trans-2-[3-(4-tert-Butylphenyl)-2-methyl-2-propenylidene]malononitrile

• CAS: 300364-84-5
• Catalog Number: ACM300364845
• Category: Other Products; Alkanes
• Molecular Weight: 250.34
• Molecular Formula: C₁₇H₁₈N₂
• Hazard Statements: H225-H304-H315-H336-H410
• RIDADR: NONH for all modes of transport
• Symbol: GHS02

Case Study

Trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malononitrile as a Matrix for Mass Spectrometry Analysis of Nanoparticles

Dass, Amala, et al. Journal of the American Chemical Society, 2008, 130(18), 5940-5946.

Intact molecular ions of the organothiolate-protected nanoparticle Au25(SCH2CH2Ph)18, identifiable at 7391 Da as both 1- and 1+ ions in negative and positive modes, respectively, can be detected using MALDI-TOF mass spectrometry. This is achieved through the application of threshold laser pulse intensities and the use of trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malononitrile (DCTB) as a matrix.
Previous MALDI-TOF experiments with different matrices have experienced significant fragmentation of both the nanoparticle and thiolate ligands. The lack of fragmentation in this study allows for accurate assessment of mixed monolayer compositions on nanoparticles produced via ligand exchange and thiol mixture synthesis. Optimal reaction conditions for creating mixed monolayers with only one or a few functional ligands can be easily discerned. Increasing the laser pulse intensity leads to initial fragmentation in the Au25(SCH2CH2Ph)18 nanoparticle, resulting in the loss of AuL units, particularly Au4(SCH2CH2Ph)4.
DCTB is known to facilitate electron transfer to and from the analyte. In this study, the relative absorbance ratios (AMPC/AMATRIX) of Au25 nanoparticles in various matrices at 337 nm under standard dilution conditions (1:1000 mole ratio of MPC to matrix) are 0.002 for DCTB, 0.004 for SA, 0.006 for UMM, and 0.009 for HABA. These results indicate that while DCTB is indeed a more effective optical absorber than the other matrices, the difference is relatively modest. Consequently, a higher optical absorbance may contribute somewhat to the efficiency of DCTB as a nanoparticle MALDI matrix.

Trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malononitrile Matrix for MALDI-MS Measurement

Fleissner, Sarah, et al. Rapid Communications in Mass Spectrometry, 2022, 36(10), e9281.

A combination of classical vacuum MALDI reflectron TOF-MS and intermediate pressure MALDI QTOF-MS techniques was utilized to analyze the ionization behavior and structural characteristics of organometallic compounds. Various sample preparations were investigated in detail, including two selected MALDI matrices [trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malononitrile (DCTB) and 2,2':5',2"-terthiophene (TTP)] in combination with different solvents for MALDI-MS measurements. And the correct isotopic distribution of the observed molecular ions was investigated.
MALDI-MS under both vacuum and medium-pressure conditions enabled successful identification of all the studied organometallic compounds. The correct ion masses of molecular ion species including [M-Cl]+, [M]+ and [M+Na]+ were established through MALDI QTOF-MS analysis which achieved mass errors below ±5 ppm throughout all tested compounds.
The analysis demonstrated that different MALDI matrices TTP and DCTB detected the analytes with no significant variations in mass spectra results. Besides, the successful examination of the compounds depended heavily on the correct combination of analyte and matrix solvent mixture.

Custom Q&A

What is the molecular formula of trans-2-[3-(4-tert-Butylphenyl)-2-methyl-2-propenylidene]malononitrile?

The molecular formula is C17H18N2.

What is the molecular weight of trans-2-[3-(4-tert-Butylphenyl)-2-methyl-2-propenylidene]malononitrile?

The molecular weight is 250.34 g/mol.

What is the IUPAC name of trans-2-[3-(4-tert-Butylphenyl)-2-methyl-2-propenylidene]malononitrile?

The IUPAC name is 2-[(E)-3-(4-tert-butylphenyl)-2-methylprop-2-enylidene]propanedinitrile.

What is the InChI of trans-2-[3-(4-tert-Butylphenyl)-2-methyl-2-propenylidene]malononitrile?

The InChI is InChI=1S/C17H18N2/c1-13(10-15(11-18)12-19)9-14-5-7-16(8-6-14)17(2,3)4/h5-10H,1-4H3/b13-9+.

What is the InChIKey of trans-2-[3-(4-tert-Butylphenyl)-2-methyl-2-propenylidene]malononitrile?

The InChIKey is OIASAVWSBWJWBR-UKTHLTGXSA-N.

What is the canonical SMILES of trans-2-[3-(4-tert-Butylphenyl)-2-methyl-2-propenylidene]malononitrile?

The canonical SMILES is CC(=CC1=CC=C(C=C1)C(C)(C)C)C=C(C#N)C#N.

What is the isomeric SMILES of trans-2-[3-(4-tert-Butylphenyl)-2-methyl-2-propenylidene]malononitrile?

The isomeric SMILES is C/C(=C\C1=CC=C(C=C1)C(C)(C)C)/C=C(C#N)C#N.

What is the CAS number of trans-2-[3-(4-tert-Butylphenyl)-2-methyl-2-propenylidene]malononitrile?

The CAS number is 300364-84-5.

What is the EC number of trans-2-[3-(4-tert-Butylphenyl)-2-methyl-2-propenylidene]malononitrile?

The EC number is 627-251-4.