Standard Article

Ethyl 2-(diphenoxyphosphinyl) acetate

  1. Marie-Noelle Roy

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01590

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Roy, M.-N. 2013. Ethyl 2-(diphenoxyphosphinyl) acetate. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. Université de Montréal, Montreal, QC, Canada

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

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(Ethyl 2-(diphenoxyphosphinyl) acetate)

[16139-79-0] C16H17O5P (MW: 320.28)

InChI = 1S/C16H17O5P/c1-2-19-16(17)13-22(18,20-14-9-5-3-6-10-14)21-15-11-7-4-8-12-15/h3-12H,2,13H2,1H3

InChIKey = UQMFCYBSUVRGNU-UHFFFAOYSA-N

((Z)-selective Horner–Wadsworth–Emmons reagent for the synthesis of α,β-unsaturated esters)

Alternative Name:Ando's phosphonate.

Physical Data: bp 220 °C/3 mm Hg, colorless oil.

Solubility: soluble in THF and MeCN. Slightly soluble in Et2O and toluene.

Form Supplied in: oil. Commercially available.

Preparative Method:Ethyl 2-(diphenoxyphosphinyl) acetate is prepared in two steps from commercially available triethyl phosphonoacetate, using phosphorus pentachloride (PCl5) and phenol in 60% overall yield.1, 2 It can also be prepared by acylation of diphenyl methylphosphonate or nucleophilic substitution of ethyl bromoacetate with diphenylphosphite3 or ethyl diphenylphosphite.4

Purification: Silica gel chromatography.

Handling, Storage, and Precautions: no special techniques are required for handling.

Featured Compounds

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  1. 1 - 74
Compound Information
Molecular Weight:320.2769
Molecular Formula:C16H17O5P
InChIKey:UQMFCYBSUVRGNU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:Not Available
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Compound Information
Molecular Weight:167.2481
Molecular Formula:C10H17NO
InChIKey:NDKBVBUGCNGSJJ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.4831
Molecular Formula:C6H18KNSi2
InChIKey:IUBQJLUDMLPAGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:264.3154
Molecular Formula:C12H24O6
InChIKey:XEZNGIUYQVAUSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:23.99771
Molecular Formula:HNa
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:213.2304
Molecular Formula:C10H15NO4
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:152.2367
Molecular Formula:C9H16N2
InChIKey:GQHTUMJGOHRCHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:149.89424
Molecular Formula:INa
InChIKey:FVAUCKIRQBBSSJ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:283.386
Molecular Formula:C14H21NO3S
InChIKey:DWZFDRUSFWDPPA-CYBMUJFWSA-N
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Compound Information
Molecular Weight:353.476
Molecular Formula:C18H27NO4S
InChIKey:NNKLILMKHVQJEH-HLRDLLSLSA-N
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Compound Information
Molecular Weight:313.412
Molecular Formula:C15H23NO4S
InChIKey:DTHYKPNZZBDQLV-CYBMUJFWSA-N
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Compound Information
Molecular Weight:383.502
Molecular Formula:C19H29NO5S
InChIKey:QRRZPTAJABHYRK-ZBTGYSDGSA-N
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Compound Information
Molecular Weight:299.386
Molecular Formula:C14H21NO4S
InChIKey:GINBOENRUDKVMJ-LBPRGKRZSA-N
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Compound Information
Molecular Weight:369.476
Molecular Formula:C18H27NO5S
InChIKey:ASOAJKBVVJFEAK-KVPUOBJLSA-N
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Compound Information
Molecular Weight:345.11
Molecular Formula:C15H30OSn
InChIKey:CFYSHKVJPQDYOW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:415.2
Molecular Formula:C19H36O2Sn
InChIKey:KMTHOKRNALYMAE-XAFAPRIGSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:LRRGYHJHSLSATF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:334.3035
Molecular Formula:C17H19O5P
InChIKey:UCJROHIRYPUQFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.3175
Molecular Formula:C15H20O3
InChIKey:JBZVXBFJJKOZRS-BENRWUELSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:KXRGCMHBLSLIKJ-GKAPJAKFSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:399.173
Molecular Formula:C16H16BrO5P
InChIKey:ZXWGBUDTVCODAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:478.069
Molecular Formula:C16H15Br2O5P
InChIKey:OGYZPERTWPFEGF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:432.4465
Molecular Formula:C23H29O6P
InChIKey:NQNVNIOOBDZKRG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.2594
Molecular Formula:C11H18O2
InChIKey:HLIUWXDTNGKNBX-CLFYSBASSA-N
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Compound Information
Molecular Weight:544.6592
Molecular Formula:C31H45O6P
InChIKey:FTSZIPLWBLZCPR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:446.4731
Molecular Formula:C24H31O6P
InChIKey:KSACTQZJHBEBHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:IISIVLZRIYEJCU-CSKARUKUSA-N
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Compound Information
Molecular Weight:558.6857
Molecular Formula:C32H47O6P
InChIKey:XFSIKYNAVWCGNS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:458.4838
Molecular Formula:C25H31O6P
InChIKey:PWLIRHNYDHMPOT-VIZOYTHASA-N
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Compound Information
Molecular Weight:208.2967
Molecular Formula:C13H20O2
InChIKey:BUDIIJYBQADQOX-PNQPDEHRSA-N
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Compound Information
Molecular Weight:570.6964
Molecular Formula:C33H47O6P
InChIKey:BMFJUSBBCGGNRR-CPNJWEJPSA-N
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Compound Information
Molecular Weight:474.5263
Molecular Formula:C26H35O6P
InChIKey:ROVGYEAZBQQFFX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.3392
Molecular Formula:C14H24O2
InChIKey:SMZGTTZMSNGTHB-ZRDIBKRKSA-N
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Compound Information
Molecular Weight:586.7389
Molecular Formula:C34H51O6P
InChIKey:VAZYVFFIELCFKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:488.5528
Molecular Formula:C27H37O6P
InChIKey:FVHGXSICUBTGGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.3657
Molecular Formula:C15H26O2
InChIKey:KHLFMZDGADSQGR-ACCUITESSA-N
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Compound Information
Molecular Weight:600.7655
Molecular Formula:C35H53O6P
InChIKey:XCYHJLQYMCYCKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:500.5635
Molecular Formula:C28H37O6P
InChIKey:WBOUDHRDKHDXPB-VCHYOVAHSA-N
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Compound Information
Molecular Weight:250.3764
Molecular Formula:C16H26O2
InChIKey:LFHHOCMVYAATBH-HEEUSZRZSA-N
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Compound Information
Molecular Weight:612.7762
Molecular Formula:C36H53O6P
InChIKey:QRJNVGRVDTVCTN-CJLVFECKSA-N
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Compound Information
Molecular Weight:516.606
Molecular Formula:C29H41O6P
InChIKey:MJMFXMWQSXMKEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.4189
Molecular Formula:C17H30O2
InChIKey:HQOGMMDUGNEROI-FYWRMAATSA-N
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Compound Information
Molecular Weight:628.8186
Molecular Formula:C37H57O6P
InChIKey:WHKKVZDAYNSTML-UHFFFAOYSA-N
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Compound Information
Molecular Weight:532.6054
Molecular Formula:C29H41O7P
InChIKey:BTEJDWRDQCPGRH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.4183
Molecular Formula:C17H30O3
InChIKey:DXOGQOUMQPDAJQ-FOWTUZBSSA-N
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Compound Information
Molecular Weight:644.818
Molecular Formula:C37H57O7P
InChIKey:MDYMSBVBRBPTGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:544.6592
Molecular Formula:C31H45O6P
InChIKey:KKNIBXKREIMXDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:294.4721
Molecular Formula:C19H34O2
InChIKey:LSFKIWMIWCOYPU-FBMGVBCBSA-N
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Compound Information
Molecular Weight:656.8718
Molecular Formula:C39H61O6P
InChIKey:JRCBJKCIJKBHSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:502.5794
Molecular Formula:C28H39O6P
InChIKey:QUHPOXBNJRSCLC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.3923
Molecular Formula:C16H28O2
InChIKey:MMQOZCABHUMXAR-SQFISAMPSA-N
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Compound Information
Molecular Weight:614.7921
Molecular Formula:C36H55O6P
InChIKey:UKFHFORNRMTLRY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:518.5788
Molecular Formula:C28H39O7P
InChIKey:SOYHVJAIUJYAJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.3917
Molecular Formula:C16H28O3
InChIKey:KZXLRUPAQJUFJZ-RVDMUPIBSA-N
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Compound Information
Molecular Weight:630.7915
Molecular Formula:C36H55O7P
InChIKey:UNSDOQNPWGDAQW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:672.8712
Molecular Formula:C39H61O7P
InChIKey:DFEOLZIKWTYJAF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.4715
Molecular Formula:C19H34O3
InChIKey:XXPFRKZOGNNOQX-SDXDJHTJSA-N
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Compound Information
Molecular Weight:686.8978
Molecular Formula:C40H63O7P
InChIKey:ZREFNPLYEGVWOS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:324.498
Molecular Formula:C20H36O3
InChIKey:SXIPSRJXXYGDFJ-MNDPQUGUSA-N
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