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P28263

Sigma-Aldrich

2-Phenylphenol

99%

Synonym(s):

2-Hydroxybiphenyl

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About This Item

Linear Formula:
C6H5C6H4OH
CAS Number:
Molecular Weight:
170.21
Beilstein:
606907
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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vapor pressure

7 mmHg ( 140 °C)

Quality Level

Assay

99%

form

solid

bp

282 °C (lit.)

mp

57-59 °C (lit.)

fluorescence

λex 231 nm; λem 356 nm

SMILES string

Oc1ccccc1-c2ccccc2

InChI

1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H

InChI key

LLEMOWNGBBNAJR-UHFFFAOYSA-N

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General description

2-Phenylphenol, also known as o-phenylphenol, is commonly used as a chemical intermediate for the synthesis of pharmaceuticals, dyes, and fragrances.[1][2][3]

Application

2-Phenylphenol can be used as a precursor in the synthesis of:
  • Dibenzofurans via palladium-catalyzed, phenol-directed C-H activation/C-O cyclization[4] or copper-catalyzed aerobic C-H activation, followed by cycloetherification.[5]
  • 6H-Dibenzo[b,d]pyran-6-ones via ruthenium-catalyzed carbonylative C-H cyclization.[6]
  • o-Phenylenes, a class of conjugated oligomers via an iterative sequence of Suzuki-Miyaura coupling reactions.[7]
  • o,o,p-Oligophenylenes via palladium-catalyzed C-H arylation.[8]

Signal Word

Danger

Hazard Statements

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

255.2 °F - closed cup

Flash Point(C)

124 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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1 of 1

Cu-catalyzed oxidative C (sp2)-H cycloetherification of o-arylphenols for the preparation of dibenzofurans.
Zhao J, et al.
Organic Letters, 14(4), 1078-1081 (2012)
Ruthenium-Catalyzed Carbonylative C?H Cyclization of 2-Arylphenols: A Novel Synthetic Route to 6 H-Dibenzo [b, d] pyran-6-ones.
Inamoto K, et al.
Organic Letters, 15(15), 3962-3965 (2013)
Parent o-phenylene oligomers: synthesis, conformational behavior, and characterization.
Mathew S M and Hartley C S
Macromolecules, 44(21), 8425-8432 (2011)
Synthesis of dibenzofurans via Palladium-catalyzed phenol-directed C?H activation/C?O cyclization.
Xiao B, et al.
Journal of the American Chemical Society, 2011, 9250-9253 (2011)
Repetitive synthetic method for o, o, p-oligophenylenes using C?H arylation.
Manabe K and Kimura T
Organic Letters, 15(2), 374-377 (2013)

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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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