Iodoethane-d5

• CAS: 6485-58-1
• Catalog Number: ACM6485581
• Category: Main Products
• Molecular Weight: 161.00
• Molecular Formula: C2D5I
• Synonyms: IODOETHANE-D5
• Appearance: Clear Colourless Oil

Case Study

Iodoethane-d5 as Deuterated Alkylating Agent for Isotopically Labeled Synthesis

Peters, Jonathan, et al. Analytical and bioanalytical chemistry 405.22 (2013): 7061.

This study explored the fragmentation behavior of deuterated rhodamine B derivatives, specifically decarboxyrhodamine B, using laser photodissociation with visible light and collision-induced dissociation (CID) in a Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometer. By synthesizing four differently deuterated decarboxyrhodamine B compounds using iodoethane-d5 as the deuterated alkylating agent, the researchers traced the origin of hydrogen atoms in the eliminated propane and distinguished between concerted and two-step radical mechanisms.
Experimental Protocol: Four decarboxyrhodamine B compounds with different deuterium labeling patterns were synthesized by alkylation of m-aminophenol with iodoethane or iodoethane-d5, followed by condensation with benzaldehyde. Compounds were characterized by electrospray ionization FT-ICR mass spectrometry at 9.4 Tesla. Fragmentation was induced by two methods: laser photodissociation at 514.5 nm with 0.5-1 W power and 0.1 s irradiation, and sustained off-resonance irradiation collision-induced dissociation (SORI CID) with argon at 3.5-4.5% power.
Performance Evaluation: The mass spectra of the deuterated compounds confirmed that the dominant fragmentation pathway is the sequential loss of two propane molecules. No hydrogen-deuterium scrambling occurs between alkyl substituents and the aromatic backbone, indicating that the carbon skeleton of the xanthene core does not participate in the fragmentation. The mass accuracy of the eliminated C3D8 fragment (measured 52.1132 Da vs. theoretical 52.1128 Da, error 0.4 mDa) provided high-confidence validation. The results support a concerted mechanism for propane elimination rather than a stepwise radical pathway. Differences in fragment ion intensities between photodissociation and CID spectra were attributed to the different internal energy deposition of the two activation methods.

Iodoethane-d5 as a Deuterium Labeling Reagent for Selective Analysis of Sulfur-Containing Species in Crude Oil by Ultrahigh Resolution Mass Spectrometry

Wang, Xuxiao, et al. International Journal of Molecular Sciences 16.12 (2015): 30133-30143.

Iodoethane-d5 (C2D5I) serves as a selective deuterium labeling reagent for the alkylation of sulfur-containing compounds in heavy crude oil. In combination with silver tetrafluoroborate (AgBF4), it enables the selective derivatization of polycyclic aromatic sulfur heterocycles (PASHs), allowing their unambiguous detection by electrospray ionization mass spectrometry without prior fractionation.
Experimental Protocol: A heavy crude oil sample was treated with AgBF4 in anhydrous dichloroethane to form Ag+-sulfur coordination complexes, followed by addition of C2D5I. The resulting S-ethyl-d5 sulfonium salts were analyzed directly by positive-ion ESI on a high-field Orbitrap FTMS (resolving power 480,000 at m/z 400) and 7 T FT-ICR MS. The deuterium label (C2D5, +5 Da shift) allowed clear differentiation of derivatized sulfur species from non-derivatized compounds.
Performance Evaluation: The reaction showed high selectivity toward sulfur over nitrogen and oxygen compounds; standard mixtures containing anthracene, acridine, and dibenzofuran showed no derivatization, while dibenzothiophene was quantitatively converted (99% yield by ¹H NMR). In crude oil, the dominant classes detected after C2D5I treatment were S1 (DBE 4-24) and S2 (DBE 1-25), which were otherwise not ionized by ESI. The method selectively detected aliphatic sulfides and thiophenic species, enabling detailed heteroatom class distribution analysis.

Custom Q&A

What is the molecular formula of Iodoethane-d5?

The molecular formula of Iodoethane-d5 is C2H5I.

What is the molecular weight of Iodoethane-d5?

The molecular weight of Iodoethane-d5 is 161.00 g/mol.

What is the IUPAC name of Iodoethane-d5?

The IUPAC name of Iodoethane-d5 is 1,1,1,2,2-pentadeuterio-2-iodoethane.

What is the InChI of Iodoethane-d5?

The InChI of Iodoethane-d5 is InChI=1S/C2H5I/c1-2-3/h2H2,1H3/i1D3,2D2.

What is the InChIKey of Iodoethane-d5?

The InChIKey of Iodoethane-d5 is HVTICUPFWKNHNG-ZBJDZAJPSA-N.

What is the Canonical SMILES of Iodoethane-d5?

The Canonical SMILES of Iodoethane-d5 is CCI.

What is the CAS number of Iodoethane-d5?

The CAS number of Iodoethane-d5 is 6485-58-1.

What is the DSSTox Substance ID of Iodoethane-d5?

The DSSTox Substance ID of Iodoethane-d5 is DTXSID90369259.

What is the XLogP3-AA value of Iodoethane-d5?

The XLogP3-AA value of Iodoethane-d5 is 2.1.

Is Iodoethane-d5 a canonicalized compound?

Yes, Iodoethane-d5 is a canonicalized compound.