Riluzole supplier | CasNO.1744-22-5

Name
Riluzole
EINECS 605-724-6
CAS No. 1744-22-5
Density 1.572 g/cm³
Solubility DMSO: ≥25 mg/mL
Melting Point 116-118 °C
Formula C₈H₅F₃N₂OS
Boiling Point 296.3 °C at 760 mmHg
Molecular Weight 234.202
Flash Point 133 °C
Transport Information UN 2811 6.1/PG 3
Appearance white crystalline solid
Safety 45
Risk Codes 25
Molecular Structure
Hazard Symbols T,Xi
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;
PSA 76.38000
LogP 3.35830

Synthetic route

: 461-82-5
4-(trifluoromethoxy)aniline

: 333-20-0
potassium thioacyanate

: 1744-22-5
Riluzole

Conditions

Conditions	Yield
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

Conditions	Yield
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 acetonitrile	80%

: 461-82-5
4-(trifluoromethoxy)aniline

: 3674-54-2
tetrabutylammonium thiocyanate

: 1744-22-5
Riluzole

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With bromine; acetic acid at 10 - 27℃; for 6.83333h;

: 1606922-37-5
C10H8F3N3O2S*ClH

: 1744-22-5
Riluzole

Conditions

Conditions	Yield
With blood peptidase

: C11H10F3N3O2S*ClH

: 1744-22-5
Riluzole

Conditions

Conditions	Yield
With blood peptidase

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

: 1744-22-5
Riluzole

Conditions

Conditions	Yield
With blood peptidase

: C15H16F3N3O4S*ClH

: 1744-22-5
Riluzole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane / 2 h 2: blood peptidase View Scheme

: C16H18F3N3O4S*ClH

: 1744-22-5
Riluzole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane / 2 h 2: blood peptidase View Scheme

: C16H18F3N3O4S*ClH

: 1744-22-5
Riluzole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane / 2 h 2: blood peptidase View Scheme

: 142229-74-1
N-<4-(trifluoromethoxy)phenyl>thiourea

: 1744-22-5
Riluzole

Conditions

Conditions	Yield
With bromine; acetic acid; lithium bromide at 40℃;

: 461-82-5
4-(trifluoromethoxy)aniline

: 1744-22-5
Riluzole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic acid / Isopropyl acetate / 16 h / Reflux 2: acetic acid; lithium bromide; bromine / 40 °C View Scheme

: 3582-05-6
trifluoromethyl trifluoromethanesulfonate

: 1744-22-5
Riluzole

: 1,3-bis(6-(trifluoromethoxy)benzo[d]thiazol-2-yl)urea

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	96%

: 1744-22-5
Riluzole

: 57-06-7
N-allyl isothiocyanate

: 1-allyl-3-(6-trifluoromethoxy-1,3-benzothiazol-2-yl)thiourea

Conditions

Conditions	Yield
In ethanol for 16h; Reflux;	95%

: (5R,8R)-9-oxo-5,6,7,9-tetrahydro-8H-5,8-methanobenzo[7]annulene-8-carboxylic acid

: 1744-22-5
Riluzole

: (5R,8R)-9-oxo-N-(6-(trifluoromethoxy)benzo[d]thiazol-2-yl)-5,6,7,9-tetrahydro-8H-5,8-methanobenzo[7]annulene-8-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 15h;	94%

: 763903-09-9
2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic acid

: 1744-22-5
Riluzole

: 1392441-96-1
N1-(6-(trifluoromethoxy)-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	93%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 24h;	80%
Stage #1: Riluzole With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Stage #2: 2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic acid In dichloromethane at 25℃; for 24h;	80%

: 40465-45-0
p-cyanophenyl isocyanate

: 1744-22-5
Riluzole

: 1343448-00-9
1-(4-cyanophenyl)-3-(6-trifluoromethoxybenzothiazol 2-yl)urea

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 5h;	93%

: 67-56-1
methanol

: 1744-22-5
Riluzole

: 133840-97-8
N-methyl-6-(trifluoromethoxy)benzo[d]thiazol-2-amine

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydroxide at 150℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;	92%

: 1195-45-5
para-fluorophenyl isocyanate

: 1744-22-5
Riluzole

: 1343447-98-2
1-(4-fluorophenyl)-3-(6-trifluoromethoxybenzothiazol-2-yl)urea

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 5h;	91%

: 1744-22-5
Riluzole

: 133840-98-9
2-hydrazinyl-6-(trifluoromethoxy)benzo[d]thiazole

Conditions

Conditions	Yield
With hydrazine dihydrochloride; hydrazine hydrate In ethylene glycol at 140℃; for 2h;	90%
With hydrazine hydrate; hydrazinium sulfate In water at 130℃; for 4h; Inert atmosphere;	75%
With hydrazinium sulfate; hydrazine In ethylene glycol at 140℃; for 2.5h;	65%
With hydrazine
With hydrogenchloride; hydrazine hydrate for 5h; Reflux;

: 1744-22-5
Riluzole

: 71-36-3
butan-1-ol

: 1353280-38-2
2-(N-n-butylamine)-6-trifluoromethoxy-benzothiazole

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydroxide at 150℃; for 12h; Inert atmosphere; regioselective reaction;	90%

: 201230-82-2
carbon monoxide

: N-(2'-iodo-[1,1'-biphenyl]-2-yl)-N-methylacrylamide

: 1744-22-5
Riluzole

: (aR,S)-2-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-N-(6-(trifluoromethoxy)benzo[d]thiazol-2-yl)acetamide

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); C25H23OP; caesium carbonate In toluene at 40℃; under 760.051 Torr; for 10h; Schlenk technique; stereoselective reaction;	88%

...Expand

: 1744-22-5
Riluzole

: 100-51-6
benzyl alcohol

: 1307865-22-0
N-benzyl-6-(trifluoromethoxy)benzo[d]thiazol-2-amine

Conditions

Conditions	Yield
With copper(l) chloride; sodium hydroxide In para-xylene at 160℃; for 12h; Inert atmosphere; regioselective reaction;	87%

: 5416-93-3
4-Methoxyphenyl isocyanate

: 1744-22-5
Riluzole

: 1343447-99-3
1-(4-methoxyphenyl)-3-(6-(trifluoromethoxy)benzo[d]thiazol-2-yl)urea

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 5h;	84%

: 68-11-1
mercaptoacetic acid

: 6334-18-5
2,3-dichlorobenzylaldehyde

: 1744-22-5
Riluzole

: 3-(6-trifluoromethoxy-benzo[d]thiazol-2-yl)-2-(2,3-dichlorophenyl)thiazolidin-4-one

Conditions

Conditions	Yield
In ethanol at 100℃; for 0.5h; Sealed tube; Microwave irradiation;	84%

...Expand

: 67-56-1
methanol

: 42248-31-7
6-Chloro-4-oxo-4H-chromene-3-carbaldehyde

: 1744-22-5
Riluzole

: C19H12ClF3N2O4S

Conditions

Conditions	Yield
at 30 - 40℃; for 10h; stereoselective reaction;	82%

...Expand

: 1357099-42-3
(E)-2-(2-methoxy-5-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)phenoxy)acetic acid

: 1744-22-5
Riluzole

: 1379509-97-3
N1-(6-(trifluoromethoxy)-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)-1-propenyl]phenoxy}acetamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	81%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 24h;	80%
Stage #1: Riluzole With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Stage #2: (E)-2-(2-methoxy-5-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)phenoxy)acetic acid In dichloromethane at 25℃; for 24h;	80%

: 2,6-difluorophenyl isocyanate

: 1744-22-5
Riluzole

: 1343448-03-2
1-(2,6-difluorophenyl)-3-(6-trifluoromethoxybenzothiazol-2-yl)urea

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 5h;	81%

: 1392443-96-7
2-{5-[1-acetyl-3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-5-pyrazolyl]-2-methoxyphenoxy}acetic acid

: 1744-22-5
Riluzole

: 1392442-07-7
N1-(6-(trifluoromethoxy)-1,3-benzothiazol-2-yl)-2-{5-[1-acetyl-3-(3,4,5-trimethoxy phenyl)-4,5-dihydro-1H-5-pyrazolyl]-2-methoxyphenoxy}acetamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 24h;	80%
Stage #1: Riluzole With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Stage #2: 2-{5-[1-acetyl-3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-5-pyrazolyl]-2-methoxyphenoxy}acetic acid In dichloromethane at 25℃; for 24h;	80%

: 684-16-2
Hexafluoroacetone

: 1744-22-5
Riluzole

: N-(2,2,2-trifluoro-1-trifluoromethylethylidene)-6-(trifluoromethoxy)benzothiazol-2-ylamine

Conditions

Conditions	Yield
Stage #1: Hexafluoroacetone; Riluzole With pyridine In benzene at 20℃; for 0.5h; Stage #2: With thionyl chloride In benzene for 1h;	79%

: 13089-11-7
methyl 3,3,3-trifluoropyruvate

: 1744-22-5
Riluzole

: methyl 3,3,3-trifluoro-2-(6-(trifluoromethoxy)benzothiazol-2-ylimino)propionate

Conditions

Conditions	Yield
Stage #1: methyl 3,3,3-trifluoropyruvate; Riluzole With pyridine In benzene at 20℃; for 0.5h; Stage #2: With thionyl chloride In benzene for 1h;	78%

: 3878-55-5
methyl hydrogen succinate

: 1744-22-5
Riluzole

: 1394929-73-7
N-(6-trifluoromethoxy-benzothiazol-2-yl)-succinamic acid methyl ester

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 96h;	77%

: 1744-22-5
Riluzole

: 144864-70-0
2-amino-4-bromo-6-trifluoromethoxy-benzothiazole hydrobromide

Conditions

Conditions	Yield
With bromine In acetic acid at 50℃; for 12h;	76%

: 84501-28-0
2-hydroxy-5-t-butylisophthalaldehyde

: 1744-22-5
Riluzole

: C20H17F3N2O3S

Conditions

Conditions	Yield
In ethanol at 20℃;	75%

: 124-63-0
methanesulfonyl chloride

: 1744-22-5
Riluzole

: N-[6-(trifluoromethoxy)benzo[d]thiazol-2-yl]methanesulfonamide

Conditions

Conditions	Yield
With triethylamine In benzene for 2h;	75%

: 1744-22-5
Riluzole

: 109-61-5
propoxycarbonyl chloride

: 1394929-66-8
(6-trifluoromethoxy-benzothiazol-2-yl)-carbamic acid propyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	74%

: 6557-86-4
cycloheptanecarbonyl chloride

: 1744-22-5
Riluzole

: N-[6-(trifluoromethoxy)benzothiazol-2-yl]cycloheptanecarboxamide

Conditions

Conditions	Yield
In dichloromethane at 20℃;	73%
In dichloromethane at 20℃;

: 83-38-5
2,6-dichlorobenzaldehyde

: 68-11-1
mercaptoacetic acid

: 1744-22-5
Riluzole

: 3-(6-trifluoromethoxy-benzo[d]thiazol-2-yl)-2-(2,6-dichlorophenyl)thiazolidin-4-one

Conditions

Conditions	Yield
In ethanol at 100℃; for 0.5h; Sealed tube; Microwave irradiation;	73%

...Expand

: 6092-54-2
n-hexyl chloroformate

: 1744-22-5
Riluzole

: (6-trifluoromethoxy-benzothiazol-2-yl)-carbamic acid hexyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	72%

Riluzole 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.

Product Name

Riluzole

Synthetic route

Riluzole Specification

Related Products

Hot Products