| Revision as of 15:42, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465849149 of page 2,2,2-Trichlorethoxycarbonyl_chloride for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 05:09, 16 September 2023 edit GreenC bot (talk | contribs)Bots2,548,645 edits Reformat 1 URL (Wayback Medic 2.5) |
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{{redirect|Troc|the car|Volkswagen T-Roc}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 457645484 |
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| verifiedrevid = 477198803 |
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| Reference = <ref> at ]</ref> |
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| Reference = <ref> {{Webarchive|url=https://archive.today/20120909093657/http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/23258 |date=2012-09-09 }} at ]</ref> |
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| ImageFile=2,2,2-Trichlorethoxycarbonyl chloride.svg |
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| ImageFile =2,2,2-Trichlorethoxycarbonyl chloride.svg |
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| ImageName = Skeletal formula of 2,2,2-Trichlorethoxycarbonyl chloride |
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| ImageName = Skeletal formula of 2,2,2-Trichlorethoxycarbonyl chloride |
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| ImageFile1=2,2,2-Trichlorethoxycarbonyl chloride-3D.png |
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| ImageFile1 =2,2,2-Trichlorethoxycarbonyl chloride-3D.png |
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| ImageName1 = Ball-and-stick model of the 2,2,2-Trichlorethoxycarbonyl chloride molecule |
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| ImageName1 = Ball-and-stick model of the 2,2,2-Trichlorethoxycarbonyl chloride molecule |
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| PIN = 2,2,2-Trichloroethyl carbonochloridate |
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| IUPACName=2,2,2-Trichlorethoxycarbonyl chloride |
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| OtherNames= Trichloroethyl chloroformate |
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| OtherNames = 2,2,2-Trichlorethoxycarbonyl chloride<br />Trichloroethyl chloroformate |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 17341-93-4 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 78534 |
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| ChemSpiderID = 78534 |
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| EC_number = 241-363-7 |
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| PubChem = 87063 |
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| UNII = 99UY6LZN4R |
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| InChI = 1/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2 |
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| InChI = 1/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2 |
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| InChIKey = LJCZNYWLQZZIOS-UHFFFAOYAA |
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| InChIKey = LJCZNYWLQZZIOS-UHFFFAOYAA |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LJCZNYWLQZZIOS-UHFFFAOYSA-N |
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| StdInChIKey = LJCZNYWLQZZIOS-UHFFFAOYSA-N |
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| SMILES =O=C(OCC(Cl)(Cl)Cl)Cl |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 17341-93-4 --> |
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| PubChem=10387 |
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| SMILES=O=C(OCC(Cl)(Cl)Cl)Cl |
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| Section1 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=3 | H=2 | Cl=4 | O=2 |
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| C=3 |
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| Density =1.539 g/cm<sup>3</sup> |
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| H=2 |
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| Cl=4 |
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| MeltingPtC = 0 |
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| MeltingPt_notes = |
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| O=2 |
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| BoilingPtC = 171 to 172 |
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| Density=1.539 g/cm<sup>3</sup> |
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| BoilingPt_notes = |
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| MeltingPt=0 °C |
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| BoilingPt=171−172 °C |
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|Section3={{Chembox Hazards |
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| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}} |
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| Section2={{Chembox Hazards |
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| GHSSignalWord = Danger |
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| EUClass=Toxic ('''T'''), Corrosive ('''C''') |
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| HPhrases = {{H-phrases|302|314|330|331}} |
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| RPhrases={{R23}}, {{R34}} |
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| PPhrases = {{P-phrases|260|261|264|270|271|280|284|301+312|301+330+331|303+361+353|304+340|305+351+338|310|311|320|321|330|363|403+233|405|501}} |
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| SPhrases={{S26}}, {{S36/37/39}} |
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'''Trichloroethyl chloroformate''' is used in ] for the introduction of the trichloroethyl chloroformate (Troc) ] for ]s, ] and ]. It readily cleaves vs other carbamates and can be used in an overall protecting group strategy. |
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The troc group is traditionally removed ''via'' Zn insertion in the presence of acetic acid, resulting in elimination and decarboxylation. |
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== Amine protection – 2,2,2-Trichloroethoxycarbonyl (Troc) == |
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:]{{clear-left}} |
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2,2,2-Trichloroethoxycarbonyl ('''Troc''') group is largely used as a ] for ] in ]. |
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=== Most common amine protection methods === |
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* 2,2,2-Trichloroethyl chloroformate, ] or aqueous ] at ambient temperature<ref>{{Cite journal|last=Marullo|first=N. P.|last2=Wagener|first2=E. H.|date=1969-01-01|title=Structural organic chemistry by nmr. III. Isomerization of compounds containing the carbon-nitrogen double bond|journal=Tetrahedron Letters|volume=10|issue=30|pages=2555–2558|doi=10.1016/S0040-4039(01)88566-X}}</ref> |
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:]{{clear-left}} |
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* ] |
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* ] |
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== References == |
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{{reflist}} |
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{{DEFAULTSORT:Trichlorethoxycarbonyl chloride, 2,2,2-}} |
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] |
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] |
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] |