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Noyori Oxidation (Sodium Tungstate Dihydrate, Hydrogen Peroxide, Methyltri-n-octylammonium Hydrogen Sulfate, Phosphonic Acid)

  1. Yoshihiro Kon,
  2. Kazuhiko Sato

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01596

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Kon, Y. and Sato, K. 2013. Noyori Oxidation (Sodium Tungstate Dihydrate, Hydrogen Peroxide, Methyltri-n-octylammonium Hydrogen Sulfate, Phosphonic Acid). e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. National Institute of Advanced Industrial Science and Technology (AIST), Tokyo, Japan

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

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(Sodium tungstate dihydrate)[10213-10-2] H4Na2O6W (MW 329.85)

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Hydrogen peroxide

[7722-84-1] H2O2 (MW 34.01)

InChI = 1S/H2O2/c1-2/h1-2H

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(Methyltri-n-octylammonium Hydrogen Sulfate)

[59158-14-4] C25H55NO4S (MW 465.77)

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Phenylphosphonic Acid

[1571-33-1] C6H7O3P (MW 158.09)

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(Aminomethyl)phosphonic Acid

[1066-51-9] CH6NO3P (MW 111.04)

Physical Data: Na2WO4·2H2O: mp 698 °C. 30% H2O2: mp −25.7 °C; bp 106.2 °C; d 1.108 g cm−1. Me(n-octyl)3NHSO4: solid at 20 °C (mp is unknown and unclear). PhPO3H2: mp 160–165 °C. NH2CH2PO3H2: mp 120 °C.

Solubility: Na2WO4·2H2O: soluble in H2O. H2O2: mix with H2O; soluble in EtOH, MeOH, 1,4-dioxane, MeCN, THF, and acetic acid. Me(n-octyl)3NHSO4: soluble in EtOH. PhPO3H2: soluble in H2O. NH2CH2PO3H2: soluble in H2O.

Form Supplied in: Na2WO4·2H2O: colorless crystals; widely available. 30% H2O2: liquid; widely available. Me(n-octyl)3NHSO4: pale yellow solid; widely available. PhPO3H2: colorless crystals; widely available. NH2CH2PO3H2: white solid; widely available.

Handling, Storage, and Precautions: Na2WO4·2H2O: air and moisture stable; irritant; avoid inhalation, ingestion, and skin contact. Use in a fume hood. 30% H2O2: H2O2 at a concentration of 66% or more may explode violently. Before solvent evaporation, ensure absence of peroxide species. After the reaction, excess H2O2 should be decomposed by treatment with MnO2, Na2SO3 aq., or Na2S2O3 aq. to avoid explosion due to peroxides; irritant; avoid inhalation, ingestion, and skin contact. Use in a fume hood. For H2O2 in detail, see Hydrogen Peroxide. Me(n-octyl)3NHSO4: air and moisture stable; irritant; avoid inhalation, ingestion, and skin contact. Use in a fume hood. PhPO3H2: air and moisture stable; irritant; avoid inhalation, ingestion, and skin contact. Use in a fume hood. NH2CH2PO3H2: air and moisture stable; irritant; avoid inhalation, ingestion, and skin contact. Use in a fume hood.

Featured Compounds

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Compound Information
Molecular Weight:329.85
Molecular Formula:H4Na2O6W
InChIKey:WPZFLQRLSGVIAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:465.774
Molecular Formula:C25H55NO4S
InChIKey:MWSPFHZPVVWJCO-UHFFFAOYSA-M
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Compound Information
Molecular Weight:124.203
Molecular Formula:C7H8S
InChIKey:HNKJADCVZUBCPG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.203
Molecular Formula:C7H8OS
InChIKey:JXTGICXCHWMCPM-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:186.273
Molecular Formula:C12H10S
InChIKey:Not Available
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Compound Information
Molecular Weight:218.272
Molecular Formula:C12H10O2S
InChIKey:Not Available
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Compound Information
Molecular Weight:158.0917
Molecular Formula:C6H7O3P
InChIKey:Not Available
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Compound Information
Molecular Weight:232.341
Molecular Formula:C14H16OS
InChIKey:BNGZOVKNCKGBPG-BXUZGUMPSA-N
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Compound Information
Molecular Weight:264.34
Molecular Formula:C14H16O3S
InChIKey:OFXZEGYAMCXQDE-BXUZGUMPSA-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:130.2279
Molecular Formula:C8H18O
InChIKey:Not Available
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:ZPVFWPFBNIEHGJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.2279
Molecular Formula:C8H18O
InChIKey:KBPLFHHGFOOTCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:WWZKQHOCKIZLMA-UHFFFAOYSA-N
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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:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1213
Molecular Formula:C7H6O2
InChIKey:WPYMKLBDIGXBTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.3184
Molecular Formula:C12H24O
InChIKey:IHOLJZJZVIFXKA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.3025
Molecular Formula:C12H22O
InChIKey:OPLPMLGBZCNBGS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.319
Molecular Formula:C12H24
InChIKey:CRSBERNSMYQZNG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.3184
Molecular Formula:C12H24O
InChIKey:MPGABYXKKCLIRW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:111.037
Molecular Formula:CH6NO3P
InChIKey:MGRVRXRGTBOSHW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2918
Molecular Formula:C11H22O
InChIKey:SKBIQKQBLQHOSU-MDZDMXLPSA-N
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Compound Information
Molecular Weight:186.2912
Molecular Formula:C11H22O2
InChIKey:XTWFTQGRBSRDCS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:GRWFGVWFFZKLTI-IUCAKERBSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:NQFUSWIGRKFAHK-BGPATTHWSA-N
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Compound Information
Molecular Weight:142.042
Molecular Formula:Na2O4S
InChIKey:PMZURENOXWZQFD-UHFFFAOYSA-L
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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:97.9952
Molecular Formula:H3O4P
InChIKey:NBIIXXVUZAFLBC-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:146.1412
Molecular Formula:C6H10O4
InChIKey:WNLRTRBMVRJNCN-UHFFFAOYSA-N
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