Product Name

  • Name

    Afloqualone

  • EINECS
  • CAS No. 56287-74-2
  • Density 1.31 g/cm3
  • Solubility
  • Melting Point 195-196 °C
  • Formula C16H14FN3O
  • Boiling Point 492.541 °C at 760 mmHg
  • Molecular Weight 283.305
  • Flash Point 251.68 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 56287-74-2 (Afloqualone)
  • Hazard Symbols
  • Synonyms 6-Amino-2-(fluoromethyl)-3-(2-methylphenyl)quinazolin-4(3H)-one;4(3H)-Quinazolinone, 6-amino-2-(fluoromethyl)-3-(2-methylphenyl)- (9CI);Aroft;Arofuto;Afloqualona;Afloqualon;
  • PSA 60.91000
  • LogP 3.32700

Synthetic route

6-acetamido-2-fluoromethyl-3-(2-methylphenyl)-4(3H)-1,3-phthalazinone
61899-79-4

6-acetamido-2-fluoromethyl-3-(2-methylphenyl)-4(3H)-1,3-phthalazinone

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
56287-74-2

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 70℃; for 2h;88.5%
2-fluoromethyl-3-(o-hydroxymethylphenyl)-6-nitro-4(3H)-quinazolinone
56287-73-1

2-fluoromethyl-3-(o-hydroxymethylphenyl)-6-nitro-4(3H)-quinazolinone

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
56287-74-2

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
With stannous chloride In hydrogenchloride; methanol; chloroform; water; isopropyl alcohol84%
With hydrogenchloride; palladium-carbon In hydrogen72%
With acetic acid; palladium-carbon In chloroform; hydrogen52.5%
isatoic anhydride
118-48-9

isatoic anhydride

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
56287-74-2

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sulfuric acid; nitric acid / 2 h / 0 - 10 °C
2.1: hydrogen / tetrahydrofuran / 2 h / 60 °C / 15001.5 Torr
2.2: 1 h / 20 °C
3.1: ethanol / 4 h / Reflux
4.1: acetic acid / 4.33 h / Reflux
5.1: potassium fluoride; tetrabutylammomium bromide / acetonitrile / 4 h / Reflux
6.1: sodium hydroxide / ethanol; water / 2 h / 70 °C
View Scheme
6-nitroisatoic anhydride
4693-02-1

6-nitroisatoic anhydride

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
56287-74-2

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogen / tetrahydrofuran / 2 h / 60 °C / 15001.5 Torr
1.2: 1 h / 20 °C
2.1: ethanol / 4 h / Reflux
3.1: acetic acid / 4.33 h / Reflux
4.1: potassium fluoride; tetrabutylammomium bromide / acetonitrile / 4 h / Reflux
5.1: sodium hydroxide / ethanol; water / 2 h / 70 °C
View Scheme
N-(2,4-dioxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)acetamide
353759-49-6

N-(2,4-dioxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)acetamide

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
56287-74-2

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethanol / 4 h / Reflux
2: acetic acid / 4.33 h / Reflux
3: potassium fluoride; tetrabutylammomium bromide / acetonitrile / 4 h / Reflux
4: sodium hydroxide / ethanol; water / 2 h / 70 °C
View Scheme
N-(2-amino-5-acetamidobenzoyl)-o-toluidine
64102-81-4

N-(2-amino-5-acetamidobenzoyl)-o-toluidine

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
56287-74-2

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid / 4.33 h / Reflux
2: potassium fluoride; tetrabutylammomium bromide / acetonitrile / 4 h / Reflux
3: sodium hydroxide / ethanol; water / 2 h / 70 °C
View Scheme
6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
56287-74-2

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone

Acetoxyacetyl chloride
13831-31-7

Acetoxyacetyl chloride

6-acetoxyacetamido-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
87265-98-3

6-acetoxyacetamido-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;93.8%
glycolic Acid
79-14-1

glycolic Acid

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
56287-74-2

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone

2-fluoromethyl-6-hydroxyacetamido-3-(o-tolyl)-4(3H)-quinazolinone
87081-79-6

2-fluoromethyl-6-hydroxyacetamido-3-(o-tolyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 6h; Ambient temperature;35.2%
6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone
56287-74-2

6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone

2-fluoromethyl-6-hydroxyacetamido-3-(o-tolyl)-4(3H)-quinazolinone
87081-79-6

2-fluoromethyl-6-hydroxyacetamido-3-(o-tolyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93.8 percent / tetrahydrofuran / Ambient temperature
2: 80.9 percent / NaHCO3 / methanol; H2O / 1 h / Heating
View Scheme

Afloqualone Specification

The CAS registry number of Afloqualone is 56287-74-2. In addition, the molecular formula is C16H14FN3O and the molecular weight is 283.30. Its IUPAC name is 6-amino-2-(fluoromethyl)-3-(2-methylphenyl)quinazolin-4-one. What's more, it is an analogue of methaqualone. It has sedative and muscle relaxant effects, and has had some clinical use.

Physical properties about Afloqualone are: (1)ACD/LogP: 0.85; (2)ACD/LogD (pH 5.5): 0.851; (3)ACD/LogD (pH 7.4): 0.852; (4)ACD/BCF (pH 5.5): 2.61; (5)ACD/BCF (pH 7.4): 2.614; (6)ACD/KOC (pH 5.5): 69.142; (7)ACD/KOC (pH 7.4): 69.233; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 58.69 Å2; (12)Index of Refraction: 1.642; (13)Molar Refractivity: 78.098 cm3; (14)Molar Volume: 216.248 cm3; (15)Polarizability: 30.96 ×10-24cm3; (16)Surface Tension: 47.295 dyne/cm; (17)Density: 1.31 g/cm3; (18)Flash Point: 251.68 °C; (19)Enthalpy of Vaporization: 75.949 kJ/mol; (20)Boiling Point: 492.541 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc1ccccc1n2c(nc3ccc(cc3c2=O)N)CF
(2)Std. InChI: InChI=1S/C16H14FN3O/c1-10-4-2-3-5-14(10)20-15(9-17)19-13-7-6-11(18)8-12(13)16(20)21/h2-8H,9,18H2,1H3
(3)Std. InChIKey: VDOSWXIDETXFET-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 272mg/kg (272mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983.
mouse LD50 oral 397mg/kg (397mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983.
mouse LD50 subcutaneous 591mg/kg (591mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983.
rat LD50 intraperitoneal 385mg/kg (385mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983.
rat LD50 oral 249mg/kg (249mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983.
rat LD50 subcutaneous 823mg/kg (823mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 991, 1983.

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