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9(10H)-ACRIDONE

9(10H)-ACRIDONE structure

CAS No:
578-95-0
Formula:
C13H9NO
Chemical Name:
9(10H)-ACRIDONE
Synonyms:
AURORA KA-3719;acridin-9-(10H)-one;ACRIDONE, FOR FLUORESCENCE;9,10-Dihydro-9-oxoacridone;9(10H)-Acridone,99%;9(10H)-Acridone,97%;9(10H)-Acridone, pract., 96%;ACRIDONE(RG)
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

YELLOW CRYSTALLINE POWDER

Acridone is a member of the class of acridines that is 9,10-dihydroacridine substituted by an oxo group at position 9. It is a member of acridines and a cyclic ketone.

Dissolve ~1g in ca 1% NaOH (100mL), add 3M HCl to pH 4 when acridone separates as a pale yellow solid with m just above 350o (sharp). It can be recrystallised from large volumes of H2O to give a few mg. It is soluble in 160 parts of boiling EtOH (540 parts at 22o) [Albert & Phillips J Chem Soc 1294 1956]. Afew decigms are best crystallised as the hydrochloride from 400 parts of 10N HCl (90% recovery) from which the free base is obtained by washing the salt with H2O. A small quantity can be recrystallised (as the neutral species) from boiling AcOH. Larger quantities are best recrystallised from a mixture of 5 parts of freshly distilled aniline and 12.5 parts of glacial acetic acid. Acridone distils unchanged at atmospheric pressure, but the boiling point was not recorded, and some sublimation occurs below 350o. It has UV: 399nm. [see max Albert, The Acridines Arnold Press pp 201, 372 1966; for pKa see Kalatzis J Chem Soc (B) 96 1969, Beilstein 23/9 V 7.]

9(10H)-ACRIDONE Basic Attributes

Molecular Weight：

195.22

Exact Mass：

195.22

BRN：

7104

EC Number：

209-434-7

UNII：

6BK306GUQA

NSC Number：

408196|7664|138672

TSCA：

TSCA listed

DSSTox ID：

DTXSID8060371

Color/Form：

Yellow

HScode：

29339900

Characteristics

λmax：

380 nm399 nm (2nd)

PSA：

29.1

XLogP3：

Appearance：

light yellow to gold crystalline powder

Density：

1.1266 (rough estimate)

Melting Point：

>300 °C (lit.)

Boiling Point：

331.88°C (rough estimate)

Flash Point：

155.0±19.7 °C

Refractive Index：

1.6060 (estimate)

Water Solubility：

Insoluble in benzene, chloroform, ether, water and ethanol.

Storage Conditions：

Refrigerator

PKA：

-0.30±0.30(Predicted)

Critical Temperature & Pressure：

Sealed in dry,Room Temperature

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

22-24/25-37/39-26-36

RTECS Number：

AR6976000

Marks：

Xn:Harmful

Precautionary statement(s)：

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

Hazard Statements：

36/37/38-22-40

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 2 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

9(10H)-acridone

9(10H)-ACRIDONE Use and Manufacturing

Uses

9(10H)-Acridone is a catabolic product of carbamazepine (C175840) metabolite and can be used as a fluorescent tag for antibody catalysis.

9(10H)-Acridone is used in the preparation of methyl 9,10-dihydro-9-oxoacridine-10-pentanoate, use for dyeing the organic materials.

Manufacturing Info：

9(10H)-Acridinone: ACTIVE

Computed Properties

Molecular Weight:195.22
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:195.068413911
Monoisotopic Mass:195.068413911
Topological Polar Surface Area:29.1
Heavy Atom Count:15
Complexity:239
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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