Deuterated chloroform

Short description: Chemical compound

Deuterated chloroform  | Stereo, skeletal formula of deuterated chloroform | Spacefill model of deuterated chloroform

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Names
IUPAC name

trichloro(deuterio)methane[1]

Preferred IUPAC name

trichloro(²H)methane

Other names

Chloroform-d
Deuterochloroform

Identifiers

CAS Number

* 865-49-6 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 1697633
ChEBI |

* CHEBI:85365 Y

ChemSpider |

* 64654 Y

EC Number |

* 212-742-4

PubChem CID

* 71583

UNII |

* P1NW4885VT Y

UN number | 1888

InChI

* InChI=1S/CHCl3/c2-1(3)4/h1H/i1D Y

Key: HEDRZPFGACZZDS-MICDWDOJSA-N Y

* InChI=1/CHCl3/c2-1(3)4/h1H/i1D

Key: HEDRZPFGACZZDS-MICDWDOJEH

SMILES

* [2H]C(Cl)(Cl)Cl

Properties

Chemical formula

| CDCl

Molar mass | 120.384 g/mol
Appearance  | Colorless liquid
Odor | chloroform-like
Density | 1.500 g/cm3
Melting point |  −64 °C (−83 °F; 209 K)
Boiling point |  61 °C (142 °F; 334 K)
Hazards
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H302, H315, H319, H331, H336, H351, H361, H372, H373

GHS precautionary statements

| P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+312, P302+352, P304+340, P305+351+338, P308+313, P311, P312, P314, P321, P330, P332+313, P337+313, P362, P403+233, P405, P501
NFPA 704 (fire diamond)  |

Related compounds

Related compounds

| Chloroform

Deuterated dichloromethane

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Deuterated chloroform, also known as chloroform-d, is the organic compound with the formula CDCl
3. Deuterated chloroform is a common solvent used in NMR spectroscopy.[2] The properties of CDCl
3 and ordinary CHCl
3 (chloroform) are virtually identical.

Deuterochloroform was first made in 1935 during the years of research on deuterium.[3]

## Contents

* 1 Preparation
* 2 NMR solvent
* 3 Hazards
* 4 References

## Preparation

Deuterated chloroform is commercially available. It is more easily produced and less expensive than deuterated dichloromethane.[4] Deuterochloroform is produced by the reaction of hexachloroacetone with deuterium oxide, using pyridine as a catalyst. The large difference in boiling points between the starting material and product facilitate purification by distillation.[5][6]

O=C(CCl

2 \+ D
2O → 2 CDCl
3 \+ CO

Treating chloral with sodium deuteroxide (NaOD) gives deuterated chloroform.[7][8]

## NMR solvent

In proton NMR spectroscopy, deuterated solvent (enriched to >99% deuterium) is typically used to avoid recording a large interfering signal or signals from the proton(s) (i.e., hydrogen-1) present in the solvent itself. If nondeuterated chloroform (containing a full equivalent of protium) were used as solvent, the solvent signal would almost certainly overwhelm and obscure any nearby analyte signals. In addition, modern instruments usually require the presence of deuterated solvent, as the field frequency is locked using the deuterium signal of the solvent to prevent frequency drift. Commercial chloroform-d does, however, still contain a small amount (0.2% or less) of non-deuterated chloroform; this results in a small singlet at 7.26 ppm, known as the residual solvent peak, which is frequently used as an internal chemical shift reference.

In carbon-13 NMR spectroscopy, the sole carbon in deuterated chloroform shows a triplet at a chemical shift of 77.16 ppm with the three peaks being about equal size, resulting from splitting by spin coupling to the attached spin-1 deuterium atom (CHCl
3 has a chemical shift of 77.36 ppm).[4]

Deuterated chloroform is a general purpose NMR solvent, as it is not very chemically reactive and unlikely to exchange its deuterium with its solute,[9] and its low boiling point allows for easy sample recovery. It, however, it is incompatible with strongly basic, nucleophilic, or reducing analytes, including many organometallic compounds.

## Hazards

Chloroform reacts photochemically with oxygen to form chlorine, phosgene and hydrogen chloride. To slow this process and reduce the acidity of the solvent, chloroform-d is stored in brown-tinted bottles, often over copper chips or silver foil as stabilizer. Instead of metals, a small amount of a neutralizing base like potassium carbonate may be added.[10] It is less toxic to the liver and kidneys than CHCl
3 due to the stronger C–D bond as compared to the C–H bond, making it somewhat less prone to form the destructive trichloromethyl radical (•CCl
3).[11][12]

## References

1. ↑ "Chloroform-d". https://pubchem.ncbi.nlm.nih.gov/compound/Chloroform-D.
2. ↑ Fulmer, Gregory R.; Miller, Alexander J. M.; Sherden, Nathaniel H.; Gottlieb, Hugo E.; Nudelman, Abraham; Stoltz, Brian M.; Bercaw, John E.; Goldberg, Karen I. (2010). "NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist". Organometallics 29 (9): 2176–2179. doi:10.1021/om100106e. https://authors.library.caltech.edu/18475/2/om100106e_si_001.pdf.
3. ↑ Breuer, F. W. (1935). "Chloroform-d (Deuteriochloroform)1". Journal of the American Chemical Society 57 (11): 2236–2237. doi:10.1021/ja01314a058. Bibcode: 1935JAChS..57.2236B.
4. ↑ 4.0 4.1 "The Theory of NMR – Solvents for NMR spectroscopy". http://orgchem.colorado.edu/Spectroscopy/nmrtheory/nmrsolvents.html.
5. ↑ Paulsen, P. J.; Cooke, W. D. (1 September 1963). "Preparation of Deuterated Solvents for Nuclear Magnetic Resonance Spectrometry.". Analytical Chemistry 35 (10): 1560. doi:10.1021/ac60203a072.
6. ↑ Zaharani, Lia; Johan, Mohd Rafie Bin; Khaligh, Nader Ghaffari (2022). "Cost and Energy Saving Process for the Laboratory-Scale Production of Chloroform-d". Organic Process Research & Development 26 (11): 3126–3129. doi:10.1021/acs.oprd.2c00260.
7. ↑ Kluger, Ronald (1964). "A Convenient Preparation of Chloroform-d1". The Journal of Organic Chemistry 29 (7): 2045–2046. doi:10.1021/jo01030a526.
8. ↑ Breuer, F. W. (1935). "Chloroform-d (Deuteriochloroform)1". Journal of the American Chemical Society 57 (11): 2236–2237. doi:10.1021/ja01314a058. Bibcode: 1935JAChS..57.2236B.
9. ↑ Sabot, Cyrille; Kumar, Kanduluru Ananda; Antheaume, Cyril; Mioskowski, Charles (2007-06-01). "Triazabicyclodecene: An Effective Isotope Exchange Catalyst in CDCl3" (in en). The Journal of Organic Chemistry 72 (13): 5001–5004. doi:10.1021/jo070307h. ISSN 0022-3263. PMID 17530896. https://pubs.acs.org/doi/10.1021/jo070307h.
10. ↑ Teipel, Jan; Gottstein, Vera; Hölzle, Eva; Kaltenbach, Katja; Lachenmeier, Dirk W.; Kuballa, Thomas (2022). "An Easy and Reliable Method for the Mitigation of Deuterated Chloroform Decomposition to Stabilise Susceptible NMR Samples" (in en). Chemistry 4 (3): 776–785. doi:10.3390/chemistry4030055. ISSN 2624-8549.
11. ↑ Goldstein, Robin S. (2013). Toxic interactions. Hewitt, William R., Hook, Jerry B.. Burlington: Elsevier Science. ISBN 978-1-4832-6970-2. OCLC 896796140.
12. ↑ Ahmadizadeh, M.; Kuo, C.-H.; Hook, J.B. (1981-07-01). "Nephrotoxicity and hepatotoxicity of chloroform in mice: Effect of deuterium substitution". Journal of Toxicology and Environmental Health 8 (1–2): 105–111. doi:10.1080/15287398109530054. ISSN 0098-4108. PMID 7328696. Bibcode: 1981JTEH....8..105A. https://doi.org/10.1080/15287398109530054.

* v
* t
* e

Deuterated NMR Solvents

Deuterated|

* Deuterated acetone \- (CD3)2C=O
* Deuterated benzene \- C6D6
* Deuterated chloroform \- CDCl3
* Deuterated dichloromethane \- CD2Cl2
* Deuterated DMF \- (CD3)2NCOD
* Deuterated DMSO \- (CD3)2S=O
* Deuterated ethanol \- C2D5OD
* Deuterated methanol \- CD3OD
* Deuterated THF \- (C4D8)O
* Deuterated water \- D2O

Reference

1H and 13C chemical shifts

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Original source: https://en.wikipedia.org/wiki/Deuterated chloroform. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Deuterated_chloroform&oldid=3843683"
*[CID]: Compound ID
*[H302]: Harmful if swallowed
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H331]: Toxic if inhaled
*[H336]: May cause drowsiness or dizziness
*[H351]: Suspected of causing cancer
*[H361]: Suspected of damaging fertility or the unborn child
*[H372]: Causes damage to organs through prolonged or repeated exposure
*[H373]: May cause damage to organs through prolonged or repeated exposure
*[P201]: Obtain special instructions before use
*[P202]: Do not handle until all safety precautions have been read and understood
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P281]: Use personal protective equipment as required
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P308+313]: IF exposed or concerned: Get medical advice/attention
*[P311]: Call a POISON CENTER or doctor/physician
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P314]: Get Medical advice/attention if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P330]: Rinse mouth
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …
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