ChemicalBook > CAS DataBase List > 1,4-Dihydroxyanthraquinone

1,4-Dihydroxyanthraquinone

Product Name
1,4-Dihydroxyanthraquinone
CAS No.
81-64-1
Chemical Name
1,4-Dihydroxyanthraquinone
Synonyms
QUINIZARINE;DSD ACID;QUINIZARIN;Solvent Orange 86;QUINAZARIN;1,4-Dihydroxy-9,10-anthraquinone;1,4-dihydroxyanthracene-9,10-dione;1,4-Doa;CI 58050;1,4-DHAQ
CBNumber
CB7730041
Molecular Formula
C14H8O4
Formula Weight
240.21
MOL File
81-64-1.mol
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1,4-Dihydroxyanthraquinone Property

Melting point:
195-200 °C
Boiling point:
450 °C
Density 
1.3032 (rough estimate)
vapor density 
8.3 (vs air)
vapor pressure 
1 mm Hg ( 196.7 °C)
refractive index 
1.5430 (estimate)
Flash point:
222 °C
storage temp. 
Store below +30°C.
solubility 
<1g/l
pka
pK (18°) 9.51
Colour Index 
58050
form 
powder
color 
red-brown
Water Solubility 
<1 g/L (20 ºC)
Merck 
14,8064
BRN 
1914036
InChIKey
GUEIZVNYDFNHJU-UHFFFAOYSA-N
LogP
4.2 at 25℃
CAS DataBase Reference
81-64-1(CAS DataBase Reference)
NIST Chemistry Reference
9,10-Anthracenedione, 1,4-dihydroxy-(81-64-1)
EPA Substance Registry System
Quinizarin (81-64-1)
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Safety

Hazard Codes 
Xi,N
Risk Statements 
36/37/38-43-50/53
Safety Statements 
22-24/25-36/37-26-61-60
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
2
RTECS 
CB6600000
TSCA 
Yes
HS Code 
2914 69 80
PackingGroup 
III
Hazardous Substances Data
81-64-1(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: > 5000 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.20259
Product name
1,4-Dihydroxyanthraquinone
Purity
for synthesis
Packaging
5G
Price
$45.6
Updated
2024/03/01
Sigma-Aldrich
Product number
8.20259
Product name
1,4-Dihydroxyanthraquinone
Purity
for synthesis
Packaging
250g
Price
$69.8
Updated
2024/03/01
Sigma-Aldrich
Product number
37480
Product name
1,4-Dihydroxyanthraquinone
Purity
purum, ≥98.0% (HPLC), powder, red-brown
Packaging
50g
Price
$54.3
Updated
2023/06/20
Sigma-Aldrich
Product number
37480
Product name
1,4-Dihydroxyanthraquinone
Purity
purum, ≥98.0% (HPLC), powder, red-brown
Packaging
250g
Price
$120
Updated
2023/06/20
TCI Chemical
Product number
D0243
Product name
Quinizarin
Purity
>97.0%(HPLC)
Packaging
25g
Price
$96
Updated
2024/03/01
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1,4-Dihydroxyanthraquinone Chemical Properties,Usage,Production

Chemical Properties

orange to red-brown crystalline powder

Uses

1,4-Dihydroxyanthraquinone, also known as quinizarin, is of great importance in manufacturing disperse, acid, and vat dyes.

Uses

1,4-Dihydroxyanthraquinone is used to color gasoline and some heating oils. It is used as an intermediate for the synthesis of indanthrene- and alizarin-derived dyes. It is also used to form lake pigments with calcium, barium and lead. It may be used in the synthesis of cyclopentanoids by cyclization of α,β-unsaturated aldehyde with 1,4-Dihydroxyanthraquinone. It has been studied as a long range emissive ratiometric fluorescent probe for live cell imaging.

Uses

Antioxidant in synthetic lubricants, dyes.

Definition

ChEBI: Quinizarin is a dihydroxyanthraquinone having the two hydroxy substituents at the 1- and 4-positions; formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxy groups It has a role as a dye.

Manufacturing Process

1,4-Dihydroxyanthraquinone is commonly known as Quinizarin.
(a) Boric acid, boric acid and mercury, boric acid and nitrous acid or nitrous acid and mercury in the presence of Anthracene-9,10-dione with sulfuric acid;
(b) In the presence of boric acid and nitrous acid, treated with sulfuric acid 1-Hydroxyanthracene-9,10-dione or 2-Hydroxyanthracene-9,10-dione,
(c)In the presence of boric acid, treated with sulfuric acid 1-Hydroxy-4-nitroanthracene-9,10-dione or 1,4-Dichloroanthracene-9,10-dione;
(d) in the Boric acid and where did in the presence of sulfuric acid, Phthalic anhydride and 4-Chlorophenol ;or Hydroquinone condensation, closed loop.

Synthesis Reference(s)

Synthesis, p. 633, 1974 DOI: 10.1055/s-1974-23387
Tetrahedron Letters, 28, p. 1533, 1987 DOI: 10.1016/S0040-4039(01)81035-2

General Description

1,4-Dihydroxyanthraquinone is an organic dye molecule with an aromatic structure. It is a derivative of anthraquinone bearing hydroxyl moieties. They may find uses in pharmacological, biochemical and dye industries. Anthraquinone dye are resistant to degradation.

Flammability and Explosibility

Non flammable

Safety Profile

Poison by intravenous route. Moderately toxic by intraperitoneal route. Mutation data reported. An eye irritant. A weak allergen. When heated todecomposition it emits acrid smoke and irritating fumes.

Synthesis

At 250 DEG C, heat boric acid 10h, obtain boric acid dehydration compound; Recording boric anhydride in boric acid dehydration compound through ultimate analysis is 99.3%, tetraboric acid 0.7%;In condensation reaction still, add oleum 350kg, phthalic anhydride 120kg, boric acid dehydration compound 40kg, para-chlorophenol 100kg(oleum: phthalic anhydride: metaboric acid: para-chlorophenol=3.5:1.2:0.4:1); Oil bath is warmed up to material 100 DEG C, accurately controls temperature of reaction 100 ~ 105 DEG C, is incubated 0.5 hour; Binder is in the hydrolysis kettle being added with 300L water, and adjustment temperature to 50 DEG C, 50 DEG C of insulations 0.1 hour, discharging press filtration, is washed to neutrality, dries up and obtains 1,4-hydroxyanthraquinone tide product 400.2kg, detect water ratio 54.2%, give money as a gift product 183.3kg, passes through liquid-phase chromatographic analysis, 1, the content of 4-hydroxyanthraquinone reaches 98.74%, dry product purity 97.12%, and yield is 94.1%.

Properties and Applications

orange. Orange red powder. Insoluble in water, soluble in ether, in strong base in certain solubility, but soluble in organic solvent oil, etc. In concentrated sulfuric acid in green yellow fluorescence. Mainly used for oil coloring. Also used in all kinds of plastic and resin, light industry products coloring.

Purification Methods

Crystallise quinizarin from glacial acetic acid. [Beilstein 8 H 450, 8 IV 3260.]

1,4-Dihydroxyanthraquinone Preparation Products And Raw materials

Raw materials

Orthoboric acid Hydroquinone Phthalic anhydride 4-Chlorophenol Sulfuric acid

Preparation Products

Solvent Blue 59 1,4-Diamino-2,3-dihydroanthraquinone Solvent Blue 36 Mordant Black 13 Solvent Green 3 Acid Green 25 HYDROQUININE (ANTHRAQUINONE-1 4-DIYL) Solvent Blue 104 Tracid Light Yellow G Solvent Blue 35 Solvent Blue 122 ACID BLUE 80 DISPERSE DYE Acid Violet 43 1,4-Diamino anthraquinone Disperse Blue 3 Solvent Violet 13 Solvent Blue 97 ACID BLUE 25 Transparent Blue Disperse Blue 14 ACID GREEN 27 (C.I. 61580)
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1,4-Dihydroxyanthraquinone Suppliers

Americas 1 Belgium 3 Brazil 1 China 405 Czech Republic 1 Europe 4 France 1 Germany 7 India 36 Italy 1 Japan 5 Mexico 1 Norway 1 Slovakia 1 South Africa 1 Spain 1 Switzerland 2 The Netherlands 3 Ukraine 1 United Kingdom 16 United States 44 Global 536
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View Lastest Price from 1,4-Dihydroxyanthraquinone manufacturers

Jinan Finer Chemical Co., Ltd
Product
1,4-Dihydroxyanthraquinone 81-64-1
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
≥98%;≥96%
Supply Ability
500mt/year
Release date
2021-08-31
Yancheng Green Chemicals Co.,Ltd
Product
1.4-Dihydroxyanthaquinone 81-64-1
Price
US $0.00/Kg/Bag
Min. Order
100KG
Purity
99
Supply Ability
1000
Release date
2021-11-08
Gansu Jinyuantai New Material Co., Ltd.
Product
1,4-Dihydroxyanthraquinone 81-64-1
Price
US $0.00/kg
Min. Order
25kg
Purity
96, 98.5
Supply Ability
10000
Release date
2023-06-15

81-64-1, 1,4-DihydroxyanthraquinoneRelated Search:

Solvent Red 43 1-Hydroxy anthraquinone Anthraquinone Solvent Blue 36 DITHIANON disodium 2,2-(5,8-dihydroxyanthraquinone-1,4-diyldiimino)bis(5-methylbenzenesulphonate) PURPURIN 1,2,5,8-TETRAHYDROXYANTHRAQUINONE Mitoxantrone HCL for Injection (Lyophilized Power) SOLVENT OIL 5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-1,4-dihydroxyanthraquinon Alizarin 1,5-DIHYDROXYANTHRAQUINONE 1,8-Dihydroxyanthraquinone Alizarin Red S 4,8-diamino-2-bromo-1,5-dihydroxyanthraquinone 2,6-DIHYDROXYANTHRAQUINONE Anthracene-1,4,9,10-tetraol

  • DSD ACID
  • CI NO 58050
  • CI 58050
  • LABOTEST-BB LT00052844
  • 1,4-dihydroxy-10-anthracenedione
  • 1,4-dihydroxy-9,10(9H,10H)anthracenedione
  • 1,4-Dihydroxy-9,10-anthraquinone
  • 1,4-Dihydroxyanthra-9,10-quinone
  • 1,4-Dihydroxyanthrachinon
  • 9,10-anthracenedione,1,4-dihydroxy-
  • Anthraquinone, 1,4-dihydroxy-
  • anthraquinone,1,4-dihydroxy-
  • Chinizarin
  • Macrolex Orange GG
  • Quinizalin
  • Quinizarin,CI 58050
  • Smoke orange r
  • smokeoranger
  • PIGMENT VIOLET 12
  • QUINAZARIN
  • QUINIZARINE
  • QUINIZARIN
  • Solvent Orange 86
  • 1,4-Dihydroxyantraquinone
  • QUINIZARIN REGULAR/TECH
  • QUINIZARIN, SUBLIMED
  • 1,4-Dihydroxy-9,10-anthracenedione C.I. 58050 Quinizarin Solvent Orange 86
  • 1,4-dihydroxyanthracene-9,10-dione
  • 1,4-dihydroxy-9,10-anthracenedione
  • 1,4-DIHYDROXYANTHRAQUINONE
  • 1,4 DIHYROXY AQ
  • 4-Dihydroxyanthraquinone
  • 1,4-dihydroxyanthrachinon(czech)[qr]
  • 1,4-dihydroxy-anthraquinon
  • 1,4-Dioxyanthraquinone
  • 1,4-dioxyanthraquinone(russian)[qr]
  • 1,4-Doa
  • 1,4-doa(russian)[qr]
  • 1,4-dihydrxyanthraquinone
  • 10-Anthracenedione,1,4-dihydroxy-9
  • Quinizarin,, Technical
  • 1,4-Dihydroxyanthraquinone, tech., 95%
  • Quinizarin,98%
  • 1,4-Dihydroxyanthraquinone,96%
  • Solvent Orange G
  • Transparent Orange G
  • 9, 10-Antnracenedlone, 1, 4-dihydroxy
  • Keyplast Yellow GG
  • Naviplast Orange G
  • Smoke Orange 18
  • Sudan S Orange 261.
  • QUINIZARIN(RG)
  • C.I.Solvent Orange 86
  • Smoke pigment
  • 1,4-Dihydroxyanthraq
  • 1,4-Dihydroxyanthraquinone, 96% 100GR
  • 1,4-Dihydroxyanthraquinone, 96% 5GR
  • 1,4- twohydroxy anthraquinone