture Sensitive
• Solubility.: water: soluble50mg/mL, clear, colorless
• Water Solubility.: Hydrolyzes in water. Solubility in methanol (almost transparency).
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 110.048012819
• Heavy Atom Count: 8
• Complexity: 103

Purity/Quality:

99%min ^*data from raw suppliers

1-Acetylimidazole ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N1C=CN=C1
• Uses: Acetylating agent for capping unreacted amino groups in peptide synthesis. It is a mild acylating agent and its reactivity can be enhanced by quaternization with, e.g. benzyl bromide. 1-Acetylimidazole was used as acetylation reagent for amino groups. It was also employed for acetylation of histones. It is relatively specific reagent for tyrosyl residue acetylatioa dn a reagent used in the synthesis of annulated imidazole derivatives. Relatively specific reagent for tyrosyl residue acetylation. Reagent used in the synthesis of annulated imidazole derivatives.

Technology Process of N-Acetylimidazole

There total 42 articles about N-Acetylimidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

1H-imidazole (288-32-4) + acetic anhydride (108-24-7) → N-Acetylimidazole (2466-76-4)

Guidance literature:

In tetrahydrofuran; for 0.5h; Inert atmosphere;

Reference yield: 96.0%

1H-imidazole (288-32-4) + acetyl chloride (75-36-5) → N-Acetylimidazole (2466-76-4)

Guidance literature:

In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1021/jacs.8b12331

Reference yield: 96.0%

acetyl chloride (75-36-5) + 1-(Trimethylsilyl)imidazole (18156-74-6) → N-Acetylimidazole (2466-76-4)

Guidance literature:

DOI:10.1016/S0022-328X(00)82809-0

upstream raw materials:

1H-imidazole

Isopropenyl acetate

acetyl chloride

1-Acetyl-4(1H)-pyridinon

Downstream raw materials:

Acetanilid

N,N-dihexylacetamide

2-[4-((S)-2-Acetylamino-2-{1-[(S)-2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-ethyl)-phenyl]-malonic acid di-tert-butyl ester

{4-[(S)-2-Acetylamino-2-(1-{(S)-2-carbamoyl-1-[3-(5-methyl-indol-1-yl)-propylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-ethyl]-benzyl}-phosphonic acid di-tert-butyl ester

Refernces

• 1、 Gelas,Horton. "-". . p. 323,324, 325. Retrieved 1978.
• 2、 Gopalakrishnan, Ganesa,Hogg, John L.. "Differentiation of Nucleophilic and General Base Catalysis in the Hydrolysis of N-Acetylbenzotriazole Using the Proton Inventory Technique". . p. 4959 - 4964. Retrieved 1981.
• 3、 Wenck,H.,Schallies,M.. "-". . p. 3059 - 3071. Retrieved 1973.
• 4、 Khim, Leang,Han, Juan,Willetts, Lynsey,Brady, Kevin,Gillece, Pauline,Rached, Ouannassa,Thomas, Neil R.,Stylianou, Eleni. "Complementary PCAF-Coenzyme a mutagenesis: Chemoenzymatic synthesis of a novel enlarged coenzyme a analogue and evaluation of its biological activity". . p. 2100 - 2103. Retrieved 2010.
• 5、 Kalkhambkar, Rajesh G.,Laali, Kenneth K.,Malunavar, Shruti S.,Prabhala, Pavankumar,Savanur, Hemantkumar M.,Sutar, Suraj M.. "Facile one-pot synthetic access to libraries of diversely substituted 3-aryl (Alkyl)-coumarins using ionic liquid (IL) or conventional base/solvent, and an IL-mediated approach to novel coumarin-bearing diaryl-ethynes". supporting information. . Retrieved 2020/04/08.
• 6、 Li, Yao-Wei,Zhang, Pei-Ming,Li, Rui,Bai, Yan,Yu, Yu,Gan, Zong-Jie. "Efficient CDI/CH3SO3H-catalyzed, microwave-assisted synthesis of 2-substituted benzothiazoles". supporting information. p. 34 - 39. Retrieved 2019/05/04.