Standard Article

(R)-2-Hydroxy-2′-methoxy-1,1′-binaphthyl

  1. Kazuaki Ishihara,
  2. Hisashi Yamamoto,
  3. Dominic Fiset

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn00119.pub2

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Ishihara, K., Yamamoto, H. and Fiset, D. 2013. (R)-2-Hydroxy-2′-methoxy-1,1′-binaphthyl. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. Nagoya University, Nagoya, Japan

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

original image

[79547-82-3] C21H16O2 (MW 300.36)

(reagent used as chiral proton source or chiral ligand in several enantioselective reactions)

Physical Data: mp 89–91 °C; [α]D27 +38.9 [c 0.68, THF, 99.3% ee (R)], inline image −44.8 (c 1.4, CHCl3, 99.3% ee (R)]; HPLC [CHIRALCEL OD, 5% i-PrOH–hexane, retention time for the (R)-enantiomer, 25.12 min; for the (S)-enantiomer, 35.47 min]; IR (Nujol) 3478 cm−1; 1H NMR (300 MHz, CDCl3) δ3.81 (s, 3H), 4.91 (s, 1H, exchangeable with D2O), 7.04 (br d, 1H, J = 7.7 Hz), 7.14–7.40 (m, 6H), 7.49 (d, 1H, J = 9.3 Hz), 7.86 (br d, 1H, J = 8.0 Hz), 7.90 (d, 2H, J = 8.5 Hz), 8.06 (d, 1H, J = 9.1 Hz); MS m/z = 300 (M+, 100%).

Solubility: soluble in alcohol, diethyl ether, toluene, and most organic solvents.

Form Supplied in: white solid.

Preparative Methods:(R)-2-hydroxy-2′-methoxy-1,1′-binaphthyl [(R)-BINOL-Me] can be prepared from commercially available (R)-1,1′-bi-2-naphthol [(R)-BINOL] by the use of 1 mol equiv of methyl iodide and sodium hydride in N,N-dimethylformamide (DMF)1a or by the use of Mitsunobu reaction.1b

Purity: recrystallization from toluene–hexane or purification by silica gel column chromatography from a hexane– AcOEt (8:1) eluent.

Handling, Storage, and Precaution: very stable in air.

Featured Compounds

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  1. 1 - 138
Compound Information
Molecular Weight:300.3505
Molecular Formula:C21H16O2
InChIKey:SYSSVMYYSHYMAQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:294.5367
Molecular Formula:C15H26O2Si2
InChIKey:VGWBRZKYHYAIID-MPEURRAXSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:UDDIWRLVXQHDBU-HUSUTMORSA-N
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Compound Information
Molecular Weight:286.324
Molecular Formula:C20H14O2
InChIKey:PPTXVXKCQZKFBN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.52
Molecular Formula:Cl4Sn
InChIKey:Not Available
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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:328.4037
Molecular Formula:C23H20O2
InChIKey:XINNOXGBOUMCOO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:294.5367
Molecular Formula:C15H26O2Si2
InChIKey:MMPFDGLVMGJLFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:YPGCWEMNNLXISK-ZETCQYMHSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:246.4201
Molecular Formula:C15H22OSi
InChIKey:AGNAFTSIVDFRQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:DRLVMOAWNVOSPE-NSHDSACASA-N
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Compound Information
Molecular Weight:295.01
Molecular Formula:C13H20Sn
InChIKey:CHRRAFUDGGVWAI-XQZINANISA-N
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Compound Information
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:CHPXLAPHLQIKCA-VIFPVBQESA-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:335.07
Molecular Formula:C16H24Sn
InChIKey:ZAFNUGMBDZBWCE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2661
Molecular Formula:C13H16
InChIKey:KFODIVKLRHZZTF-CYBMUJFWSA-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:228.2863
Molecular Formula:C15H16O2
InChIKey:LCMDTTHOXHEUIJ-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: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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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:108.642
Molecular Formula:C3H9ClSi
InChIKey:IJOOHPMOJXWVHK-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:236.3929
Molecular Formula:C16H28O
InChIKey:KOICZDDAVPYKKX-NCZFFCEISA-N
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Compound Information
Molecular Weight:236.3929
Molecular Formula:C16H28O
InChIKey:YPZUZOLGGMJZJO-BHUMPYGKSA-N
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Compound Information
Molecular Weight:236.3929
Molecular Formula:C16H28O
InChIKey:YPZUZOLGGMJZJO-RGWLBATNSA-N
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Compound Information
Molecular Weight:236.3929
Molecular Formula:C16H28O
InChIKey:YPZUZOLGGMJZJO-VMIYWNJYSA-N
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Compound Information
Molecular Weight:236.3929
Molecular Formula:C16H28O
InChIKey:YPZUZOLGGMJZJO-ZMLGBVNGSA-N
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Compound Information
Molecular Weight:230.3453
Molecular Formula:C16H22O
InChIKey:GWMVTXXXCDWZQS-SDNWHVSQSA-N
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Compound Information
Molecular Weight:230.3453
Molecular Formula:C16H22O
InChIKey:UDJCZXGJYFBOFE-HOCLYGCPSA-N
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Compound Information
Molecular Weight:230.3453
Molecular Formula:C16H22O
InChIKey:UDJCZXGJYFBOFE-GOEBONIOSA-N
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Compound Information
Molecular Weight:390.43
Molecular Formula:C27H18O3
InChIKey:LGATZCXGWOMONE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.3453
Molecular Formula:C16H22O
InChIKey:OSNYSUVPOZLCFR-NTCAYCPXSA-N
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Compound Information
Molecular Weight:404.5842
Molecular Formula:C28H36O2
InChIKey:LANVSBHRQSQXQI-NKWSUHGFSA-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:356.4984
Molecular Formula:C23H32O3
InChIKey:IRIRWEACXZOQKC-SKWRMQMOSA-N
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Compound Information
Molecular Weight:106.42
Molecular Formula:Pd
InChIKey:KDLHZDBZIXYQEI-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:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-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:482.7715
Molecular Formula:C33H42OSi
InChIKey:GZTAXXMWDFGUCU-OGLMXYFKSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:DVRNZIIXOYTWET-DOTOQJQBSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:NOZWPHLEVRSGCH-MRXNPFEDSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:UTKDXTOHYADWAQ-MRXNPFEDSA-N
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Compound Information
Molecular Weight:261.4621
Molecular Formula:C16H36FN
InChIKey:FPGGTKZVZWFYPV-UHFFFAOYSA-M
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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:394.437
Molecular Formula:C27H19FO2
InChIKey:SDGOGTATDZIGDY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.0233
Molecular Formula:C2HF3O2
InChIKey:DTQVDTLACAAQTR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:286.4516
Molecular Formula:C20H30O
InChIKey:QXNWVJOHUAQHLM-AZUAARDMSA-N
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Compound Information
Molecular Weight:482.7715
Molecular Formula:C33H42OSi
InChIKey:XGKLHMQGXJICRL-MTDXEUNCSA-N
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Compound Information
Molecular Weight:286.4085
Molecular Formula:C19H26O2
InChIKey:GNUXXTMPJILJCB-PKOBYXMFSA-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:61.04
Molecular Formula:CH3NO2
InChIKey:LYGJENNIWJXYER-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:ZQKGWPOFOVJYTD-YQQAZPJKSA-N
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Compound Information
Molecular Weight:310.5161
Molecular Formula:C23H34
InChIKey:MWKLPYLIXRGXIN-KDXVVQHGSA-N
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Compound Information
Molecular Weight:310.5161
Molecular Formula:C23H34
InChIKey:JVDVQORKNFGWKQ-SQOUVECCSA-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:120.1485
Molecular Formula:C8H8O
InChIKey:KWOLFJPFCHCOCG-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:255.501
Molecular Formula:C6H14BaO2
InChIKey:CPUJSIVIXCTVEI-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:410.1
Molecular Formula:C17H14Br2O2
InChIKey:MLGZXFKRYXXISS-BETUJISGSA-N
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Compound Information
Molecular Weight:158.1965
Molecular Formula:C11H10O
InChIKey:IXJYPGQHNBVWDL-ONGXEEELSA-N
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Compound Information
Molecular Weight:64.055
Molecular Formula:C4H9Li
InChIKey:MZRVEZGGRBJDDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:306.284
Molecular Formula:C21H15LiO2
InChIKey:JLKUJEAPMBFNLI-UHFFFAOYSA-M
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Compound Information
Molecular Weight:422.558
Molecular Formula:C30H30O2
InChIKey:HUUDFMUNTPOULG-QOCHGBHMSA-N
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Compound Information
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:Not Available
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Compound Information
Molecular Weight:172.695
Molecular Formula:C10H17Cl
InChIKey:JDMWYZSPJDXSOB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:436.5846
Molecular Formula:C31H32O2
InChIKey:JSCVZTKZTTYYKQ-ATJXCDBQSA-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:526.6641
Molecular Formula:C37H34O3
InChIKey:OLQMMCJOSVGIQP-PNHLSOANSA-N
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Compound Information
Molecular Weight:594.662
Molecular Formula:C38H33F3O3
InChIKey:HDQHYQYSJBICPQ-RWEWTDSWSA-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:98.143
Molecular Formula:C6H10O
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:399.135
Molecular Formula:C23H21GaO2
InChIKey:PRMHJKOLPFGBDX-UHFFFAOYSA-M
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Compound Information
Molecular Weight:475.231
Molecular Formula:C29H25GaO2
InChIKey:ZIKVIHZGEIIRRQ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:441.214
Molecular Formula:C26H27GaO2
InChIKey:RSYRYSGQXQRDHS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:350.735
Molecular Formula:C20H12ClO2P
InChIKey:OVSINNBCLPSKAZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:614.6244
Molecular Formula:C41H27O4P
InChIKey:BTSBFMKYYAOWSV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.669
Molecular Formula:C11H14ClN2P
InChIKey:FEBHKVGIZHAOBC-XHDPSFHLSA-N
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Compound Information
Molecular Weight:504.5586
Molecular Formula:C32H29N2O2P
InChIKey:WJGALKUSULZTDJ-KJICVINHSA-N
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Compound Information
Molecular Weight:252.3077
Molecular Formula:C17H16O2
InChIKey:UVJZGFKZGQSKDV-OUKQBFOZSA-N
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Compound Information
Molecular Weight:178.184
Molecular Formula:C7H7NaO2S
InChIKey:KFZUDNZQQCWGKF-UHFFFAOYSA-M
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Compound Information
Molecular Weight:348.458
Molecular Formula:C22H20O2S
InChIKey:AQZHDBHVKNISCQ-SAPNQHFASA-N
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Compound Information
Molecular Weight:365.89
Molecular Formula:C6H10Cl2Pd2
InChIKey:OTBRMLNJALKXGN-UHFFFAOYSA-L
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Compound Information
Molecular Weight:132.1146
Molecular Formula:C5H8O4
InChIKey:BEPAFCGSDWSTEL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:324.3704
Molecular Formula:C20H20O4
InChIKey:RTUIHIVPYZLWPB-BUHFOSPRSA-N
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Compound Information
Molecular Weight:98.1423
Molecular Formula:C2H3KO2
InChIKey:Not Available
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Compound Information
Molecular Weight:71.121
Molecular Formula:C4H9N
InChIKey:RWRDLPDLKQPQOW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:263.3767
Molecular Formula:C19H21N
InChIKey:XCONIJJQUDHKSN-BUHFOSPRSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:WEHWNAOGRSTTBQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:293.4458
Molecular Formula:C21H27N
InChIKey:UFBLFQWAOWYJRX-FOCLMDBBSA-N
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Compound Information
Molecular Weight:158.1519
Molecular Formula:C7H10O4
InChIKey:ZWWQRMFIZFPUAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.1678
Molecular Formula:C7H12O4
InChIKey:NFOQJNGQQXICBY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:406.072
Molecular Formula:C16H24BF4Rh
InChIKey:Not Available
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Compound Information
Molecular Weight:197.059
Molecular Formula:C7H10Cl2O2
InChIKey:YEVOJQLHVBRLQG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:479.394
Molecular Formula:C28H24Cl2O3
InChIKey:NVUOSCZIDKBJSV-XGCWNURASA-N
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Compound Information
Molecular Weight:479.394
Molecular Formula:C28H24Cl2O3
InChIKey:NVUOSCZIDKBJSV-SOKVYYICSA-N
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Compound Information
Molecular Weight:190.647
Molecular Formula:C7H7ClO2S
InChIKey:YYROPELSRYBVMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1038
Molecular Formula:C4H6N2
InChIKey:MCTWTZJPVLRJOU-UHFFFAOYSA-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:334.669
Molecular Formula:C15H18Cl3NO
InChIKey:RXDMAYSSBPYBFW-BFVZDQMLSA-N
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Compound Information
Molecular Weight:929.0016
Molecular Formula:C63H45O6P
InChIKey:PHLWOTCTRLHSFO-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:118.1757
Molecular Formula:C9H10
InChIKey:QROGIFZRVHSFLM-QHHAFSJGSA-N
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Compound Information
Molecular Weight:28.0101
Molecular Formula:CO
InChIKey:UGFAIRIUMAVXCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:DIBSCKQIZZVKMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:258.0336
Molecular Formula:C7H7O4Rh
InChIKey:BZCAWKOPWNIDOC-FGSKAQBVSA-M
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Compound Information
Molecular Weight:202.1889
Molecular Formula:C12H11OP
InChIKey:ASUOLLHGALPRFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:468.5248
Molecular Formula:C33H25OP
InChIKey:KRWTWSSMURUMDE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.0314
Molecular Formula:C4F6O3
InChIKey:QAEDZJGFFMLHHQ-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:224.51
Molecular Formula:C4H6O4Pd
InChIKey:YJVFFLUZDVXJQI-UHFFFAOYSA-L
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Compound Information
Molecular Weight:578.6183
Molecular Formula:C39H32OP2
InChIKey:CXNIUSPIQKWYAI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.452
Molecular Formula:Cl3HSi
InChIKey:ZDHXKXAHOVTTAH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:993.083
Molecular Formula:C59H42F6O4S2
InChIKey:AFHCONMSXDPXHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:993.083
Molecular Formula:C59H42F6O4S2
InChIKey:SIIZTARCBROVSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1021.136
Molecular Formula:C61H46F6O4S2
InChIKey:KCDZLQLNAFKOOD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1021.136
Molecular Formula:C61H46F6O4S2
InChIKey:GELPBGRQWLFYLJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1049.189
Molecular Formula:C63H50F6O4S2
InChIKey:SZWXVAKPQJRREN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1049.189
Molecular Formula:C63H50F6O4S2
InChIKey:FJXVMYYRKCXJJA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1077.242
Molecular Formula:C65H54F6O4S2
InChIKey:NGXFCZYJIMCDTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1077.242
Molecular Formula:C65H54F6O4S2
InChIKey:VMTCJFTWEAMOMN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1105.295
Molecular Formula:C67H58F6O4S2
InChIKey:OQTWAONQQXSFIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1105.295
Molecular Formula:C67H58F6O4S2
InChIKey:VOAMLDHIFQUKFZ-UHFFFAOYSA-N
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