- Hexamethylphosphoramide
chembox Verifiedfields changed Watchedfields changed verifiedrevid 400104650 Name Hexamethylphosphoramide ImageFile HMPA 2D skeletal.png ImageName Chemical structure of HMPA ImageFile1 Hexamethylphosphoramide from xtal 3D balls.png ImageName1 3D stick model of HMPA PIN Hexamethylphosphoric triamide IUPACName Hexamethylphosphoramide OtherNames Hexametapol br HMPA Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 12158 PubChem 12679 InChI 1 C6H18N3OP c1 7 2 11 10,8 3 4 9 5 6 h1 6H3 InChIKey GNOIPBMMFNIUFM UHFFFAOYAP StdInChI Ref stdinchicite correct chemspider StdInChI 1S C6H18N3OP c1 7 2 11 10,8 3 4 9 5 6 h1 6H3 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey GNOIPBMMFNIUFM UHFFFAOYSA N CASNo Ref cascite correct CAS CASNo 680 31 9 KEGG Ref keggcite changed kegg KEGG C19250 ChEBI Ref ebicite changed EBI ChEBI 24565 SMILES O P N C C N C C N C C Section2 Chembox Properties C 6 H 18 N 3 O 1 P 1 MolarMass 179.20 g mol Density 1.03 g cm sup 3 sup MeltingPtC 7.20 BoilingPtC 232.5 Boiling notes CRC ref CRC91 page 3 280 ref Section7 Chembox Hazards ExternalMSDS http msds.chem.ox.ac.uk HE hexamethylphosphoramide.html Oxford MSDS EUClass Hazchem Xn Hexamethylphosphoramide , often abbreviated HMPA, is a phosphoramide i.e. an amide of phosphoric acid having the chemical formula formula CH sub 3 sub sub 2 sub N sub 3 sub PO. This colorless liquid is a useful polar aprotic solvent and additive in organic synthesis . Structure and reactivity HMPA is the oxide of the highly basic tertiary phosphine hexamethylphosphorous triamide HMPT , P NMe sub 2 sub sub 3 sub . Like other phosphine oxides e.g., triphenylphosphine oxide , the molecule has a tetrahedral core and a P O bond that is highly polarized, with significant negative charge residing on the oxygen atom. Compounds containing a nitrogen phosphorus bond typically are degraded by hydrochloric acid to form a protonated amine and phosphate. Applications HMPA is used as a solvent for polymer ... more details
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- 1,3-Dimethyl-2-imidazolidinone
chembox Verifiedfields changed verifiedrevid 456364183 ImageFile Dimethylimidazolidinone.png ImageSize 150px IUPACName 1,3 Dimethyl 2 imidazolidinone OtherNames Dimethylethyleneurea br N,N Dimethylimidazolidinone Section1 Chembox Identifiers Abbreviations DMI ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 6409 InChI 1 C5H10N2O c1 6 3 4 7 2 5 6 8 h3 4H2,1 2H3 InChIKey CYSGHNMQYZDMIA UHFFFAOYAB SMILES1 CN1CCN C1 O C ChEMBL Ref ebicite changed EBI ChEMBL 12338 StdInChI Ref stdinchicite correct chemspider StdInChI 1S C5H10N2O c1 6 3 4 7 2 5 6 8 h3 4H2,1 2H3 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey CYSGHNMQYZDMIA UHFFFAOYSA N CASNo Ref cascite correct CAS CASNo 80 73 9 PubChem 6661 SMILES O C1N C CCN1C Section2 Chembox Properties Formula C sub 5 sub H sub 10 sub N sub 2 sub O MolarMass 114.1457 Appearance Clear liquid Density MeltingPtC 8.2 BoilingPtC 225 Solubility Section3 Chembox Hazards MainHazards FlashPt 120 C Autoignition 1,3 Dimethyl 2 imidazolidinone DMI is a cyclic urea used as a high boiling polar aprotic solvent . It is colourless, transparent, highly polar and has high thermal and chemical stability. It is a Homology chemistry homolog of the related solvent DMPU . In many applications, DMI as well as DMPU can be used as a substitute or replacement for the carcinogenic solvent Hexamethylphosphoramide HMPA . ref cite journal author Lo, Chi Chu year 1992 title Replacement of carcinogenic solvent HMPA by DMI in insect sex pheromone synthesis journal Journal of Chemical Ecology volume 18 issue 2 doi 10.1007 BF00982095 pages 3245 last2 Chao first2 Pei Min ref DMI has a boiling point of 225 C, a flash point of 120 C and a melting point of 8.2 C. ref http www.mitsuichemicals.com dmi.htm DMI at Mitsui Chemicals ref DMI has excellent solvating ability for both inorganic and organic compounds. DMI can is used in a variety of applications including detergents, dyestuffs, electronic materials and in the manufacture of polymers. DMI is ... more details
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- Pinacol coupling reaction
in a system of samarium II iodide and Hexamethylphosphoramide HMPA Ref 4 . Two examples ... more details
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- Potassium tert-butoxide
sulfoxide DMSO , hexamethylphosphoramide HMPA , and 18 crown 6 interact with the potassium ... more details
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- DMPU
chembox verifiedrevid 414403521 ImageFile DMPU.png ImageSize 150px IUPACName 1,3 Dimethyltetrahydropyrimidin 2 1 H one OtherNames N,N Dimethyl N,N trimethyleneurea br N,N Dimethylpropyleneurea br 1,3 Dimethyl 3,4,5,6 tetrahydro 2 1H pyrimidinone Section1 Chembox Identifiers Abbreviations DMPU ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 73671 InChI 1 C6H12N2O c1 7 4 3 5 8 2 6 7 9 h3 5H2,1 2H3 InChIKey GUVUOGQBMYCBQP UHFFFAOYAB ChEMBL Ref ebicite correct EBI ChEMBL 12284 StdInChI Ref stdinchicite correct chemspider StdInChI 1S C6H12N2O c1 7 4 3 5 8 2 6 7 9 h3 5H2,1 2H3 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey GUVUOGQBMYCBQP UHFFFAOYSA N CASNo 7226 23 5 EINECS 230 625 6 PubChem 81646 SMILES O C1N C CCCN1C InChI RTECS MeSHName ChEBI KEGG Ref keggcite correct kegg KEGG ATCCode prefix ATCCode suffix ATC Supplemental Section2 Chembox Properties C 6 H 12 N 2 O 1 MolarMass Appearance Density 1.064 g cm sup 3 sup MeltingPtK 253 Melting notes BoilingPtC 246 Boiling notes Solubility miscible SolubleOther RefractiveIndex 1.4875 1.4895 Solvent pKa pKb Section7 Chembox Hazards EUClass EUIndex MainHazards ExternalMSDS http fscimage.fishersci.com msds 26622.htm External MSDS NFPA H NFPA F NFPA R NFPA O RPhrases R22 R41 R62 SPhrases S26 S36 37 39 S45 RSPhrases FlashPt 121 C Autoignition ExploLimits PEL 1,3 Dimethyl 3,4,5,6 tetrahydro 2 1H pyrimidinone DMPU is a cyclic urea sometimes used as a polar, aprotic organic solvent . In 1985, Dieter Seebach showed that it is possible to substitute the relatively toxic hexamethylphosphoramide HMPA with DMPU. ref cite journal title Substitution of HMPT by the cyclic urea DMPU as a cosolvent for highly reactive nucleophiles and bases author Triptikumar Mukhopadhyay, Dieter Seebach journal Helvetica Chimica Acta volume 65 issue 1 pages 385 391 year 1982 url doi 10.1002 hlca.19820650141 ref References Reflist Further reading cite journal title Phase Transfer Catalytic Preparation of the Dipolar Aprotic Solven ... more details
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- Acyloin
Image Acyloin.PNG thumb right size The structure of a typical acyloin. Acyloins also referred to as ketols are a class of organic compound s in organic chemistry sharing a common functional group consisting of a hydroxyl group placed on the position of a carbonyl group. Nomenclature Common types of ketols include Alpha ketols have the hydroxyl group adjacent to the keto group. Beta ketols have the hydroxyl group at the second carbon from the keto group. Gamma ketols have the hydroxyl group at the third carbon from the keto group. Synthesis of acyloins This section is linked from Organic reaction Classic organic reactions exist for the synthesis of acyloins. The acyloin condensation is a reductive coupling of esters The benzoin condensation is condensation reaction between aldehydes catalyzed by a nucleophile Oxidation of carbonyl s is possible with molecular oxygen but not selective Better alternative is oxidation of corresponding silyl enol ethers with mCPBA in the Rubottom oxidation MoOPH oxidation of carbonyl s is a system with molybdenum peroxide , pyridine and hexamethylphosphoramide . Enolate oxidation by sulfonyloxaziridines Enolate s can be oxidized by oxaziridine sulfonyloxaziridines ref Synthesis of .alpha. hydroxycarbonyl compounds acyloins direct oxidation of enolates using 2 sulfonyloxaziridines Franklin A. Davis, Lal C. Vishwakarma, Joanne G. Billmers, John Finn J. Org. Chem. 1984 49 17 3241 3243. http pubs.acs.org cgi bin abstract.cgi joceah 1984 49 i17 f jo00191a048.pdf Abstract ref ref Asymmetric Oxidation of Ester and Amide Enolates Using New Camphorylsulfony1 oxaziridines Davis, F. A. Haque, M. S. Ulatowski, T. G. Towson, J. C. J. Org. Chem. 1986 , 51, 2402. http pubs.acs.org cgi bin abstract.cgi joceah 1986 51 i12 f jo00362a053.pdf Abstract ref . The enolate reacts by nucleophilic displacement at the electron deficient oxygen of the oxaziridine ring. Image Enolate oxidation sulfonyloxazirines.png 600px Enolate oxidation by sulfonyloxaziridine T ... more details
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- Trisulfur
way to make it is with polysulfide dissolved in hexamethylphosphoramide where it gives a blue colour ... solutions of alkali polysulfides in hexamethylphosphoramide. author T. Chivers, I. Drummond journal ... more details
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- Twaron
HMPT hexamethylphosphoramide . Despite heavy research DuPont now also uses the AKZO patent to use ... more details
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- Molecular sieve
10 Adsorbs di n butylamine not tri n butylamine . Used for drying hexamethylphosphoramide HMPA . ref ... more details
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- List of IARC Group 2B carcinogens
Hexachloroethane Hexachlorocyclohexane s Hexamethylphosphoramide HMPA Human immunodeficiency ... more details
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- Dimethylformamide
chembox verifiedrevid 458446617 Name N , N Dimethylformamide ImageFileL1 Dimethylformamide 2D skeletal.svg ImageNameL1 Chemical structure of dimethylformamide ImageFileR1 DMF 3D balls.png ImageNameR1 Dimethylformamide IUPACName N , N Dimethylmethanamide OtherNames DMF Dimethylformamide N , N Dimethylformamide DMFA Section1 Chembox Identifiers DrugBank Ref drugbankcite correct drugbank DrugBank DB01844 StdInChI Ref stdinchicite correct chemspider StdInChI 1S C3H7NO c1 4 2 3 5 h3H,1 2H3 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey ZMXDDKWLCZADIW UHFFFAOYSA N SMILES O CN C C ChEMBL Ref ebicite correct EBI ChEMBL 268291 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 5993 UNII Ref fdacite correct FDA UNII 8696NH0Y2X InChI 1S C3H7NO c1 4 2 3 5 h3H,1 2H3 InChIKey ZMXDDKWLCZADIW UHFFFAOYSA N CASNo 68 12 2 CASNo Ref cascite correct CAS RTECS LQ2100000 ChEBI Ref ebicite correct EBI ChEBI 17741 PubChem 6228 KEGG Ref keggcite correct kegg KEGG C03134 Section2 Chembox Properties Formula C sub 3 sub H sub 7 sub NO MolarMass 73.09 g mol Appearance Clear liquid Density 0.944 g cm sup 3 sup , liquid Solubility Miscible MeltingPtC 61 BoilingPtC 153 VaporPressure 0.3 kPa 20 C pKa pKb Viscosity 0.92 Poise cP at 20 C RefractIndex 1.4305 20 C , Dielectric constant sub r sub 36.71 25 C Section3 Chembox Structure Dipole 3.86 Debye D 25 C Section7 Chembox Hazards ExternalMSDS http msds.chem.ox.ac.uk DI N,N dimethylformamide.html MSDS MainHazards flammable NFPA H 1 NFPA F 2 NFPA R 0 FlashPt 58 C RPhrases R61 R20 21 R36 SPhrases S53 S45 TLV TWA 10 ppm ref http sciencelab.com msds.php?msdsId 9923813 ScienceLab.com MSDS ref Section8 Chembox Related Function amide s OtherFunctn Acetamide , br Formamide , br hexamethylphosphoramide OtherCpds Dimethyl sulfoxide , br acetonitrile , br N Methylformamide Dimethylformamide is an organic compound with the chemical formula formula Methyl CH sub 3 sub sub 2 sub NC O H. Commonly abbreviated as DMF though this acronym is s ... more details
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- National Emissions Standards for Hazardous Air Pollutants
680 31 9 Hexamethylphosphoramide 110 54 3 Hexane 302 01 2 Hydrazine 7647 01 0 Hydrogen chloride ... more details
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- Divinylcyclopropane-cycloheptadiene rearrangement
in dry tetrahydrofuran THF 1 mL mmol of chloride was added, followed by dry hexamethylphosphoramide ... more details
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- Base-promoted epoxide isomerization
padding top 30px 3 span center File EpIsoMech2.png center In many cases when hexamethylphosphoramide ... more details
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- Common reagents
first7 Ward T. last8 Roos first8 Bj rn O. last9 Vallance first9 Claire ref Hexamethylphosphoramide ... more details
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- N-Butyllithium
TMEDA , hexamethylphosphoramide HMPA , and 1,4 diazabicyclo 2.2.2 octane DABCO further polarize ... more details
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- Desulfonylation reactions
volume 46 pages 211 ref in the presence of hexamethylphosphoramide HMPA , SmI sub 2 sub is able to effect .... Hexamethylphosphoramide increases the reducing power of SmI sub 2 sub substantially. Tin halide ... more details
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- Kevlar
chains in the fiber s direction. Hexamethylphosphoramide HMPA was the solvent initially used ... more details
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- Dimethyl sulfoxide
N methyl 2 pyrrolidone , and Hexamethylphosphoramide HMPA . DMSO is frequently used as a solvent for chemical ... more details
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- Reductions with samarium(II) iodide
Reductions with samarium II iodide involve the conversion of various classes of organic compounds into reduced products through the action of samarium II iodide, a mild one electron reducing agent. ref name OrgReact cite journal last1 Molander first1 Gary A. title Reductions with Samarium II Iodide year 2004 doi 10.1002 0471264180.or046.03 ref Introduction In 1979, Kagan observed the reduction of a variety of organic functional groups by samarium iodide under mild reaction conditions. ref name orig cite journal last1 Girard first1 P. last2 Namy first2 J. L. last3 Kagan first3 H. B. title Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents journal Journal of the American Chemical Society volume 102 pages 2693 year 1980 doi 10.1021 ja00528a029 issue 8 ref Since that time, samarium iodide has been employed in a variety of contexts in organic synthesis for both functional group manipulation and carbon carbon bond formation. ref cite journal last1 Molander first1 Gary A. last2 Harris first2 Christina R. title Sequencing Reactions with Samarium II Iodide journal Chemical Reviews volume 96 pages 307 year 1996 doi 10.1021 cr950019y pmid 11848755 issue 1 ref Samarium iodide is a one electron reductant, and typically effects reduction through a series of electron transfer and proton transfer from protic solvent steps. Reducible functional groups include Functionalized carbonyl compounds Ketones and aldehydes Carboxylic acids under strongly acidic or basic conditions Organic halides Nitro compounds Some examples of functionality reduced by SmI sub 2 sub are provided below. span style float right padding right 50px padding top 30px 1 span center File SmI2Gen.png center The reactivity of SmI sub 2 sub is significantly affected by the choice of solvent. The use of hexamethylphosphoramide HMPA as a co solvent in samarium iodide reductions allows the reaction to be carried o ... more details
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- Solvent
Benzonitrile 1.01 1 Methyl 2 pyrrolidinone 1.028 . Hexamethylphosphoramide 1.03 1,4 Dioxane 1.033 ... more details
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- Aldol reaction
E enolates. The addition of Hexamethylphosphoramide HMPA is known to reverse the stereoselectivity ... more details
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