Biphenyl-2,2'-dicarboxaldehyde

• CAS: 1210-05-5
• Catalog Number: ACM1210055
• Category: Main Products
• Molecular Weight: 210.23
• Molecular Formula: C₁₄H₁₀O₂
• Synonyms: (1,1'-biphenyl)-2,2'-dicarboxaldehyde;(1,1'-Biphenyl)-2,2'-dicarboxaldehyde;[1,1'-Biphenyl]-2,2'-dicarbaldehyde;2,2'-biphenyldicarboxaldehyde;2,2'-Biphenyldicarbaldehyde;2,2'-Biphenyldicarboxaldehyde;Biphenyl-2,2'-dialdehyde;Diphenic dialdehyde
• IUPAC Name: 2-(2-formylphenyl)benzaldehyde
• Canonical SMILES: C1=CC=C(C(=C1)C=O)C2=CC=CC=C2C=O
• InChI Key: HJFGULDHUDIPDA-UHFFFAOYSA-N
• Boiling Point: 179ºC / 2mmHg
• Melting Point: 64ºC
• Flash Point: 151.1ºC
• Density: 1.18g/cm³
• Exact Mass: 210.06800
• H-Bond Acceptor: 2
• H-Bond Donor: 0

Case Study

Biphenyl-2,2'-Dicarboxaldehyde for the Synthesis of Polycyclododecene via Horner-Emmons Cyclization

Agranat I, et al. The Journal of Organic Chemistry, 1979, 44(12), 1936-1941.

(9E,14E,24E,29E)hexabenzo[d,f,jk,o,q,uu]dodecalene(1a) was synthesized in 0.3% yield via the Homer-Emmons reaction between biphenyl-2,2'-dicarboxaldehyde (4) and biphenyl-2,2',6,6'-tetrakis(diethyl methylphosphonate) (8). The double Homer-Emmons reaction between biphenyl-2,2'-dicarboxaldehyde (4) and biphenyl-Z,2'-bis(diethyl methylphosphonate) (7) gave (9E,19E)-tetrabenzo[a,c,g,i]cyclododecene (2a) in 8.0% yield.
Synthesis procedure between 4 and 8
· A suspension of sodium hydride (50%, 1.05 g, 22 mmol) in dry DMF (250 mL) was treated with a solution of compound 4 (2.10 g, 10 mmol) in dry DMF (100 mL) and a solution of compound 8 (crude, 3.77 g, 5 mmol) in dry DMF (100 mL). The addition process lasted for 4 hours, followed by stirring for a further 18 hours.
· The reaction mixture was then decomposed and processed according to standard procedures. The crude product was subjected to chromatography on a silica gel column (100 g) using CsHe as the eluent. Subsequent PLC chromatography of the eluted product on silica PLC plates with a hexane-benzene mixture (7:1) resulted in the formation of compound 1a as a pale yellow solid. The yield obtained was 0.3% (0.008 g).

Biphenyl-2,2'-Dicarboxaldehyde as a Marker for Ambient Air Studies

Tomaz S, et al. Atmospheric Environment, 2017, 161, 144-154.

This work investigated the total concentrations of 80 polycyclic aromatic hydrocarbons (PACs) in ambient air (gaseous and particulate) and performed an extended chemical characterization of the aerosols. The results showed that 6H-dibenzo[b,d]pyran-6-one, biphenyl-2,2'-dicarboxaldehyde and 3-nitrophenanthrene were selected as the best markers for the oxidation processes of PACs in ambient air.
· Biphenyl-2,2'-dicarboxaldehyde has been detected at very low levels in primary emissions from biomass burning. It has been found to form as a secondary compound in the gas phase reaction of phenanthrene with OH radical, NO3 radical, and O3. Additionally, this compound has been identified as a byproduct of the heterogeneous reaction of phenanthrene with ozone.
· Using concentrations in both the gaseous and particulate phases, ratios of oxy- or nitro-PAHs to their parent PAHs have been analyzed to study relative reactivity of PAHs and the sources of oxy- and nitro-PAHs. Overall, the concentration ratios of 6Hdibenzo[b,d]pyran-6-one, 3-nitrophenanthrene, and biphenyl-2,2'-compounds such as 1-nitropyrene and benz[a]anthracene-7,12- dione did not follow the same trend. The peak values for concentration ratios in November were observed for all compounds, which could be attributed to the very low levels of both parent PAHs and PAH derivatives.