Standard Article

The Catalytic Asymmetric Strecker Reaction

  1. Masakatsu Shibasaki,
  2. Motomu Kanai,
  3. Tsuyoshi Mita

Published Online: 16 JUN 2008

DOI: 10.1002/0471264180.or070.01

Organic Reactions

Organic Reactions

How to Cite

Shibasaki, M., Kanai, M. and Mita, T. 2008. The Catalytic Asymmetric Strecker Reaction. Organic Reactions. 70:1:1–119.

Author Information

  1. The University of Tokyo, Graduate School of Pharmaceutical Sciences, Bunkyo-ku, Tokyo, Japan

Publication History

  1. Published Online: 16 JUN 2008

Chemistry Terms

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Abstract

Alpha-amino acids are important building blocks for proteins, peptides, and pharmaceuticals. Among a variety of methods to synthesize optically active alpha-amino acids, the Strecker reaction is one of the simplest and most powerful. This reaction consists of three steps (1) condensation of an aldehyde or ketone with an amine to produce and imine, (2) nucleophilic attack of cyanide on the imine to produce and amino nitrile, and (3) hydrolysis of the amino nitrile to the corresponding alpha-amino acid. These steps can be conducted in one pot. Conversion of the nitrile group to amide, amine, or aldehyde functionalities is also possible. The catalytic promotion and enantiocontrol of the cyanide addition to the imines is the main focus of the Strecker reaction. Therefore, isolated and purified imines are normally used as substrates. The catalyst turnover efficiency and enantioselectivity of this step are intimately related to the electronic and steric characteristics of the substrate imines, with nitrogen substituent greatly contributing to these factors. However, since optically active alpha-amino acids are generally the synthetic target of the catalytic asymmetric Strecker reaction, the accessibilty of the starting imines and ease of final deprotection of the product are also important considerations. This chapter focuses on catalytic enantioselective Strecker and Reissert reactions.

Keywords:

  • Strecker reaction;
  • alpha-amino acids;
  • mechanisms;
  • imines;
  • catalytic asymmetric reactions;
  • enantioselective reactions;
  • Reissert reaction;
  • method comparisons;
  • experimental conditions;
  • aldimines;
  • chiral metal complex;
  • Ketimines;
  • cyanides;
  • toxicity

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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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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:365.3373
Molecular Formula:C21H17FNO2P
InChIKey:CCJDVVFGYDVKOK-BSYVCWPDSA-N
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Compound Information
Molecular Weight:215.2478
Molecular Formula:C13H13NO2
InChIKey:OWSZMZAENZHDLB-LBPRGKRZSA-N
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Compound Information
Molecular Weight:55.0785
Molecular Formula:C3H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:237.361
Molecular Formula:C13H19NOS
InChIKey:HBDRAOQMCVOLDL-SDNWHVSQSA-N
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Compound Information
Molecular Weight:304.331
Molecular Formula:C13H15F3N2OS
InChIKey:HHZROTJQLLZVNN-MPBGBICISA-N
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Compound Information
Molecular Weight:1606.43
Molecular Formula:C96H84O2P4Pd2
InChIKey:DGZZGBPFANNTAX-UHFFFAOYSA-R
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Compound Information
Molecular Weight:143.1852
Molecular Formula:C10H9N
InChIKey:PBYMYAJONQZORL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:285.18
Molecular Formula:C12H17BrN2O
InChIKey:XVIQBTADMQDVNT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:105.9884
Molecular Formula:CNa2O3
InChIKey:CDBYLPFSWZWCQE-UHFFFAOYSA-L
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Compound Information
Molecular Weight:392.3627
Molecular Formula:C22H18FN2O2P
InChIKey:ANHUYRBNRDCCFN-JOCHJYFZSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:268.3071
Molecular Formula:C17H16O3
InChIKey:XAPKUWHYZJZRGF-OUKQBFOZSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:416.3
Molecular Formula:C21H19Cl2N3O2
InChIKey:KAAHAFPVBOYTKD-WBVHZDCISA-N
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Compound Information
Molecular Weight:130.529
Molecular Formula:C5H3ClO2
InChIKey:OFTKFKYVSBNYEC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.9368
Molecular Formula:MnO2
InChIKey:Not Available
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Compound Information
Molecular Weight:529.5907
Molecular Formula:C35H33NP2
InChIKey:GYKMEKRMASHMIH-VSJLXWSYSA-N
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Compound Information
Molecular Weight:255.3117
Molecular Formula:C16H17NO2
InChIKey:MPAHLASUCNUDOC-HNNXBMFYSA-N
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Compound Information
Molecular Weight:480.4682
Molecular Formula:C28H20N2O6
InChIKey:WYOSLLUWZYUSDC-NDEPHWFRSA-N
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Compound Information
Molecular Weight:383.679
Molecular Formula:C16H36O4Zr
InChIKey:BGGIUGXMWNKMCP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:249.3502
Molecular Formula:C18H19N
InChIKey:ZNCHEIPCEFBETR-XDHOZWIPSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:156.1393
Molecular Formula:C6H8N2O3
InChIKey:LAOZSCRCYVBSJA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:360.401
Molecular Formula:C19H22F2N4O
InChIKey:QXWNESOGWFJDFR-PBHICJAKSA-N
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Compound Information
Molecular Weight:219.1605
Molecular Formula:C9H8F3NO2
InChIKey:FUPRWUOOEKSLDF-MRVPVSSYSA-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:206.2841
Molecular Formula:C12H18N2O
InChIKey:RHBRDTJXGNWOGY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:Not Available
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Compound Information
Molecular Weight:406.072
Molecular Formula:C16H24BF4Rh
InChIKey:YIGBBHUYQJBDQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.729
Molecular Formula:C12H17ClN2O
InChIKey:UWBLXSCBMCSQIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:WGQKYBSKWIADBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:385.4981
Molecular Formula:C26H27NO2
InChIKey:HDCBZHATHZHGAC-QHCPKHFHSA-N
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Compound Information
Molecular Weight:302.2821
Molecular Formula:C15H14N2O5
InChIKey:BSNWLIKSXXSKQV-AGIUHOORSA-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:135.07
Molecular Formula:C5H7ArN2
InChIKey:DAOGFTMDHJVLQP-RXMQYKEDSA-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:284.151
Molecular Formula:C15H10BrN
InChIKey:SJBAPHJRDIIHMB-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:Not Available
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InChIKey:Not Available
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Compound Information
Molecular Weight:284.213
Molecular Formula:C12H28O4Ti
InChIKey:VXUYXOFXAQZZMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:399.4418
Molecular Formula:C24H21N3O3
InChIKey:LRNXTKJSKBQEOG-KRWDZBQOSA-N
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Compound Information
Molecular Weight:222.2851
Molecular Formula:C15H14N2
InChIKey:PLGRKAWXNOCOFU-OAHLLOKOSA-N
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Compound Information
Molecular Weight:84.0066
Molecular Formula:CHNaO3
InChIKey:UIIMBOGNXHQVGW-UHFFFAOYSA-M
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Compound Information
Molecular Weight:253.725
Molecular Formula:C13H16ClNO2
InChIKey:HSIDOHKQHALOQR-OVCLIPMQSA-N
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Compound Information
Molecular Weight:191.2264
Molecular Formula:C11H13NO2
InChIKey:ACEPYLDNGYGKDY-SNVBAGLBSA-N
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Compound Information
Molecular Weight:150.1778
Molecular Formula:C8H10N2O
InChIKey:KIYRSYYOVDHSPG-SSDOTTSWSA-N
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Compound Information
Molecular Weight:208.2139
Molecular Formula:C10H12N2O3
InChIKey:NTUPLVQSRKPQED-VGMNWLOBSA-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:185.129
Molecular Formula:C9H9ArN2
InChIKey:AEONJPQWUWMGJS-SECBINFHSA-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:192.1235
Molecular Formula:C6H8O7
InChIKey:KRKNYBCHXYNGOX-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:230.3055
Molecular Formula:C14H18N2O
InChIKey:FZPLWCRMAPIKSF-ZDUSSCGKSA-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:260.29
Molecular Formula:C17H12N2O
InChIKey:ISINJAULVPSFFZ-OAHLLOKOSA-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:512.145
Molecular Formula:CeN6O18
InChIKey:HGTPFADPABTGKP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3059
Molecular Formula:C17H14N2O
InChIKey:DQOBVSPPSFCOLF-OAHLLOKOSA-N
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Compound Information
Molecular Weight:94.1112
Molecular Formula:C6H6O
InChIKey:ISWSIDIOOBJBQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:295.3755
Molecular Formula:C19H21NO2
InChIKey:Not Available
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Compound Information
Molecular Weight:120.034
Molecular Formula:ArH2NO2S
InChIKey:CLHNQOQLSAZCGR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.2521
Molecular Formula:C15H10N2O2
InChIKey:VUJBNBLXFORPGS-GFCCVEGCSA-N
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Compound Information
Molecular Weight:316.07
Molecular Formula:C13H27NSn
InChIKey:GMYAQHAKWKXYHG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.928
Molecular Formula:C4H10BF3O
InChIKey:MZTVMRUDEFSYGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.497
Molecular Formula:C2H3ClO2
InChIKey:Not Available
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Compound Information
Molecular Weight:290.574
Molecular Formula:C8H10F3NO3Zn
InChIKey:DREJEJOLBVFGMU-FXRZFVDSSA-L
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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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:444.116
Molecular Formula:C20H12Br2O2
InChIKey:BRTBEAXHUYEXSY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:302.3267
Molecular Formula:C19H14N2O2
InChIKey:KWBRKCROTGJRQJ-MJGOQNOKSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula: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:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:26.0174
Molecular Formula:CHN
InChIKey:XFXPMWWXUTWYJX-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:98.078
Molecular Formula:H2O4S
InChIKey:QAOWNCQODCNURD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.2515
Molecular Formula:C15H10N2O3
InChIKey:PYYXBOWVBLMWPX-YUTCNCBUSA-N
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Compound Information
Molecular Weight:234.2479
Molecular Formula:C13H14O4
InChIKey:CTNKPEYDCQNTPN-CMDGGOBGSA-N
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Compound Information
Molecular Weight:214.22
Molecular Formula:C12H10N2O2
InChIKey:YCWALPNQBFDXJJ-GFCCVEGCSA-N
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Compound Information
Molecular Weight:157.0911
Molecular Formula:C4H6F3NO2
InChIKey:JBQBFDPQDFDHEC-GSVOUGTGSA-N
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Compound Information
Molecular Weight:131.1729
Molecular Formula:C6H13NO2
InChIKey:NPDBDJFLKKQMCM-BYPYZUCNSA-N
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Compound Information
Molecular Weight:414.285
Molecular Formula:C21H17Cl2N3O2
InChIKey:KRUKPBAOYUIOBP-OAHLLOKOSA-N
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Compound Information
Molecular Weight:293.191
Molecular Formula:C15H14Cl2N2
InChIKey:SHVMKZUEVILMGB-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:261.3593
Molecular Formula:C16H23NO2
InChIKey:QEVBMDXKNLWPAX-INIZCTEOSA-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:296.3651
Molecular Formula:C21H16N2
InChIKey:ZJFFUOZYHVKNDS-FQEVSTJZSA-N
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Compound Information
Molecular Weight:22.98976928
Molecular Formula:HNa
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.2326
Molecular Formula:C11H13NO4
InChIKey:XHGLVMDBZZZXDP-LLVKDONJSA-O
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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:199.156
Molecular Formula:C10H11ArN2
InChIKey:KTDZPJNEXGDULG-SNVBAGLBSA-N
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Compound Information
Molecular Weight:234.2
Molecular Formula:C14H12ArN
InChIKey:HOTWOOWTRSBFDY-LFIBNONCSA-N
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Compound Information
Molecular Weight:172.13
Molecular Formula:C9H10ArN
InChIKey:CLFSHBJWUIDRAP-DHZHZOJOSA-N
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Compound Information
Molecular Weight:231.2143
Molecular Formula:C11H12F3NO
InChIKey:WDPAGNQIJBVMQI-RGURZIINSA-N
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Compound Information
Molecular Weight:383.3961
Molecular Formula:C24H17NO4
InChIKey:ZTPQUSDWZJAQMX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:207.2258
Molecular Formula:C11H13NO3
InChIKey:SZATXVFGSXZJHE-XYOKQWHBSA-N
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Compound Information
Molecular Weight:138.2055
Molecular Formula:CK2O3
InChIKey:BWHMMNNQKKPAPP-UHFFFAOYSA-L
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Compound Information
Molecular Weight:236.3116
Molecular Formula:C16H16N2
InChIKey:HLFDNKVYUJIQJD-MRXNPFEDSA-N
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Compound Information
Molecular Weight:258.2396
Molecular Formula:C12H13F3N2O
InChIKey:ANBJCSHHBRHBIC-WDEREUQCSA-N
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Compound Information
Molecular Weight:155.194
Molecular Formula:C7H8O2S
InChIKey:FXJVNINSOKCNJP-UHFFFAOYSA-M
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Compound Information
Molecular Weight:231.079
Molecular Formula:C7H6ArF3N2O
InChIKey:RLLUCEVZVOUWAR-RXMQYKEDSA-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:86.1754
Molecular Formula:C6H14
InChIKey:VLKZOEOYAKHREP-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:1494.21
Molecular Formula:C88H68O2P4Pd2
InChIKey:QNYKFVMGLCDOMX-UHFFFAOYSA-R
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Compound Information
Molecular Weight:171.034
Molecular Formula:C7H7Br
InChIKey:AGEZXYOZHKGVCM-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:88.1051
Molecular Formula:C4H8O2
InChIKey:XEKOWRVHYACXOJ-UHFFFAOYSA-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:277.306
Molecular Formula:C12H14F3NOS
InChIKey:AWXLZIPEFCRBKW-GANRHZMWSA-N
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Compound Information
Molecular Weight:264.386
Molecular Formula:C14H20N2OS
InChIKey:GRYWGZYIBHSJHP-IKJXHCRLSA-N
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Compound Information
Molecular Weight:261.225
Molecular Formula:C15H13ArN2
InChIKey:MZZVNVPZFBCUJP-AWEZNQCLSA-N
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Compound Information
Molecular Weight:108.045
Molecular Formula:C4H6ArN
InChIKey:VJRVHIGFKRYZPH-GQCTYLIASA-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:42.04
Molecular Formula:CH2N2
InChIKey:YXHKONLOYHBTNS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:290.05
Molecular Formula:C12H28Sn
InChIKey:Not Available
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Compound Information
Molecular Weight:379.4474
Molecular Formula:C20H29NO6
InChIKey:FWVOPPVENYQBEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.3926
Molecular Formula:C11H24O2Si
InChIKey:YTNNMAIKEURUTO-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:141.939
Molecular Formula:CH3I
InChIKey:INQOMBQAUSQDDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.2863
Molecular Formula:C15H15N
InChIKey:JATCPLSBWDXCNE-DTQAZKPQSA-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:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.3388
Molecular Formula:C18H17FN2O
InChIKey:JRUJPVWVHMYIQA-ACJLOTCBSA-N
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Compound Information
Molecular Weight:111.1211
Molecular Formula:C5H10AlN
InChIKey:KWMUAEYVIFJZEB-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:334.51
Molecular Formula:C9H21GdO3
InChIKey:VJLSFXQJAXVOEQ-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:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-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: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:284.2668
Molecular Formula:C15H12N2O4
InChIKey:OLKMQNFUDVXHIZ-UPJWGTAASA-N
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Compound Information
Molecular Weight:240.2573
Molecular Formula:C14H12N2O2
InChIKey:OFICTPJIUIDVCW-AWEZNQCLSA-N
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Compound Information
Molecular Weight:276.3755
Molecular Formula:C19H20N2
InChIKey:FZYWTHRIOYSXPQ-KRWDZBQOSA-N
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Compound Information
Molecular Weight:46.0254
Molecular Formula:CH2O2
InChIKey:BDAGIHXWWSANSR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.635
Molecular Formula:C12H10ClP
InChIKey:XGRJZXREYAXTGV-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:106.508
Molecular Formula:C3H3ClO2
InChIKey:PQLFROTZSIMBKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:276.2894
Molecular Formula:C17H12N2O2
InChIKey:IORLRXPBHUEZMQ-QGZVFWFLSA-N
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Compound Information
Molecular Weight:269.3134
Molecular Formula:C17H16FNO
InChIKey:WKLAZAMSKXVPSP-OHEASWGXSA-N
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Compound Information
Molecular Weight:823.24
Molecular Formula:C48H44O2P2Pd
InChIKey:BHKFDFQIOHGCTM-UHFFFAOYSA-P
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Compound Information
Molecular Weight:236.1992
Molecular Formula:C11H9FN2O3
InChIKey:LXANPKRCLVQAOG-NSHDSACASA-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:120.557
Molecular Formula:C4H10AlCl
InChIKey:YNLAOSYQHBDIKW-UHFFFAOYSA-M
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Compound Information
Molecular Weight:235.2392
Molecular Formula:C11H13N3O3
InChIKey:XCWDWEXBEUNPGD-VIFPVBQESA-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:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-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:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-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:120.976
Molecular Formula:C3H5Br
InChIKey:BHELZAPQIKSEDF-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:123.1525
Molecular Formula:C7H9NO
InChIKey:FEDLEBCVFZMHBP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:62.842
Molecular Formula:CH3BNNa
InChIKey:Not Available
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Compound Information
Molecular Weight:767.14
Molecular Formula:C44H36O2P2Pd
InChIKey:LBTCWWBUYVSVMS-UHFFFAOYSA-P
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Compound Information
Molecular Weight:1155.56
Molecular Formula:C72H60P4Pd
InChIKey:NFHFRUOZVGFOOS-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:380.225
Molecular Formula:C17H15Cl2N3O3
InChIKey:UCKHICKHGAOGAP-UONOGXRCSA-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:36.461
Molecular Formula:ClH
InChIKey:VEXZGXHMUGYJMC-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:381.223
Molecular Formula:C19H13BrN2O2
InChIKey:KPRWUJHUJGDPMQ-IBGZPJMESA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:DKGAVHZHDRPRBM-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:348.5551
Molecular Formula:C19H32N2O2Si
InChIKey:WSIFUGUEVJLNKD-MRXNPFEDSA-N
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Compound Information
Molecular Weight:194.183
Molecular Formula:C7H8NaO3S
InChIKey:KVCGISUBCHHTDD-UHFFFAOYSA-M
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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:33.0299
Molecular Formula:H3NO
InChIKey:AVXURJPOCDRRFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:376.425
Molecular Formula:C15H24N2O7S
InChIKey:DAQAKHDKYAWHCG-RWTHQLGUSA-N
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Compound Information
Molecular Weight:150.603
Molecular Formula:C6H11ClO2
InChIKey:JUUBFHLPTCPVBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.3678
Molecular Formula:C14H26N2O3
InChIKey:UKFJLHLYPJBMCY-NEPJUHHUSA-N
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Compound Information
Molecular Weight:426.348
Molecular Formula:C19H28BrN3O3
InChIKey:CWYAJAQBLZTNJR-AWEZNQCLSA-N
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Compound Information
Molecular Weight:164.2077
Molecular Formula:C8H12N4
InChIKey:OZAIFHULBGXAKX-VAWYXSNFSA-N
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Compound Information
Molecular Weight:221.2524
Molecular Formula:C12H15NO3
InChIKey:PZSDOVPSRMYTQU-MDWZMJQESA-N
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Compound Information
Molecular Weight:227.004
Molecular Formula:C8Cl2N2O2
InChIKey:HZNVUJQVZSTENZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:221.297
Molecular Formula:C16H15N
InChIKey:LBOJYSIDWZQNJS-CVEARBPZSA-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:155.055
Molecular Formula:C5H7ArO3
InChIKey:AMWNQVJZMPQKKB-NSCUHMNNSA-N
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Compound Information
Molecular Weight:99.2065
Molecular Formula:C4H9NSi
InChIKey:Not Available
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Compound Information
Molecular Weight:205.2545
Molecular Formula:C15H11N
InChIKey:LPCWDYWZIWDTCV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:444.116
Molecular Formula:C20H12Br2O2
InChIKey:OORIFUHRGQKYEV-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:419.4368
Molecular Formula:C23H24F3NO3
InChIKey:SCBPGGIGWNGOGC-VPHMPFFRSA-N
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Compound Information
Molecular Weight:150.1778
Molecular Formula:C8H10N2O
InChIKey:FJEVKYZLIRAAKE-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:202.2954
Molecular Formula:C13H18N2
InChIKey:NQEXMNYCHAHCKT-LBPRGKRZSA-N
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Compound Information
Molecular Weight:323.3685
Molecular Formula:C20H22NOP
InChIKey:KOZLDJGLVNQMNN-QZQOTICOSA-N
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Compound Information
Molecular Weight:158.104
Molecular Formula:C8H8ArN
InChIKey:LQQDAUOGWXHPLM-JXMROGBWSA-N
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Compound Information
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:QIFZMFUCASLNCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.566
Molecular Formula:C7H5ClO3
InChIKey:NHQDETIJWKXCTC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:269.3398
Molecular Formula:C20H15N
InChIKey:ZCKRGDXLIAHRLE-KGENOOAVSA-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:258.7
Molecular Formula:C15H11ClO2
InChIKey:IRXSLJNXXZKURP-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:261.225
Molecular Formula:C15H13ArN2
InChIKey:MZZVNVPZFBCUJP-CQSZACIVSA-N
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Compound Information
Molecular Weight:26.0174
Molecular Formula:CHN
InChIKey:XFXPMWWXUTWYJX-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:455.5482
Molecular Formula:C28H29N3O3
InChIKey:XJWUXUDAUHFJIX-NRFANRHFSA-N
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Compound Information
Molecular Weight:381.897
Molecular Formula:C19H28ClN3O3
InChIKey:UQABCTSOYXEZKL-AWEZNQCLSA-N
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Compound Information
Molecular Weight:143.1836
Molecular Formula:C7H13NO2
InChIKey:CXQTTWVBUDFUNO-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:350.3939
Molecular Formula:C21H23N2OP
InChIKey:MFLKWROXVPIKMQ-OAQYLSRUSA-N
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Compound Information
Molecular Weight:302.3267
Molecular Formula:C19H14N2O2
InChIKey:WWRAEQYXDAEQPO-LJQANCHMSA-N
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Compound Information
Molecular Weight:258.2396
Molecular Formula:C12H13F3N2O
InChIKey:ANBJCSHHBRHBIC-QWRGUYRKSA-N
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Compound Information
Molecular Weight:304.331
Molecular Formula:C13H15F3N2OS
InChIKey:HHZROTJQLLZVNN-FKIZINRSSA-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:112.1696
Molecular Formula:C7H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:75.0666
Molecular Formula:C2H5NO2
InChIKey:DHMQDGOQFOQNFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:305.801
Molecular Formula:C20H16ClN
InChIKey:ZOKRSDBOXKNGIS-PXLXIMEGSA-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:139.1949
Molecular Formula:C8H13NO
InChIKey:BFACPIXBZSWFSV-CMDGGOBGSA-N
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Compound Information
Molecular Weight:248.2448
Molecular Formula:C11H15F3N2O
InChIKey:IFKVAQRWDTXVID-MRVPVSSYSA-N
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Compound Information
Molecular Weight:332.826
Molecular Formula:C21H17ClN2
InChIKey:AKDCTBNWLFDSRO-HXUWFJFHSA-N
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Compound Information
Molecular Weight:288.182
Molecular Formula:C15H14BrN
InChIKey:UQDRDQVOQSVTPT-SFQUDFHCSA-N
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Compound Information
Molecular Weight:262.3489
Molecular Formula:C18H18N2
InChIKey:NOUDWMXEOIUPOB-KRWDZBQOSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:LRHPLDYGYMQRHN-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:320.45
Molecular Formula:C17H24N2O2S
InChIKey:SBWXBICFELAPMN-MRXNPFEDSA-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:252.311
Molecular Formula:C16H16N2O
InChIKey:IJUFCQBWJJMVGR-MRXNPFEDSA-N
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Compound Information
Molecular Weight:286.3273
Molecular Formula:C19H14N2O
InChIKey:YRECLDIGZJDNEM-SFHVURJKSA-N
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Compound Information
Molecular Weight:261.3178
Molecular Formula:C18H15NO
InChIKey:NUDJAGRGKRKASN-XMHGGMMESA-N
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Compound Information
Molecular Weight:201.3074
Molecular Formula:C14H19N
InChIKey:AOHMTCJLTJHSDT-NTCAYCPXSA-N
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Compound Information
Molecular Weight:85.1045
Molecular Formula:C4H7NO
InChIKey:MWFMGBPGAXYFAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:277.383
Molecular Formula:C18H15NS
InChIKey:XFAPGONXFWIGBN-XMHGGMMESA-N
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Compound Information
Molecular Weight:255.3117
Molecular Formula:C16H17NO2
InChIKey:RCOQPJOYIKDRIT-INIZCTEOSA-N
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Compound Information
Molecular Weight:277.4033
Molecular Formula:C20H23N
InChIKey:VEXVACFDKDSDNN-LTGZKZEYSA-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:271.3557
Molecular Formula:C20H17N
InChIKey:Not Available
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Compound Information
Molecular Weight:339.342
Molecular Formula:C19H17NO5
InChIKey:FQZUQFMPDPNRMW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:221.297
Molecular Formula:C16H15N
InChIKey:CMKNKHFDZGOMFO-GZTJUZNOSA-N
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Compound Information
Molecular Weight:223.2683
Molecular Formula:C12H17NO3
InChIKey:JVLGDDNDVOSMSI-JTQLQIEISA-N
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Compound Information
Molecular Weight:129.157
Molecular Formula:C6H11NO2
InChIKey:NJLZXBZFWMPWSO-RFZPGFLSSA-N
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Compound Information
Molecular Weight:562.025
Molecular Formula:C3F9InO9S3
InChIKey:Not Available
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Compound Information
Molecular Weight:235.3236
Molecular Formula:C17H17N
InChIKey:KOAHVZHHTXMYNY-VBOCQNEXSA-N
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Compound Information
Molecular Weight:306.4445
Molecular Formula:C21H26N2
InChIKey:WRYOZQZWOVETDV-FQEVSTJZSA-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:305.801
Molecular Formula:C20H16ClN
InChIKey:KPDVCLRKIMCLPL-PXLXIMEGSA-N
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Compound Information
Molecular Weight:324.3408
Molecular Formula:C17H19F3N2O
InChIKey:UQYCIZBYOYLRSV-AWEZNQCLSA-N
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Compound Information
Molecular Weight:264.3648
Molecular Formula:C18H20N2
InChIKey:NSGIHCWCGYZCEE-QGZVFWFLSA-N
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