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:

99.00% ^*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:

(E)-3-(anthracen-9-yl)acrylic acid

(Z)-3-(anthracen-9-yl)-2-phenylacrylonitrile

(E)-3-(anthracen-9-yl)-1-(2-hydroxyphenyl)prop-2-en-3-one

[9]anthryl-benzoyloxy-acetonitrile

Refernces

New enantiopure NHCs derived from camphor

10.1039/b911476a

The research focuses on developing a novel class of enantiopure carbene precursors based on camphor, an inexpensive and readily available chiral starting material. The purpose of this study is to explore the potential of these new carbene precursors in catalytic reactions, particularly in enantioselective transformations. The researchers synthesized several carbene precursors (5a–c) from camphor-derived diamine 3 using standard transformations with reagents such as MesCH2Cl, benzaldehyde, and anthracene-9-carbaldehyde. They also prepared salt 7 by reacting amine 6 with 2,4,6-trimethylbenzyl chloride. The carbenes derived from these precursors were tested in a formal [2+2] reaction of ketenes and aldehydes, yielding optically active β-lactones with good enantiomeric excess (ee) values, up to 92% ee in some cases. This study concludes that these new carbenes, with their unique structural features, can effectively catalyze enantioselective reactions, offering a promising avenue for asymmetric catalysis. Future work will involve exploring these carbenes as ligands in metal-catalyzed reactions.

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