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A90004

Sigma-Aldrich

Anthraquinone

97%

Synonym(s):

1,4,11,12-Tetrahydro-9,10-anthraquinone, 9,10-Anthraquinone, Anthracene-9,10-quinone, Anthradione

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About This Item

Empirical Formula (Hill Notation):
C14H8O2
CAS Number:
84-65-1
Molecular Weight:
208.21
Beilstein:
390030
EC Number:
201-549-0
MDL number:
MFCD00001188
UNSPSC Code:
12352100
PubChem Substance ID:
24891393
NACRES:
NA.22

vapor density

7.16 (vs air)

vapor pressure

1 mmHg ( 190 °C)

Assay

97%

form

powder

bp

379-381 °C (lit.)

mp

284-286 °C (lit.)

SMILES string

O=C1c2ccccc2C(=O)c3ccccc13

InChI

1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H

InChI key

RZVHIXYEVGDQDX-UHFFFAOYSA-N

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Application

Anthraquinone (AQ) can be used:
  • In the synthesis of water-soluble anthraquinone derivatives such as 9,10-anthraquinone-2,6-disulfonic acid, disodium salt (AQ-2,6) and 9,10-anthraquinone-2-sulfonic acid, monosodium salt (AQ-2). These AQ derivatives are useful as redox catalysts for aeration in Becher process.
  • As an indicator to determine the acid strength of poly(4-vinylpyridinium) hydrogen sulfate (P(4-VPH)HSO4) catalyst.
  • As a pulping catalyst.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H317,H350

Hazard Classifications

Carc. 1B - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

482.0 °F - closed cup

Flash Point(C)

250 °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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Anthraquinone-A review of the rise and fall of a pulping catalyst.
Hart PW and Rudie AW
Tappi Journal, 13(10), 23-31 (2014)
Preparation, characterization and use of poly (4-vinylpyridinium) hydrogen sulfate salt as an eco-benign, efficient and reusable solid acid catalyst for the chemoselective 1, 1-diacetate protection and deprotection of aldehydes.
Khaligh NG and Shirini F
J. Mol. Catal. A: Chem., 348(1-2), 20-29 (2011)
The application of anthraquinone redox catalysts for accelerating the aeration step in the becher process.
Bruckard WJ, et al.
Hydrometallurgy, 73(1-2), 111-121 (2004)
Emilio M Ungerfeld et al.
Microorganisms, 8(6) (2020-05-30)
Ameliorating methane (CH4) emissions from ruminants would have environmental benefits, but it is necessary to redirect metabolic hydrogen ([H]) toward useful sinks to also benefit animal productivity. We hypothesized that inhibiting rumen methanogenesis would increase de novo synthesis of microbial
Erin E Podlesny et al.
The Journal of organic chemistry, 78(2), 466-476 (2012-12-20)
The development of the first asymmetric synthesis of a chiral anthraquinone dimer is outlined, resulting in the first total synthesis of (S)-bisoranjidiol. Rather than a biomimetic dimerization retrosynthetic disconnection, the anthracenyl ring systems are generated after formation of the axially
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