Standard Article

Carbonyl Methylenation and Alkylidenation Using Titanium-Based Reagents

  1. Stanley H. Pine

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or043.01

Organic Reactions

Organic Reactions

How to Cite

Pine, S. H. 2004. Carbonyl Methylenation and Alkylidenation Using Titanium-Based Reagents. Organic Reactions. 43:1:1–91.

Author Information

  1. California State University, Department of Chemistry and Biochemistry, Los Angeles, California

Publication History

  1. Published Online: 15 OCT 2004

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Abstract

Alkylidenation of the carbonyl group of ketones and aldehydes is among the most useful reactions of organic synthesis. The Wittig reaction of phosphoranes is probably the most widely used method of alkylidenation, although a variety of other approaches have been developed to accomplish this transformation.

The observation that titanium-based reagents can accomplish such a transformation has provided a new approach to alkylidenation. Not only do these reagents accomplish alkylidenation of the carbonyl group of aldehydes and ketones, but they are also effective with esters, lactones, amides, thioesters, and certain other carboxylic acid derivatives. Alkylidenation of the carbonyl group of carboxylic acid derivatives cannot normally be accomplished by the Wittig reaction.

Initial interest in the reaction focused on methylenation using the titanium–aluminum complex known as the Tebbe reagent.

Reactions of the Tebbe reagent with carboxylic esters and observed their conversion to enol ethers in high yield.

Furthermore, the Tebbe reagent was also found to methylenate aldehydes and ketones, sometimes more effectively than the Wittig method. The related titanium metallacycles, which are prepared from the Tebbe reagent and an alkene in the presence of a Lewis base, accomplish similar alkylidenations.

During the same period a still undefined reagent was prepared from zinc, a dihalomethane, and titanium tetrachloride that was shown to methylenate aldehydes and ketones. Modification of this mixture provides a reagent that accomplishes methylenation and alkylidenation of carboxylic acid derivatives. An alternative preparation of this reagent has also received wide use.

Reagents for carbonyl alkylidenation involving titanium–magnesium, zirconium, tantalum, tungsten, molybdenum, boron, and chromium have also been studied, but none has found such broad use in synthesis.

Keywords:

  • carbonyl methylenation;
  • alkylidenation;
  • mechanism;
  • titanium catalysts;
  • carboxylic acid derivatives;
  • ketones;
  • aldehydes;
  • functional group selectivity;
  • Tebbe reagent;
  • experimental procedures;
  • esters;
  • amides;
  • amides;
  • experimental procedures;
  • scope;
  • limitations

Featured Compounds

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  1. 1 - 250
Compound Information
Molecular Weight:164.158
Molecular Formula:C9H8O3
InChIKey:YLHXLHGIAMFFBU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:530.8759
Molecular Formula:C27H42O5Si3
InChIKey:CNYAXNXGFQPSFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:RUXXCJKMTULKGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.3556
Molecular Formula:C14H26O
InChIKey:UTZQAZKLUBACEC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.3031
Molecular Formula:C12H22
InChIKey:IQOLXDPLPXAWCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.1832
Molecular Formula:C11H9F3O2
InChIKey:UTCZANJRXCJUGL-QPJJXVBHSA-N
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Compound Information
Molecular Weight:402.5992
Molecular Formula:C23H34O4Si
InChIKey:GNHKOIULFSUMAV-NSGLVBLXSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:SYBYTAAJFKOIEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2445
Molecular Formula:C14H12O
InChIKey:QGLIJZOAHZFXJK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:YCMDQZKAIQBLJD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1852
Molecular Formula:C10H10O2
InChIKey:LYJHVEDILOKZCG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.3028
Molecular Formula:C15H18O
InChIKey:SIJFHOPZJILLGW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:203.2802
Molecular Formula:C13H17NO
InChIKey:ZPFVOSLKDUUSTC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:ZNZYLDJKNNOZEN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.3233
Molecular Formula:C14H22O2
InChIKey:OSLODJVQKSQSGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:404.572
Molecular Formula:C22H32O5Si
InChIKey:OUQZYVBBFHYEAC-QYBKLKLPSA-N
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Compound Information
Molecular Weight:238.3657
Molecular Formula:C15H26O2
InChIKey:DMCFFFVYXPGQCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.4186
Molecular Formula:C20H26O3
InChIKey:PNUFGFIOVVNKQC-SLHNCBLASA-N
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Compound Information
Molecular Weight:173.835
Molecular Formula:CH2Br2
InChIKey:FJBFPHVGVWTDIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:290.3542
Molecular Formula:C17H22O4
InChIKey:ACJJNFYWMWGFPR-DISOXQEGSA-N
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Compound Information
Molecular Weight:198.2173
Molecular Formula:C13H10O2
InChIKey:FCJSHPDYVMKCHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:300.509
Molecular Formula:C16H32O3Si
InChIKey:AJCWZLHLKVYKCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2759
Molecular Formula:C11H20O
InChIKey:YKFHFQUALOYSGO-BQYQJAHWSA-N
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Compound Information
Molecular Weight:688.877
Molecular Formula:C36H52O11Si
InChIKey:MOMVOOHPQGXQEE-PNSKYSHKSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:OTMGWWSNCUTXDW-MDZDMXLPSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:FJTRNRFAIZEJJJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:538.6302
Molecular Formula:C34H34O6
InChIKey:BUBVLQDEIIUIQG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.2655
Molecular Formula:C13H16O
InChIKey:AVTFAEMJVINZMY-JXMROGBWSA-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:138.2069
Molecular Formula:C9H14O
InChIKey:QKJMGSNDKSAPCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:OPWUAEHFQVJOCM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:FGYJVOVIGVLVBN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:PJCYWOOAQHDOPF-GQCTYLIASA-N
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Compound Information
Molecular Weight:170.2918
Molecular Formula:C11H22O
InChIKey:KYWIYKKSMDLRDC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:DULCUDSUACXJJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:676.8663
Molecular Formula:C35H52O11Si
InChIKey:MAHLUYAOQXIJAA-RBUQPCERSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:DSFNTAVCWZDPEB-VOTSOKGWSA-N
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Compound Information
Molecular Weight:208.3398
Molecular Formula:C14H24O
InChIKey:UBUGETHWZNEPMN-CMDGGOBGSA-N
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Compound Information
Molecular Weight:212.2439
Molecular Formula:C14H12O2
InChIKey:YLZJSGAIAOIPRG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2473
Molecular Formula:C11H17F3O
InChIKey:VHSGMOOERPTHKG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.0779
Molecular Formula:C3H6O3
InChIKey:IEJIGPNLZYLLBP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:IRWNFSMZBFIURE-XBXARRHUSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:VDMUEUFLAGSQBS-VQHVLOKHSA-N
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Compound Information
Molecular Weight:109.1259
Molecular Formula:C6H7NO
InChIKey:OLNMPDGRBKUJRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:276.239
Molecular Formula:C17H24Ti
InChIKey:KDIOAUWUUYOEEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.3981
Molecular Formula:C15H30O
InChIKey:XSYWFEMDEVMTDC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:FFWSICBKRCICMR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.2167
Molecular Formula:C13H10O3
InChIKey:ROORDVPLFPIABK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:ZNWBXXLWBPWQAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:SAQDSFALZQOEGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.3709
Molecular Formula:C14H28O2
InChIKey:VZWGRQBCURJOMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.319
Molecular Formula:C12H24
InChIKey:SJVKHZYVCVKEGM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.1267
Molecular Formula:C6H7F3O
InChIKey:Not Available
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Compound Information
Molecular Weight:256.427
Molecular Formula:C13H20OS2
InChIKey:FIKNPWFPYAZRIF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:288.4122
Molecular Formula:C13H24O5Si
InChIKey:CSPFISYOAJFKHD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:VHYFNPMBLIVWCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.132
Molecular Formula:C8H6O2
InChIKey:ACZGCWSMSTYWDQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.3126
Molecular Formula:C13H22O2
InChIKey:WXNKIPHTQFZSCH-BQYQJAHWSA-N
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Compound Information
Molecular Weight:132.1592
Molecular Formula:C9H8O
InChIKey:RNIMKRYOMAMHMJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:QWMKTUSPLFTXFA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.186
Molecular Formula:C15H20Ti
InChIKey:NFUMJSZIIBFNCS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:KYSNXNXYOUWOPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:633.2106
Molecular Formula:C31H68O5Si4
InChIKey:BVGVPKFIZJQXJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.2655
Molecular Formula:C13H16O
InChIKey:YIUGFKYVPGNWAK-XBXARRHUSA-N
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Compound Information
Molecular Weight:114.1648
Molecular Formula:C6H15Al
InChIKey:CDHICTNQMQYRSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.2103
Molecular Formula:C12H11F3O
InChIKey:PAXAQMWPWXAEJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2112
Molecular Formula:C11H12O3
InChIKey:ZEKCEJRLNUCAAN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:UOGXIPLKDOHXRA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.3612
Molecular Formula:C16H24O
InChIKey:KRTRQXIWZRANDC-TWGQIWQCSA-N
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Compound Information
Molecular Weight:202.2921
Molecular Formula:C14H18O
InChIKey:CIMUPCBHXATUGO-WEVVVXLNSA-N
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Compound Information
Molecular Weight:182.647
Molecular Formula:C10H11ClO
InChIKey:ISAUUJJGMQGHDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.2091
Molecular Formula:C12H11F3O3
InChIKey:LCEHIDVXHXRJDE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:BCJDCKZAIWXJDZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:MTZQAGJQAFMTAQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:ISZWTVCVSJVEOL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:FLHLBRIXYFDMIU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.578
Molecular Formula:C13H15ClTi
InChIKey:UZPFRYZZTZHHBF-UHFFFAOYSA-M
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:IFDDMADVXCXDPD-QHHAFSJGSA-N
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Compound Information
Molecular Weight:264.3615
Molecular Formula:C19H20O
InChIKey:QGKKYGLFLIXXHQ-ONNFQVAWSA-N
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Compound Information
Molecular Weight:194.3132
Molecular Formula:C13H22O
InChIKey:URCKUMRYNXRELV-PKNBQFBNSA-N
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Compound Information
Molecular Weight:877.1887
Molecular Formula:C56H64O7Si
InChIKey:RDFDXJTUWDNEIF-UZQUDJGMSA-N
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Compound Information
Molecular Weight:276.239
Molecular Formula:C17H24Ti
InChIKey:OFWGQBCMYYWTNQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:LPMWJCMGEXFYLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1144
Molecular Formula:C6H7F3O
InChIKey:ZFUOVLZLJCJNCP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:XJUMADFCBHRJQU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.0621
Molecular Formula:C3H4O3
InChIKey:Not Available
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Compound Information
Molecular Weight:174.1944
Molecular Formula:C8H14O4
InChIKey:XWEOGMYZFCHQNT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:FEXQDZTYJVXMOS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:879.1615
Molecular Formula:C55H62O8Si
InChIKey:SLPXNNMPWDMQOZ-ZQKCHVEUSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:SIZDIMDMQQFWLM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:189.679
Molecular Formula:Cl4Ti
InChIKey:Not Available
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Compound Information
Molecular Weight:194.3132
Molecular Formula:C13H22O
InChIKey:AAUVMWXXRMULTG-UKTHLTGXSA-N
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:RCBGGJURENJHKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:OWWIWYDDISJUMY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.4192
Molecular Formula:C20H26O2
InChIKey:WMWQDJRSYPBRDH-LTFPLMDUSA-N
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Compound Information
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:SWLGTNLRTUGMHV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.593
Molecular Formula:C8H7ClO2
InChIKey:LXNFVVDCCWUUKC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:OZZYKXXGCOLLLO-TWTPFVCWSA-N
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Compound Information
Molecular Weight:316.4345
Molecular Formula:C20H28O3
InChIKey:WNKREPLOBQWSNO-DXBWTPJFSA-N
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Compound Information
Molecular Weight:280.404
Molecular Formula:C20H24O
InChIKey:BWLXMVMGRXZLFN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:NRRQXLYOHDBBBS-CMDGGOBGSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:KKOJGCIZAWTKLI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:LYDRKKWPKKEMNZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.2632
Molecular Formula:C11H19F3O
InChIKey:KERQIJSACSVZMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:CEXNNRYBRPKTPC-ONEGZZNKSA-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:318.4073
Molecular Formula:C19H26O4
InChIKey:QEWOQAZPLHSARN-HJRFIPHPSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:QPJVMBTYPHYUOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.2103
Molecular Formula:C12H11F3O
InChIKey:KJXWSNAMUUKELA-VMPITWQZSA-N
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Compound Information
Molecular Weight:266.3343
Molecular Formula:C18H18O2
InChIKey:LNNKUFSDAXTLIO-YCRREMRBSA-N
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Compound Information
Molecular Weight:230.1832
Molecular Formula:C11H9F3O2
InChIKey:JRJRIRGAYXPMNH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:CATSNJVOTSVZJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:528.9031
Molecular Formula:C28H44O4Si3
InChIKey:VSAWPQGGLSNDQY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.0851
Molecular Formula:C3H9Al
InChIKey:Not Available
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:QYOVCBKZFRCMCG-NSCUHMNNSA-N
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Compound Information
Molecular Weight:111.0987
Molecular Formula:C5H5NO2
InChIKey:UMFMHWCXQBESPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:RQRDCTRBECQWBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.3386
Molecular Formula:C14H24O3
InChIKey:WOJDBOWEFVOMQD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:596.8262
Molecular Formula:C34H48O7Si
InChIKey:VKIKRXGBTRKWPM-SWJFXVHUSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:AVQPWRZDVLERPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:ZPVFWPFBNIEHGJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1739
Molecular Formula:C9H10O3
InChIKey:DDIZAANNODHTRB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:UHEPJGULSIKKTP-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:686.9042
Molecular Formula:C37H54O10Si
InChIKey:PBVVRVGYJVMLJD-VLDSTHNNSA-N
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Compound Information
Molecular Weight:220.3505
Molecular Formula:C15H24O
InChIKey:MSYWSEHICMADAS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:598.799
Molecular Formula:C33H46O8Si
InChIKey:ACMHBGPWSNFHBO-AARHSHDHSA-N
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Compound Information
Molecular Weight:56.1063
Molecular Formula:C4H8
InChIKey:VQTUBCCKSQIDNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.2745
Molecular Formula:C12H19F3
InChIKey:ZTOCFGVJNZAASH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2967
Molecular Formula:C13H20O2
InChIKey:FLNOPDNEFTWELZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.5362
Molecular Formula:C17H34O2Si
InChIKey:XSWQIOQBPGMAFX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:BFVBKTGHPWCEQG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.506
Molecular Formula:C16H26O2S2
InChIKey:WFCXLLKVOAPIEM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:596.8262
Molecular Formula:C34H48O7Si
InChIKey:BZSHXUWNRQAAMA-GGEKVXJASA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:QSSJZLPUHJDYKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.4
Molecular Formula:C12H18O2S2
InChIKey:GPZDMRXNWAROSD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:536.6573
Molecular Formula:C35H36O5
InChIKey:ZMPUERSSNVHHJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:ODLDELPCBCOGLK-XVNBXDOJSA-N
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Compound Information
Molecular Weight:224.3392
Molecular Formula:C14H24O2
InChIKey:ICHWKXNOJJNQKM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.3663
Molecular Formula:C15H26O
InChIKey:UUIIBDWDDHMOSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.2363
Molecular Formula:C13H13F3O2
InChIKey:JALDPRVRAXGWFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:KGDJMNKPBUNHGY-RMKNXTFCSA-N
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Compound Information
Molecular Weight:196.3291
Molecular Formula:C13H24O
InChIKey:DJHSWUJNEALLGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.2046
Molecular Formula:C6H16N2
InChIKey:KWYHDKDOAIKMQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:GFTLDFWHZXYZAG-GXSJLCMTSA-N
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Compound Information
Molecular Weight:148.1586
Molecular Formula:C9H8O2
InChIKey:VMUXSMXIQBNMGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.184
Molecular Formula:C10H10O4
InChIKey:NIQCNGHVCWTJSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:PXVSPVHVPWJJAI-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:164.2441
Molecular Formula:C11H16O
InChIKey:DJSDRMFUNRNVQQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1852
Molecular Formula:C10H10O2
InChIKey:CCRCUPLGCSFEDV-BQYQJAHWSA-N
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Compound Information
Molecular Weight:126.2392
Molecular Formula:C9H18
InChIKey:FBEDQPGLIKZGIN-UHFFFAOYSA-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:635.1834
Molecular Formula:C30H66O6Si4
InChIKey:DFWVIFANXWWLOK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:YTFKODRXTIXMOG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:DONSTYDPUORSDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:RIFKADJTWUGDOV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.3285
Molecular Formula:C13H24O2
InChIKey:JVVUEGHYKUMGQR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:HIGQPQRQIQDZMP-DHZHZOJOSA-N
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Compound Information
Molecular Weight:202.1731
Molecular Formula:C10H9F3O
InChIKey:SIPINRRNUJITJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:560.7511
Molecular Formula:C30H44O8Si
InChIKey:HCMTWUMNEXKZTC-OJHKMLFLSA-N
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Compound Information
Molecular Weight:238.2812
Molecular Formula:C16H14O2
InChIKey:NGHOLYJTSCBCGC-VAWYXSNFSA-N
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Compound Information
Molecular Weight:113.1576
Molecular Formula:C6H11NO
InChIKey:GGYVTHJIUNGKFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:MZONMYOSAYHGAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:604.8036
Molecular Formula:C32H48O9Si
InChIKey:NWMZXMYUGVVKAJ-WMYFCZKQSA-N
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Compound Information
Molecular Weight:208.122
Molecular Formula:C12H16Ti
InChIKey:TZDDBGXAOLSWEH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1852
Molecular Formula:C10H10O2
InChIKey:AEUULUMEYIPECD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2921
Molecular Formula:C14H18O
InChIKey:QHDJXTPJWFOEJS-XBXARRHUSA-N
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Compound Information
Molecular Weight:316.479
Molecular Formula:C15H24O3S2
InChIKey:WJQBDUMERXUHDX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:464.8917
Molecular Formula:C19H44O5Si4
InChIKey:ZDPLHGWSGHFLSX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:286.4393
Molecular Formula:C14H26O4Si
InChIKey:KAESLRZEMSNAQS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.0872
Molecular Formula:C5H5F3O2
InChIKey:KDETVIXRIFXUGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.584
Molecular Formula:C13H18AlClTi
InChIKey:HUESUCODIPYQPI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.0995
Molecular Formula:C5H5F3O2
InChIKey:Not Available
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-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:146.1858
Molecular Formula:C10H10O
InChIKey:SKVLAYXNJMOXCS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.14
Molecular Formula:CH2AlCl5Ti
InChIKey:JZYQNIYWSXWFSM-UHFFFAOYSA-I
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Compound Information
Molecular Weight:602.8308
Molecular Formula:C33H50O8Si
InChIKey:OKSTUDSLRJCMCO-OLFJEZDDSA-N
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Compound Information
Molecular Weight:166.217
Molecular Formula:C10H14O2
InChIKey:GZJFWHARFQQZDU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.62
Molecular Formula:C9H9ClO2
InChIKey:ANPPGQUFDXLAGY-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:558.7782
Molecular Formula:C31H46O7Si
InChIKey:OXJVUOAKPBHMDI-CMPUJJQDSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:VHMYBWIOLGKSHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2921
Molecular Formula:C14H18O
InChIKey:MZDWFEVXCVQHLN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:OQRQHBKEEIMXMP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.959
Molecular Formula:C10H10Cl2Ti
InChIKey:UPQNXBCFKDPPEC-UHFFFAOYSA-L
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Compound Information
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:DQGSJTVMODPFBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:QHPKNUCFNTUWOB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:VNWHDWWIWOLKEH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:288.3814
Molecular Formula:C18H24O3
InChIKey:LISKWUQXEYTNJE-DQVOVIAYSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:XARSCEOUIZQPSI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:JRYQHTGXOBAUPA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:WYGZHSAEEWRUKM-YVMONPNESA-N
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Compound Information
Molecular Weight:122.1213
Molecular Formula:C7H6O2
InChIKey:WPYMKLBDIGXBTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.3768
Molecular Formula:C19H22O2
InChIKey:OKESDINPVMAQMH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:HRSXWUSONDBHSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:674.8935
Molecular Formula:C36H54O10Si
InChIKey:CJCHNIBTVVWMJM-UZJKACDHSA-N
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Compound Information
Molecular Weight:226.236
Molecular Formula:C10H17F3O2
InChIKey:MGRWEFWRZHQSRH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2378
Molecular Formula:C12H14O3
InChIKey:OFRHMGVEWXXDBG-CMDGGOBGSA-N
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Compound Information
Molecular Weight:168.62
Molecular Formula:C9H9ClO
InChIKey:AEHOEMCYBWBLLM-UHFFFAOYSA-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:194.2701
Molecular Formula:C12H18O2
InChIKey:VKAMQZDEZYFWSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.1459
Molecular Formula:C9H7F3O2
InChIKey:GMYUKHZXDVBIQE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3083
Molecular Formula:C17H16O
InChIKey:VEEDIQJQVJFAKA-OUKQBFOZSA-N
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Compound Information
Molecular Weight:196.3291
Molecular Formula:C13H24O
InChIKey:ZOKLAFZVUCBKFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:65.409
Molecular Formula:Zn
InChIKey:HCHKCACWOHOZIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:PDNJMHZLMGTCDU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:MQNAWGURFBPDMW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2759
Molecular Formula:C11H20O
InChIKey:HORHVIVEFFTLPK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:598.799
Molecular Formula:C33H46O8Si
InChIKey:OEKBSBUFIRIZOA-FLXAVSGSSA-N
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Compound Information
Molecular Weight:196.1999
Molecular Formula:C10H12O4
InChIKey:LMCUQDGELGASMZ-XVKPBYJWSA-N
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Compound Information
Molecular Weight:206.3239
Molecular Formula:C14H22O
InChIKey:YDPPTBCKWWOCLE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:GFQWQNCDDFRRRK-GFGVWQOPSA-N
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Compound Information
Molecular Weight:466.8645
Molecular Formula:C18H42O6Si4
InChIKey:VNGTZLYNGGLPIZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.0995
Molecular Formula:C5H5F3O2
InChIKey:Not Available
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Compound Information
Molecular Weight:154.1267
Molecular Formula:C6H7F3O
InChIKey:Not Available
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Compound Information
Molecular Weight:154.0872
Molecular Formula:C5H5F3O2
InChIKey:XIVPVSIDXBTZLM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1144
Molecular Formula:C6H7F3O
InChIKey:XPRNZUKKKWIHBQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:558.7782
Molecular Formula:C31H46O7Si
InChIKey:OXJVUOAKPBHMDI-RLXMVLCYSA-N
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Compound Information
Molecular Weight:676.8663
Molecular Formula:C35H52O11Si
InChIKey:MAHLUYAOQXIJAA-JXYZXQKGSA-N
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Compound Information
Molecular Weight:674.8935
Molecular Formula:C36H54O10Si
InChIKey:CJCHNIBTVVWMJM-JFKPNKMPSA-N
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Compound Information
Molecular Weight:879.1615
Molecular Formula:C55H62O8Si
InChIKey:SLPXNNMPWDMQOZ-UGGATUBOSA-N
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Compound Information
Molecular Weight:877.1887
Molecular Formula:C56H64O7Si
InChIKey:RDFDXJTUWDNEIF-CGUSVCNXSA-N
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Compound Information
Molecular Weight:604.8036
Molecular Formula:C32H48O9Si
InChIKey:NWMZXMYUGVVKAJ-UHCKPCJQSA-N
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Compound Information
Molecular Weight:602.8308
Molecular Formula:C33H50O8Si
InChIKey:OKSTUDSLRJCMCO-ASSZPPITSA-N
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Compound Information
Molecular Weight:212.3285
Molecular Formula:C13H24O2
InChIKey:AZTBFNAJPXPWGK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.3556
Molecular Formula:C14H26O
InChIKey:VLQXEVAOQMRBBF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:424.7323
Molecular Formula:C25H48O3Si
InChIKey:GUOHVBYFXDVSSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:336.5411
Molecular Formula:C19H32O3Si
InChIKey:KZHBVCPZOZZUMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:IDNRIYVQXZTTIF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:364.3897
Molecular Formula:C19H24O7
InChIKey:JGJBINXDUHECHI-LDUSWNGDSA-N
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Compound Information
Molecular Weight:198.3034
Molecular Formula:C15H18
InChIKey:RUURNCFYSRCRKM-ARBRNUSQSA-N
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Compound Information
Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:VRXDKYFSWOOJLO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2429
Molecular Formula:C11H16O3
InChIKey:VNWBIXDWILNBDM-VAOFZXAKSA-N
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Compound Information
Molecular Weight:234.3355
Molecular Formula:C18H18
InChIKey:QHAABQWHYVLCAF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2713
Molecular Formula:C12H18
InChIKey:MWDGNPZVRLTTMD-OUAUKWLOSA-N
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Compound Information
Molecular Weight:174.827
Molecular Formula:CH2Br2
InChIKey:FJBFPHVGVWTDIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:KWOLFJPFCHCOCG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:272.382
Molecular Formula:C18H24O2
InChIKey:IPVPJTPFIPEDNQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.2457
Molecular Formula:C12H16O4
InChIKey:KWSKUYPUOGGGBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.3511
Molecular Formula:C15H24
InChIKey:RDOCEKCPYPRXQM-JBAPVGOWSA-N
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Compound Information
Molecular Weight:480.871
Molecular Formula:C27H52O3Si2
InChIKey:UDELGVVPLXAYBE-XUTLUUPISA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:LANUXSZTHAVTPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.2259
Molecular Formula:C11H14O5
InChIKey:PJTOGTPGKZREEX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2967
Molecular Formula:C13H20O2
InChIKey:UXOPQCCKRDRWAI-BQYQJAHWSA-N
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Compound Information
Molecular Weight:294.3859
Molecular Formula:C17H26O4
InChIKey:JBRCNSRRUTUJDD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:DRLVMOAWNVOSPE-UHFFFAOYSA-N
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