Standard Article

Cobalt, [5,10,15,20-tetraphenyl-21H,23H-porphinato(2−)-κN21,κN22,κN23,κN24]-

  1. Sanjay K. Singh1,
  2. Steven J. Collier2

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01602

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Singh, S. K. and Collier, S. J. 2013. Cobalt, [5,10,15,20-tetraphenyl-21H,23H-porphinato(2−)-κN21,κN22,κN23,κN24]-. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. 1

    AMRI, Singapore

  2. 2

    Codexis Laboratories Singapore Pte Ltd., Singapore

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

(a catalyst for various oxidation reactions)

Alternative Names: Cobalt 5,10,15,20-tetraphenylporphyrin; Co(II) meso-tetraphenylporphyrinate; (tetraphenylporphinato)cobalt(II); Co(II)TPP.

Physical Data:  >300 °C (dec.).1

Solubility: Soluble in MeOH, CHCl3, and CH2Cl2.

Form Supplied in: Commercially available as a dark brown powder.

Analysis of Reagent Purity: by 1H NMR2 and UV-Vis spectroscopy.3

Preparative Method: Cobalt(II)TPP is commercially available, and synthetic protocols for its preparation are also reported. It is most commonly made via a two-step reaction sequence. First the porphyrin skeleton is constructed, and then the metal is coordinated to the ring of the free porphyrin. However, given the commercial availability of meso-tetraphenylporphyrin (H2TPP), only incorporation of the metal is discussed here. In general, a solution of the Co(II) salt, most commonly CoCl24-6 or Co(OAc)27-9 is heated with a solution of H2TPP to incorporate the metal center. For example, CoCl2 in methanol was added to a solution of H2TPP in CHCl3, and the resulting mixture was heated at reflux for several hours. Upon cooling, the reaction mixture was washed with brine, dried over anhydrous Na2SO4, and the resulting solution was evaporated to dryness. Recrystallization from CHCl3/hexanes afforded Co(II)TPP (eq 1).10 A mixture of Co(Cl)2·6H2O, NaOAc, and TPP in refluxing AcOH also provides high yields of Co(II)TPP.11 Use of microwave irradiation with either DMF8 or the ionic liquid [bmim][BF4]6 as solvent provides Co(II)TPP with very short reaction times. A one-pot method for the synthesis of Co(II)TPP starting from pyrrole and benzaldehyde has also been reported.5

original image(1)

Handling, Storage, and Precautions: stable at room temperature.

Featured Compounds

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  1. 1 - 130
Compound Information
Molecular Weight:614.7358
Molecular Formula:C44H30N4
InChIKey:YNHJECZULSZAQK-LWQDQPMZSA-N
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Compound Information
Molecular Weight:671.6531
Molecular Formula:C44H28CoN4
InChIKey:LSZLYWSRWXFMOI-DAJBKUBHSA-N
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Compound Information
Molecular Weight:129.839
Molecular Formula:Cl2Co
InChIKey:Not Available
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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:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-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:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:WVDDGKGOMKODPV-UHFFFAOYSA-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:84.1595
Molecular Formula:C6H12
InChIKey:Not Available
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:HGCIXCUEYOPUTN-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:72.1057
Molecular Formula:C4H8O
InChIKey:AMIMRNSIRUDHCM-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:168.2328
Molecular Formula:C10H16O2
InChIKey:VCJFBQACKACAPP-BLHCBFLLSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:FKIPMHAKVUNNPS-BQYQJAHWSA-N
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Compound Information
Molecular Weight:116.2767
Molecular Formula:C6H16Si
InChIKey:AQRLNPVMDITEJU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.095
Molecular Formula:C3H8O
InChIKey:KFZMGEQAYNKOFK-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:122.1677
Molecular Formula:C7H10N2
InChIKey:VHYFNPMBLIVWCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:HJOVHMDZYOCNQW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:AYJXHIDNNLJQDT-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:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-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:80.1277
Molecular Formula:C6H8
InChIKey:Not Available
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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:198.2158
Molecular Formula:C10H14O4
InChIKey:VDGAZJWPUNUMLR-UWVGGRQHSA-N
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Compound Information
Molecular Weight:198.2158
Molecular Formula:C10H14O4
InChIKey:VDGAZJWPUNUMLR-AOOOYVTPSA-N
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Compound Information
Molecular Weight:224.51
Molecular Formula:C4H6O4Pd
InChIKey:YJVFFLUZDVXJQI-UHFFFAOYSA-L
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Compound Information
Molecular Weight:110.1106
Molecular Formula:C6H6O2
InChIKey:QIGBRXMKCJKVMJ-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:88.1051
Molecular Formula:C4H8O2
InChIKey:XEKOWRVHYACXOJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:GWYPDXLJACEENP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.2423
Molecular Formula:C11H16O4
InChIKey:UADLQVRRAURCBG-PHIMTYICSA-N
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Compound Information
Molecular Weight:212.2423
Molecular Formula:C11H16O4
InChIKey:UADLQVRRAURCBG-GHMZBOCLSA-N
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Compound Information
Molecular Weight:108.0948
Molecular Formula:C6H4O2
InChIKey:AZQWKYJCGOJGHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1699
Molecular Formula:C10H8O
InChIKey:KJCVRFUGPWSIIH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.1528
Molecular Formula:C10H6O3
InChIKey:CSFWPUWCSPOLJW-UHFFFAOYSA-N
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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:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:144.1699
Molecular Formula:C10H8O
InChIKey:JWAZRIHNYRIHIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2292
Molecular Formula:C14H10
InChIKey:MWPLVEDNUUSJAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2121
Molecular Formula:C14H8O2
InChIKey:RZVHIXYEVGDQDX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:740.087
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:274.3117
Molecular Formula:C16H18O4
InChIKey:RKRWHUXXTPLPAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:ZRSNZINYAWTAHE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:272.2958
Molecular Formula:C16H16O4
InChIKey:Not Available
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Compound Information
Molecular Weight:214.2631
Molecular Formula:C13H14N2O
InChIKey:CMNUYDSETOTBDE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.256
Molecular Formula:C12H8OS
InChIKey:NGDPCAMPVQYGCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.257
Molecular Formula:C12H8S
InChIKey:IYYZUPMFVPLQIF-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:149.1467
Molecular Formula:C8H7NO2
InChIKey:YFZHODLXYNDBSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.1607
Molecular Formula:C8H8N2O3
InChIKey:GFNBZVFYQPTWRK-RMKNXTFCSA-N
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Compound Information
Molecular Weight:165.1461
Molecular Formula:C8H7NO3
InChIKey:YQYGPGKTNQNXMH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:103.1198
Molecular Formula:C4H9NO2
InChIKey:IOGXOCVLYRDXLW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1852
Molecular Formula:C10H10O2
InChIKey:NUMHUJZXKZKUBN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:193.1992
Molecular Formula:C10H11NO3
InChIKey:OKULDYWFOINMTE-YRNVUSSQSA-N
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Compound Information
Molecular Weight:178.1846
Molecular Formula:C10H10O3
InChIKey:QNTSFZXGLAHYLC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.594
Molecular Formula:C8H7Cl
InChIKey:KTZVZZJJVJQZHV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:169.608
Molecular Formula:C8H8ClNO
InChIKey:KAXTWDXRCMICEQ-POHAHGRESA-N
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Compound Information
Molecular Weight:154.594
Molecular Formula:C8H7ClO
InChIKey:BUZYGTVTZYSBCU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:JHNRZXQVBKRYKN-VQHVLOKHSA-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:118.1757
Molecular Formula:C9H10
InChIKey:JLBJTVDPSNHSKJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:149.1897
Molecular Formula:C9H11NO
InChIKey:XAAUYUMBCPRWED-CSKARUKUSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:GNKZMNRKLCTJAY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:KBLWLMPSVYBVDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.2203
Molecular Formula:C9H15NO3
InChIKey:BFTLULGDLBCOIB-YFHOEESVSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:GWCTUKHUBWMAMI-GQCTYLIASA-N
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Compound Information
Molecular Weight:173.2096
Molecular Formula:C8H15NO3
InChIKey:NVOQPUWHJBRFKO-CLFYSBASSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:Not Available
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Compound Information
Molecular Weight:171.2368
Molecular Formula:C9H17NO2
InChIKey:DCVKYISODMBDSI-KTKRTIGZSA-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:129.157
Molecular Formula:C6H11NO2
InChIKey:GSQUWYUOUSOTQH-SREVYHEPSA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:MMFCJPPRCYDLLZ-CMDGGOBGSA-N
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Compound Information
Molecular Weight:185.2634
Molecular Formula:C10H19NO2
InChIKey:IGGQVXCZCLURRD-KHPPLWFESA-N
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Compound Information
Molecular Weight:284.3927
Molecular Formula:C19H24O2
InChIKey:YEWSFUFGMDJFFG-WFZCBACDSA-N
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Compound Information
Molecular Weight:315.4067
Molecular Formula:C19H25NO3
InChIKey:ALPVAQARJWKHPM-WIOLPFNZSA-N
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Compound Information
Molecular Weight:282.3768
Molecular Formula:C19H22O2
InChIKey:DKVSUQWCZQBWCP-WFZCBACDSA-N
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Compound Information
Molecular Weight:313.3908
Molecular Formula:C19H23NO3
InChIKey:RJNIREGRIOZKSX-WIOLPFNZSA-N
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Compound Information
Molecular Weight:199.2469
Molecular Formula:C10H17NO3
InChIKey:QFGXCHPKJMHBAN-OHFYBLQUSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:FZWWRLGSAKEQQI-OWZSENBOSA-N
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Compound Information
Molecular Weight:247.2897
Molecular Formula:C14H17NO3
InChIKey:FENMWWVCBUMKOI-JWIYKGGMSA-N
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Compound Information
Molecular Weight:244.3288
Molecular Formula:C16H20O2
InChIKey:TUNCIMCBFXQXSJ-ZYUHXDNHSA-N
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Compound Information
Molecular Weight:275.3428
Molecular Formula:C16H21NO3
InChIKey:QQUPFMQUQZTWSU-UDUOVWRXSA-N
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Compound Information
Molecular Weight:335.3963
Molecular Formula:C21H21NO3
InChIKey:NCMMCCKJJSTCGX-LIRSHIKOSA-N
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Compound Information
Molecular Weight:366.4104
Molecular Formula:C21H22N2O4
InChIKey:IJGPZIXUGOYGLE-BDNXVVLJSA-N
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Compound Information
Molecular Weight:237.2518
Molecular Formula:C12H15NO4
InChIKey:VRQYWTUVYZDTNC-YTXTXJHMSA-N
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Compound Information
Molecular Weight:268.2658
Molecular Formula:C12H16N2O5
InChIKey:PQWRYUXKFWPXOQ-GKPGWJKISA-N
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Compound Information
Molecular Weight:207.3119
Molecular Formula:C13H21NO
InChIKey:OXAHIKPZMCZCEX-YIORLJKJSA-N
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Compound Information
Molecular Weight:238.326
Molecular Formula:C13H22N2O2
InChIKey:MXPQNQWZYPPJAG-BYKJOZEVSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:RPKNZSIKTLYYKD-BSWSSELBSA-N
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Compound Information
Molecular Weight:183.2475
Molecular Formula:C10H17NO2
InChIKey:FXHNXIYFOXYTPB-VEQVDCDKSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:BATOPAZDIZEVQF-MQQKCMAXSA-N
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Compound Information
Molecular Weight:127.1412
Molecular Formula:C6H9NO2
InChIKey:XGZSXDRTYRGBRO-FDTUMDBZSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:164.1216
Molecular Formula:C6H4N4O2
InChIKey:CZZVSJPFJBUBDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.2185
Molecular Formula:C13H10
InChIKey:NIHNNTQXNPWCJQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:300.3108
Molecular Formula:C19H12N2O2
InChIKey:JGQXGMZVBXQSJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:WPDAVTSOEQEGMS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:448.4296
Molecular Formula:C26H16N4O4
InChIKey:PNYYZCPCURRELI-ZQZMJUSDSA-N
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Compound Information
Molecular Weight:119.1836
Molecular Formula:C9H12
InChIKey:NCCMLVRJQAWFKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.2997
Molecular Formula:C15H16N2O2
InChIKey:KYZANBCMYXKVQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.2182
Molecular Formula:C10H14
InChIKey:ZJMWRROPUADPEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.3263
Molecular Formula:C16H18N2O2
InChIKey:LYBUXVREFNBQRB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:YNQLUTRBYVCPMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.2732
Molecular Formula:C14H14N2O2
InChIKey:QJEBNIICHOYJDH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.2573
Molecular Formula:C14H12N2O2
InChIKey:NOFYGCNWOSJRBF-RVDMUPIBSA-N
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Compound Information
Molecular Weight:168.2344
Molecular Formula:C13H12
InChIKey:CZZYITDELCSZES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:304.3425
Molecular Formula:C19H16N2O2
InChIKey:RCFJRHRJIZVTEP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:302.3267
Molecular Formula:C19H14N2O2
InChIKey:UBFYKRUAAWHJTG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.2307
Molecular Formula:C13H10N2O2
InChIKey:NYJOAZXGKLCRSV-GXDHUFHOSA-N
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Compound Information
Molecular Weight:153.569
Molecular Formula:C6H4ClN3
InChIKey:HZVGOEUGZJFTNN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.678
Molecular Formula:C13H10ClN
InChIKey:NWCAQYVAHZWHIO-XNTDXEJSSA-N
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Compound Information
Molecular Weight:149.15
Molecular Formula:C7H7N3O
InChIKey:PPKDSHDYUBDVKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.2591
Molecular Formula:C14H13NO
InChIKey:Not Available
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Compound Information
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:KKKHINJUWJIDIH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:VIMLGHZWCCDDGQ-OCAPTIKFSA-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:164.2011
Molecular Formula:C10H12O2
InChIKey:GMKWCKAQJHUARU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:IFYRNPQCRFNEBN-UHFFFAOYSA-N
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