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1744-22-5

Basic Information
CAS No.: 1744-22-5
Name: Riluzole
Molecular Structure:
Molecular Structure of 1744-22-5 (Riluzole)
Formula: C8H5F3N2OS
Molecular Weight: 234.202
Synonyms: Benzothiazole,2-amino-6-(trifluoromethoxy)- (7CI,8CI);6-(Trifluoromethoxy)-1,3-benzothiazol-2-amine;6-(Trifluoromethoxy)-2-aminobenzothiazole;6-Trifluoromethoxybenzothiazol-2-ylamine;PK 26124;RP 54274;Rilutek;
EINECS: 605-724-6
Density: 1.572 g/cm3
Melting Point: 116-118 °C
Boiling Point: 296.3 °C at 760 mmHg
Flash Point: 133 °C
Solubility: DMSO: ≥25 mg/mL
Appearance: white crystalline solid
Hazard Symbols: ToxicT,IrritantXi
Risk Codes: 25
Safety: 45
Transport Information: UN 2811 6.1/PG 3
PSA: 76.38000
LogP: 3.35830
Synthetic route
461-82-5

4-(trifluoromethoxy)aniline

333-20-0

potassium thioacyanate

1744-22-5

Riluzole

Conditions
ConditionsYield
With bromine; acetic acid at 0 - 20℃; for 16h; Inert atmosphere;95%
Stage #1: 4-(trifluoromethoxy)aniline; potassium thioacyanate In acetic acid at 20℃; for 0.333333h;
Stage #2: With bromine In acetic acid at 20℃;
94%
Stage #1: 4-(trifluoromethoxy)aniline; potassium thioacyanate With acetic acid for 0.166667h;
Stage #2: With bromine
86%
461-82-5

4-(trifluoromethoxy)aniline

1147550-11-5

ammonium thiocyanate

1744-22-5

Riluzole

Conditions
ConditionsYield
With benzyltrimethylazanium tribroman-2-uide In acetonitrile at 20℃; for 24h;80%
With benzyltrimethylazanium tribroman-2-uide In acetonitrile at 20℃; for 24h;80%
With benzyltrimethylazanium tribroman-2-uide In acetonitrile80%
461-82-5

4-(trifluoromethoxy)aniline

3674-54-2

tetrabutylammonium thiocyanate

1744-22-5

Riluzole

Conditions
ConditionsYield
With benzyltrimethylazanium tribroman-2-uide In dichloromethane at 20℃; for 18h;74%

3-(2-hydroxyethyl)-6-trifluoromethoxy-2-benzothiazoline hydrobromide

1744-22-5

Riluzole

131395-13-6

2-amino-4-nitro-6-trifluoromethoxy-benzothiazole

131395-12-5

2-amino-5-nitro-6-trifluoromethoxy-benzothiazole

1744-22-5

Riluzole

Conditions
ConditionsYield
In water
133840-98-9

2-hydrazinyl-6-(trifluoromethoxy)benzo[d]thiazole

1744-22-5

Riluzole

ammonium thiocyanate

461-82-5

4-(trifluoromethoxy)aniline

1744-22-5

Riluzole

Conditions
ConditionsYield
With bromine; acetic acid at 10 - 27℃; for 6.83333h;
1606922-37-5

C10H8F3N3O2S*ClH

1744-22-5

Riluzole

Conditions
ConditionsYield
With blood peptidase

C11H10F3N3O2S*ClH

1744-22-5

Riluzole

Conditions
ConditionsYield
With blood peptidase

2-(methylamino)-N-[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]acetamide hydrochloride

1744-22-5

Riluzole

Conditions
ConditionsYield
With blood peptidase
Downstream Products
133840-96-7
133840-98-9
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    Riluzole Basic information Product Name: Riluzole Synonyms: 6-TRIFLUOROMETHOXYBENZOTHIAZOLE-2-YL-AMINE;6-(TRIFLUOROMETHOXY)-1,3-BENZOTHIAZOL-2-AMINE;6-TRIFLUOROMETHOXY-BENZOTHIAZOL-2-YLAMINE;6-trifluoromethoxy-2-aminobenzothiazole;6-(TRIFLUORO

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Specification

The Riluzole is an organic compound with the formula C8H5F3N2OS. The IUPAC name of this chemical is 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine. With the CAS registry number 1744-22-5, it is also named as 2-Amino-6-trifluoromethoxybenzothiazole. The product's categories are Neuroprotective; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; GABA/Glycine Receptor; Glutamate. Besides, it may have clinical use in mood and anxiety disorders. It has been shown to have antidepressant properties in the treatment of refractory depression and as an anxiolytic in obsessive-compulsive disorder and in GAD.

Physical properties about Riluzole are: (1)ACD/LogP: 2.84; (2)ACD/LogD (pH 5.5): 2.84; (3)ACD/LogD (pH 7.4): 2.84; (4)ACD/BCF (pH 5.5): 84.23; (5)ACD/BCF (pH 7.4): 85.18; (6)ACD/KOC (pH 5.5): 828.83; (7)ACD/KOC (pH 7.4): 838.14; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 53.6 Å2; (12)Index of Refraction: 1.614; (13)Molar Refractivity: 51.94 cm3; (14)Molar Volume: 148.9 cm3; (15)Polarizability: 20.59×10-24cm3; (16)Surface Tension: 49.2 dyne/cm; (17)Density: 1.572 g/cm3; (18)Flash Point: 133 °C; (19)Enthalpy of Vaporization: 53.6 kJ/mol; (20)Boiling Point: 296.3 °C at 760 mmHg; (21)Vapour Pressure: 0.00145 mmHg at 25°C.

Preparation: this chemical can be prepared by 4-trifluoromethoxy aniline and NH4CNS. This reaction will need reagent Acetic acid and bromine. The yield is about 75%.



Uses of Riluzole: it can be used to produce 2-hydrazino-6-trifluoromethoxy-benzothiazole at temperature of 140 °C. It will need reagent hydrazine hydrate, hydrazine dihydrochloride and solvent ethane-1,2-diol with reaction time of 2 hours. The yield is about 90%.

When you are using this chemical, please be cautious about it as the following:
It is toxic if swallowed. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: FC(F)(F)Oc1ccc2nc(sc2c1)N
(2)InChI: InChI=1/C8H5F3N2OS/c9-8(10,11)14-4-1-2-5-6(3-4)15-7(12)13-5/h1-3H,(H2,12,13)
(3)InChIKey: FTALBRSUTCGOEG-UHFFFAOYAB
(4)Std. InChI: InChI=1S/C8H5F3N2OS/c9-8(10,11)14-4-1-2-5-6(3-4)15-7(12)13-5/h1-3H,(H2,12,13)
(5)Std. InChIKey: FTALBRSUTCGOEG-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 46mg/kg (46mg/kg)   European Patent Application. Vol. #50551,
mouse LD50 intravenous 34500ug/kg (34.5mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 41, Pg. 1973, 1999.
mouse LD50 oral 67mg/kg (67mg/kg)   European Patent Application. Vol. #50551,
rat LD50 intravenous 22mg/kg (22mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 41, Pg. 1973, 1999.
rat LD50 oral 45mg/kg (45mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 41, Pg. 1973, 1999.