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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 443516111 |
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| Watchedfields = changed |
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| Name = Chloroacetaldehyde |
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| verifiedrevid = 443517733 |
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| ImageFileL1 = Chloroacetald.png |
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| Name = Chloroacetaldehyde |
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| ImageSizeL1 = 115 |
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| ImageFileL1 = Chloroacetald.png |
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| ImageNameL1 = Structural formula |
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| ImageSizeL1 = 115 |
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| ImageFileR1 = Chloroacetaldehyde-3D-balls.png |
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| ImageNameL1 = Structural formula |
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| ImageSizeR1 = 125 |
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| ImageFileR1 = Chloroacetaldehyde-3D-balls.png |
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| ImageNameR1 = Ball-and-stick model |
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| ImageSizeR1 = 125 |
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| IUPACName = Chloroacetaldehyde |
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| ImageNameR1 = Ball-and-stick model |
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| SystematicName = Chloroethanal |
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| PIN = Chloroacetaldehyde <!-- the locant ‘2’ for acetaldehyde is not cited --> |
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| Section1 = {{Chembox Identifiers |
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| SystematicName = Chloroethanal |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| OtherNames = 2-Chloroacetaldehyde<br />2-Chloroethanal |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = CF069F5D9C |
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| UNII = CF069F5D9C |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = 61S63ROQ1E |
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| UNII1_Comment = (hydrate) |
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| ChemSpiderID = 32 |
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| ChemSpiderID = 32 |
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| PubChem = 33 |
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| ChEBI = 27871 |
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| CASNo = 107-20-0 |
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| CASNo = 107-20-0 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASOther = (hydrate: 34789-09-8, 7737-02-2) |
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| CASNo2 = 34789-09-8 |
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| CASNo_Ref = {{cascite}} |
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| CASNo2_Comment =(hydrate) |
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| RTECS = |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| RTECS = |
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| InChI = 1S/C2H3ClO/c3-1-2-4/h2H,1H2 |
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| InChIKey = QSKPIOLLBIHNAC-UHFFFAOYSA-N |
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| SMILES = C(C=O)Cl |
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| EINECS = 203-472-8 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>2</sub>H<sub>3</sub>Cl |
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| Formula = C<sub>2</sub>H<sub>3</sub>ClO |
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| MolarMass = 78.50 g mol<sup>-1</sup> |
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| MolarMass = 78.50 g mol<sup>−1</sup> |
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| Appearance = Colourless liquid |
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| Appearance = Colourless liquid |
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| Odor = acrid, penetrating<ref name=":me">{{Cite book|title=The Merck index|date=1996|publisher=Merck|others=S Budavari, M O'Neil, A Smith|isbn=9780911910124|edition=12|pages=2108}}</ref> |
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| Density = |
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| Density = 1.117 g/mL |
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| Solubility = Soluble as hydrate |
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| Solubility = soluble<ref name=":me"/> |
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| MeltingPt = |
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| SolubleOther = organic solvents |
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| BoilingPt = 85–85.5 °C |
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| pKa = |
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| MeltingPtC = -16.3 |
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| MeltingPt_notes = hydrate melts at 43–50 °C<ref name=":me" /> |
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| BoilingPtC = 85 to 85.5 |
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| BoilingPt_notes = |
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| pKa = |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = alkylating agent |
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| MainHazards = alkylating agent |
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| NFPA-H = |
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| NFPA-H = |
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| NFPA-F = |
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| NFPA-F = |
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| Reactivity= |
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| NFPA-R = |
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| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS08}}{{GHS09}} |
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| NFPA-R = |
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| FlashPt = |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|311|314|330|351|400}} |
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| RPhrases = |
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| FlashPt = {{convert|87.7|C|F}} (closed cup) |
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| SPhrases = |
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| PEL = C 1 ppm (3 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0118}}</ref> |
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| REL = C 1 ppm (3 mg/m<sup>3</sup>)<ref name=PGCH/> |
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| IDLH = 45 ppm<ref name=PGCH/> |
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| LD50 = 89 mg/kg (oral, rat)<br/>82 mg/kg (oral, mouse)<ref>{{cite web |url = https://www.cdc.gov/niosh/idlh/107200.html |title = Chloroacetaldehyde |publisher = National Institute for Occupational Safety and Health | date = 4 December 2014 |access-date = 20 February 2015}}</ref> |
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| LC50 = 200 ppm (rat, 1 hr)<ref>{{IDLH|107200|Chloroacetaldehyde}}</ref> |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| OtherCpds = ], ] |
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| OtherCompounds = ], ] |
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'''Chloroacetaldehyde''' is the ] with the formula ClCH<sub>2</sub>CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous ]. The compound is not normally encountered in the ] form, but rather as the hydrate (]), ClCH<sub>2</sub>CH(OH)<sub>2</sub>. Chloroacetaldehyde is a useful intermediate in the synthesis, e.g. of 2-aminothiazole or many pharmaceutical compounds. |
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'''Chloroacetaldehyde''' is an ] with the formula ClCH<sub>2</sub>CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous ]. The compound is not normally encountered in the ] form, but rather as the ] (ClCH<sub>2</sub>CH(OH))<sub>2</sub>O. |
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Another use is to facilitate bark removal from tree trunks. |
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Chloroacetaldehyde is a metabolite of the antineoplastic ] and believed to be responsible for some of the toxicity observed with ifosfamide. |
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==Synthesis and reactions== |
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The hydrate of chloroacetaldehyde is produced by the ] of aqueous ] using ]: |
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:ClCH=CH<sub>2</sub> + Cl<sub>2</sub> + H<sub>2</sub>O → ClCH<sub>2</sub>CHO + 2 HCl |
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It can also be prepared from ].<ref name=Ullmann>Reinhard Jira, Erwin Kopp, Blaine C. McKusick, Gerhard Röderer, Axel Bosch, Gerald Fleischmann “Chloroacetaldehydes“ in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a06_527.pub2}}</ref> |
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==Synthesis and occurrence== |
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Being bifunctional, chloroacetaldehyde is a versatile precursor to many ]s. It condenses with thiourea derivatives to give ]s. This reaction was once important as a precursor to ], one of the first sulfa drugs.<ref name=Ullmann/> |
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Hydrated chloroacetaldehyde is produced by the ] of aqueous ]: |
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:ClCH=CH<sub>2</sub> + Cl<sub>2</sub> + H<sub>2</sub>O → ClCH<sub>2</sub>CHO + 2 HCl |
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It can also be prepared from ]<ref name="Ullmann">{{Ullmann|doi=10.1002/14356007.a06_527.pub2|title= Chloroacetaldehydes|year=2007|last1=Jira|first1=Reinhard|last2=Kopp|first2=Erwin|last3=McKusick|first3=Blaine C.|last4= Röderer|first4=Gerhard|last5=Bosch|first5=Axel|last6=Fleischmann|first6=Gerald|isbn=978-3527306732}}</ref> or by careful chlorination of ].<ref name=":me" /> The related bromoacetaldehyde is prepared via bromination of ]. It also rapidly forms an acetals in the presence of alcohols.<ref>S. M. McElvain and D. Kundiger "Bromoacetal" Organic Syntheses 1943, volume 23, p. 8. {{doi|10.15227/orgsyn.023.0008}}.</ref> |
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Water free chloroacetaldehyde is prepared from the hydrate by ] with ], ], or ]. Anhydrous chloroacetaldehyde reversibly converts to ].<ref name=":0">{{Cite journal|last=Keiji|first=T|date=1992-10-30|title=α-Chlorocarbonyl Compounds: Their Synthesis and Applications (Commemoration Issue Dedicated to Professor Shigeo Tanimoto On the Occasion of His Retirement)|journal=Bulletin of the Institute for Chemical Research, Kyoto University|volume=70|issue=3|pages=341|hdl=2433/77455|issn=0023-6071}}</ref><ref name=":me" /> Less reactive chloroacetaldehyde derivatives might be used instead to obtain chloroacetaldehyde or bypass its intermediate formation completely: e.g. chloroacetaldehyde dimethyl acetal (2-chloro-1,1-dimethoxyethane) hydrolyzes in acidic conditions to give chloroacetaldehyde, which may then quickly react with the other reagents<ref name=":0" /> instead of polymerizing. |
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Relevant to its occurrence in humans, it arises via the isomerization of ], a metabolite of ].<ref>{{cite journal |doi=10.1093/toxsci/kfq371 |title=Endogenous versus Exogenous DNA Adducts: Their Role in Carcinogenesis, Epidemiology, and Risk Assessment |year=2011 |last1=Swenberg |first1=J. A. |last2=Lu |first2=K. |last3=Moeller |first3=B. C. |last4=Gao |first4=L. |last5=Upton |first5=P. B. |last6=Nakamura |first6=J. |last7=Starr |first7=T. B. |journal=Toxicological Sciences |volume=120 |issue=Suppl 1 |pages=S130–S145 |pmid=21163908 |pmc=3043087 }}</ref> |
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==Reactions== |
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Chloroacetaldehyde readily hydrates: |
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Being bifunctional, chloroacetaldehyde is a precursor to many ]s. It condenses with ] derivatives to give ]s. This reaction was once used in the preparation of ], one of the first sulfa drugs.<ref name=Ullmann/> Chloroacetaldehyde is a building block in the synthesis of the pharmaceuticals ], ], ], and ].<ref name=":0" /> Chloroacetaldehyde is an ]. It reacts with ] and ] to give cyclic products containing a fused ] group. This reaction is related to the possible mutagenic properties of chloroacetaldehyde.<ref>{{cite journal |doi=10.1006/rtph.1996.0002 |title=DNA Damage: Chemistry, Repair, and Mutagenic Potential |year=1996 |last1=Singer |first1=B. |journal=Regulatory Toxicology and Pharmacology |volume=23 |issue=1 Pt 1 |pages=2–13 |pmid=8628915 }}</ref> |
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==Environmental aspects== |
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==Environmental aspects== |
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Chloroacetaldehyde is a ] in the degradation of ], which initially converts to ]. This metabolic pathway is topical since billions of kilograms of 1,2-dichloroethane have been produced as a precursor to ].<ref>Janssen, D. B.; van der Ploeg, J. R. and Pries, F., "Genetics and biochemistry of 1,2-dichloroethane degradation", Biodegradation, 1994, 5, 249-57.{{DOI|10.1007/BF00696463}}</ref> |
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Chloroacetaldehyde is a ] in the degradation of ], which initially converts to ]. This metabolic pathway is topical because 1,2-dichloroethane is produced on a large scale as a precursor to ].<ref>Janssen, D. B.; van der Ploeg, J. R. and Pries, F., "Genetics and Biochemistry of 1,2-Dichloroethane Degradation", Biodegradation, 1994, 5, 249-57.{{doi|10.1007/BF00696463}}</ref> |
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==Safety== |
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Chloroacetaldehyde is corrosive to ]s. It irritates eyes, skin and respiratory tract.<ref name=":me"/> |
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Based on data collected from human studies in 1962, exposures to 45 ppm of chloroacetaldehyde were found to be disagreeable and caused conjunctival irritation to the subjects.<ref></ref> The ] established a ] at a ceiling of 1 ppm (3 mg/m<sup>3</sup>) for exposures to chloroacetaldehyde.<ref></ref> |
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==See also== |
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* ] |
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* ] |
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==References== |
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==References== |
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