2,2'-Biimidazole

Base Information

• Chemical Name: 2,2'-Biimidazole
• CAS No.: 492-98-8
• Molecular Formula: C6H6N4
• Molecular Weight: 134.14
• Hs Code.: 2933290090
• European Community (EC) Number: 207-768-8
• NSC Number: 522950
• UNII: WEZ56MM6EC
• DSSTox Substance ID: DTXSID30197715
• Nikkaji Number: J182.242J
• Wikidata: Q72443471
• ChEMBL ID: CHEMBL333830
• Mol file: 492-98-8.mol

Synonyms:2,2'-biimidazole;H2BiIm

Chemical Property of 2,2'-Biimidazole

Chemical Property:

• Melting Point: >350°C
• Boiling Point: 455.5 °C at 760 mmHg
• PKA: pK1: 5.01(+1) (25°C,μ= 0.3)
• Flash Point: 238.1 °C
• PSA: 57.36000
• Density: 1.371 g/cm³
• LogP: 0.79980
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 134.059246208
• Heavy Atom Count: 10
• Complexity: 102

Purity/Quality:

98% ^*data from raw suppliers

1H,1''H-2,2''-Biimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=C(N1)C2=NC=CN2
• Uses: 1H,1''H-2,2''-Biimidazole is used in the preparation of complexes that exhibits photoluminescence and optical properties. Also used in the preparation of bismuth biimidazoles as semi-conductors.

Technology Process of 2,2'-Biimidazole

There total 13 articles about 2,2'-Biimidazole 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: 86.0%

Bis-N-(2,2-dimethoxyethylacetamidine) dihydrochloride (106536-97-4) → 2,2'-biimidazole (492-98-8)

Guidance literature:

With toluene-4-sulfonic acid; at 170 ℃; for 0.333333h;

DOI:10.1055/s-1986-31607

Reference yield: 60.4%

1,2-dihydroxyethylenediamine dihydrochloride (93241-62-4) → 2,2'-biimidazole (492-98-8)

Guidance literature:

With sodium acetate; In water; at 90 ℃; for 2h;

DOI:10.1007/BF00473456

Reference yield: 53.2%

Glyoxal (131543-46-9,107-22-2) → 2,2'-biimidazole (492-98-8)

Guidance literature:

Glyoxal; With ammonium acetate; In water; at 20 - 40 ℃; for 3h;

With water; pH=5 - 7; Product distribution / selectivity;

upstream raw materials:

3,3,3-trichloro-2-hydroxy-propionic acid

Glyoxal

ammonium acetate

glyoxal sulfate

Downstream raw materials:

1,1′-dibenzyl-2,2′-biimidazole

1,1'-dimethyl-2,2'-biimidazole

N-benzyl-2,2'-bi-1H-imidazole

4-benzyl-2,2'-bi-1H-imidazole

Refernces

• 1、 Akutagawa, Tomoyuki,Saito, Gunzi. "Multiplex Proton-Transfer and Electron-Transfer Natures Based on the 2,2'-Bi-1H-imidazole System. I. Acid Dissociation Constants and Redox Properties in Solution". . p. 1753 - 1774. Retrieved 1995.
• 2、 Xia, Yu,Chen, Qingchang,Qin, Xiuying,Sun, Dongdong,Zhang, Jingnan,Liu, Jie. "Studies of ruthenium(ii)-2,2′-bisimidazole complexes on binding to G-quadruplex DNA and inducing apoptosis in HeLa cells". . p. 3706 - 3715. Retrieved 2013.
• 3、 Lewczuk, Rafa?,Szala, Mateusz,Re?ko, Judyta,Klap?tke, Thomas M.,Cudzi?o, Stanis?aw. "Synthesis and Properties of 4,4',5,5'-Tetranitro-1H,1'H-2,2'-Biimidazole Salts: Semicarbazidium, 3-Amino-1,2,4-Triazolium, and 5-Aminotetrazolium Derivatives". . p. 697 - 701. Retrieved 2017.
• 4、 Duranti,Balsamini. "-". . p. 815,816. Retrieved 1974.
• 5、 Klapoetke, Thomas M.,Preimesser, Andreas,Stierstorfer, Joerg. "Energetic derivatives of 4, 4',5, 5'-Tetranitro-2, 2'-bisimidazole (TNBI)". . p. 1278 - 1286. Retrieved 2012.
• 6、 Tang, Yongxing,Imler, Gregory H.,Parrish, Damon A.,Shreeve, Jean'ne M.. "C6N10O4: Thermally Stable Nitrogen-Rich Inner Bis(diazonium) Zwitterions". . p. 8201 - 8204. Retrieved 2019.
• 7、 Léval, Alexander,Agapova, Anastasiya,Steinlechner, Christoph,Alberico, Elisabetta,Junge, Henrik,Beller, Matthias. "Hydrogen production from formic acid catalyzed by a phosphine free manganese complex: Investigation and mechanistic insights". supporting information. p. 913 - 920. Retrieved 2020/02/27.