1-methyl-1H-indazole-3-carbaldehyde

Base Information

• Chemical Name: 1-methyl-1H-indazole-3-carbaldehyde
• CAS No.: 4002-83-9
• Molecular Formula: C9H8N2O
• Molecular Weight: 160.17
• Hs Code.: 2933998090
• European Community (EC) Number: 640-823-8
• DSSTox Substance ID: DTXSID00428164
• Wikidata: Q82240958
• Mol file: 4002-83-9.mol

Synonyms:1-methyl-1H-indazole-3-carbaldehyde;4002-83-9;1-methylindazole-3-carbaldehyde;1-Methyl-1H-indazole-3-carboxaldehyde;MFCD08060478;4-Iodoimidazole(IIMD);1-methyl-3-formylindazole;SCHEMBL465585;DTXSID00428164;KYDLGYCLCFKUHY-UHFFFAOYSA-N;AKOS006220920;CS-W021348;PB10491;PS-4952;AM803847;SY097414;FT-0704990;EN300-66939;1-methyl-1H-indazole-3-carbaldehyde, AldrichCPR;J-504876;Z1065726002

Chemical Property of 1-methyl-1H-indazole-3-carbaldehyde

Chemical Property:

• Vapor Pressure: 0.000549mmHg at 25°C
• Melting Point: 61 °C
• Refractive Index: 1.622
• Boiling Point: 311.8 °C at 760 mmHg
• Flash Point: 142.4 °C
• PSA: 34.89000
• Density: 1.21 g/cm³
• LogP: 1.38580
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 160.063662883
• Heavy Atom Count: 12
• Complexity: 183

Purity/Quality:

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

1-Methyl-1H-indazole-3-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C(=N1)C=O

Technology Process of 1-methyl-1H-indazole-3-carbaldehyde

There total 4 articles about 1-methyl-1H-indazole-3-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: 86.0%

(1-methyl-1H-indazol-3-yl)methanol (1578-96-7) → 1-methyl-1H-indazole-3-carbaldehyde (4002-83-9)

Guidance literature:

(1-methyl-1H-indazol-3-yl)methanol; With Dess-Martin periodane; In dichloromethane; for 0.5h;

With sodium hydroxide; water; In diethyl ether; dichloromethane; for 0.166667h;

Reference yield: 80.0%

1H-indazole-3-carboxaldehyde (5235-10-9) + methyl iodide (74-88-4) → 1-methyl-1H-indazole-3-carbaldehyde (4002-83-9)

Guidance literature:

1H-indazole-3-carboxaldehyde; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.75h; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 3h;

DOI:10.1021/acs.jmedchem.8b00661

Reference yield:

1-methyl-1H-indazole-3-carboxylic acid (50890-83-0) → 1-methyl-1H-indazole-3-carbaldehyde (4002-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isobutyl chloroformate / tetrahydrofuran / 0.5 h / -18 °C

1.2: 1 h

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

2.2: 0.5 h / 20 °C

With oxalyl dichloride; dimethyl sulfoxide; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;

upstream raw materials:

(1-methyl-1H-indazol-3-yl)methanol

1H-indazole-3-carboxaldehyde

methyl iodide

1-methyl-1H-indazole-3-carboxylic acid

Downstream raw materials:

C₁₅H₁₃IN₂O

Refernces

• 1、 Ann, Jihyae,Czikora, Agnes,Saini, Amandeep S.,Zhou, Xiaoling,Mitchell, Gary A.,Lewin, Nancy E.,Peach, Megan L.,Blumberg, Peter M.,Lee, Jeewoo. "α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands". supporting information. p. 6261 - 6276. Retrieved 2018/06/11.