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291390

Sigma-Aldrich

p-Tolyl acetate

99%

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Synonym(s):
p-Cresyl acetate
Linear Formula:
CH3CO2C6H4CH3
CAS Number:
Molecular Weight:
150.17
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

refractive index

n20/D 1.501 (lit.)

bp

210-211 °C (lit.)

density

1.047 g/mL at 25 °C (lit.)

SMILES string

CC(=O)Oc1ccc(C)cc1

InChI

1S/C9H10O2/c1-7-3-5-9(6-4-7)11-8(2)10/h3-6H,1-2H3

InChI key

CDJJKTLOZJAGIZ-UHFFFAOYSA-N

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This Item
N850525371510914
p-Tolyl acetate 99%

Sigma-Aldrich

291390

p-Tolyl acetate

1-Naphthyl acetate ≥98% (C)

Sigma-Aldrich

N8505

1-Naphthyl acetate

Isopropenyl acetate produced by Wacker Chemie AG, Burghausen, Germany, ≥99.0% (GC)

Sigma-Aldrich

10914

Isopropenyl acetate

refractive index

n20/D 1.501 (lit.)

refractive index

-

refractive index

n20/D 1.6345 (lit.)

refractive index

n20/D 1.401 (lit.)

bp

210-211 °C (lit.)

bp

-

bp

237 °C (lit.), 62 °C/0.3 mmHg (lit.)

bp

94 °C (lit.)

density

1.047 g/mL at 25 °C (lit.)

density

-

density

-

density

0.922 g/mL at 20 °C, 0.909 g/mL at 25 °C (lit.)

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

General description

The Fries rearrangement of p-tolyl acetate has been investigated using the H-form of various zeolites as catalysts. Mechanism of photo-Fries rearrangement of p-tolyl acetate has been studied.

Application

p-Tolyl acetate has been used in the total synthesis of (−)-incrustoporin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

194.0 °F - closed cup

Flash Point(C)

90 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Mechanistic studies of the photo-Fries reaction.
Sandner MR, et al.
Journal of the American Chemical Society, 90(26), 7249-7254 (1968)
Fries rearrangement over zeolitic catalysts.
Vogt A, et al.
Applied Catalysis A: General, 123(1), 37-49 (1995)
Q Yu et al.
Journal of Asian natural products research, 1(3), 183-188 (2001-03-20)
(-)-Incrustoporin (1) has been synthesized using aldol condensation of ethyl p-tolyl-acetate (2) and (2R)-benzoyloxy-butanal (3), followed by acid-catalyzed deprotection of the benzoyl group, lactone ring-closure, and elimination of the beta-OH in a one-pot manner. The aldehyde 3 was prepared from
Alfonso Pérez-Garrido et al.
Bioorganic & medicinal chemistry, 17(2), 896-904 (2008-12-06)
This paper reports a QSAR study for predicting the complexation of a large and heterogeneous variety of substances (233 organic compounds) with beta-cyclodextrins (beta-CDs). Several different theoretical molecular descriptors, calculated solely from the molecular structure of the compounds under investigation

Articles

The Fries rearrangement reaction is an organic name reaction which involves the conversion of phenolic esters into hydroxyaryl ketones on heating in the presence of a catalyst. Suitable catalysts for this reaction are Brønsted or Lewis acids such as HF, AlCl3, BF3, TiCl4, or SnCl4. The Fries rearrangement reaction is an ortho, para-selective reaction, and is used in the preparation of acyl phenols. This organic reaction has been named after German chemist Karl Theophil Fries.

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