1,1,2,3-Tetramethylbenzo[e]indol-3-ium

Base Information

• Chemical Name: 1,1,2,3-Tetramethylbenzo[e]indol-3-ium
• CAS No.: 58464-25-8
• Molecular Formula: C16H18IN
• Molecular Weight: 351.23
• European Community (EC) Number: 624-703-2
• DSSTox Substance ID: DTXSID80382674
• Nikkaji Number: J1.375.589B
• Wikidata: Q72507507
• ChEMBL ID: CHEMBL1358777
• Mol file: 58464-25-8.mol

Synonyms:1,1,2,3-tetramethylbenzo[e]indol-3-ium;1,1,2,3-tetramethyl-1H-benzo[e]indolium;MLS000584195;58464-25-8;SMR000203358;SCHEMBL2966154;CHEMBL1358777;BDBM53612;cid_2783649;DTXSID80382674;REGID_for_CID_2783649;HMS2603M10;1,1,2,3-tetramethylbenz[e]indol-3-ium;1,1,2,3-Tetramethyl-1H-benzo[e]indole-3-ium

Chemical Property of 1,1,2,3-Tetramethylbenzo[e]indol-3-ium

Chemical Property:

• Melting Point: 220 °C (dec.)(lit.)
• PSA: 3.01000
• LogP: 0.82850
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 224.143924578
• Heavy Atom Count: 17
• Complexity: 353

Purity/Quality:

98%Min ^*data from raw suppliers

1,1,2,3-TETRAMETHYL-1H-BENZ[E]INDOLIUM IODIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=[N+](C2=C(C1(C)C)C3=CC=CC=C3C=C2)C

Technology Process of 1,1,2,3-Tetramethylbenzo[e]indol-3-ium

There total 9 articles about 1,1,2,3-Tetramethylbenzo[e]indol-3-ium 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: 100.0%

2,3,3-trimethylbenzo[e]indole (41532-84-7) + methyl iodide (74-88-4) → 1,1,2,3-tetramethyl-1H-benz[e]indol-3-ium iodide (58464-25-8)

Guidance literature:

In acetonitrile; at 110 ℃; for 48h; Inert atmosphere;

DOI:10.1021/ja105937q

Reference yield: 94.0%

2,3,3-trimethyl-3H-benzo[g]indole (74470-85-2) + methyl iodide (74-88-4) → 1,1,2,3-tetramethyl-1H-benz[e]indol-3-ium iodide (58464-25-8)

Guidance literature:

at 20 ℃; for 24h;

Reference yield:

2-naphthylhydrazine hydrochloride (2243-58-5) → 1,1,2,3-tetramethyl-1H-benz[e]indol-3-ium iodide (58464-25-8)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / 24 h / 100 °C

2: acetonitrile / 100 °C

With acetic acid; In acetonitrile; 1: |Fischer Indole Synthesis;

DOI:10.3390/molecules23020226

upstream raw materials:

2,3,3-trimethylbenzo[e]indole

methyl iodide

3-methyl-butan-2-one

2-hydrazinonaphthalene

Downstream raw materials:

C₂₇H₃₁N₂⁽¹⁺⁾*I^(1-)

C₄₀H₄₂N₂O₂

1,1,3-trimethyl-2-((1E,3E,5E)-5-(1,1,3-trimethyl-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dien-1-yl)-1H-benzo[e]indol-3-ium iodide

1,3,3-trimethyl-1',2'-diphenylspiro[benzo[e]indoline-2,7'-furo[3,2-f]chromene]

Refernces

• 1、 Sun, Yue,Fan, Shanwei,Zhao, Dong,Duan, Lian,Li, Ruifeng. "A fluorescent turn-on probe based on benzo [E] indolium for cyanide ion in water with high selectivity". . p. 1255 - 1261. Retrieved 2013.
• 2、 Li, Zhang-Yi,Cui, Xiao-Ling,Yan, Ye-Hao,Che, Qiao-Ling,Miao, Jun-Ying,Zhao, Bao-Xiang,Lin, Zhao-Min. "A novel endoplasmic reticulum-targeted ratiometric fluorescent probe based on FRET for the detection of SO2 derivatives". . . Retrieved 2021.
• 3、 Fortibui, Maxine Mambo,Yoon, Dae Wui,Lim, Ja-Yun,Lee, Sohyun,Choi, Minsun,Heo, June Seok,Kim, Jinkwan,Kim, Jinheung. "A cancer cell-specific benzoxadiazole-based fluorescent probe for hydrogen sulfide detection in mitochondria". . p. 2545 - 2554. Retrieved 2021.
• 4、 Gong, Yige,Jia, Juan,Niu, Weifen,Wang, Yandan,Wei, Zhiwen. "Ratiometric fluorimetric and colorimetric probe for sensing and imaging pH changes in living cells". . . Retrieved 2022/03/27.
• 5、 Dumur, Frédéric,Gigmes, Didier,Lalevée, Jacques,Mokbel, Haifaa,Noirbent, Guillaume. "Towards new NIR dyes for free radical photopolymerization processes". supporting information. p. 2067 - 2076. Retrieved 2021/08/23.