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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:
90-43-7
Molecular Weight:
170.21
Beilstein:
606907
EC Number:
201-993-5
MDL number:
MFCD00002208
UNSPSC Code:
12352100
PubChem Substance ID:
24898365
NACRES:
NA.22

vapor pressure

7 mmHg ( 140 °C)

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.

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 or copper-catalyzed aerobic C-H activation, followed by cycloetherification.
  • 6H-Dibenzo[b,d]pyran-6-ones via ruthenium-catalyzed carbonylative C-H cyclization.
  • o-Phenylenes, a class of conjugated oligomers via an iterative sequence of Suzuki-Miyaura coupling reactions.
  • o,o,p-Oligophenylenes via palladium-catalyzed C-H arylation.

Signal Word

Danger

Hazard Statements

H315,H318,H335,H410

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Parent o-phenylene oligomers: synthesis, conformational behavior, and characterization.
Mathew S M and Hartley C S
Macromolecules, 44(21), 8425-8432 (2011)
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)
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)
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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