Standard Article

3,5-Di-tert-butyl-1,2-benzoquinone

  1. Vaclav Horak1,
  2. Youco Mermersky1,
  3. Vijay Nair2,3,
  4. Ani Deepthi2,3

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rd057.pub2

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Horak, V., Mermersky, Y., Nair, V. and Deepthi, A. 2013. 3,5-Di-tert-butyl-1,2-benzoquinone. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. 1

    Georgetown University, Washington, DC, USA

  2. 2

    National Institute for Interdisciplinary Science and Technology (CSIR), Thiruvananthapuram, India

  3. 3

    University of Kerala, Thiruvananthapuram, India

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

original image

[3383-21-9] C14H20O2 (MW 220.31)

(reacts with primary amines to give different products depending on the alkyl substituent: benzoxazoles from primary amines and α-amino acids; ketones from s-alkyl primary amines; dioxazepines from cyclopropylamines; aromatic aldehydes from vic-aminobenzyl alcohols; skatole from tryptophan)

Alternate Name: DTBBQ.

Physical Data: mp 114–115 °C.

Solubility: sol most organic solvents; insol water.

Form Supplied in: dark red needles; commercially available.

Analysis of Reagent Purity: by TLC (silica gel plate Bakerflex-IBF, hexane/methylene chloride (1∶1), Rf 0.53);5 UV–vis λmax 402 (ε = 821).3

Preparative Methods: by PbO2 oxidation of 3,5-di-t-butylcatechol;7 by chemical and electrochemical oxidation of 3,5-di-t-butyl-2-hydroxyaniline.3

Purification: recrystallization from toluene or by vacuum sublimation.

Handling, Storage, and Precautions: avoid exposure to light; toxicity unknown.

Featured Compounds

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  1. 1 - 100
Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:NOUZOVBGCDDMSX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:61.0831
Molecular Formula:C2H7NO
InChIKey:HZAXFHJVJLSVMW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.3593
Molecular Formula:C16H23NO2
InChIKey:KLDYWWYTCUAAED-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:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1796
Molecular Formula:C8H11N
InChIKey:BHHGXPLMPWCGHP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:321.4559
Molecular Formula:C22H27NO
InChIKey:TXXIPWRVVZNPHD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:99.1741
Molecular Formula:C6H13N
InChIKey:PAFZNILMFXTMIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:221.3385
Molecular Formula:C14H23NO
InChIKey:IVVMNEWWVJXCLX-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:421.6148
Molecular Formula:C28H39NO2
InChIKey:OGSCXTIYBPFZTR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:133.1903
Molecular Formula:C9H11N
InChIKey:OYRBDGKUVUVWRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:335.4825
Molecular Formula:C23H29NO
InChIKey:NBEXHARWQJTECP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:335.4825
Molecular Formula:C23H29NO
InChIKey:ACGFNIHNOUIKLE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.323
Molecular Formula:C11H17NO2S
InChIKey:BPJSOEZUCFZROW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.214
Molecular Formula:C8H8OS
InChIKey:QRVYABWJVXXOTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.2316
Molecular Formula:C10H15NO2
InChIKey:XIBKRBZBFLHCOW-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: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:204.2252
Molecular Formula:C11H12N2O2
InChIKey:Not Available
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Compound Information
Molecular Weight:131.1745
Molecular Formula:C9H9N
InChIKey:ZFRKQXVRDFCRJG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:45.0837
Molecular Formula:C2H7N
InChIKey:Not Available
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Compound Information
Molecular Weight:249.3917
Molecular Formula:C16H27NO
InChIKey:XZFBFWBVNSIGLQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.1368
Molecular Formula:C4H11N
InChIKey:HPNMFZURTQLUMO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:277.4448
Molecular Formula:C18H31NO
InChIKey:NHAMIIMXMWRAFJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:85.1475
Molecular Formula:C5H11N
InChIKey:Not Available
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Compound Information
Molecular Weight:289.4555
Molecular Formula:C19H31NO
InChIKey:FHMDTLUHRKJASB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:87.1204
Molecular Formula:C4H9NO
InChIKey:YNAVUWVOSKDBBP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:291.4284
Molecular Formula:C18H29NO2
InChIKey:FTSKCEBKLSQHBJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2316
Molecular Formula:C10H14N2
InChIKey:YZTJYBJCZXZGCT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:366.5396
Molecular Formula:C24H34N2O
InChIKey:JLMFDLRAWNGBOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.3541
Molecular Formula:C17H20N2
InChIKey:NWVNXDKZIQLBNM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:456.6621
Molecular Formula:C31H40N2O
InChIKey:WNIBKIHXARTUBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1356
Molecular Formula:C4H10N2
InChIKey:GLUUGHFHXGJENI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:494.7516
Molecular Formula:C32H50N2O2
InChIKey:HVAMYFKNXSVBCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.3038
Molecular Formula:C18H14
InChIKey:BULLHRADHZGONG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:450.6112
Molecular Formula:C32H34O2
InChIKey:SAQYQWZVFVEUEV-BHWQQCGTSA-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:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:324.4565
Molecular Formula:C22H28O2
InChIKey:GSDLQLMAFMZTST-DVUUYJHRSA-N
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Compound Information
Molecular Weight:268.3502
Molecular Formula:C18H20O2
InChIKey:AVLHPXMYTYNPLL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.928
Molecular Formula:C4H10BF3O
InChIKey:KZMGYPLQYOPHEL-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:102.1332
Molecular Formula:C8H6
InChIKey:UEXCJVNBTNXOEH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:322.4406
Molecular Formula:C22H26O2
InChIKey:MPWGUENBCPZSCI-VGOFRKELSA-N
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Compound Information
Molecular Weight:322.4406
Molecular Formula:C22H26O2
InChIKey:QMUACJAISKEMJV-QRQCRPRQSA-N
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Compound Information
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:VANVKDJJYBYKEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:352.5097
Molecular Formula:C24H32O2
InChIKey:QUENEQHFAMFSAB-UXHICEINSA-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:384.4685
Molecular Formula:C29H20O
InChIKey:Not Available
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Compound Information
Molecular Weight:604.7759
Molecular Formula:C43H40O3
InChIKey:FPNWLQOFOHDAHR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:444.7268
Molecular Formula:C29H40N2Si
InChIKey:KETIQWGEOUNMFJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:665.0342
Molecular Formula:C43H60N2O2Si
InChIKey:HGYUFIONCVQNRO-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:169.608
Molecular Formula:C8H8ClNO
InChIKey:CWLYVEMDVAPUMV-NTMALXAHSA-N
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Compound Information
Molecular Weight:353.4547
Molecular Formula:C22H27NO3
InChIKey:GRUXLGCUMXAOBJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:353.4547
Molecular Formula:C22H27NO3
InChIKey:UPAWFPZMZAHFNL-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:202.2093
Molecular Formula:C11H10N2O2
InChIKey:CKVPGBCNCMKWTC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:394.5033
Molecular Formula:C25H30O4
InChIKey:VCUSLVNLNUDGOG-PIHPCUNDSA-N
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Compound Information
Molecular Weight:212.2439
Molecular Formula:C14H12O2
InChIKey:JTTIGLYPLMYHAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.1121
Molecular Formula:C5H6N2O4
InChIKey:UFAZHCVBGMSJHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:486.5541
Molecular Formula:C27H34O8
InChIKey:KYAPFTLEWBZUHX-OSMGYRLQSA-N
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Compound Information
Molecular Weight:486.5541
Molecular Formula:C27H34O8
InChIKey:QNHCCDXKPWKUEI-OSMGYRLQSA-N
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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:109.1689
Molecular Formula:C7H11N
InChIKey:XYZMOVWWVXBHDP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1094
Molecular Formula:C6H6O4
InChIKey:VHILMKFSCRWWIJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:471.5858
Molecular Formula:C27H37NO6
InChIKey:KFOLTRBPRXJPPL-SLMZUGIISA-N
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Compound Information
Molecular Weight:471.5858
Molecular Formula:C27H37NO6
InChIKey:BMQZDIXPUQMLNB-SLMZUGIISA-N
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Compound Information
Molecular Weight:160.1711
Molecular Formula:C6H12N2O3
InChIKey:HEGRRSZUIAOCHY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.0785
Molecular Formula:C3H7O2
InChIKey:IJLLVMKZQUARBE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:436.4954
Molecular Formula:C23H32O8
InChIKey:QPFWKBXPQSZFDC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:436.4954
Molecular Formula:C23H32O8
InChIKey:GIEZPDKRDHEHNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.1586
Molecular Formula:C9H7N
InChIKey:AWJUIBRHMBBTKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:491.5754
Molecular Formula:C29H33NO6
InChIKey:TZWVGVWGVKDUQH-OEXUWWALSA-N
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Compound Information
Molecular Weight:491.5754
Molecular Formula:C29H33NO6
InChIKey:LAKNHWQGJFYEIL-OEXUWWALSA-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:137.333
Molecular Formula:Cl3P
InChIKey:FAIAAWCVCHQXDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:359.656
Molecular Formula:C14H22Cl3O2P
InChIKey:QOVRUTVSWGCASX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:362.4168
Molecular Formula:C20H26O6
InChIKey:XLSACYLPDOXPCF-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:353.3961
Molecular Formula:C24H20NP
InChIKey:PTLOPIHJOPWUNN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:295.4186
Molecular Formula:C20H25NO
InChIKey:QJFGFKMTUWBTJU-HEHNFIMWSA-N
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Compound Information
Molecular Weight:386.5292
Molecular Formula:C26H30N2O
InChIKey:JCFRPUWHBOMGRB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:626.248
Molecular Formula:C24H26BBiF4O
InChIKey:OXNKVGRULREDQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:318.4504
Molecular Formula:C20H30O3
InChIKey:CFGXZZHVLBVXDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:416.5934
Molecular Formula:C26H40O4
InChIKey:PBHSOAZRCGHSDT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.212
Molecular Formula:C4H9KO
InChIKey:LPNYRYFBWFDTMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.4203
Molecular Formula:C12H26Si
InChIKey:AKQHUJRZKBYZLC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:362.6214
Molecular Formula:C22H38O2Si
InChIKey:UNJCUAOHHYNGIM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:319.218
Molecular Formula:I2Zn
InChIKey:UAYWVJHJZHQCIE-UHFFFAOYSA-L
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Compound Information
Molecular Weight:114.2609
Molecular Formula:C6H14Si
InChIKey:HYWCXWRMUZYRPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:SBNXVUJSMPOKEL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.315
Molecular Formula:Cl2Zn
InChIKey:Not Available
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Compound Information
Molecular Weight:502.373
Molecular Formula:C9H15Br3Ga2
InChIKey:LLWHSHPUQJIPPV-UHFFFAOYSA-K
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Compound Information
Molecular Weight:262.3871
Molecular Formula:C17H26O2
InChIKey:CMRVWUYKZXQQTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:149.89424
Molecular Formula:INa
InChIKey:FVAUCKIRQBBSSJ-UHFFFAOYSA-M
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