Diphenaldehyde

Base Information

• Chemical Name: Diphenaldehyde
• CAS No.: 1210-05-5
• Molecular Formula: C14H10 O2
• Molecular Weight: 210.232
• Hs Code.: 2912299000
• European Community (EC) Number: 635-014-1
• NSC Number: 314066
• UNII: DK4V67PK7P
• DSSTox Substance ID: DTXSID00153101
• Nikkaji Number: J53.934A
• Wikidata: Q83019932
• Mol file: 1210-05-5.mol

Synonyms:diphenaldehyde

Chemical Property of Diphenaldehyde

Chemical Property:

• Melting Point: 64 ºC
• Refractive Index: 1.5681 (estimate)
• Boiling Point: 179 ºC / 2mmHg
• Flash Point: 151.1°C
• PSA: 34.14000
• Density: 1.18g/cm³
• LogP: 2.97860
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 210.068079557
• Heavy Atom Count: 16
• Complexity: 223

Purity/Quality:

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

Biphenyl-2,2''-dicarboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C=O)C2=CC=CC=C2C=O

Technology Process of Diphenaldehyde

There total 61 articles about Diphenaldehyde 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-formylbenzene boronic acid (40138-16-7) + ortho-bromobenzaldehyde (6630-33-7) → Biphenyl-2,2'-dicarbaldehyde (1210-05-5)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium fluoride dihydrate; tri-tert-butylphosphonium hydrogen tetrafluoroborate; In tetrahydrofuran; Inert atmosphere;

DOI:10.1002/anie.201201374

Reference yield: 98.0%

2-iodobenzaldehyde (26260-02-6) → Biphenyl-2,2'-dicarbaldehyde (1210-05-5)

Guidance literature:

With copper(I) thiophene-2-carboxylate; copper; In dimethyl sulfoxide; at 65 ℃;

DOI:10.1016/j.tet.2016.07.063

Reference yield: 95.0%

ortho-bromobenzaldehyde (6630-33-7) → Biphenyl-2,2'-dicarbaldehyde (1210-05-5)

Guidance literature:

With copper(I) thiophene-2-carboxylate; copper; In dimethyl sulfoxide; at 65 ℃;

DOI:10.1016/j.tet.2016.07.063

upstream raw materials:

ethanol

2,2′‐bis(dibromomethyl)‐1,1′‐biphenyl

potassium oxalate

phenanthrene

Downstream raw materials:

9,10-phenanthrenequinone

phenanthrene

2'-hydroxymethyl-biphenyl-2-carboxylic acid

<1,1'-biphenyl>-2,2'-dicarboxaldehyde dioxime

Refernces

NEW ALKENE-FORMING REACTION: PHENANTHRENES FROM 2-(2-FORMYLPHENYL)BENZALDEHYDE BIS-TOSYLHYDRAZONE DECOMPOSITION

10.1016/0040-4039(91)80677-X

The research aims to develop a new method for converting dicarbonyl compounds into alkenes, specifically focusing on the synthesis of phenanthrenes from 2-(2-formylphenyl)benzaldehydes. The study explores various routes to achieve this transformation, including heating the dilithium or disodium salts of the bistosylhydrazones derived from the aldehydes. The researchers initially attempted methods such as the Bacon procedure and titanium coupling but faced challenges, especially with steric hindrance in the synthesis of 4,5-dimethoxyphenanthrene. They then explored the formation of bis-diazoalkanes from bistosylhydrazones, which upon heating, could cyclize to form phenanthrenes. Tosylhydrazine is used as a key reagent to convert the 2-(2-formylphenyl)benzaldehydes into their corresponding bistosylhydrazones. Sodium hydride (NaH) is employed to deprotonate the bistosylhydrazones, forming their sodium salts. The study concludes that this new method is effective for the preparation of sterically hindered phenanthrenes and represents a significant advancement in the field of alkene formation from dicarbonyl compounds.