Standard Article

2,2,2-Trifluoro-1-methoxyethanol

  1. G. K. Surya Prakash,
  2. Zhe Zhang,
  3. Fang Wang

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01620

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Prakash, G. K. S., Zhang, Z. and Wang, F. 2013. 2,2,2-Trifluoro-1-methoxyethanol. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. University of Southern California, Los Angeles, CA, USA

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

original image

[431-46-9] C3H5F3O2 (MW 130.07)

InChI = 1S/C3H5F3O2/c1-8-2(7)3(4,5)6/h2,7H,1H3

InChIKey = GWTBCUWZAVMAQV-UHFFFAOYSA-N

(a CF3-containing synthon with various synthetic applications)

Alternate Names: fluoral methyl hemiacetal; trifluoroacetaldehyde methyl hemiacetal.

Physical Data: bp 96.0–96.5 °C (729 Torr).1 d20 1.326 g cm−3.

Solubility: soluble in H2O (and rapidly hydrolyzes to trifluoroacetaldehyde hydrate), THF, diethyl ether, CH2Cl2, MeOH, and other organic solvents.

Form Supplied in: colorless liquid; commercially available.

Purification: by distillation.

Handling, Storage, and Precautions: avoid contact with skin and eyes. Avoid inhalation. Moisture sensitive. Recommended to be stored under anhydrous conditions in a refrigerator. Use in a well-ventilated fume hood.

Preparative Methods: the title compound was originally prepared through the reaction of trifluoroacetaldehyde (CF3CHO) with anhydrous methyl alcohol (CH3OH) at −78 °C. The resulting product was further purified by distillation through a semimicro fractionating column (eq 1).1

original image(1)

Alternatively, the preparation of trifluoroacetaldehyde methyl hemiacetal (CF3CH(OH)OMe) was achieved via the reaction between tetramethoxysilane and trifluoroacetaldehyde–hydrogen fluoride complex (CF3CHO·HF). The latter was achieved by the gas-phase halogen exchange of chloral (CCl3CHO) with excess hydrogen fluoride, namely a Swarts-type reaction (eq 2).2, 3

original image(2)

It has been shown that the CF3CH(OH)OMe could also be prepared through the direct nucleophilic trifluoromethylation of methyl formates with fluoroform (eq 3).4

original image(3)

Featured Compounds

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  1. 1 - 134
Compound Information
Molecular Weight:130.0658
Molecular Formula:C3H5F3O2
InChIKey:GWTBCUWZAVMAQV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.0239
Molecular Formula:C2HF3O
InChIKey:JVTSHOJDBRTPHD-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:147.388
Molecular Formula:C2HCl3O
InChIKey:HFFLGKNGCAIQMO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:20.00634
Molecular Formula:FH
InChIKey:KRHYYFGTRYWZRS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.0303
Molecular Formula:C2H2F4O
InChIKey:HZPZMZOSTCWEPB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2212
Molecular Formula:C4H12O4Si
InChIKey:Not Available
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:Not Available
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Compound Information
Molecular Weight:69.0059
Molecular Formula:CHF3
InChIKey:NYKUFCUBMAFLFF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.4831
Molecular Formula:C6H18KNSi2
InChIKey:IUBQJLUDMLPAGT-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:117.1479
Molecular Formula:C8H7N
InChIKey:SIKJAQJRHWYJAI-UHFFFAOYSA-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
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Compound Information
Molecular Weight:752.9589
Molecular Formula:C50H57O4P
InChIKey:AGQAQYPGJDBIQR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.1525
Molecular Formula:C7H9NO
InChIKey:BHAAPTBBJKJZER-UHFFFAOYSA-N
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Compound Information
Molecular Weight:235.203
Molecular Formula:C10H12F3NO2
InChIKey:ISIYFPNINBKFAI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.202
Molecular Formula:C7H8O3S
InChIKey:JOXIMZWYDAKGHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.1678
Molecular Formula:C7H12O4
InChIKey:IYXGSMUGOJNHAZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:363.3289
Molecular Formula:C16H20F3NO5
InChIKey:TUTZBHWVYGSWAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.3065
Molecular Formula:C17H16O4
InChIKey:RYFCSKVXWRJEOB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:487.4677
Molecular Formula:C26H24F3NO5
InChIKey:YFLWOFIHTNQXFH-UHFFFAOYSA-N
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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:335.2757
Molecular Formula:C14H16F3NO5
InChIKey:RLIXQJAWXGVDOR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.1764
Molecular Formula:C9H11F3O4
InChIKey:RMSGBTXDUFHCEV-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:Not Available
Molecular Formula:Not Available
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Molecular Weight:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:364.3152
Molecular Formula:C19H15F3O4
InChIKey:ULTLLHBHZNPMIL-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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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:212.1233
Molecular Formula:C7H7F3O4
InChIKey:ICGXEJXIILKMIG-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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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:225.2082
Molecular Formula:C9H14F3NO2
InChIKey:VXFIAJALPYGHMZ-ZETCQYMHSA-N
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Compound Information
Molecular Weight:120.368
Molecular Formula:MgO4S
InChIKey:CSNNHWWHGAXBCP-UHFFFAOYSA-L
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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:1.00794
Molecular Formula:H
InChIKey:GPRLSGONYQIRFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:213.1975
Molecular Formula:C8H14F3NO2
InChIKey:QDYJCSPZDOHOIG-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:301.3041
Molecular Formula:C15H18F3NO2
InChIKey:XBPQSTUNDTVOFA-OLZOCXBDSA-N
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Compound Information
Molecular Weight:171.217
Molecular Formula:C7H9NO2S
InChIKey:LMYRWZFENFIFIT-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:189.679
Molecular Formula:Cl4Ti
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:118.97
Molecular Formula:Cl2OS
InChIKey:FYSNRJHAOHDILO-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:73.1368
Molecular Formula:C4H11N
InChIKey:DAZXVJBJRMWXJP-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:140.2584
Molecular Formula:C6H12N2Si
InChIKey:YKFRUJSEPGHZFJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:257.3254
Molecular Formula:C9H18F3NO2Si
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:151.90385
Molecular Formula:CsF
InChIKey:Not Available
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Compound Information
Molecular Weight:176.2581
Molecular Formula:C11H16N2
InChIKey:IQXXEPZFOOTTBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:346.4632
Molecular Formula:C16H25F3N2OSi
InChIKey:AZONQAJEJDTHSU-UHFFFAOYSA-N
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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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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:222.258
Molecular Formula:C4H9F3O3SSi
InChIKey:FTVLMFQEYACZNP-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:89.1362
Molecular Formula:C4H11NO
InChIKey:Not Available
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Compound Information
Molecular Weight:169.1449
Molecular Formula:C6H10F3NO
InChIKey:KENMAISXTXACCY-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:103.1628
Molecular Formula:C5H13NO
InChIKey:NWYYWIJOWOLJNR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.1715
Molecular Formula:C7H12F3NO
InChIKey:JLMJFFHXSADZTF-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:117.1894
Molecular Formula:C6H15NO
InChIKey:Not Available
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Compound Information
Molecular Weight:197.1981
Molecular Formula:C8H14F3NO
InChIKey:IYTIXZWGGKYGOR-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:117.1894
Molecular Formula:C6H15NO
InChIKey:JBULSURVMXPBNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:197.1981
Molecular Formula:C8H14F3NO
InChIKey:HPXXXKGDPAYBCW-UHFFFAOYSA-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
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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:135.228
Molecular Formula:C5H13NOS
InChIKey:MIQJGZAEWQQAPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.236
Molecular Formula:C7H12F3NOS
InChIKey:AZIGFBFORSEYND-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:181.2331
Molecular Formula:C13H11N
InChIKey:SXZIXHOMFPUIRK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:351.4382
Molecular Formula:C18H20F3NOSi
InChIKey:JWWPICQAVQFYBQ-UHFFFAOYSA-N
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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:175.58
Molecular Formula:C5H9ClF3N
InChIKey:NTXOWAXRHYWWNJ-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:36.461
Molecular Formula:ClH
InChIKey:VEXZGXHMUGYJMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.3
Molecular Formula:C3H5KOS2
InChIKey:JCBJVAJGLKENNC-UHFFFAOYSA-M
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:262.27
Molecular Formula:C7H9F3O3S2
InChIKey:GBJCWNXHXCSAMR-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:238.679
Molecular Formula:C5H6ClF3OS2
InChIKey:KYELFCXRGPCIRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.239
Molecular Formula:Cl5P
InChIKey:UHZYTMXLRWXGPK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:68.0773
Molecular Formula:C3H4N2
InChIKey:RAXXELZNTBOGNW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1012
Molecular Formula:C5H5F3N2O
InChIKey:UEYYZTGTKXAZTJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1012
Molecular Formula:C5H5F3N2O
InChIKey:MKTAGPGPPNUHJX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:264.1252
Molecular Formula:C7H6F6N2O2
InChIKey:AQEGTAOTYVBEDM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:67.0892
Molecular Formula:C4H5N
InChIKey:KAESVJOAVNADME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.1871
Molecular Formula:C10H9F3N2
InChIKey:BPICCHOQHDQPCU-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:582.3438
Molecular Formula:C24H10F12N4
InChIKey:WVGOEXOYKRVJPB-OTHQCIQNSA-N
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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:326.4326
Molecular Formula:C20H26N2O2
InChIKey:LJOQGZACKSYWCH-MYUJHIMRSA-N
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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:67.806
Molecular Formula:BF3
InChIKey:WTEOIRVLGSZEPR-UHFFFAOYSA-N
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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
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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:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:83.1317
Molecular Formula:C5H9N
InChIKey:JAMNHZBIQDNHMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:241.2076
Molecular Formula:C9H14F3NO3
InChIKey:XTVXBXDRHZTDNC-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:256.32
Molecular Formula:C15H12O2S
InChIKey:PEQHNBAATLMGFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:334.359
Molecular Formula:C17H13F3N2S
InChIKey:WSCSSEVGQDYNEQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:77.0825
Molecular Formula:C2H7NO2
InChIKey:USFZMSVCRYTOJT-UHFFFAOYSA-N
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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:503.566
Molecular Formula:C21H33N3O9S
InChIKey:JSUQXDLAAYLMNS-BYXVQRNISA-N
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Compound Information
Molecular Weight:292.288
Molecular Formula:C11H17O5PS
InChIKey:RCSDMTWWPNXXPP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.211
Molecular Formula:C9H7F3O2S
InChIKey:MXCAYGIFNXCLMK-VOTSOKGWSA-N
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Compound Information
Molecular Weight:285.2964
Molecular Formula:C12H19N3O5
InChIKey:KIBLVBPHQCVUFG-SOYHJAILSA-N
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Compound Information
Molecular Weight:379.3316
Molecular Formula:C15H20F3N3O5
InChIKey:SRGDYIWQQQZYDJ-NBIDRCSRSA-N
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