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Anthraquinone

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Anthraquinone Basic information

Product Name:
Anthraquinone
CAS:
84-65-1
MF:
C14H8O2
MW:
208.21
EINECS:
201-549-0
Mol File:
84-65-1.mol
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Anthraquinone Chemical Properties

Melting point:
284-286 °C(lit.)
Boiling point:
379-381 °C(lit.)
Density 
1.438
vapor density 
7.16 (vs air)
vapor pressure 
1 mm Hg ( 190 °C)
refractive index 
1.5681 (estimate)
Flash point:
365 °F
storage temp. 
Storage temperature: no restrictions.
solubility 
0.00007g/l
form 
Powder
color 
Yellow-green to khaki to tan
Water Solubility 
<0.1 g/100 mL at 23 ºC
Merck 
14,687
BRN 
390030
Stability:
Stable. Incompatible with strong oxidizing agents. Combustible.
InChIKey
RZVHIXYEVGDQDX-UHFFFAOYSA-N
CAS DataBase Reference
84-65-1(CAS DataBase Reference)
IARC
2B (Vol. 101) 2013
NIST Chemistry Reference
9,10-Anthraquinone(84-65-1)
EPA Substance Registry System
Anthraquinone (84-65-1)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
43-36/37/38
Safety Statements 
36/37-37/39-26-24
RIDADR 
3077
WGK Germany 
1
RTECS 
CB4725000
Autoignition Temperature
650 °C
TSCA 
Yes
HS Code 
2914 61 00
HazardClass 
9
PackingGroup 
III
Hazardous Substances Data
84-65-1(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: > 5000 mg/kg

MSDS

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Anthraquinone Usage And Synthesis

Chemical Properties

dull yellow powder

Chemical Properties

Anthraquinone is a combustible, light yellow to green crystalline solid.

Uses

bird repellant, irritant

Uses

A precursor for dye formation

Uses

Starting material for the manufacture of dyes; bird repellent.

Definition

ChEBI: An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.

Definition

A colorless crystalline quinone used in producing dyestuffs such as alizarin.

Definition

anthraquinone: A colourless crystallingquinone; m.p. 154°C. It maybe prepared by reacting benzenewith phthalic anhydride. The compoundis the basis of a range ofdyestuffs.

Production Methods

Anthraquinone is obtained by oxidation of anthracene using sodium dichromate plus sulfuric acid, and is purified by dissolving in concentrated sulfuric acid at 130 °C and pouring into boiling water, whereupon anthraquinone separates as pure solid, and is recovered by filtration. Further purification may be accomplished by sublimation or crystallization from nitrobenzene, aniline or tetrachloroethane.

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 1457, 1980 DOI: 10.1021/ja00524a059
The Journal of Organic Chemistry, 29, p. 987, 1964 DOI: 10.1021/jo01027a538
Tetrahedron Letters, 24, p. 5499, 1983 DOI: 10.1016/S0040-4039(00)94122-4

General Description

Yellow crystals or powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Anthraquinone is incompatible with strong oxidizing agents.

Hazard

Possible carcinogen.

Fire Hazard

Anthraquinone is combustible.

Agricultural Uses

Repellent, Seed treatment: Used as a seed dressing or protectant. Banned in EU.

Trade name

(p)ANTHRAPEL®; FLIGHT CONTROL- PLUS®; HOELITE®; MORKIT®; REPELL®

Pharmacology

Anthraquinone is a secondary repellent and affects birds by causing post-ingestional distress (40). Sometimes, ingestion of anthraquinone-treated food produces vomiting, but often vomiting does not occur and the bird just sits quietly until the discomfort passes. Unlike methiocarb, anthraquinone doe not affect the bird’s nervous system and does not immobilize affected birds. Presumably, the emetic response is produced through irritation of the gut lining, but the actual mechanism is unclear. It is clear, however, that anthraquinone is not a taste repellent or contact irritant. Birds do not hesitate to eat treated food, and they exhibit no sign that treated food is unpalatable to them. The post-ingestional discomfort that results from eating anthraquinone-treated food produces a conditioned aversion to that food type. Birds need to experience the adverse consequences before learning to avoid the protected food. Thus, it is not reasonable to expect losses to cease immediately upon application of the repellent. There will be some level of loss in the crop as the depredating birds acquire the learned avoidance response.

Safety Profile

Moderately toxic by intraperitoneal route. A mild allergen. Mutation data reported. Combustible when exposed to heat or flame. To fight fire, use water, foam, CO2, water spray or mist, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Anthraquinone is an important starting material for vat dye manufacture. Also used in making organics; and used as a bird repellent in seeds.

Shipping

UN3143 Dyes, solid, toxic, n.o.s. or Dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Crystallise anthraquinone from CHCl3 (38mL/g), *benzene, or boiling acetic acid, wash it with a little EtOH and dry it under vacuum over P2O5. [Beilstein 7 IV 2556.]

Toxicity evaluation

Anthraquinone is a stable compound that is virtually insoluble in water. It is not phytotoxic and does not inhibit germination of rice seeds or growth of sprouts. It has very low toxicity to birds and mammals, and it appears to be innocuous to insects as well. There is no known hazard to nontarget species from repellent applications of Flight Control.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

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AnthraquinoneSupplierMore

Hangzhou QiFei Chemical Co., Ltd. Gold
Tel:
18058801870
Email:
hzqifeihuagong@163.com;
J & K SCIENTIFIC LTD.
Tel:
400-666-7788 010-82848833-
Email:
jkinfo@jkchemical.com;market6@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel:
400-660-8290 21-61259100-
Email:
sh@meryer.com
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel:
18930552037 821-50328103-801
Email:
3bsc@sina.com
Alfa Aesar
Tel:
400-610-6006
Email:
saleschina@alfa-asia.com
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