9-Anthraldehyde

Base Information

• Chemical Name: 9-Anthraldehyde
• CAS No.: 642-31-9
• Deprecated CAS: 1781226-16-1
• Molecular Formula: C15H10O
• Molecular Weight: 206.244
• Hs Code.: 2912.29
• European Community (EC) Number: 211-383-0
• NSC Number: 15
• UNII: 353S277YHY
• DSSTox Substance ID: DTXSID9060940
• Nikkaji Number: J45.218A
• Wikipedia: Anthracene-9-carbaldehyde
• Wikidata: Q63396302
• ChEMBL ID: CHEMBL4447118
• Mol file: 642-31-9.mol

Synonyms:9-Anthraldehyde(6CI,7CI,8CI);9-Anthracenecarbaldehyde;9-Anthracenemethanal;9-Formylanthracene;NSC 15;

Chemical Property of 9-Anthraldehyde

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 8.58E-07mmHg at 25°C
• Melting Point: 103-105 °C(lit.)
• Refractive Index: 1.745
• Boiling Point: 405.7 °C at 760 mmHg
• Flash Point: 269.2 °C
• PSA: 17.07000
• Density: 1.217 g/cm³
• LogP: 3.80550
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: Soluble in toluene.
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 206.073164938
• Heavy Atom Count: 16
• Complexity: 238

Purity/Quality:

99% ^*data from raw suppliers

9-Anthraldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 24/25-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C=C3C=CC=CC3=C2C=O
• Uses: 9-Anthraldehyde is used to prepare asymmetrical tridentate Schiff base ligands, 2-(9-anthrylmethyl-ideneamino)-4-methyl-phenol and functionalized ligand like 2-(anthracen-9-ylidene)-4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione through Knoevenangel condensation with the diphosphine ligand 4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione. It is also used as an intermediate for dyes, pigment, active pharmaceutical ingredients and other organic compounds. Further, it is involved in the Diels Alder reaction with benzenediazonium-2-carboxylate.

Technology Process of 9-Anthraldehyde

There total 91 articles about 9-Anthraldehyde 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: 64.0%

9-hydroxymethylanthracene (1468-95-7) → 9,10-phenanthrenequinone (84-65-1) + 9-anthracene aldehyde (642-31-9)

Guidance literature:

With osmium(VIII) oxide; trimethylamine-N-oxide; In tetrahydrofuran; pyridine; water; at 65 ℃;

DOI:10.1246/cl.2001.48

Reference yield: 28.0%

malonic acid (141-82-2) + anthracene (120-12-7) → anthracen-9-carboxylic acid (723-62-6) + 9-acetoxyanthracene (1499-12-3) + α,α-diacetoxy-9-methylanthracene (111354-83-7) + 9-anthracene aldehyde (642-31-9)

Guidance literature:

With manganese triacetate; In acetic acid; for 0.0166667h; Heating;

DOI:10.1246/bcsj.62.545

Reference yield: 28.0%

malonic acid (141-82-2) + anthracene (120-12-7) + acetic acid (64-19-7,77671-22-8) → anthracen-9-carboxylic acid (723-62-6) + 9-acetoxyanthracene (1499-12-3) + α,α-diacetoxy-9-methylanthracene (111354-83-7) + 9-anthracene aldehyde (642-31-9)

Guidance literature:

With manganese triacetate; for 0.0166667h; Product distribution; Mechanism; Heating; Mn(III)-mediated formylation of various aromatic compounds;

DOI:10.1246/bcsj.62.545

upstream raw materials:

chloromethylene-formamidine

anthracene

N,N-dimethyl-formamide

N-methyl-N-phenylformamide

Downstream raw materials:

(anthracen-9-yl)-N,N-dimethylmethanamine

3-anthracen-9-ylmethylene-5-p-tolyl-3H-furan-2-one

3-[1-Anthracen-9-yl-meth-(E)-ylidene]-5-(4-methoxy-phenyl)-3H-furan-2-one

(Anthryl-(9)-methylen)-acetessigester

Refernces

• 1、 Salimi, Mehri,Zamanpour, Azadeh. "Ag nanoparticle immobilized on functionalized magnetic hydrotalcite (Fe3O4/HT-SH-Ag) for clean oxidation of alcohols with TBHP". . . Retrieved 2020.
• 2、 Singh,Roy. "Bacteriorhodopsin analogue from anthryl chromophores". . p. 383 - 389. Retrieved 1990.
• 3、 Gao, Shouhai,Wang, Wei,Wang, Binghe. "A new OsO4-mediated carbon-carbon bond cleavage reaction leading to the formation of anthraquinone". . p. 48 - 49. Retrieved 2001.
• 4、 Farhid, Hassan,Hajishaabanha, Fatemeh,Rashidi Vahid, Adina,Shaabani, Ahmad,Shaabani, Shabnam. "A bagasse-supported magnetic manganese dioxide nanoparticle: applications in the selective aerobic oxidation of alcohols and one-pot tandem oxidative synthesis of quinazolinones". . . Retrieved 2022/01/24.
• 5、 Isakovskaya,Nikovskii,Nelyubina, Yu. V.. "New Low-Dimensional Perovskites Based on Lead Bromide". . p. 365 - 375. Retrieved 2021/07/16.