1,2,3,3-Tetramethyl-3H-indolium iodide

Base Information

• Chemical Name: 1,2,3,3-Tetramethyl-3H-indolium iodide
• CAS No.: 5418-63-3
• Deprecated CAS: 1425113-48-9
• Molecular Formula: C12H16N^.I
• Molecular Weight: 301.17
• Hs Code.: 2933990090
• European Community (EC) Number: 226-526-2
• NSC Number: 10498
• DSSTox Substance ID: DTXSID30883489
• ChEMBL ID: CHEMBL2393299
• Mol file: 5418-63-3.mol

Synonyms:1,2,3,3-Tetramethyl-3H-indolium iodide;5418-63-3;1,2,3,3-tetramethyl-3H-indol-1-ium iodide;3H-Indolium, 1,2,3,3-tetramethyl-, iodide;EINECS 226-526-2;MFCD00013333;NSC 10498;2,2,3,4-Tetramethylbenzazolium iodide;1,2,3,3-tetramethylindol-1-ium;iodide;3H-Indolium,1,2,3,3-tetramethyl-, iodide;3H-Indolium, 1,2,3,3-tetramethyl-, iodide (1:1);1,2,3,3-Tetramethyl-3H-indoliumiodide;1,2,3,3-Tetramethyl-1-indolium Iodide;SCHEMBL1865228;CHEMBL2393299;C12H16N.I;AMY4519;DTXSID30883489;BCP31259;C12-H16-N.I;NSC10498;2,3,4-Tetramethylbenzazolium iodide;NSC-10498;ZB0952;AKOS002318819;CS-W009434;DS-6640;BP-22914;LS-83579;SY066669;3H-Indolium,2,3,3-tetramethyl-, iodide;1,2,3,3-Tetramethyl-3H-indolium;FT-0635691;T3979;N-methyl-2,3,3-trimethyl[3H]indolium iodide;H10787;1,2,3,3-Tetramethyl-3H-indolium iodide, 98%;N-methyl-2,3,3-trimethyl [3H] indolium iodide;A830019;W-105662;46149-03-5

Chemical Property of 1,2,3,3-Tetramethyl-3H-indolium iodide

Chemical Property:

• Melting Point: 258 °C (dec.)(lit.)
• PSA: 3.01000
• LogP: -0.32470
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 301.03275
• Heavy Atom Count: 14
• Complexity: 250

Purity/Quality:

98%, ^*data from raw suppliers

1,2,3,3-Tetramethyl-3H-indolium iodide 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=[N+](C2=CC=CC=C2C1(C)C)C.[I-]

Technology Process of 1,2,3,3-Tetramethyl-3H-indolium iodide

There total 26 articles about 1,2,3,3-Tetramethyl-3H-indolium iodide 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: 89.0%

2,3,3-trimethylindoleniune (1640-39-7) + ethyl iodide (75-03-6) → 1,2,3,3-tetramethyl-3H-indolium iodide (5418-63-3)

Guidance literature:

In acetonitrile; for 24h; Reflux;

DOI:10.1016/j.saa.2018.04.076

Reference yield: 60.0%

3-methyl-butan-2-one (563-80-4) + N-methylaniline (100-61-8) → 1,2,3,3-tetramethyl-3H-indolium iodide (5418-63-3)

Guidance literature:

N-methylaniline; With acetic acid; sodium nitrite; In water; at 20 ℃; for 0.75h;

3-methyl-butan-2-one; With acetic acid; zinc; for 0.5h; Heating;

With hydrogen iodide; In ethanol;

DOI:10.1002/jhet.5570410117

Reference yield:

3-methyl-butan-2-one (563-80-4) → 1,2,3,3-tetramethyl-3H-indolium iodide (5418-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / 16 h / 120 °C

2: acetonitrile / 12 h / Reflux

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

DOI:10.1002/cmdc.201300090

upstream raw materials:

indole

methanol

methyl iodide

2-methyl-1H-indole

Downstream raw materials:

1,3-bis-(1,3,3-trimethyl-3H-indol-2-yl)-trimethinium ; iodide

1,,3,3,1',3',3'-hexamethylindocarbocyanine perchlorate

trans-2--1',3',3'-trimethylindolium iodide

C₁₈H₁₈N₂O

Refernces

• 1、 Zhou, Quan,Zhu, Yong,Sheng, Pengtao,Wu, Zeming,Cai, Qingyun. "A highly selective and reversible fluorescent Cu2+ and S2- probe under physiological conditions and in live cells". . p. 46951 - 46954. Retrieved 2014.
• 2、 Zhu, Yingzhong,Du, Wei,Zhang, Mingzhu,Xu, Ying,Song, Leilei,Zhang, Qiong,Tian, Xiaohe,Zhou, Hongping,Wu, Jieying,Tian, Yupeng. "A series of water-soluble A-π-A′ typological indolium derivatives with two-photon properties for rapidly detecting HSO3-/SO32- in living cells". . p. 3862 - 3869. Retrieved 2017.
• 3、 Liu, Yu,Li, Kun,Wu, Ming-Yu,Liu, Yan-Hong,Xie, Yong-Mei,Yu, Xiao-Qi. "A mitochondria-targeted colorimetric and ratiometric fluorescent probe for biological SO2 derivatives in living cells". . p. 10236 - 10239. Retrieved 2015.
• 4、 Cui, Lixia,Zhang, Honghong,Zhang, Guomei,Zhou, Ying,Fan, Li,Shi, Lihong,Zhang, Caihong,Shuang, Shaomin,Dong, Chuan. "Substituent effect on the acid-induced isomerization of spiropyran compounds". . p. 13 - 17. Retrieved 2018.
• 5、 Gosi, Mahesh,Marepu, Nagaraju,Sunandamma, Yeturu. "Cyanine-based Fluorescent Probe for Cyanide Ion Detection". . p. 1409 - 1415. Retrieved 2021.
• 6、 Yan, Jin-Wu,Zhu, Jia-Ying,Zhou, Kai-Xiang,Wang, Jin-Sheng,Tan, Hui-Ya,Xu, Zhong-Yong,Chen, Shuo-Bin,Lu, Yu-Ting,Cui, Meng-Chao,Zhang, Lei. "Neutral merocyanine dyes: For: in vivo NIR fluorescence imaging of amyloid-β plaques". . p. 9910 - 9913. Retrieved 2017.
• 7、 Zhu, Yuedong,Pan, Haiting,Song, Yanyan,Jing, Chao,Gan, Jia-An,Zhang, Junji. "Mitochondria-targeted fluorescent probe for rapid detection of thiols and its application in bioimaging". . . Retrieved 2021.
• 8、 St. Lorenz, Anna,Buabeng, Emmanuel Ramsey,Taratula, Oleh,Taratula, Olena,Henary, Maged. "Near-Infrared Heptamethine Cyanine Dyes for Nanoparticle-Based Photoacoustic Imaging and Photothermal Therapy". . p. 8798 - 8805. Retrieved 2021/06/28.