837-45-6

Basic information

• Product Name: PHENANTHRENE-9-CARBOXALDEHYDE
• Synonyms: 9-Phenanthrenecarboxylic acid;9-Phenanthroic acid;Phenanthrene-9-carboxylic acid
• CAS NO: 837-45-6
• Molecular Formula: C₁₅H₁₀O₂
• Molecular Weight: 222.24
• Mol File: 837-45-6.mol

Chemical Properties

• Melting Point: 249-251℃
• Boiling Point: 323.41°C (rough estimate)
• Flash Point: 194.8°C
• Appearance: /
• Density: 1.305
• Vapor Pressure: 2.37E-08mmHg at 25°C
• Refractive Index: 1.6600 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: PHENANTHRENE-9-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENANTHRENE-9-CARBOXALDEHYDE(837-45-6)
• EPA Substance Registry System: PHENANTHRENE-9-CARBOXALDEHYDE(837-45-6)

Safety Data

• Hazardous Substances Data: 837-45-6(Hazardous Substances Data)

Usage

Uses

1-Iodo-4-pentylbenzene is a polycyclic aromatic hydrocarbon. An environmental pollutant.

Synthesis Reference(s)

The Journal of Organic Chemistry, 36, p. 1769, 1971 DOI: 10.1021/jo00812a010

InChI:InChI=1/C15H10O2/c16-15(17)14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9H,(H,16,17)

Upstream product

• 71910-54-8 (E)-3-(2-Aminophenyl)-2-phenyl-2-propenoic acid 
• 19319-28-9 (Z)-3-(2-chlorophenyl)-2-phenyl acrylic acid 
• 89346-67-8 (E)-2-(2-Carboxy-2-phenylethenyl)benzenediazonium tetrafluoroborate 
• 75-05-8 acetonitrile 
• 124-38-9 carbon dioxide 
• 85-01-8 phenanthrene 
• 951-05-3 9-(chloromethyl)phenanthrene 
• 64-19-7 acetic acid 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 79-37-8 oxalyl dichloride 
• 219-92-1 dibenzocycloheptene 
• 7647-01-0 hydrogenchloride 
• 71-43-2 benzene 

Downstream Products

• 67293-13-4 phenanthrene-9-carboxylic acid-(2-diethylamino-ethyl ester); hydrochloride 
• 124-38-9 carbon dioxide 
• 85-01-8 phenanthrene 
• 84-11-7 9,10-phenanthrenequinone 
• 83665-40-1 3-(p-methoxyphenyl)-2-(9-phenanthryl)oxacyclohepta-2,4-dien 
• 74357-23-6 (E)-3-(p-methoxyphenyl)-2-propenyl 9-phenanthrenecarboxylate 
• 83665-34-3 (E)-4-(p-methoxyphenyl)-3-butenyl 9-phenanthrenecarboxylate 
• 74357-24-7 (E)-5-(p-methoxyphenyl)-4-pentenyl 9-phenanthrenecarboxylate 
• 128622-56-0 (E)-2-(p-methoxyphenyl)-2-butenyl 9-phenanthrenecarboxylate 
• 74357-25-8 (Z)-2-(p-methoxyphenyl)-2-butenyl 9-phenanthrenecarboxylate 
• 129887-63-4 (Z)-6-(p-methoxyphenyl)-5-hexenyl 9-phenanthrenecarboxylate 
• 128622-55-9 (E)-6-(p-methoxyphenyl)-5-hexenyl 9-phenanthrenecarboxylate 
• 83665-35-4 (E)-3-(p-methoxyphenyl)-3-pentenyl 9-phenanthrenecarboxylate 
• 74357-26-9 (E)-4-(p-methoxyphenyl)-4-hexenyl 9-phenanthrenecarboxylate 

Relevant articles and documents

Reductive photocarboxylation of phenantnrene: A mechanistic investigation

Irradiation of a solution of phenanthrene (PHN) in DMSO saturated with CO2 in the presence of N,N-dimethylaniline (DMA) produced 9,10-dihydrophenanthrene-9-carboxylic acid (1) in 55% yield, trans-9,10-dihydrophenanthrene-9,10-dicarboxylic acid (2) in 11% yield, a trace of phenanthrene-9-carboxylic acid (3), and a trace of 10-[p-(N,N-dimethylamino)phenyl]-9,10-dihydrophenanthrene-9-carboxylic acid (5). Addition of cumene, a hydrogen donor, or water, a proton donor, decreased the yield of 2, while addition of certain salts increased its yield. 9-Carboxy-9,10-dihydrophenanthr-10-yl, generated by irradiation of phenanthrene-9-carboxylic acid in the presence of DMA, is proposed to be an intermediate in the formation of the acids. The quantum yield for the formation of 2 increased to a maximum of 0.13 with increasing light intensity. High CO2 concentrations in DMSO changed the reaction pathway, greatly reducing the yields of 1 and 2, and phenanthrene-9-carboxylic acid (3) and 10-[p-(N,N-dimethylamino)phenyl]-9,10-dihydrophenanthrene-9-carboxylic acid (5) were formed instead. On the basis of these results reduction of 9-carboxy-9,10-dihydrophenanthr-10-yl with the phenanthrene radical anion is proposed to be a step in the mechanism accounting for trans-9,10-dihydrophenanthrene-9,10-dicarboxylic acid formation. Transient spectroscopic evidence in support of this proposal is presented.

The Baeyer-Villiger Reaction of Polycyclic Aromatic Aldehydes: Preparation of Polycyclic Phenols

Baeyer-Villiger reactions of such polycyclic aromatic aldehydes as 2-dibenzofurancarbaldehyde with various peroxy compounds have been studied in detail, giving predominantly the corresponding phenols.

PHOTOCATALYSIS OF THE PSCHORR REACTION BY TRIS-(2,2'-BIPYRIDYL)RUTHENIUM(II) IN THE PHENANTHRENE SERIES

The photocatalytic conversion of the tetrafluoroborate salt of the stilbenediazonium ion (1) into the corresponding phenanthrene (2) (Pschorr reaction) by Ru(bpy)3(2+) (bpy = 2,2'-bipyridyl) has been investigated.We have shown that this particular Pshorr

Reactions of Halogenated α-Phenylcinnamic Acids with Potassium Amide in Liquid Ammonia : Part I - Reactions of cis- and trans-2-Chloro-α-phenylcinnamic Acids

Reaction of trans- and cis-2-chloro-α-phenylcinnamic acids (1) with KNH2 in liquid ammonia gives phenanthrene-9-carboxylic acids (2) and 3-phenylcarbostyrils (8).Under similar conditions 3-chloro-α-phenylcinnamic acids (5) furnish 3-phenylcoumarins (6).