Standard Article

The α-Hydroxy Ketone (α-Ketol) and Related Rearrangements

  1. Leo A. Paquette,
  2. John E. Hofferberth

Published Online: 15 APR 2004

DOI: 10.1002/0471264180.or062.03

Organic Reactions

Organic Reactions

How to Cite

Paquette, L. A. and Hofferberth, J. E. 2004. The α-Hydroxy Ketone (α-Ketol) and Related Rearrangements . Organic Reactions. 62:3:477–567.

Author Information

  1. The Ohio State University, Evans Chemical Laboratories, Columbus, Ohio

Publication History

  1. Published Online: 15 APR 2004

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Abstract

Treatment of suitable alpha-hydroxy aldehydes and ketones with a base, a Bronsted or Lewis acid, or simply with heat has long been know to induce the 1,2-shift of an alkyl or aryl substituent to form an isomeric product. The synthetic utility of the process was considerably expanded when applied to steroidal D-ring homoannulations, and has more recently encompassed novel ring expansion to numerous complex target ring systems. The classical alpha-ketol rearrangement shares, in common with other base-promoted ketogenic isomerizations, the property of advancing from an alkoxide to a carbonyl group as the migrating center relocates its bonding electrons to the adjacent trigonal center. A distinctive feature of the title reaction, however, is its reversibility, such that the more stable alpha-hydroxy carbonyl isomer is favored. The process has sometimes been termed the acyloin rearrangement.

This chapter focuses on the isomerization of alpha-hydroxy ketones, aldehydes, and imines under various reaction conditions exclusive of photochemical activation. The literature coverage extends to 2000.

Since many of the steroidal transformations were carried out in early days when products were not always adequately characterized; errors in structural assignment were occasionally made. Experimental detail was sometimes lacking. To alleviate this problem, we have included only experiments that lead to reasonably pure products of established structure.

Keywords:

  • rearrangements;
  • acyclic alpha hydroxyl ketones;
  • cyclic alpha ketols;
  • bridged alpha ketols;
  • steroidal alpha ketols;
  • complex polycyclics;
  • hydroxy aldehydes;
  • hydroxy imines;
  • tautomerization;
  • carbohydrates;
  • chain extension;
  • tosyl isocyanide;
  • enolates;
  • silyl enol ethers;
  • silyl ketene acetals;
  • experimental procedures;
  • other methods;
  • scope;
  • limitations

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:364.4327
Molecular Formula:C20H28O6
InChIKey:HVVXVLCKJVYPSI-KIOFCADYSA-N
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Compound Information
Molecular Weight:404.4535
Molecular Formula:C22H28O7
InChIKey:SYSAAGIOIANXBW-ZOGLZDRWSA-N
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Compound Information
Molecular Weight:200.662
Molecular Formula:C10H13ClO2
InChIKey:BFABGARCRJLYBH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:710.8502
Molecular Formula:C40H54O11
InChIKey:MWFJSSPLIMAZGJ-COKFHHPPSA-N
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Compound Information
Molecular Weight:198.3342
Molecular Formula:C10H18O2Si
InChIKey:STTOVMYOKACYPO-WCBMZHEXSA-N
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Compound Information
Molecular Weight:253.3389
Molecular Formula:C17H19NO
InChIKey:AOBRPVYTYRLIPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.3175
Molecular Formula:C15H19NO
InChIKey:KJBGLNVNONRBCZ-ZLDLUXBVSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:ZFOOVBJHEUWTSZ-PSASIEDQSA-N
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Compound Information
Molecular Weight:376.4865
Molecular Formula:C22H32O5
InChIKey:QRQGSCXEIGJRJJ-ODHDHZKRSA-N
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Compound Information
Molecular Weight:365.4223
Molecular Formula:C22H23NO4
InChIKey:IIVGNWCSQRORBR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:304.4238
Molecular Formula:C19H28O3
InChIKey:AKRBLZKRYPEVIK-PEMPUTJUSA-N
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Compound Information
Molecular Weight:199.395
Molecular Formula:C2H6BaO2
InChIKey:BQDSDRAVKYTTTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.2262
Molecular Formula:C14H10O5
InChIKey:MENMHKJXOBNOAE-RBQUTUCGSA-N
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Compound Information
Molecular Weight:214.2598
Molecular Formula:C14H14O2
InChIKey:KKOXMHIDZVPACX-OSMZGAPFSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:RMLMTLCQCHBROG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:304.4238
Molecular Formula:C19H28O3
InChIKey:AKRBLZKRYPEVIK-PEMPUTJUSA-N
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Compound Information
Molecular Weight:364.4327
Molecular Formula:C20H28O6
InChIKey:NWVCDBDOQSCWFE-QPMMVAKTSA-N
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Compound Information
Molecular Weight:184.3614
Molecular Formula:C13H28
InChIKey:IIYFAKIEWZDVMP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:NCFCVASWTHARRW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:99.9943
Molecular Formula:CrO3
InChIKey:WGLPBDUCMAPZCE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:658.851
Molecular Formula:C35H50O10Si
InChIKey:HWHJTOVPIRHJCM-CFJSPBJFSA-N
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Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:JLECCXUJWYXKRG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.133
Molecular Formula:C2H6OS
InChIKey:IAZDPXIOMUYVGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:LWYNFVHUPFHDEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.9368
Molecular Formula:MnO2
InChIKey:Not Available
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:XMLYCEVDHLAQEL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:QNODIIQQMGDSEF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.9092
Molecular Formula:C10H14NiO4
InChIKey:BMGNSKKZFQMGDH-FDGPNNRMSA-L
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Compound Information
Molecular Weight:306.3536
Molecular Formula:C17H22O5
InChIKey:QIJVQGMVFNZRDB-GYBOFCAGSA-N
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Compound Information
Molecular Weight:670.8186
Molecular Formula:C35H46O11Si
InChIKey:SCHMCJIOOTXQBL-XZZREGDJSA-N
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Compound Information
Molecular Weight:466.7275
Molecular Formula:C29H42O3Si
InChIKey:YXHMMALCSIJOSC-OQBGCQOXSA-N
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Compound Information
Molecular Weight:408.4853
Molecular Formula:C22H32O7
InChIKey:BWZMHXPIONECNR-YYNSWQSCSA-N
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Compound Information
Molecular Weight:236.3068
Molecular Formula:C14H20O3
InChIKey:LWWDGGWFYUVCFW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:CREMWICPHOFKBR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:487.53
Molecular Formula:C27H36O3Se
InChIKey:XHIDRLJCTXWTQT-ASUBQVAYSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:AAHFAABFNIYXPY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:332.3909
Molecular Formula:C19H24O5
InChIKey:YZFGNJMOHZWTGC-ABBGJRKUSA-N
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Compound Information
Molecular Weight:378.4624
Molecular Formula:C27H22O2
InChIKey:AGAPSCCHXUILLU-HHHXNRCGSA-N
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Compound Information
Molecular Weight:229.3175
Molecular Formula:C15H19NO
InChIKey:DXYNFNXJDMKBNW-PYAOFISZSA-N
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Compound Information
Molecular Weight:210.228
Molecular Formula:C14H10O2
InChIKey:WURBFLDFSFBTLW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.3175
Molecular Formula:C15H19NO
InChIKey:YWRRIYGOFQEXKY-TYNCELHUSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:KHCUSEDRQWYNDS-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:600.6136
Molecular Formula:C30H36N2O11
InChIKey:WYNQJRJMYZNWOY-CBKTXTTESA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:NUDSBKBQLBSBNN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.2699
Molecular Formula:C15H14O3
InChIKey:QCNLTGUEIGKCMY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:CRJPFEAQVHYDRO-JBVFEPGOSA-N
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Compound Information
Molecular Weight:456.6498
Molecular Formula:C25H36N2O4Si
InChIKey:GPTYXIPTUMKVKM-TWAZMVPOSA-N
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Compound Information
Molecular Weight:365.4223
Molecular Formula:C22H23NO4
InChIKey:ZJSNXQJRHMYJBC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.823
Molecular Formula:CCl4
InChIKey:VZGDMQKNWNREIO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.2262
Molecular Formula:C14H10O5
InChIKey:HZBLCFLOAUFUDA-RPZVGCSNSA-N
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Compound Information
Molecular Weight:402.6529
Molecular Formula:C27H46O2
InChIKey:SSABWNGICXCRRY-FRPSKHSRSA-N
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Compound Information
Molecular Weight:360.401
Molecular Formula:C20H24O6
InChIKey:YSSSPARMOAYJTE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:572.8479
Molecular Formula:C33H52O6Si
InChIKey:GGEHIGJDYMXSIH-ZNPPEQIRSA-N
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Compound Information
Molecular Weight:334.4498
Molecular Formula:C20H30O4
InChIKey:SDBITTRHSROXCY-OKFBFAQVSA-N
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Compound Information
Molecular Weight:56.1056
Molecular Formula:HKO
InChIKey:KWYUFKZDYYNOTN-UHFFFAOYSA-M
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Compound Information
Molecular Weight:168.1898
Molecular Formula:C9H12O3
InChIKey:YXNDTMBYXGJLKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:446.4902
Molecular Formula:C24H30O8
InChIKey:OTQNDWNLHJPTPI-BVAHMKKKSA-N
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Compound Information
Molecular Weight:334.4498
Molecular Formula:C20H30O4
InChIKey:NCQOZVNJXVOGIA-WMFBCXMOSA-N
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Compound Information
Molecular Weight:60.0843
Molecular Formula:O2Si
InChIKey:VYPSYNLAJGMNEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.016
Molecular Formula:C8H15B
InChIKey:FEJUGLKDZJDVFY-OCAPTIKFSA-N
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Compound Information
Molecular Weight:214.2598
Molecular Formula:C14H14O2
InChIKey:VKKLKKIHXXXYQG-SCDSUCTJSA-N
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Compound Information
Molecular Weight:196.2429
Molecular Formula:C11H16O3
InChIKey:RWUOELKZDKWLIZ-KWQFWETISA-N
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Compound Information
Molecular Weight:208.2536
Molecular Formula:C12H16O3
InChIKey:KNMCBHDRXKAVRY-JFUSQASVSA-N
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Compound Information
Molecular Weight:196.2429
Molecular Formula:C11H16O3
InChIKey:JSMAZWJURYJWPV-KWQFWETISA-N
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Compound Information
Molecular Weight:326.4326
Molecular Formula:C20H26N2O2
InChIKey:XNYRYILFKATWJF-FFGOWVMKSA-N
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Compound Information
Molecular Weight:114.0233
Molecular Formula:C2HF3O2
InChIKey:DTQVDTLACAAQTR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:AHQHVUBVTPKJQW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:466.4783
Molecular Formula:C23H30O10
InChIKey:HWIDPGBLMUWOFF-IKJWTTDMSA-N
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Compound Information
Molecular Weight:212.2439
Molecular Formula:C14H12O2
InChIKey:VNQMMVYBOYFHGI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:LZHOUVXPEIFRFA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:VTSRHCVLJWZVEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:596.1
Molecular Formula:C24H54OSn2
InChIKey:APQHKWPGGHMYKJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.679
Molecular Formula:C10H15ClO
InChIKey:XFRHGFVWDJESGC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:440.638
Molecular Formula:C27H36O3S
InChIKey:UKOADAUZYOTPFP-ASUBQVAYSA-N
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Compound Information
Molecular Weight:126.583
Molecular Formula:C7H7Cl
InChIKey:KCXMKQUNVWSEMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:340.4113
Molecular Formula:C18H28O6
InChIKey:UFAGQQVEBTVEOV-UAXVXCKYSA-N
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Compound Information
Molecular Weight:141.928
Molecular Formula:C4H10BF3O
InChIKey:MZTVMRUDEFSYGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:SEBPXHSZHLFWRL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:513.7425
Molecular Formula:C32H39NO3Si
InChIKey:LBRFMBMINFIBDW-AFOZTUFKSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:TWNAIGXHWABTTR-RCOVLWMOSA-N
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Compound Information
Molecular Weight:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.599
Molecular Formula:Cl2Ni
InChIKey:QMMRZOWCJAIUJA-UHFFFAOYSA-L
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Compound Information
Molecular Weight:34.0147
Molecular Formula:H2O2
InChIKey:MHAJPDPJQMAIIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.078
Molecular Formula:H2O4S
InChIKey:QAOWNCQODCNURD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:JAZUVJLINDCCOW-OFQRNFBNSA-N
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Compound Information
Molecular Weight:440.638
Molecular Formula:C27H36O3S
InChIKey:BSDCRRBICORGBY-IWSZWWFDSA-N
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Compound Information
Molecular Weight:424.4416
Molecular Formula:C21H28O9
InChIKey:KEPMWRXWAHKDMK-VXMFEQTDSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:SHPGKCBAUUCRQT-RCOVLWMOSA-N
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Compound Information
Molecular Weight:487.53
Molecular Formula:C27H36O3Se
InChIKey:RXILELDWKZCHKR-IWSZWWFDSA-N
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Compound Information
Molecular Weight:332.4339
Molecular Formula:C20H28O4
InChIKey:PVDCOHXOKYZQQP-VPCNSNALSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:IBWFPYRVHYLXEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.2699
Molecular Formula:C15H14O3
InChIKey:PVSFIFPJPUEHPO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:466.7259
Molecular Formula:C26H46O5Si
InChIKey:SNVRKMOTRFSRTM-OLMQDNSDSA-N
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Compound Information
Molecular Weight:154.1632
Molecular Formula:C8H10O3
InChIKey:DXODJUXMNZSTFU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:DCHOTFPTCDONQH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.3225
Molecular Formula:C12H27AlO3
InChIKey:MDDPTCUZZASZIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:HNPKHDXYGBZFNU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:308.3695
Molecular Formula:C17H24O5
InChIKey:WXTGXLKXKMJCCU-JBLLWJKWSA-N
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Compound Information
Molecular Weight:324.2489
Molecular Formula:C15H12CrO5
InChIKey:DCGNTBJKYADBIB-KLPQJWFNSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:FEVLDOXHQONPAV-UHIISALHSA-N
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Compound Information
Molecular Weight:362.4168
Molecular Formula:C20H26O6
InChIKey:MRWXTWINAFVAOZ-RJHWBGITSA-N
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Compound Information
Molecular Weight:22.98976928
Molecular Formula:HNa
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:JKAKPUWJSRMKFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:382.4911
Molecular Formula:C21H34O6
InChIKey:CUCKUZMNFYMAJL-QVOQPVJZSA-N
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Compound Information
Molecular Weight:158.0339
Molecular Formula:KMnO4
InChIKey:VZJVWSHVAAUDKD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.2582
Molecular Formula:C11H17NO2
InChIKey:XFOOGLFDAIWEMW-FXPVBKGRSA-N
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Compound Information
Molecular Weight:600.6136
Molecular Formula:C30H36N2O11
InChIKey:FAEMIAOFQIBIJX-MPXIVFSASA-N
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Compound Information
Molecular Weight:138.2055
Molecular Formula:CK2O3
InChIKey:BWHMMNNQKKPAPP-UHFFFAOYSA-L
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Compound Information
Molecular Weight:486.7171
Molecular Formula:C31H38O3Si
InChIKey:YKOAPBNKTKXYTR-WMKNUWDHSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:FAHGKVJAELJFRC-DABQJJPHSA-N
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Compound Information
Molecular Weight:302.3664
Molecular Formula:C21H18O2
InChIKey:FLUZLQFUGOLAHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:NNBZCPXTIHJBJL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.2428
Molecular Formula:C9H21AlO3
InChIKey:SMZOGRDCAXLAAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:XEKOWRVHYACXOJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.212
Molecular Formula:C4H9KO
InChIKey:LPNYRYFBWFDTMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.1898
Molecular Formula:C9H12O3
InChIKey:AIUJDIPTMFTDJG-CBAPKCEASA-N
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Compound Information
Molecular Weight:552.6552
Molecular Formula:C32H40O8
InChIKey:SDGDWRYYHQOQOJ-XXMLZKCSSA-N
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Compound Information
Molecular Weight:212.2439
Molecular Formula:C14H12O2
InChIKey:ISAOCJYIOMOJEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.3288
Molecular Formula:C16H20O2
InChIKey:HAJFGGSCOVCXRA-BBRMVZONSA-N
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Compound Information
Molecular Weight:466.7275
Molecular Formula:C29H42O3Si
InChIKey:DNZVHMUNJXTNOY-YACJIIDUSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:SYAVYWAMVZKGTF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:350.4492
Molecular Formula:C20H30O5
InChIKey:VEFQDSXSELSHMX-ZSZNEMJYSA-N
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Compound Information
Molecular Weight:301.3834
Molecular Formula:C17H23N3O2
InChIKey:CSGQGLBCAHGJDR-HUUCEWRRSA-N
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Compound Information
Molecular Weight:253.3389
Molecular Formula:C17H19NO
InChIKey:WMRCVTRGHBYCMT-SOGDLCAJSA-N
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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:111.1211
Molecular Formula:C5H10AlN
InChIKey:KWMUAEYVIFJZEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.2705
Molecular Formula:C15H14O2
InChIKey:WMEOMAYOFHGZIF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:KICREDOLXPKCLZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:101.9613
Molecular Formula:Al2O3
InChIKey:TWNQGVIAIRXVLR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:RYHBNJHYFVUHQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.642
Molecular Formula:C3H9ClSi
InChIKey:IJOOHPMOJXWVHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:PDCCLRAOJRADOX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.2223
Molecular Formula:C14H10CrO5
InChIKey:BQAJDULSODSPGQ-CEARTAFTSA-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:195.2582
Molecular Formula:C11H17NO2
InChIKey:ODQOXHWCBUTREH-KKZNHRDASA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:GWLDODYPRFUJTK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:554.6711
Molecular Formula:C32H42O8
InChIKey:QNOTXCPSNGZSSB-BCMFHKCLSA-N
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Compound Information
Molecular Weight:572.8479
Molecular Formula:C33H52O6Si
InChIKey:FEIYACJASGSWJO-JLTHPNNSSA-N
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Compound Information
Molecular Weight:331.2
Molecular Formula:N2O6Pb
InChIKey:RLJMLMKIBZAXJO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:264.3169
Molecular Formula:C15H20O4
InChIKey:ZWMQGXMHSMRYFW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:390.4269
Molecular Formula:C21H26O7
InChIKey:MJIJLRRIQCJXDC-SNZIJEOUSA-N
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Compound Information
Molecular Weight:253.3389
Molecular Formula:C17H19NO
InChIKey:QMZFHYVMCUNEII-KRWDZBQOSA-N
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Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:YDSVPCCNBNSGDJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:IUTZKYSQEWMGLS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:466.7259
Molecular Formula:C26H46O5Si
InChIKey:YSEFLGYFBLWSQA-VUGJSQTMSA-N
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Compound Information
Molecular Weight:318.4073
Molecular Formula:C19H26O4
InChIKey:QTWRPMSYNHXFLG-ZNZDAUKMSA-N
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Compound Information
Molecular Weight:208.2536
Molecular Formula:C12H16O3
InChIKey:SGMBNIHEHBIMJD-ZHAHWJHGSA-N
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Compound Information
Molecular Weight:226.2705
Molecular Formula:C15H14O2
InChIKey:DIVXVZXROTWKIH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:42.0367
Molecular Formula:C2H2O
InChIKey:CCGKOQOJPYTBIH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.339
Molecular Formula:C7H7BrMg
InChIKey:DVXDIGKNJYSMFM-UHFFFAOYSA-M
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:KTYOVFDWYUQIRA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:326.4326
Molecular Formula:C20H26N2O2
InChIKey:NZPIGOSHOZHMPJ-VNTMZGSJSA-N
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Compound Information
Molecular Weight:159.808
Molecular Formula:Br2
InChIKey:GDTBXPJZTBHREO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:QMYUGOQCDHOJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:36.461
Molecular Formula:ClH
InChIKey:VEXZGXHMUGYJMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:487.53
Molecular Formula:C27H36O3Se
InChIKey:YGOYLSINLBNWTE-KNLYACDFSA-N
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:GFSAUGGAKFZDTM-MNUQUWEESA-N
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Compound Information
Molecular Weight:456.6498
Molecular Formula:C25H36N2O4Si
InChIKey:UWQZCPXTVXNARS-VADBWAETSA-N
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:QMJJXMUQSRZCGB-PNZRWIHMSA-N
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Compound Information
Molecular Weight:554.6711
Molecular Formula:C32H42O8
InChIKey:QPGUFRUTQPENPE-YNTGXQQRSA-N
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Compound Information
Molecular Weight:126.1531
Molecular Formula:C7H10O2
InChIKey:LKXVIJIJFZGCMD-FSPLSTOPSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:LZRCVDRYTAYYPI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:378.4624
Molecular Formula:C27H22O2
InChIKey:OQVIAYNISMWGBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:408.4422
Molecular Formula:C21H28O8
InChIKey:ZMBGSDMRHSWIKO-IFOODVJBSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:RHRLAJUVPLESGE-SCDSUCTJSA-N
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Compound Information
Molecular Weight:332.3909
Molecular Formula:C19H24O5
InChIKey:ORRBRZSYXWGNHQ-IZROQAOKSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:186.635
Molecular Formula:C9H11ClO2
InChIKey:XPVGFJWSNJOZIB-CBAPKCEASA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:ODZTXUXIYGJLMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:466.7275
Molecular Formula:C29H42O3Si
InChIKey:AFXWTTTTZUBJPI-JEAJKEDXSA-N
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Compound Information
Molecular Weight:236.3068
Molecular Formula:C14H20O3
InChIKey:SDBJHEGPFHEGIS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:710.8502
Molecular Formula:C40H54O11
InChIKey:DGALPQLAZVBZFJ-PFUCQIAMSA-N
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Compound Information
Molecular Weight:126.1531
Molecular Formula:C7H10O2
InChIKey:JHBSKDNYIGMOQF-CAHLUQPWSA-N
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Compound Information
Molecular Weight:308.3695
Molecular Formula:C17H24O5
InChIKey:ZDBOARAEZGVLCY-CYSHUZOXSA-N
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Compound Information
Molecular Weight:522.6292
Molecular Formula:C31H38O7
InChIKey:RWNOAZBELWILOC-HXLRRGCXSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:XTHFKEDIFFGKHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:67.806
Molecular Formula:BF3
InChIKey:WTEOIRVLGSZEPR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:NPXXWGTWGWBUTC-SUHUHFCYSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:DVWPFGYTZFAHKY-OSMZGAPFSA-N
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Compound Information
Molecular Weight:229.3175
Molecular Formula:C15H19NO
InChIKey:DXYNFNXJDMKBNW-JIHUWAALSA-N
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Compound Information
Molecular Weight:229.3175
Molecular Formula:C15H19NO
InChIKey:KJBGLNVNONRBCZ-OSAQELSMSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:DCHOTFPTCDONQH-GFCCVEGCSA-N
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Compound Information
Molecular Weight:31.9988
Molecular Formula:O2
InChIKey:MHAJPDPJQMAIIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:264.3169
Molecular Formula:C15H20O4
InChIKey:DDLLIYKVDWPHJI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:ZFOOVBJHEUWTSZ-SCZZXKLOSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:NPXXWGTWGWBUTC-SCDSUCTJSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:DVWPFGYTZFAHKY-SCDSUCTJSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:NPXXWGTWGWBUTC-OSMZGAPFSA-N
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Compound Information
Molecular Weight:214.2598
Molecular Formula:C14H14O2
InChIKey:VKKLKKIHXXXYQG-OSMZGAPFSA-N
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Compound Information
Molecular Weight:125.1457
Molecular Formula:C7H10O2
InChIKey:PMWNWADHKSRBRV-VDTYLAMSSA-N
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Compound Information
Molecular Weight:125.1457
Molecular Formula:C7H10O2
InChIKey:PMWNWADHKSRBRV-CAHLUQPWSA-N
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Compound Information
Molecular Weight:20.0276
Molecular Formula:H2O
InChIKey:Not Available
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Compound Information
Molecular Weight:440.638
Molecular Formula:C27H36O3S
InChIKey:UKOADAUZYOTPFP-KNLYACDFSA-N
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Compound Information
Molecular Weight:304.4238
Molecular Formula:C19H28O3
InChIKey:AKRBLZKRYPEVIK-PEMPUTJUSA-N
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Compound Information
Molecular Weight:402.6529
Molecular Formula:C27H46O2
InChIKey:AYXDXVGGAIDTQI-LWNVLZJFSA-N
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Compound Information
Molecular Weight:402.6529
Molecular Formula:C27H46O2
InChIKey:AYXDXVGGAIDTQI-FRPSKHSRSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:412.517
Molecular Formula:C22H36O7
InChIKey:NXCYBYJXCJWMRY-GBDIVFEWSA-N
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Compound Information
Molecular Weight:408.4422
Molecular Formula:C21H28O8
InChIKey:ZMBGSDMRHSWIKO-FOMISVOBSA-N
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Compound Information
Molecular Weight:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.3068
Molecular Formula:C14H19NO
InChIKey:WDMAXURLTRQIBS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:404.4535
Molecular Formula:C22H28O7
InChIKey:SYSAAGIOIANXBW-ZOGLZDRWSA-N
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Compound Information
Molecular Weight:610.8737
Molecular Formula:C32H59AlO7Si
InChIKey:YSJGZFNGZDOZJL-NUONAIDBSA-N
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Compound Information
Molecular Weight:168.1898
Molecular Formula:C9H12O3
InChIKey:PGSOOIKBEIIBGR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:289.3264
Molecular Formula:C16H19NO4
InChIKey:GMPFDUMVFKRPNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2701
Molecular Formula:C12H18O2
InChIKey:WLWOEMHYDJAWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:ZFOOVBJHEUWTSZ-WCBMZHEXSA-N
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Compound Information
Molecular Weight:285.361
Molecular Formula:C16H15NO2S
InChIKey:XBGXGWNKJBMMPR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:370.4421
Molecular Formula:C21H26N2O4
InChIKey:OOHBHMKPDXKZIM-KODHJQJWSA-N
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Compound Information
Molecular Weight:231.3333
Molecular Formula:C15H21NO
InChIKey:WNABJQWOGGCFLO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.217
Molecular Formula:C10H14O2
InChIKey:ZCNCQJYPGGXZPW-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:355.3844
Molecular Formula:C20H21NO5
InChIKey:SBEDWYLFYCSPGC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:355.3844
Molecular Formula:C20H21NO5
InChIKey:GCKVGKZRKKGWAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:471.5906
Molecular Formula:C29H33N3O3
InChIKey:UMSLVOMOXCPOQD-QLPLNKDJSA-N
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Compound Information
Molecular Weight:395.4483
Molecular Formula:C23H25NO5
InChIKey:KCYRWBIJAFKWSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1412
Molecular Formula:C6H10O4
InChIKey:VUQLHQFKACOHNZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.2054
Molecular Formula:C12H10O4
InChIKey:QMDDGSDYNJVKNY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:SXJPAABWNSGWDY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.2116
Molecular Formula:C13H10CrO5
InChIKey:VFJSAFLAPCJKDV-IOAPNJDHSA-N
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Compound Information
Molecular Weight:332.3909
Molecular Formula:C19H24O5
InChIKey:KKBZCSLFNQAXOK-GFFVYYNQSA-N
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Compound Information
Molecular Weight:217.3068
Molecular Formula:C14H19NO
InChIKey:GQCLTEGYKISXIL-NTCAYCPXSA-N
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Compound Information
Molecular Weight:427.4917
Molecular Formula:C27H25NO4
InChIKey:MJBQXXAZTXDLJJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:HNGVETQUKUGWHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:485.5741
Molecular Formula:C29H31N3O4
InChIKey:UKCINPJKOKJORH-QZNVCQCUSA-N
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Compound Information
Molecular Weight:232.3612
Molecular Formula:C16H24O
InChIKey:GPXKYPSSEWHTSX-IMJJTQAJSA-N
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Compound Information
Molecular Weight:146.1412
Molecular Formula:C6H10O4
InChIKey:YJVOWRAWFXRESP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.2164
Molecular Formula:C10H14O3
InChIKey:LWZCGNJKEPLPLA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1736
Molecular Formula:C6H14O3
InChIKey:SBZXBUIDTXKZTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:658.851
Molecular Formula:C35H50O10Si
InChIKey:HWHJTOVPIRHJCM-NIWDXWTNSA-N
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Compound Information
Molecular Weight:257.3706
Molecular Formula:C17H23NO
InChIKey:ZLFUVTNLJFQWFY-NSCUHMNNSA-N
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Compound Information
Molecular Weight:203.2802
Molecular Formula:C13H17NO
InChIKey:KKHRPQNLRZGTFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:203.2802
Molecular Formula:C13H17NO
InChIKey:WBCIWUOGKNFQQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:313.5093
Molecular Formula:C19H27NOSi
InChIKey:JGHYPTRLVMDLIL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.232
Molecular Formula:C13H12O4
InChIKey:OWAUIKIBWKWYTF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.2108
Molecular Formula:C8H15NO
InChIKey:GACARISANCFUEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:670.8186
Molecular Formula:C35H46O11Si
InChIKey:SCHMCJIOOTXQBL-GSFQIJFHSA-N
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Compound Information
Molecular Weight:147.002
Molecular Formula:C6H4Cl2
InChIKey:RFFLAFLAYFXFSW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:544.341
Molecular Formula:C18H9Cl9
InChIKey:JDRHDKQKXPHNFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:378.4624
Molecular Formula:C27H22O2
InChIKey:AGAPSCCHXUILLU-UHFFFAOYSA-N
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