3,5,6-Trimethylpyrazine-2-carbaldehyde

Base Information

• Chemical Name: 3,5,6-Trimethylpyrazine-2-carbaldehyde
• CAS No.: 186534-02-1
• Molecular Formula: C8H10N2O
• Molecular Weight: 150.18
• Hs Code.: 2933990090
• European Community (EC) Number: 856-770-0
• DSSTox Substance ID: DTXSID80594018
• Wikidata: Q72514348
• Mol file: 186534-02-1.mol

Synonyms:3,5,6-TRIMETHYLPYRAZINE-2-CARBALDEHYDE;186534-02-1;Pyrazinecarboxaldehyde, trimethyl- (9CI);MFCD16294231;3,5,6-trimethylpyrazine-2-carboxaldehyde;Pyrazinecarboxaldehyde, trimethyl-;SCHEMBL1191060;AMY6416;DTXSID80594018;AKOS006336788;3,5,6-trimethyl-2-pyrazinecarbaldehyde;AC-27698;BS-15844;SY269959;DB-010197;CS-0137572;EN300-6496382;A880638;AR-690/43422895;Z1201628611

Chemical Property of 3,5,6-Trimethylpyrazine-2-carbaldehyde

Chemical Property:

• Refractive Index: 1.553
• Boiling Point: 231.756 °C at 760 mmHg
• PKA: 1.06±0.10(Predicted)
• Flash Point: 96.785 °C
• PSA: 42.85000
• Density: 1.101 g/cm³
• LogP: 1.21430
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 150.079312947
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,5,6-Trimethylpyrazine-2-carbaldehyde 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N=C(C(=N1)C)C=O)C

Technology Process of 3,5,6-Trimethylpyrazine-2-carbaldehyde

There total 6 articles about 3,5,6-Trimethylpyrazine-2-carbaldehyde 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-Pyrazinemethanol,3,5,6-trimethyl (75907-74-3) → 3,5,6-trimethyl-pyrazine-2-carbaldehyde (186534-02-1)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 0 - 20 ℃; for 0.5h;

DOI:10.1021/acs.jmedchem.5b01203

Reference yield:

Tetramethylpyrazine (1124-11-4) → 3,5,6-trimethyl-pyrazine-2-carbaldehyde (186534-02-1)

Guidance literature:

Multi-step reaction with 4 steps

1: dihydrogen peroxide; acetic acid / 95 °C

2: 2 h / Reflux

3: sodium hydroxide

4: phosphoric acid; dicyclohexyl-carbodiimide / dimethyl sulfoxide

With phosphoric acid; dihydrogen peroxide; acetic acid; dicyclohexyl-carbodiimide; sodium hydroxide; In dimethyl sulfoxide; 4: Pfitzner-Moffatt oxidation;

DOI:10.1111/j.1747-0285.2012.01332.x

Reference yield:

2,3,5,6-tetramethylpyrazine mono N-oxide (22978-83-2) → 3,5,6-trimethyl-pyrazine-2-carbaldehyde (186534-02-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 2 h / Reflux

2: sodium hydroxide

3: phosphoric acid; dicyclohexyl-carbodiimide / dimethyl sulfoxide

With phosphoric acid; dicyclohexyl-carbodiimide; sodium hydroxide; In dimethyl sulfoxide; 3: Pfitzner-Moffatt oxidation;

DOI:10.1111/j.1747-0285.2012.01332.x

upstream raw materials:

2-Pyrazinemethanol,3,5,6-trimethyl

Tetramethylpyrazine

2,3,5,6-tetramethylpyrazine mono N-oxide

(3,5,6-trimethylpyrazin-2-yl)methyl acetate

Downstream raw materials:

methyl 3,5,6-trimethylpyrazine-2-carboxylate

(E)-2-(3-cyanostyryl)-3,5,6-trimethylpyrazine

(E)-2-(4-methylstyryl)-3,5,6-trimethylpyrazine

(E)-2-(2-methylstyryl)-3,5,6-trimethylpyrazine

Refernces

• 1、 Zha, Gao-Feng,Qin, Hua-Li,Youssif, Bahaa G.M.,Amjad, Muhammad Wahab,Raja, Maria Abdul Ghafoor,Abdelazeem, Ahmed H.,Bukhari, Syed Nasir Abbas. "Discovery of potential anticancer multi-targeted ligustrazine based cyclohexanone and oxime analogs overcoming the cancer multidrug resistance". . p. 34 - 48. Retrieved 2017.
• 2、 Zhang, Chao,Chen, Lang-Di,Liang, Xin-Tong,Liu, Wei-Xiong,Wu, Wen-Hao. "Synthesis and biological evaluation of ligustrazine derivatives". . p. 114 - 117. Retrieved 2017.
• 3、 Bukhari, Syed Nasir Abbas. "Discovery of a new tetramethylpyrazine based chalcone with α, β-unsaturated ketone moiety as a potential anticancer agent". . p. 826 - 829. Retrieved 2020/02/25.
• 4、 -. "TRIFLUOROACETYL HYDRAZIDE COMPOUNDS AND MEDICAL USES THEREOF". Paragraph 0038. . Retrieved 2019/07/29.