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Description

Deuterated chloroform (CDCl3), also known as chloroform-d, is an excellent everyday solvent choice for scientists who demand exceptional results. Commonly used as a solvent in proton NMR (1H NMR) spectroscopy, chloroform-d can dissolve a vast array of compounds with ease due to its weak polarity. It is often used in combination with methanol-d as a cosolvent. Plus, its low boiling point makes it relatively easy to recover a sample post-NMR analysis or during organic syntheses.

Chemical Properties

colourless liquid

Uses

Labelled Chloroform, generally in trimethylsilane solution, used in NMR spectroscopy as a solvent. Unlabelled chloroform has been used an an anaesthetic due to its action on the central nervous system .

Definition

ChEBI: A deuterated compound that is is an isotopologue of chloroform in which the hydrogen atom is replaced with a deuterium. Commonly used as a solvent in proton MNR spectroscopy.

Preparation

On a large-scale, chloroform-d (CDCl3) is synthesized by treatment of a hypochlorite salt with deuterated acetone/ethanol or the reaction between chloral and sodium deuteroxide (NaOD). The NaOD is prepared from the reaction of deuterium oxide (D2O) and sodium metal, which liberate deuterium gas from the reaction mixture; therefore, this reaction has drawbacks, including the danger of explosion of the deuterium gas and high risk for use of metal sodium on larger scales. In order to avoid the above drawbacks, the convenient reaction of sodium peroxide and D2O was used to prepare NaOD.

General Description

Chloroform-d (Deuterochloroform, CDCl₃), deuterated chloroform, is a 100% isotopically enriched NMR (Nuclear Magnetic Resonance) solvent. It is widely employed in high resolution NMR studies due to its high chemical and isotopic purity. Quantitaive infrared spectral investigations of carbon-deuterium stretching bands of chloroform-d in various organic solvents have been reported. Raman difference spectroscopic studies of mixtures of chloroform-d and liquid chloroform have been conducted to evaluate frequency shifts in the in the ν₁ and ν₂ bands of CHCl₃ and CDCl₃.

References

[1] LIA ZAHARANI  Mohd R B J, NADER GHAFFARI KHALIGH*   Cost and Energy Saving Process for the Laboratory-Scale Production of Chloroform-d[J]. Organic Process Research & Development, 2022, 26 11: 3126-3129. DOI:10.1021/acs.oprd.2c00260.
[2] MEI-CHUN WU, HUA YANG*   Photoredox-Catalyzed C–H Trideuteromethylation of Quinoxalin-2(1H)-ones with CDCl3 as the “CD3” source[J]. Organic Letters, 2022, 24 35: 6412-6416. DOI:10.1021/acs.orglett.2c02439.

Questions And Answer

• Water peak

  The position of the water peak in different deuterated reagents is not the same. The water peak of heavy water is about 4.67 ppm. There is a trend that the more water the low field.
  Chloroform-D is less soluble with water and the water content is low, so its water peak near 1.59 ppm. Deuterated acetone is about 2.8 ppm and the deuterated dimethylsulfoxide has a water peak of about 3.4 ppm. If water is added to deuterated acetone, the water peak will gradually move to a low field and eventually stop at about 4.7 ppm.;

• Application

  Chloroform-d has been employed as solvent in a 1H NMR (Proton Nuclear Magnetic Resonance) spectroscopic study. It has been employed as solvent during the 31PNMR (Phosphorus-31 nuclear magnetic resonance) spectral investigation of triphenyl phosphate and tris(2-chloroethyl) phosphate. It has also been used as the deuterated solvent in the 1H NMR spectral studies of 2-(4-bromobenzyl)-3-hydroxypropanoic acid and 3-hydroxy-2-(4-methoxybenzyl)propanoic acid. It has also been used as the deuterated solvent for the 1HNMR spectral studies of  3,3′-dihydroxy-4,4′-diamino-biphenyl (HAB) and 2,2′-bis-(3,4-dicarboxy-phenyl) hexafluoropropane dianhydride (6FDA) polyimide.Chloroform-d has been employed as solvent in a 1H NMR (Proton Nuclear Magnetic Resonance) spectroscopic study. It has been employed as solvent during the 31PNMR (Phosphorus-31 nuclear magnetic resonance) spectral investigation of triphenyl phosphate and tris(2-chloroethyl) phosphate. It has also been used as the deuterated solvent in the 1H NMR spectral studies of 2-(4-bromobenzyl)-3-hydroxypropanoic acid and 3-hydroxy-2-(4-methoxybenzyl)propanoic acid. It has also been used as the deuterated solvent for the 1HNMR spectral studies of  3,3′-dihydroxy-4,4′-diamino-biphenyl (HAB) and 2,2′-bis-(3,4-dicarboxy-phenyl) hexafluoropropane dianhydride (6FDA) polyimide.;

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