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ChemicalBook >> CAS DataBase List >>1,4-Dihydroxyanthraquinone

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
Molecular Weight:
240.21
MDL Number:
MFCD00001209
MOL File:
81-64-1.mol
MSDS File:
SDS
Last updated:2024-12-18 14:08:57

1,4-Dihydroxyanthraquinone Properties

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)
EWG's Food Scores 1
FDA UNII 8S496ZV3CS
NIST Chemistry Reference 9,10-Anthracenedione, 1,4-dihydroxy-(81-64-1)
EPA Substance Registry System Quinizarin (81-64-1)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS09
Signal word  Warning
Hazard statements  H410
Precautionary statements  P273
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
NFPA 704
1
0 0

1,4-Dihydroxyanthraquinone price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.20259 1,4-Dihydroxyanthraquinone for synthesis 81-64-1 5G $45.6 2024-03-01 Buy
Sigma-Aldrich 8.20259 1,4-Dihydroxyanthraquinone for synthesis 81-64-1 250g $69.8 2024-03-01 Buy
Sigma-Aldrich 37480 1,4-Dihydroxyanthraquinone purum, ≥98.0% (HPLC), powder, red-brown 81-64-1 50g $54.3 2023-06-20 Buy
Sigma-Aldrich 37480 1,4-Dihydroxyanthraquinone purum, ≥98.0% (HPLC), powder, red-brown 81-64-1 250g $120 2023-06-20 Buy
TCI Chemical D0243 Quinizarin >97.0%(HPLC) 81-64-1 25g $96 2024-03-01 Buy
Product number Packaging Price Buy
8.20259 5G $45.6 Buy
8.20259 250g $69.8 Buy
37480 50g $54.3 Buy
37480 250g $120 Buy
D0243 25g $96 Buy

1,4-Dihydroxyanthraquinone Chemical Properties,Uses,Production

Chemical Properties

orange to red-brown crystalline powder

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

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

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%.

Purification Methods

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

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.

85-44-9
123-31-9
81-64-1
Synthesis of 1,4-Dihydroxyanthraquinone from Phthalic anhydride and Hydroquinone
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View Lastest Price from 1,4-Dihydroxyanthraquinone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
1,4-Dihydroxyanthraquinone pictures 2024-12-20 1,4-Dihydroxyanthraquinone
81-64-1
 US $0.00 / Kg/Bag 1KG ≥98%;≥96% 500mt/year Jinan Finer Chemical Co., Ltd
1.4-Dihydroxyanthaquinone pictures 2024-12-20 1.4-Dihydroxyanthaquinone
81-64-1
 US $0.00 / Kg/Bag 100KG 99 1000 Yancheng Green Chemicals Co.,Ltd
1,4-Dihydroxyanthraquinone pictures 2024-12-20 1,4-Dihydroxyanthraquinone
81-64-1
 US $0.00 / kg 25kg 96, 98.5 10000 Gansu Jinyuantai New Material Co., Ltd.
CI NO 58050 CI 58050 LABOTEST-BB LT00052844 1,4-dihydroxy-10-anthracenedione 1,4-dihydroxy-9,10(9H,10H)anthracenedione 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 1,4-Dihydroxyantraquinone QUINIZARIN REGULAR/TECH QUINIZARIN, SUBLIMED 1,4-Dihydroxy-9,10-anthracenedione C.I. 58050 Quinizarin Solvent Orange 86 1,4-dihydroxy-9,10-anthracenedione 1,4-DIHYDROXYANTHRAQUINONE 1,4 DIHYROXY AQ 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 Quinizarin 96% Quinizarin/1,4-Dihydroxyanthraquinone 1,4-DHAQ 1,4-Dihydroxyanthraquinone ISO 9001：2015 REACH C.I.Solvent Orange 86:C.I.58050 1,4-Dihydroxyanthra-9 1.4-Dihydroxyanthaquinone Dye Intermediate, 4-Dihydroxyanthraquinone CAS No 81-64-1 High quality