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84-65-1

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Identification

Name
Anthraquinone
CAS
84-65-1
Synonyms
2-METHOXYBENZOIC ACID
9,10-ANTHRAQUINONE
9,10-DIHYDRO-9,10-ANTHRACENEDIONE
9,10-dihydro-9,10-dioxoanthracene
9,10-DIOXOANTHRACENE
ALPHA RAXIL CA
Anthracenedione
ANTHRAQUINONE
CORBIT
CORBIT(R)
GAUCHO BLE
Hoelite
'LGC' (1601)
'LGC' (2410)
MORKIT
9,10(9H,10H)-anthracenedione
9,10-Anthracenedione
9,10-anthracenequinone
9,10-Anthrachinon
9,10-dihydro-9,10-dioxo-anthracen
EINECS(EC#)
201-549-0
Molecular Formula
C14H8O2
MDL Number
MFCD00001188
Molecular Weight
208.21
MOL File
84-65-1.mol

Chemical Properties

Appearance
Anthraquinone is a combustible, light yellow to green crystalline solid.
Appearance
dull yellow powder
Melting point 
284-286 °C (lit.)
mp 
284-286 °C(lit.)

Boiling point 
379-381 °C (lit.)
bp 
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)
Fp 
365 °F

storage temp. 
no restrictions.
solubility 
0.00007g/l
form 
Powder
color 
Yellow-green to khaki to tan
Stability:
Stable. Incompatible with strong oxidizing agents. Combustible.
Water Solubility 
<0.1 g/100 mL at 23 ºC
Merck 
14,687
Detection Methods
HPLC,NMR
BRN 
390030
InChIKey
RZVHIXYEVGDQDX-UHFFFAOYSA-N
CAS DataBase Reference
84-65-1(CAS DataBase Reference)
NIST Chemistry Reference
9,10-Anthraquinone(84-65-1)
IARC
2B (Vol. 101) 2013
EPA Substance Registry System
84-65-1(EPA Substance)

Safety Data

Hazard Codes 
Xi
Risk Statements 
R43:May cause sensitization by skin contact.
R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Statements 
S36/37:Wear suitable protective clothing and gloves .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S24:Avoid contact with skin .
RIDADR 
3077
WGK Germany 
1

RTECS 
CB4725000

Autoignition Temperature
650 °C
TSCA 
Yes
HazardClass 
9
PackingGroup 
III
HS Code 
29146100
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.
Hazardous Substances Data
84-65-1(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: > 5000 mg/kg

Raw materials And Preparation Products

Hazard Information

General Description
Yellow crystals or powder.
Reactivity Profile
ANTHRAQUINONE(84-65-1) is incompatible with strong oxidizing agents.
Air & Water Reactions
Insoluble in water.
Hazard
Possible carcinogen.
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.
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
Fire Hazard
This chemical is combustible.
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.
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.
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.
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.
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.
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
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.
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.

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