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			{{short description|Chemical compound}}
	{{Unreferenced|date = February 2007}}
	{{Chembox		{{Chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 401983341
			| Watchedfields = changed
⚫	| ImageFileL1 = Chloroform-d.png
		⚫	| verifiedrevid = 430329052
			| ImageFile =
		⚫	| ImageFileL1 = Deuterated chloroform.svg
	| ImageFileL1_Ref = {{chemboximage|correct|??}}		| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageSizeL1 = 121
	| ImageNameL1 = Stereo, skeletal formula of deuterated chloroform		| ImageNameL1 = Stereo, skeletal formula of deuterated chloroform
	| ImageFileR1 = Chloroform_3D.svg		| ImageFileR1 = Deuterated-chloroform-3D-vdW.png
	| ImageFileR1_Ref = {{chemboximage|correct|??}}		| ImageFileR1_Ref = {{chemboximage|correct|??}}
	| ImageSizeR1 = 121
	| ImageNameR1 = Spacefill model of deuterated chloroform		| ImageNameR1 = Spacefill model of deuterated chloroform
			| IUPACName = trichloro(deuterio)methane<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/Chloroform-D|title=Chloroform-d}}</ref>
	| IUPACName = Trichloro(<sup>2</sup>H)methane{{Citation needed|date = May 2011}}
	| OtherNames = Chloroform-d<br />		| OtherNames = Chloroform-''d''<br />Deuterochloroform
			| SystematicName =
	Deuterochloroform
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
	| CASNo = 865-49-6		| CASNo = 865-49-6
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
	| PubChem = 71583
			| UNII = P1NW4885VT
	| PubChem_Ref = {{Pubchemcite|correct|pubchem}}
	| ChemSpiderID = 64654		| PubChem = 71583
			| ChemSpiderID = 64654
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫	| EINECS = 212-742-4
			| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫	| UNNumber = 1888
	| Beilstein = 1697633		| ChEBI = 85365
		⚫	| EINECS = 212-742-4
⚫	| SMILES = C(Cl)(Cl)Cl
		⚫	| UNNumber = 1888
⚫	| StdInChI = 1S/CHCl3/c2-1(3)4/h1H/i1D
			| Beilstein = 1697633
⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| SMILES = C(Cl)(Cl)Cl
⚫	| InChI = 1/CHCl3/c2-1(3)4/h1H/i1D
		⚫	| StdInChI = 1S/CHCl3/c2-1(3)4/h1H/i1D
⚫	| StdInChIKey = HEDRZPFGACZZDS-MICDWDOJSA-N
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| InChI = 1/CHCl3/c2-1(3)4/h1H/i1D
⚫	| InChIKey = HEDRZPFGACZZDS-MICDWDOJEH
		⚫	| StdInChIKey = HEDRZPFGACZZDS-MICDWDOJSA-N
		⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| InChIKey = HEDRZPFGACZZDS-MICDWDOJEH
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	| Formula = C<sup>2</sup>HCl<sub>3</sub>		| Formula = {{chem2|CDCl3}}
	| MolarMass = 120.384 g mol<sup>-1</sup>		| MolarMass = 120.384 g/mol
			| Appearance = Colorless liquid
⚫	| ExactMass = 118.920659899 g mol<sup>-1</sup>
			| Odor = chloroform-like
	| Density = 1.500 g cm<sup>-3</sup>
		⚫	| Density = 1.500 g/cm<sup>3</sup>
	| MeltingPtC = -64
	| BoilingPtC = 61		| MeltingPtC = -64
			| BoilingPtC = 61
	}}		}}
	| Section3 = {{Chembox Hazards		| Section3 = {{Chembox Hazards
			| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}}
	| EUClass = {{Hazchem Xn}}
	| NFPA-H = 2		| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|302|315|319|331|336|351|361|372|373}}
⚫	| NFPA-F = 0
			| PPhrases = {{P-phrases|201|202|260|261|264|270|271|280|281|301+312|302+352|304+340|305+351+338|308+313|311|312|314|321|330|332+313|337+313|362|403+233|405|501}}
	| NFPA-R = 0		| NFPA-H = 2
	| RPhrases = {{R22}}, {{R38}}, {{R40}}, {{R48/20/22}}
	| SPhrases = {{S36/37}}		| NFPA-F = 0
		⚫	| NFPA-R = 0
	}}		}}
	| Section4 = {{Chembox Related		| Section4 = {{Chembox Related
	| OtherCpds = ]<br />		| OtherCompounds = ]<br />
	]		]
	}}		}}
			| Section5 =
			| Section6 =
	}}		}}
			'''Deuterated chloroform''', also known as chloroform-''d'', is the ] with the formula {{chem2|CDCl3}}. Deuterated chloroform is a common ] used in ].<ref>{{cite journal|doi=10.1021/om100106e|title=NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist|journal=Organometallics|volume=29|issue=9|pages=2176–2179|year=2010|last1=Fulmer|first1=Gregory R.|last2=Miller|first2=Alexander J. M.|last3=Sherden|first3=Nathaniel H.|last4=Gottlieb|first4=Hugo E.|last5=Nudelman|first5=Abraham|last6=Stoltz|first6=Brian M.|last7=Bercaw|first7=John E.|last8=Goldberg|first8=Karen I.|url=https://authors.library.caltech.edu/18475/2/om100106e_si_001.pdf}}</ref> The properties of {{chem2|CDCl3 and ordinary CHCl3}} (]) are virtually identical.
	'''Deuterated chloroform''' (CDCl<sub>3</sub>), is an ] of ] (CHCl<sub>3</sub>) in which the ] atom ("H") is replaced with a ] (heavy hydrogen) ] ("D"). Deuterated chloroform is the most common ] used in ].
			Deuterochloroform was first made in 1935 during the years of research on ].<ref>Chloroform-d (Deuteriochloroform), F. W. Breuer
⚫	{{List of NMR solvents}}
			, J. Am. Chem. Soc. 1935, 57, 11, 2236–2237 (November 1, 1935)
			</ref>
			==Preparation==
⚫	{{DEFAULTSORT:Deuterated Chloroform}}
			Deuterated chloroform is commercially available. It is more easily produced and less expensive than ].<ref name="colorado1">{{Cite web |url=http://orgchem.colorado.edu/Spectroscopy/nmrtheory/nmrsolvents.html |title=The Theory of NMR – Solvents for NMR spectroscopy |access-date=2014-01-23 |archive-date=2016-03-03 |archive-url=https://web.archive.org/web/20160303170619/http://orgchem.colorado.edu/Spectroscopy/nmrtheory/nmrsolvents.html |url-status=dead}}</ref> Deuterochloroform is produced by the reaction of ] with ], using ] as a catalyst. The large difference in boiling points between the starting material and product facilitate purification by distillation.<ref>{{cite journal |last1=Paulsen |first1=P. J. |last2=Cooke |first2=W. D. |title=Preparation of Deuterated Solvents for Nuclear Magnetic Resonance Spectrometry. |journal=Analytical Chemistry |date=1 September 1963 |volume=35 |issue=10 |pages=1560 |doi=10.1021/ac60203a072}}</ref><ref>{{cite journal |doi=10.1021/acs.oprd.2c00260|title=Cost and Energy Saving Process for the Laboratory-Scale Production of Chloroform-d |year=2022 |last1=Zaharani |first1=Lia |last2=Johan |first2=Mohd Rafie Bin |last3=Khaligh |first3=Nader Ghaffari |journal=Organic Process Research & Development |volume=26 |issue=11 |pages=3126–3129 |s2cid=253071632}}</ref>
⚫	]
			:{{chem2|O\dC(CCl3)2 + D2O → 2 CDCl3 + CO2}}
			Treating ] with sodium deuteroxide (NaOD) gives deuterated chloroform.<ref>Kluger, Ronald (1964). "A Convenient Preparation of Chloroform-d1". The Journal of Organic Chemistry. 29 (7): 2045-2046. doi:10.1021/jo01030a526.</ref><ref>Breuer, F. W. (1935). "Chloroform-d (Deuteriochloroform)1". Journal of the American Chemical Society. 57 (11): 2236-2237. doi:10.1021/ja01314a058.</ref>
			==NMR solvent==
			In ] 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 ] spectroscopy, the sole carbon in deuterated chloroform shows a triplet at a ] of 77.16 ppm with the three peaks being about equal size, resulting from splitting by ] to the attached spin-1 deuterium atom ({{chem2|CHCl3}} has a chemical shift of 77.36 ppm).<ref name="colorado1" />
	{{Organohalide-stub}}
			Deuterated chloroform is a general purpose NMR solvent, as it is not very chemically reactive and unlikely to exchange its deuterium with its solute,<ref>{{Cite journal |last1=Sabot |first1=Cyrille |last2=Kumar |first2=Kanduluru Ananda |last3=Antheaume |first3=Cyril |last4=Mioskowski |first4=Charles |date=2007-06-01 |title=Triazabicyclodecene: An Effective Isotope Exchange Catalyst in CDCl<sub>3</sub> |url=https://pubs.acs.org/doi/10.1021/jo070307h |journal=The Journal of Organic Chemistry |language=en |volume=72 |issue=13 |pages=5001–5004 |doi=10.1021/jo070307h |pmid=17530896 |issn=0022-3263}}</ref> 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 ], ] and ]. 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 ] may be added.<ref>{{Cite journal |last1=Teipel |first1=Jan |last2=Gottstein |first2=Vera |last3=Hölzle |first3=Eva |last4=Kaltenbach |first4=Katja |last5=Lachenmeier |first5=Dirk W. |last6=Kuballa |first6=Thomas |date=2022 |title=An Easy and Reliable Method for the Mitigation of Deuterated Chloroform Decomposition to Stabilise Susceptible NMR Samples |journal=Chemistry |language=en |volume=4 |issue=3 |pages=776–785 |doi=10.3390/chemistry4030055 |issn=2624-8549|doi-access=free}}</ref> It is less toxic to the liver and kidneys than {{chem2|CHCl3}} due to the ] {{chem2|C\sD}} bond as compared to the {{chem2|C\sH}} bond, making it somewhat less prone to form the destructive trichloromethyl radical ({{chem2|•CCl3}}).<ref>{{Cite book|last=Goldstein, Robin S.|url=https://www.worldcat.org/oclc/896796140|title=Toxic interactions|date=2013|publisher=Elsevier Science|others=Hewitt, William R., Hook, Jerry B.|isbn=978-1-4832-6970-2|location=Burlington|oclc=896796140}}</ref><ref>{{Cite journal |last1=Ahmadizadeh |first1=M. |last2=Kuo |first2=C.-H. |last3=Hook |first3=J.B. |date=1981-07-01 |title=Nephrotoxicity and hepatotoxicity of chloroform in mice: Effect of deuterium substitution |url=https://doi.org/10.1080/15287398109530054 |journal=Journal of Toxicology and Environmental Health |volume=8 |issue=1–2 |pages=105–111 |doi=10.1080/15287398109530054 |issn=0098-4108 |pmid=7328696|bibcode=1981JTEH....8..105A }}</ref>
			==References==
			{{reflist}}
		⚫	{{List of NMR solvents}}
		⚫	{{DEFAULTSORT:Deuterated Chloroform}}
		⚫	]
			]
			]
			]