Standard Article

2-[(Trimethylsilyl)oxy]-1,3,2-benzodioxaphosphole

  1. Marie S. T. Morin,
  2. Bruce A. Arndtsen

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01599

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Morin, M. S. T. and Arndtsen, B. A. 2013. 2-[(Trimethylsilyl)oxy]-1,3,2-benzodioxaphosphole. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. McGill University, Montréal, QC, Canada

Publication History

  1. Published Online: 16 SEP 2013

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Abstract

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(2-[(Trimethylsilyl)oxy]-1,3,2-benzodioxaphosphole)

[61706-76-1] C9H13O3PSi (MW 228.26)

InChI = 1S/C9H13O3PSi/c1-14(2,3)12-13-10-8-6-4-5-7-9(8)11-13/h4-7H,1-3H3

InChIKey = PFTJBCMZLWNNFO-UHFFFAOYSA-N

(Synthetically equivalent to (2-catechyl)P(OH))

Physical Data:1 colorless liquid; bp 47–62 °C/0.06 mmHg; d 1.106 g cm−3; inline image 1.4920.

Solubility: soluble in most organic solvents.

Preparative Method: (2-catechyl)P(OTMS) 1 can be prepared via a modified procedure from that originally reported by Pudovik.2 To neat 1,2-phenylene phosphorochloridite3 (23.8 mL, 200 mmol) under nitrogen at 0 °C is slowly added N,O-bis(trimethylsilyl)acetamide (49.6 mL, 200 mmol) over 15 min. After stirring at ambient temperature for 20 h, the solvent and TMSCl are carefully removed in vacuo (to minimize loss of volatile product). The product is distilled at 100–150 mTorr, 46–52 °C to yield a colorless oil (31.0 g, 68% isolated yield).4

Purification: distillation at 46–52 °C/0.1–0.15 mmHg.

Handling, Storage, and Precautions: the reagent is sensitive to hydrolysis and should be stored under nitrogen. Long-term storage should be at −30 °C. Use in a fume hood. No toxicity data has been reported for this compound. The related diaryl phosphites (ArO)2P(O)H are reported to be irritants and corrosive.5 In addition, (CH3C6H3O2)P(O)Cl has been reported to have pesticidal activity.6

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Molecular Weight:Not Available
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Compound Information
Molecular Weight:181.2331
Molecular Formula:C13H11N
InChIKey:UVEWQKMPXAHFST-SDNWHVSQSA-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:337.309
Molecular Formula:C19H16NO3P
InChIKey:ZJWFLVJVSNSCKQ-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:222.258
Molecular Formula:C4H9F3O3SSi
InChIKey:FTVLMFQEYACZNP-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:108.642
Molecular Formula:C3H9ClSi
InChIKey:IJOOHPMOJXWVHK-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:167.326
Molecular Formula:C6H18LiNSi2
InChIKey:YNESATAKKCNGOF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1094
Molecular Formula:C6H6O4
InChIKey:VHILMKFSCRWWIJ-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:84.0734
Molecular Formula:C4H4O2
InChIKey:IMAKHNTVDGLIRY-UHFFFAOYSA-N
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Molecular Weight:Not Available
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Compound Information
Molecular Weight:51.0467
Molecular Formula:C3HN
InChIKey:LNDJVIYUJOJFSO-UHFFFAOYSA-N
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Molecular Weight:Not Available
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Compound Information
Molecular Weight:73.1368
Molecular Formula:C4H11N
InChIKey:HPNMFZURTQLUMO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.1974
Molecular Formula:C10H14NO2P
InChIKey:RNMIYVBIKKKCAE-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:156.0759
Molecular Formula:C6H5O3P
InChIKey:BSZOIKKTMZSXJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.2045
Molecular Formula:C5H9F3O2Si
InChIKey:VIYXXANHGYSBLY-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:210.228
Molecular Formula:C14H10O2
InChIKey:WURBFLDFSFBTLW-UHFFFAOYSA-N
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