Standard Article

Manganese(II) tetraphenylporphyrin

  1. Naga K. Modukuru,
  2. Steven J. Collier

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01601

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Modukuru, N. K. and Collier, S. J. 2013. Manganese(II) tetraphenylporphyrin. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. Codexis Laboratories Singapore, Pte. Ltd., Singapore, Singapore

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

(catalyst for aerobic oxidation of alkenes and alkanes; model heme analog)

Alternative Names: Mn(II)TPP; 5,10,15,20-tetraphenyl-21H,23H-porphyrin manganese(II).

Physical Data: unknown.

Solubility: unknown.

Form Obtained in: usually formed in situ; purple crystals as toluene solvate: Mn(II)TPP·2PhMe.1

Analysis of Reagent Purity: UV/Vis Spectroscopy; ESR Spectroscopy.

Preparative Methods: Mn(II)TPP is generally made in situ via reduction of the more common and more stable Mn(III)(TPP)Cl species. It is also possible to directly insert Mn(II)TPP into a metal-free porphyrin.

In-situ Chemical Reduction Method: Mn(III)(TPP)Cl (18 mg, 1 equiv) was dissolved in DCM (3 mL) and the solution was degassed and kept under an argon atmosphere. Tetra-n-butylammonium borohydride (78 mg, 12 equiv) was added as a solid and the mixture was stirred at room temperature and used in situ for subsequent reactions.2

Chromous Reduction Method: Chromium(II) acetylacetonate was added to a mixture of Mn(III)(TPP)Cl in refluxing toluene until the color of the solution changed from green to deep purple. The hot solution was filtered quickly through a medium frit and heptane was added. After 1 h, the resulting precipitate was filtered to afford the crude product. Recrystallization from hot toluene/heptane provided purple crystals of desired product in 55% yield (eq 1).1

original image(1)

Manganese Insertion Method:  A mixture of tetraphenylporphyrin, manganese bromide (MnBr2), and Proton Sponge (N,N,N′,N′-tetramethylnaphthalene-1,8-diamine) in toluene and THF was heated until, upon acidification of a sample, the visible spectrum indicated lack of protonated free porphyrin at 750 nm. Degassed alumina was added and the solvents were carefully removed under reduced pressure. The desired product was obtained by column purification on a short alumina column, eluting with toluene/THF. Recrystallization from hot toluene/heptane provided purple crystals of desired product in 55% yield.1

Handling, Storage, and Precautions: unknown; recommend to form and use in situ.

Featured Compounds

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  1. 1 - 83
Compound Information
Molecular Weight:703.111
Molecular Formula:C44H28ClMnN4
InChIKey:MIUMWNDEIWVIEG-YKKPBKTHSA-M
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Compound Information
Molecular Weight:250.2119
Molecular Formula:C10H14CrO4
InChIKey:SBTJABCOFJUGCX-FDGPNNRMSA-L
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Compound Information
Molecular Weight:667.658
Molecular Formula:C44H28MnN4
InChIKey:SEVKCRJDNPAWQG-DAJBKUBHSA-N
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Compound Information
Molecular Weight:285.665
Molecular Formula:C10H14ClCrO4
InChIKey:GOWNJMQQVDNBLB-SUKNRPLKSA-K
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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:100.2019
Molecular Formula:C7H16
InChIKey:IMNFDUFMRHMDMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:HGCIXCUEYOPUTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:AMIMRNSIRUDHCM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:CTMHWPIWNRWQEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:FIEKVYPYFQSFTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:WCMSFBRREKZZFL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:DUDYJVLITCQGCP-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:120.1485
Molecular Formula:C8H8O
InChIKey:Not Available
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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:134.1751
Molecular Formula:C9H10O
InChIKey:YVCOJTATJWDGEU-APPZFPTMSA-N
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Compound Information
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:PJANXHGTPQOBST-VAWYXSNFSA-N
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Compound Information
Molecular Weight:196.2445
Molecular Formula:C14H12O
InChIKey:ARCJQKUWGAZPFX-KWCCSABGSA-N
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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:URYYVOIYTNXXBN-UPHRSURJSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:MELPJGOMEMRMPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:KWKAKUADMBZCLK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:Not Available
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Compound Information
Molecular Weight:126.2392
Molecular Formula:C9H18
InChIKey:IICQZTQZQSBHBY-HWKANZROSA-N
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Compound Information
Molecular Weight:142.2386
Molecular Formula:C9H18O
InChIKey:IKYJCWFNSKISSG-RKDXNWHRSA-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:152.2334
Molecular Formula:C10H16O
InChIKey:CCEFMUBVSUDRLG-XNWIYYODSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:OOCCDEMITAIZTP-QPJJXVBHSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:PVALSANGMFRTQM-RKDXNWHRSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:AWMVMTVKBNGEAK-QMMMGPOBSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:DTUQWGWMVIHBKE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.1059
Molecular Formula:C6H7NaO6
InChIKey:PPASLZSBLFJQEF-RXSVEWSESA-M
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Compound Information
Molecular Weight:404.156
Molecular Formula:C25H54ClN
InChIKey:XKBGEWXEAPTVCK-UHFFFAOYSA-M
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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:180.2451
Molecular Formula:C14H12
InChIKey:PJANXHGTPQOBST-QXMHVHEDSA-N
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Compound Information
Molecular Weight:196.2445
Molecular Formula:C14H12O
InChIKey:ARCJQKUWGAZPFX-OKILXGFUSA-N
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Compound Information
Molecular Weight:196.2445
Molecular Formula:C14H12O
InChIKey:ARCJQKUWGAZPFX-KBPBESRZSA-N
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Compound Information
Molecular Weight:196.2445
Molecular Formula:C14H12O
InChIKey:ARCJQKUWGAZPFX-ZIAGYGMSSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:RYPKRALMXUUNKS-HYXAFXHYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:LIESJAYIOKBLIL-RITPCOANSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:RYPKRALMXUUNKS-HWKANZROSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:LIESJAYIOKBLIL-PHDIDXHHSA-N
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Compound Information
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:FNFXSDYETCRXMJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:GRXXIEFDQZBSQD-GFCCVEGCSA-N
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Compound Information
Molecular Weight:98.1861
Molecular Formula:C7H14
InChIKey:Not Available
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:NMOFYYYCFRVWBK-SSDOTTSWSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:Not Available
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:SYQIWVMFOAHDMK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:ZWAJLVLEBYIOTI-OLQVQODUSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:Not Available
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:CATSNJVOTSVZJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:NGAZZOYFWWSOGK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:Not Available
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Compound Information
Molecular Weight:98.1861
Molecular Formula:C7H14
InChIKey:UAEPNZWRGJTJPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:VTBOTOBFGSVRMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:NDVWOBYBJYUSMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:HTSABYAWKQAHBT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:MQWCXKGKQLNYQG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:LFSAPCRASZRSKS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:UJBOOUHRTQVGRU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:VGVHNLRUAMRIEW-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:116.2013
Molecular Formula:C7H16O
InChIKey:Not Available
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:WVDDGKGOMKODPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:RDOXTESZEPMUJZ-UHFFFAOYSA-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:260.2884
Molecular Formula:C14H16N2O3
InChIKey:XZECNVJPYDPBAM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.2872
Molecular Formula:C14H16N2O5
InChIKey:SRSGJKLSFJZPAE-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:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:HJOVHMDZYOCNQW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:AYJXHIDNNLJQDT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:XTHFKEDIFFGKHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:308.3446
Molecular Formula:C17H21FO4
InChIKey:RGULPSNGHOQZTB-VDNDLQMASA-N
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Compound Information
Molecular Weight:895.0703
Molecular Formula:C60H51FN4O3
InChIKey:FPCCCTXTXHPECB-SRDDQRRLSA-N
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Compound Information
Molecular Weight:308.3446
Molecular Formula:C17H21FO4
InChIKey:YRJDJCIXIUAEKL-IIZJFRANSA-N
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Compound Information
Molecular Weight:257.307
Molecular Formula:C16H40BN
InChIKey:GMBOFJFPOCGSOI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.421
Molecular Formula:CdN2O6
InChIKey:XIEPJMXMMWZAAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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