1,4-Dihydroxyanthraquinone

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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View Lastest Price from 1,4-Dihydroxyanthraquinone manufacturers

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

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

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