Standard Article

Twofold Extrusion Reactions

  1. Lynn James Guziec,
  2. Frank S. Guziec Jr.

Published Online: 31 OCT 2012

DOI: 10.1002/0471264180.or078.03

Organic Reactions

Organic Reactions

How to Cite

James Guziec, L. and Guziec, F. S. 2012. Twofold Extrusion Reactions. Organic Reactions. 3:411–550.

Author Information

  1. Southwestern University, Department of Chemistry and Biochemistry, Georgetown, Texas

Publication History

  1. Published Online: 31 OCT 2012

Chemistry Terms

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Abstract

Twofold extrusion reactions are chemical transformations in which two small inorganic molecules or atoms connecting carbon or nitrogen atoms are lost, generating the corresponding carbon-carbon or carbon-nitrogen double bonds. These reactions are particularly useful for the preparation of sterically hindered alkenes and imines. The inorganic species liberated in twofold extrusion reactions can be molecular nitrogen, sulfur, selenium, tellurium, sulfur dioxide, sulfur monoxide, carbon dioxide or carbon monoxide.

The most common precursors for twofold extrusion reactions are 1,3,4-thiadiazolines, which thermally extrude molecular nitrogen affording thiiranes. These thiiranes can be readily desulfurized to afford the corresponding alkenes using tertiary phosphines. The corresponding 1,3,4-selenadiazolines thermally extrude both molecular nitrogen and atomic selenium directly affording alkenes. Alkenes can also be prepared by formal extrusions of molecular nitrogen plus sulfur dioxide or sulfur monoxide. Extremely sterically hindered imines can be prepared by extrusions of molecular nitrogen and sulfur or selenium from in situ generated heterocyclic precursors. Other less common twofold extrusion reactions are also reported.

The detailed preparations of the required precursors for the twofold extrusion reactions as well as the mechanisms of these extrusion processes are discussed in this chapter. The utility of twofold extrusion reactions in the preparations of ‘molecular rotors’ and other extremely sterically hindered alkenes is presented. The steric limitations of the twofold extrusion reactions are discussed along with comparisons of these reactions with other alkene- and imine-forming synthetic methods. The Tabular Survey covers material through the end of 2009.

Keywords:

  • Extrusion;
  • twofold extrusion;
  • alkene;
  • imine;
  • 1,3,4-thiadiazolines;
  • 1,3,4-selenadiazolines;
  • [nitrogen, sulfur, selenium, tellurium, sulfur dioxide, sulfur monoxide, carbon dioxide and carbon monoxide (all with extrusion)];
  • thiocarbonyl ylide;
  • tertiary phosphine;
  • diazo compounds;
  • thiones;
  • selones;
  • sulfenes;
  • selenirane;
  • azines;
  • chelotropic extrusion;
  • Barton-Kellogg reaction;
  • Staudinger-Pfenninger reaction;
  • Schönberg reaction;
  • thiadiazoline-1,1-dioxides;
  • thiirane 1,1-dioxide;
  • thiirane 1-oxide;
  • oxathiolan-4-ones;
  • lead tetraacetate;
  • barium manganate;
  • diselenium dibromide;
  • thiocarbonyl-S-imide;
  • copper powder;
  • photochemical extrusion;
  • flash vacuum pyrolysis (FVP);
  • rhodium (II) acetate;
  • 1,3-dithiacyclopentanes;
  • hydrazones;
  • thiaziridine 1,1-dioxides;
  • p-toluenesulfonylhydrazones;
  • 1,2,3-thiadiazolines;
  • alkenes (sterically hindered);
  • imines (sterically hindered);
  • N-sulfonylamines;
  • retrocyclization;
  • iminium salts (sterically hindered);
  • geminal dihalides;
  • nanoscale devices;
  • photonic devices;
  • thiophosgene;
  • O-thioesters;
  • O-selenoesters;
  • enol ethers;
  • dithioesters;
  • thioenol ethers;
  • thionolactones;
  • thioamides;
  • thiolactams;
  • trithiocarbonates;
  • ketene thioacetals;
  • thioacyl halides;
  • thionitroso compounds;
  • thiatriazoline;
  • trimethyl orthoformate;
  • hydrogen sulfide;
  • triphenylphosphoranylidene hydrazones

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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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:190.305
Molecular Formula:C12H14S
InChIKey:UBQLHWMDPOWPQG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.185
Molecular Formula:C4H9NO2S
InChIKey:IXUWFJQVIANURI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:305.23
Molecular Formula:C15H14O2Se
InChIKey:OZODTDDIYDQQQD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:332.416
Molecular Formula:C21H16O2S
InChIKey:GJSNRAJUOUOIET-UHFFFAOYSA-N
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Compound Information
Molecular Weight:316.4791
Molecular Formula:C24H28
InChIKey:AEVSUMKZJKJKQF-VHXPQNKSSA-N
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Compound Information
Molecular Weight:56.0666
Molecular Formula:C2H4N2
InChIKey:WLXALCKAKGDNAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.2913
Molecular Formula:C17H14O3
InChIKey:HMWBEURJPDOFAS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.308
Molecular Formula:C11H16O3S
InChIKey:CKMLMHQASKUVRK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.1359
Molecular Formula:C7H6N2
InChIKey:CRGRWBQSZSQVIE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1916
Molecular Formula:C9H12
InChIKey:AUHZEENZYGFFBQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.1121
Molecular Formula:C5H6N2O4
InChIKey:UFAZHCVBGMSJHS-UHFFFAOYSA-N
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Molecular Weight:415.4858
Molecular Formula:C28H21N3O
InChIKey:VNCVGERWEOZBFL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.18
Molecular Formula:C5H8O3S
InChIKey:PESGEIKVKSRVJQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:59.1103
Molecular Formula:C3H9N
InChIKey:Not Available
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Molecular Weight:197.257
Molecular Formula:C8H11N3OS
InChIKey:GDLZOMCZDSPVIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:424.514
Molecular Formula:C26H20N2O2S
InChIKey:RWHNUJNCKQZFEX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:386.5274
Molecular Formula:C30H26
InChIKey:LKYDKUSUKIGYOL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.323
Molecular Formula:C11H16N2S
InChIKey:XFIZMSIGJQOXTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.465
Molecular Formula:C8H18SSi2
InChIKey:DWLGVDALKWUQSW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:259.3434
Molecular Formula:C16H21NO2
InChIKey:DQDLZFJWIPVOSI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:LHXDLQBQYFFVNW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:324.437
Molecular Formula:C20H20O2S
InChIKey:CSCVUPPPVYEWFI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:320.835
Molecular Formula:C20H13ClS
InChIKey:YZCMDFJARMLEAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.742
Molecular Formula:C10H15ClO3S
InChIKey:BGABKEVTHIJBIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2872
Molecular Formula:C12H20
InChIKey:FJHVMZDLYBHASM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.4467
Molecular Formula:C18H32
InChIKey:BJLDJXSKAWPUSR-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:317.73
Molecular Formula:Br2Se2
InChIKey:XXFBOXZYQLMDQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1488
Molecular Formula:C5H12
InChIKey:OFBQJSOFQDEBGM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.633
Molecular Formula:C7H5ClS
InChIKey:MNUYNGXMQRGJSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:101.17
Molecular Formula:C4H7NS
InChIKey:IMWUREPEYPRYOR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:463.64
Molecular Formula:C28H48Se
InChIKey:PIPJAKUEIJIRDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.347
Molecular Formula:C16H14S
InChIKey:SWPCGPUBBAOTMY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2209
Molecular Formula:C9H14N2
InChIKey:NZIKGWMLWIJONL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:430.0392
Molecular Formula:C10H5F6IO4
InChIKey:PEZNEXFPRSOYPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:267.238
Molecular Formula:C12H24Cl2N2
InChIKey:HIXCYMVGOCFLMJ-FOCLMDBBSA-N
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Compound Information
Molecular Weight:256.32
Molecular Formula:C15H12O2S
InChIKey:GIGATHCFQIQZIB-AFYYWNPRSA-N
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Compound Information
Molecular Weight:216.387
Molecular Formula:C10H19NS2
InChIKey:DOFBAWMMAMCKBT-UHFFFAOYSA-M
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Compound Information
Molecular Weight:348.3903
Molecular Formula:C19H24O6
InChIKey:QFTHPWRGQTVAGR-OAHLLOKOSA-N
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Compound Information
Molecular Weight:462.565
Molecular Formula:C31H31N2P
InChIKey:BJTQPSMTKOKAIU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.281
Molecular Formula:C10H14O3S
InChIKey:AJTZVBCZLVLVKJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.3324
Molecular Formula:C12H24N2
InChIKey:MYKADEMIRVFALV-UTLPMFLDSA-N
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:332.437
Molecular Formula:C26H20
InChIKey:JLZUZNKTTIRERF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.19
Molecular Formula:C10H16Se
InChIKey:GNMCDOCXUWTHLT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:406.562
Molecular Formula:C27H18S2
InChIKey:YJHHYIKRPOFFFW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.343
Molecular Formula:C10H20N2O2S
InChIKey:FRAZZUMXDYACQL-YUMQZZPRSA-N
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Compound Information
Molecular Weight:205.318
Molecular Formula:C9H19NO2S
InChIKey:VHFHKAJSCOGFPM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:488.5559
Molecular Formula:C33H29O2P
InChIKey:RSPJXSUBEYZFQE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.397
Molecular Formula:C12H24N2S
InChIKey:ZITVEDITYNAJFA-RYUDHWBXSA-N
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Compound Information
Molecular Weight:244.309
Molecular Formula:C14H12O2S
InChIKey:JQCAMTODVTZCAE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:355.42
Molecular Formula:C18H32N2Se
InChIKey:FYKZDRFSOJSPAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.179
Molecular Formula:C8H11NO
InChIKey:HCXRUFOOEKOULX-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:98.1463
Molecular Formula:C5H10N2
InChIKey:ZNLNBIHMNSHXHP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.3446
Molecular Formula:C16H21N
InChIKey:MBRXZNOLPYJSPA-SAPNQHFASA-N
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Compound Information
Molecular Weight:141.2539
Molecular Formula:C9H19N
InChIKey:VCMKYJMEMATQPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:64.064
Molecular Formula:O2S
InChIKey:Not Available
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Compound Information
Molecular Weight:290.4418
Molecular Formula:C22H26
InChIKey:HAWMSPUUZWRGGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2526
Molecular Formula:C9H18N2
InChIKey:KEJDZOJSZYVXBU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.235
Molecular Formula:C7H12S
InChIKey:HNJZXUIBVXBJFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1026
Molecular Formula:C4H6N2O2
InChIKey:Not Available
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Compound Information
Molecular Weight:32.0452
Molecular Formula:H4N2
InChIKey:OAKJQQAXSVQMHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1151
Molecular Formula:CHKO3
InChIKey:TYJJADVDDVDEDZ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:205.2
Molecular Formula:C9H18Se
InChIKey:VZHILOFQEFHSLR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:87.1204
Molecular Formula:C4H9NO
InChIKey:FXHOOIRPVKKKFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.255
Molecular Formula:C9H11NS
InChIKey:WNRLGCKLMHXABJ-XLPZGREQSA-N
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Compound Information
Molecular Weight:327.41
Molecular Formula:C18H32Se
InChIKey:GKOMPFYKXUUAKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:348.4382
Molecular Formula:C22H24N2O2
InChIKey:WJIJXVOUYCVYJC-MBALSZOMSA-N
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Compound Information
Molecular Weight:160.234
Molecular Formula:C7H12O2S
InChIKey:XUZRFJBIKOACEP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.349
Molecular Formula:C7H10S3
InChIKey:FFIFYXTYVXGTRN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:ZPVOLGVTNLDBFI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:219.2796
Molecular Formula:C13H17NO2
InChIKey:OGUMNUKHZXHQEG-WOFCGZDCSA-N
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Compound Information
Molecular Weight:76.141
Molecular Formula:CS2
InChIKey:QGJOPFRUJISHPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2918
Molecular Formula:C11H22O
InChIKey:LPKATDGGXXEZFL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:247.3605
Molecular Formula:C12H30N3P
InChIKey:FDIOSTIIZGWENY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:272.4681
Molecular Formula:C20H32
InChIKey:YWDNLLRZWAMTOR-FOCLMDBBSA-N
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Compound Information
Molecular Weight:320.4248
Molecular Formula:C22H24O2
InChIKey:WQLXJKNXCMRHHS-QURGRASLSA-N
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Compound Information
Molecular Weight:133.1506
Molecular Formula:C7H7N3
InChIKey:UDLLFLQFQMACJB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:37.954
Molecular Formula:AlH4Li
InChIKey:OCZDCIYGECBNKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2792
Molecular Formula:C10H20N2
InChIKey:FQKCIYLEQYBWAA-MKICQXMISA-N
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Compound Information
Molecular Weight:204.331
Molecular Formula:C13H16S
InChIKey:AMVCTTKORDITAI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.341
Molecular Formula:C20H16
InChIKey:Not Available
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Compound Information
Molecular Weight:156.245
Molecular Formula:C8H12OS
InChIKey:SVRXPTCPQFXZSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:344.4046
Molecular Formula:C26H16O
InChIKey:MMMRULDDLHTJNH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:368.491
Molecular Formula:C18H28N2O4S
InChIKey:RFPUTOBLPSMEOM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.304
Molecular Formula:C9H18S
InChIKey:HMMKPVYDAVOBLX-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:184.2786
Molecular Formula:C10H20N2O
InChIKey:CGXDNXAYMLHFOC-YRNVUSSQSA-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:134.1751
Molecular Formula:C9H10O
InChIKey:SIZDIMDMQQFWLM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:325.3
Molecular Formula:C4H6O4Pb
InChIKey:GUWSLQUAAYEZAF-UHFFFAOYSA-L
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Compound Information
Molecular Weight:254.279
Molecular Formula:C13H18O5
InChIKey:SPYLDGSUBUVGRV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:330.531
Molecular Formula:C20H30N2S
InChIKey:CELJMXMCZUAWSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:302.4525
Molecular Formula:C23H26
InChIKey:NWMZRBOMOBWJLX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:328.382
Molecular Formula:C18H16O4S
InChIKey:ZLXXAKSGHMIORE-UHFFFAOYSA-N
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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:399.43
Molecular Formula:C22H28N2Se
InChIKey:GVRPLVKBFABWTR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:418.592
Molecular Formula:C30H26S
InChIKey:SEWNFIYDPVOKHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.1998
Molecular Formula:C10H10N2
InChIKey:YNDZVQSCSZBSOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:337.9
Molecular Formula:C14H10STe
InChIKey:KCJDUGHZXCCHHQ-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:324.32
Molecular Formula:C15H23N3Se
InChIKey:LRYLOAGIVMWXLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.267
Molecular Formula:C13H8OS
InChIKey:VKLOKHJKPPJQMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:482.616
Molecular Formula:C28H22N2O2S2
InChIKey:GCTQYKDWQGZJNP-MEFGMAGPSA-N
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Compound Information
Molecular Weight:192.216
Molecular Formula:C13H8N2
InChIKey:LOBSPZHDUJUOES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:405.48
Molecular Formula:C22H34N2Se
InChIKey:AZPMLYNEAWNFCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.299
Molecular Formula:C10H16S
InChIKey:LZCJFUYIXHJWPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.4363
Molecular Formula:C20H28
InChIKey:KRDXURLKZNAXAQ-VXPUYCOJSA-N
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Compound Information
Molecular Weight:212.31
Molecular Formula:C14H12S
InChIKey:YZGUWUYYNVDKDB-LSLKUGRBSA-N
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Compound Information
Molecular Weight:246.325
Molecular Formula:C14H14O2S
InChIKey:UKHKZGJCPDWXQY-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:251.23
Molecular Formula:C13H16Se
InChIKey:XZDDHPVGVRBXJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.2539
Molecular Formula:C9H19N
InChIKey:OSJQKOMOEHBJBR-JXMROGBWSA-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:211.011
Molecular Formula:C5H7BrO4
InChIKey:NEMOJKROKMMQBQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:NQCABGRZRRCWPC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:21.976
Molecular Formula:CH3Li
InChIKey:Not Available
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Compound Information
Molecular Weight:186.1653
Molecular Formula:C7H10N2O4
InChIKey:PSINDLUNOGABJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2367
Molecular Formula:C9H16N2
InChIKey:ZYYBWVXOJNKZJG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.3498
Molecular Formula:C15H23N
InChIKey:RVMZSLSYWTVUIJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2744
Molecular Formula:C14H14N2
InChIKey:AGQJUHLHBBRTDQ-PEZBUJJGSA-N
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Compound Information
Molecular Weight:268.3517
Molecular Formula:C21H16
InChIKey:GKUPDZCIBKBVSW-XSFVSMFZSA-N
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Compound Information
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:URLKBWYHVLBVBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.214
Molecular Formula:C8H8OS
InChIKey:IXVOVVPVAXAFIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:115.0907
Molecular Formula:C3H5N3O2
InChIKey:RXYCUKSOYJWGPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.1204
Molecular Formula:C4H10O3
InChIKey:Not Available
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Compound Information
Molecular Weight:328.515
Molecular Formula:C20H28N2S
InChIKey:QPEMOHICQCYTFY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.259
Molecular Formula:C8H12N2S
InChIKey:IKOUCNSWCSDWAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.077
Molecular Formula:CaO
InChIKey:ODINCKMPIJJUCX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.3618
Molecular Formula:C16H24
InChIKey:ACMXXCAIILDULR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:24.305
Molecular Formula:Mg
InChIKey:RBDWJDKUWZUMEV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:272.317
Molecular Formula:C12H16O5S
InChIKey:JFTGCRPPEOUCRE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1754
Molecular Formula:C6H14
InChIKey:VLKZOEOYAKHREP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:337.4
Molecular Formula:C19H30Se
InChIKey:SXLZPSJMVHJBJT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:267.989
Molecular Formula:C8H12Br2
InChIKey:HAIIKSDEVJMECE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2014
Molecular Formula:C13H8O2
InChIKey:JNELGWHKGNBSMD-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:404.467
Molecular Formula:C14H14O2P2S4
InChIKey:Not Available
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:ANQVAFUCYRTKOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.283
Molecular Formula:C10H14S
InChIKey:NKTSSCWRJVACFR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:277.428
Molecular Formula:C15H23N3S
InChIKey:MYXVTJPUXVVWHG-UHFFFAOYSA-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:322.4422
Molecular Formula:C25H22
InChIKey:RLUUIUYWPBXBTQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2319
Molecular Formula:C13H10N2
InChIKey:ITLHXEGAYQFOHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:338.486
Molecular Formula:C20H18OS2
InChIKey:JCVHAYFTZFNFLF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.2855
Molecular Formula:C18H15P
InChIKey:RIOQSEWOXXDEQQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.2839
Molecular Formula:C15H14N2O2
InChIKey:OWRNAWGCEAUIOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.263
Molecular Formula:BaMnO4
InChIKey:ZZCNKSMCIZCVDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:443.4
Molecular Formula:C8H12O8Pb
InChIKey:Not Available
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Compound Information
Molecular Weight:281.332
Molecular Formula:C15H11N3OS
InChIKey:TUFFFDXWUHTXBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.646
Molecular Formula:C4H10ClNO2S
InChIKey:WGBSTIRRHNSMRN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.2699
Molecular Formula:C15H14O3
InChIKey:RFVHVYKVRGKLNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.275
Molecular Formula:C8H14N2S
InChIKey:MMQCNLMPQMGVML-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.3621
Molecular Formula:C19H20
InChIKey:PXJUYCDEHIAYHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:42.04
Molecular Formula:CH2N2
InChIKey:YXHKONLOYHBTNS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.268
Molecular Formula:C13H8S
InChIKey:HFTBATIGSHWQBL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.427
Molecular Formula:C19H20S
InChIKey:LZYQGNHXFYNLAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.4577
Molecular Formula:C22H28
InChIKey:IGTNTQMIWYBRHX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.226
Molecular Formula:Cl3Ti
InChIKey:YONPGGFAJWQGJC-UHFFFAOYSA-K
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Compound Information
Molecular Weight:208.323
Molecular Formula:C11H16N2S
InChIKey:MFVPASHAMLFKSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.17
Molecular Formula:C9H14Se
InChIKey:OONZVYNBLYSWII-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:198.283
Molecular Formula:C13H10S
InChIKey:XDDVRYDDMGRFAZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.3172
Molecular Formula:C18H16O4
InChIKey:YOTKHEHTAIFYHG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:249.135
Molecular Formula:C14H10Cl2
InChIKey:GVLRAPLHURDGPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.335
Molecular Formula:C12H18O3S
InChIKey:LJQYWPXATDYIJL-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:232.343
Molecular Formula:C10H20N2O2S
InChIKey:MWPXJZCZFDJSBE-UHNCYFFSSA-N
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Compound Information
Molecular Weight:281.2
Molecular Formula:C14H10Cl2S
InChIKey:AFWJSEFXTYJCJF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:Not Available
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Compound Information
Molecular Weight:225.2857
Molecular Formula:C15H15NO
InChIKey:ZTYXEDOHERBZBW-NXVVXOECSA-N
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Compound Information
Molecular Weight:114.982
Molecular Formula:CCl2S
InChIKey:ZWZVWGITAAIFPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:326.5188
Molecular Formula:C22H34N2
InChIKey:FYFFIXSHCQLSNE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:286.344
Molecular Formula:C13H18O5S
InChIKey:KWIGSFPGUMCSHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2478
Molecular Formula:C13H12N2
InChIKey:QYCSNMDOZNUZIT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:VQSFHZJBTTWXIS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:308.5848
Molecular Formula:C22H44
InChIKey:UDDARUHQYSLCIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:6.941
Molecular Formula:Li
InChIKey:SIAPCJWMELPYOE-UHFFFAOYSA-N
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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:452.5409
Molecular Formula:C30H28O4
InChIKey:LXYBRRVOIQFRRL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.3776
Molecular Formula:C16H26
InChIKey:HFCIPFOWCGVSBW-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:226.294
Molecular Formula:C14H10OS
InChIKey:DTUOHSZQXBIZAM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.2038
Molecular Formula:C9H13NO4
InChIKey:JWDOSQSEIRGMAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2154
Molecular Formula:C13H8N2O
InChIKey:BUGHGJJFTXGSSC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.387
Molecular Formula:C10H19NS2
InChIKey:ITOXEXODYMKALC-UHFFFAOYSA-M
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Compound Information
Molecular Weight:611.7
Molecular Formula:C28H20Te2
InChIKey:GLNSZUWYXXYALP-DQSJHHFOSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:UEVFTEJYOXJPNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:DSSYKIVIOFKYAU-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:441.9871
Molecular Formula:C8H12O8Rh2
InChIKey:SYBXSZMNKDOUCA-UHFFFAOYSA-J
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Compound Information
Molecular Weight:193.3284
Molecular Formula:C13H23N
InChIKey:PXSSITHARNEPQQ-SDNWHVSQSA-N
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Compound Information
Molecular Weight:384.6807
Molecular Formula:C28H48
InChIKey:QXUYMZKQIOVSEP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:316.416
Molecular Formula:C21H16OS
InChIKey:NEKDGXSDJMPUPX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:276.4137
Molecular Formula:C18H28O2
InChIKey:YUPOMMHJOHRSQI-ISLYRVAYSA-N
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Compound Information
Molecular Weight:116.224
Molecular Formula:C6H12S
InChIKey:VFTLVPVEAUNVOS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:372.4425
Molecular Formula:C24H25N2P
InChIKey:BBFRHBSFAZBXHF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:426.5329
Molecular Formula:C28H31N2P
InChIKey:BWBBAOPGEROBNN-PBBVDAKRSA-N
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Compound Information
Molecular Weight:100.459
Molecular Formula:ClHO4
InChIKey:VLTRZXGMWDSKGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:SHQSVMDWKBRBGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.245
Molecular Formula:C8H12O2S
InChIKey:DFVBOZQKIKOPMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.303
Molecular Formula:C12H14O2S
InChIKey:GIVZMSJIWMPKEL-LLVKDONJSA-N
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Compound Information
Molecular Weight:172.245
Molecular Formula:C8H12O2S
InChIKey:BWHAFZXYCVTNQI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:368.683
Molecular Formula:C21H28SSi2
InChIKey:GPMRDEZGAOWCNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.2258
Molecular Formula:C11H12N2O
InChIKey:XCMSWSCZZTZCOA-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:420.588
Molecular Formula:C28H20S2
InChIKey:WEHLOVDVXGHBMD-DQSJHHFOSA-N
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Compound Information
Molecular Weight:366.516
Molecular Formula:C23H26O2S
InChIKey:OXZVUYKXNMBWIL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.3728
Molecular Formula:C20H20
InChIKey:RHJOIBZJOIPHFK-FMQUCBEESA-N
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Compound Information
Molecular Weight:119.124
Molecular Formula:C6H5N3
InChIKey:CTRLRINCMYICJO-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:90.121
Molecular Formula:C4H10O2
InChIKey:XTHFKEDIFFGKHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.343
Molecular Formula:C10H20N2O2S
InChIKey:FRAZZUMXDYACQL-OCAPTIKFSA-N
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Compound Information
Molecular Weight:482.616
Molecular Formula:C28H22N2O2S2
InChIKey:GCTQYKDWQGZJNP-SZXQPVLSSA-N
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Compound Information
Molecular Weight:420.588
Molecular Formula:C28H20S2
InChIKey:WEHLOVDVXGHBMD-BYYHNAKLSA-N
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Compound Information
Molecular Weight:316.4791
Molecular Formula:C24H28
InChIKey:AEVSUMKZJKJKQF-WCWDXBQESA-N
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Compound Information
Molecular Weight:132.181
Molecular Formula:C5H8O2S
InChIKey:NZEQJGBUXLFTTB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3887
Molecular Formula:C20H22
InChIKey:HEXRSZKHDIFUOM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.3636
Molecular Formula:C18H20N2O2
InChIKey:GHKNYIKKEJMSCR-IWGRKNQJSA-N
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Compound Information
Molecular Weight:149.1467
Molecular Formula:C8H7NO2
InChIKey:SYZVQXIUVGKCBJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.331
Molecular Formula:C13H16S
InChIKey:QAICPJWHNVFHCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2417
Molecular Formula:C11H14N2O
InChIKey:DIUDVKXAAMPXAS-QBFSEMIESA-N
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Compound Information
Molecular Weight:362.442
Molecular Formula:C22H18O3S
InChIKey:LDXLWUKXIMUXKM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:394.144
Molecular Formula:C18H18Br2
InChIKey:AJJPHVIWEKNDAK-ISLYRVAYSA-N
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Compound Information
Molecular Weight:337.446
Molecular Formula:C21H16O2S
InChIKey:Not Available
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Compound Information
Molecular Weight:154.615
Molecular Formula:C4H7ClO2S
InChIKey:ZJAOQAVOWVZRRT-NSCUHMNNSA-N
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Compound Information
Molecular Weight:282.3783
Molecular Formula:C22H18
InChIKey:ZXJYAYKVSJJDNO-JLHYYAGUSA-N
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Compound Information
Molecular Weight:245.18
Molecular Formula:C13H10Se
InChIKey:OWFCDQUCJXHNOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.127
Molecular Formula:C3H4O3S
InChIKey:AYVTTWZAVAGWEX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.288
Molecular Formula:C9H16S
InChIKey:DODPMKRONNEPQU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:290.4418
Molecular Formula:C22H26
InChIKey:OUUGVNMEZPHDHH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:VUKHQPGJNTXTPY-NSCUHMNNSA-N
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Compound Information
Molecular Weight:366.861
Molecular Formula:C21H15ClO2S
InChIKey:IHFIFLMHXTVJGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:500.1
Molecular Formula:C26H32N2Te
InChIKey:GRQMOHANJIDTDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:454.369
Molecular Formula:C16H24Cl4S3
InChIKey:BTCJUPPZEXSUOI-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:411.312
Molecular Formula:C21H15BrO2S
InChIKey:QZLJZPQYLSQQEF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.309
Molecular Formula:C14H12O2S
InChIKey:ZXQADSQBNWPCCC-OKILXGFUSA-N
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Compound Information
Molecular Weight:301.3386
Molecular Formula:C20H15NO2
InChIKey:CYXPHYXHMRNEBZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.241
Molecular Formula:C9H10S
InChIKey:MJNJRNCGQFMUOC-IONNQARKSA-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:114.2211
Molecular Formula:C4H10N2Si
InChIKey:Not Available
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Compound Information
Molecular Weight:424.517
Molecular Formula:C28H29N2P
InChIKey:WGGIIMDRWJWWAF-ZIADKAODSA-N
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Compound Information
Molecular Weight:160.2157
Molecular Formula:C10H12N2
InChIKey:QHSXXFFNWCTFPC-ZRDIBKRKSA-N
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