Tazarotene supplier | CasNO.118292-40-3

Name
Tazarotene
EINECS 601-516-4
CAS No. 118292-40-3
Article Data11
CAS DataBase
Density 1.22 g/cm³
Solubility Well soluble in water
Melting Point 97-98 °C
Formula C₂₁H₂₁NO₂S
Boiling Point 499.8 °C at 760 mmHg
Molecular Weight 351.469
Flash Point 256.1 °C
Transport Information
Appearance White solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3-Pyridinecarboxylic acid,6-[(3,4-dihydro-4,4-dimethyl-2H-1- benzothiopyran-6-yl)ethynyl]-,ethyl ester;Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate;Tazorac;Zorac;AGN 190168;
PSA 64.49000
LogP 4.43150

Synthetic route

: 4,4-dimethylbenzothiopyran-6-ylacetylene

: 49608-01-7
6-chloro-3-pyridinecarboxylic acid ethyl ester

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
With palladium on activated charcoal; potassium acetate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 5h; Temperature; Reagent/catalyst; Solvent; Sonogashira Cross-Coupling; Inert atmosphere;	86.3%

: 118292-06-1
(4,4-dimethylthiochroman-6-yl)acetylene

: 49608-01-7
6-chloro-3-pyridinecarboxylic acid ethyl ester

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
Stage #1: 6-chloro-3-pyridinecarboxylic acid ethyl ester With potassium carbonate; triphenylphosphine; 5%-palladium/activated carbon In toluene at 45 - 50℃; Stage #2: (4,4-dimethylthiochroman-6-yl)acetylene; copper(l) iodide In toluene at 45 - 115℃; Product distribution / selectivity;	60%
Stage #1: 6-chloro-3-pyridinecarboxylic acid ethyl ester With palladium on activated charcoal; potassium carbonate; sodium sulfate; triphenylphosphine In toluene at 50 - 55℃; for 2h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: (4,4-dimethylthiochroman-6-yl)acetylene With copper(l) iodide In toluene at 105 - 115℃;	9 g

: 6-[2-(4,4-dimethylthiochroman-6yl)ethynyl]nicotinic acid ethyl ester S-oxide

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
With N,N-dimethyl-formamide; phosphorus trichloride at -20℃; for 1h;	59%
With phosphorus trichloride In N,N-dimethyl-formamide at -20℃; for 1h;	59%
With phosphorus trichloride In N,N-dimethyl-formamide at -20℃; for 1h;	59%

: 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl] nicotinic acid ethyl ester hydrochloride

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 2h; pH=7.5 - 8;	55%
With sodium hydrogencarbonate In water; ethyl acetate for 2 - 4h; Product distribution / selectivity;

: 118292-06-1
(4,4-dimethylthiochroman-6-yl)acetylene

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In tetrahydrofuran for 5h; Product distribution / selectivity; Heating / reflux;
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine In tetrahydrofuran at 25 - 30℃; for 24h; Product distribution / selectivity;

: 118292-06-1
(4,4-dimethylthiochroman-6-yl)acetylene

: ethyl 6-chloronicotinoate

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
With n-butyllithium; tetrakis(triphenylphosphine)palladium (0); zinc(II) chloride In tetrahydrofuran; hexane; ethyl acetate
With n-butyllithium; tetrakis(triphenylphosphine)palladium (0); zinc(II) chloride In tetrahydrofuran; hexane; ethyl acetate

: 118292-06-1
(4,4-dimethylthiochroman-6-yl)acetylene

: bis(triphenylphosphine)palladium(II) dichloride

: 49608-01-7
6-chloro-3-pyridinecarboxylic acid ethyl ester

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
In ethyl acetate; triethylamine

...Expand

: 64-17-5
ethanol

: 118292-41-4
6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl]nicotinic acid

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
With sulfuric acid Heating / reflux;

: 78-39-7
Triethyl orthoacetate

: 118292-41-4
6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl]nicotinic acid

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
In toluene at 110 - 120℃; Product distribution / selectivity;

: 952294-18-7
6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl] nicotinic acid hydrochloride

: 78-39-7
Triethyl orthoacetate

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
In toluene at 110 - 120℃; Product distribution / selectivity;

: 112110-44-8
6-bromo-4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C 2.1: potassium carbonate; copper(l) iodide; triphenylphosphine; palladium 10% on activated carbon / 1,2-dimethoxyethane; water / 0.5 h / 20 °C 2.2: 5 h / 80 °C 3.1: sodium hydride / toluene; mineral oil / Reflux 4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere 5.1: phosphorus trichloride / N,N-dimethyl-formamide / 1 h / -20 °C View Scheme
Multi-step reaction with 5 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C 2.1: potassium carbonate; copper(l) iodide; triphenylphosphine; palladium 10% on activated carbon / 1,2-dimethoxyethane; water / 0.5 h / 20 °C 2.2: 5 h / 80 °C 3.1: sodium hydride / toluene; mineral oil / Reflux 4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere 5.1: phosphorus trichloride / N,N-dimethyl-formamide / 1 h / -20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C
2.1: potassium carbonate; copper(l) iodide; triphenylphosphine; palladium 10% on activated carbon / 1,2-dimethoxyethane; water / 0.5 h / 20 °C
2.2: 5 h / 80 °C
3.1: sodium hydride / toluene; mineral oil / Reflux
4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere
5.1: phosphorus trichloride / N,N-dimethyl-formamide / 1 h / -20 °C
View Scheme

: 4,4-dimethyl-6-bromothiochromane S-oxide

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate; copper(l) iodide; triphenylphosphine; palladium 10% on activated carbon / 1,2-dimethoxyethane; water / 0.5 h / 20 °C 1.2: 5 h / 80 °C 2.1: sodium hydride / toluene; mineral oil / Reflux 3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere 4.1: phosphorus trichloride / N,N-dimethyl-formamide / 1 h / -20 °C View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate; copper(l) iodide; triphenylphosphine; palladium 10% on activated carbon / 1,2-dimethoxyethane; water / 0.5 h / 20 °C 1.2: 5 h / 80 °C 2.1: sodium hydride / toluene; mineral oil / Reflux 3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere 4.1: phosphorus trichloride / N,N-dimethyl-formamide / 1 h / -20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: potassium carbonate; copper(l) iodide; triphenylphosphine; palladium 10% on activated carbon / 1,2-dimethoxyethane; water / 0.5 h / 20 °C
1.2: 5 h / 80 °C
2.1: sodium hydride / toluene; mineral oil / Reflux
3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere
4.1: phosphorus trichloride / N,N-dimethyl-formamide / 1 h / -20 °C
View Scheme

: 864841-54-3
4-(4,4-dimethylthiochroman-6yl)-2-methyl-3-butyn-2-ol S-oxide

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / toluene; mineral oil / Reflux 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere 3: phosphorus trichloride / N,N-dimethyl-formamide / 1 h / -20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hydride / toluene; mineral oil / Reflux 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere 3: phosphorus trichloride / N,N-dimethyl-formamide / 1 h / -20 °C View Scheme

: 864841-55-4
4,4-dimethyl-6-ethynylthiochromane S-oxide

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere 2: phosphorus trichloride / N,N-dimethyl-formamide / 1 h / -20 °C View Scheme

: tazarotene hydrochloride

: 118292-40-3
tazarotene

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 25 - 30℃;	9 g

: 118292-40-3
tazarotene

: C21H25NO2S

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol under 3800.26 Torr; for 16h;	100%

: 118292-40-3
tazarotene

: 6-[2-(4,4-dimethylthiochroman-6yl)ethynyl]nicotinic acid ethyl ester S-oxide

Conditions

Conditions	Yield
With sodium periodate In methanol; water at 10 - 20℃; for 18.5h;	90%

: 118292-40-3
tazarotene

: ethyl (Z)-6-(2-(4,4-dimethylthiochroman-6-yl)vinyl)nicotinate

Conditions

Conditions	Yield
With hydrogen In methanol under 3800.26 Torr; for 16h; Reagent/catalyst; Solvent; Green chemistry; stereoselective reaction;	85%

: 118292-40-3
tazarotene

A: ethyl (Z)-6-(2-(4,4-dimethylthiochroman-6-yl)vinyl)nicotinate

B: C21H25NO2S

Conditions

Conditions	Yield
With hydrogen In methanol under 3800.26 Torr; for 15h;	A 85% B n/a

: 14516-54-2
bromopentacarbonylmanganese(I)

: 67-64-1
acetone

: 118292-40-3
tazarotene

: fac-[MnBr(CO)3(tazarotene)]*C3H6O

Conditions

Conditions	Yield
for 0.166667h; Inert atmosphere; Darkness; Reflux;	84%

...Expand

: 118292-40-3
tazarotene

: 6-(2-(4,4-dimethylthiochroman-6-yl)-ethynyl)-pyridin-3-ylmethanol

Conditions

Conditions	Yield
In tetrahydrofuran; water; ethyl acetate
With hydrogenchloride In tetrahydrofuran; water; ethyl acetate

: 118292-40-3
tazarotene

: 94-36-0
dibenzoyl peroxide

Conditions

Conditions	Yield
With dibenzoyl peroxide

: 118292-40-3
tazarotene

: 1262228-03-4
6-[4,4-dimethyl-2-(pyridine-3-carbonyloxy)thiochroman-6-ylethynyl]nicotinic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium periodate / water; methanol / 18.5 h / 10 - 20 °C 2: 5 h / 130 °C 3: sodium ethanolate; water / tetrahydrofuran / 12 h / 75 °C 4: triethylamine / dichloromethane / 18 h / 0 - 20 °C View Scheme

: 118292-40-3
tazarotene

A: 1262228-05-6
(R)-6-[4,4-dimethyl-2-(pyridine-3-carbonyloxy)thiochroman-6-ylethynyl]nicotinic acid ethyl ester

B: 1262228-04-5
(S)-6-[4,4-dimethyl-2-(pyridine-3-carbonyloxy)thiochroman-6-ylethynyl]nicotinic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium periodate / water; methanol / 18.5 h / 10 - 20 °C 2: 5 h / 130 °C 3: sodium ethanolate; water / tetrahydrofuran / 12 h / 75 °C 4: triethylamine / dichloromethane / 18 h / 0 - 20 °C 5: OJH column / ethanol / Resolution of racemate View Scheme

: 118292-40-3
tazarotene

: 1262228-08-9
ethyl 6-((4,4-dimethyl-2-oxothiochroman-6-yl)ethynyl)nicotinate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium periodate / water; methanol / 18.5 h / 10 - 20 °C 2: 5 h / 130 °C 3: sodium ethanolate; water / tetrahydrofuran / 12 h / 75 °C 4: Dess-Martin periodane / dichloromethane / 1 h / 20 °C View Scheme

: 118292-40-3
tazarotene

: 1262228-13-6
6-(2-acetoxy-4,4-dimethylthiochroman-6-ylethynyl)nicotinic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium periodate / water; methanol / 18.5 h / 10 - 20 °C 2: 5 h / 130 °C View Scheme

: 118292-40-3
tazarotene

: 1262228-06-7
6-((2-hydroxy-4,4-dimethylthiochroman-6-yl)ethynyl)nicotinic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium periodate / water; methanol / 18.5 h / 10 - 20 °C 2.1: 5 h / 130 °C 3.1: potassium hydroxide; water / ethanol / 18.5 h / 20 °C 3.2: pH ~ 5 View Scheme

: 118292-40-3
tazarotene

: 1262228-07-8
6-((4,4-dimethyl-2-oxothiochroman-6-yl)ethynyl)nicotinic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium periodate / water; methanol / 18.5 h / 10 - 20 °C 2.1: 5 h / 130 °C 3.1: sodium ethanolate; water / tetrahydrofuran / 12 h / 75 °C 4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 5.1: potassium hydroxide; water / ethanol / 18 h / 20 °C 5.2: pH ~ 5 View Scheme

: 118292-40-3
tazarotene

: 1338704-48-5
C29H37NO5SSi

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium periodate / water; methanol / 18.5 h / 10 - 20 °C 2: 5 h / 130 °C 3: sodium ethanolate; water / tetrahydrofuran / 12 h / 75 °C 4: triethylamine / dichloromethane / 17 h / 20 °C / Inert atmosphere View Scheme

: 118292-40-3
tazarotene

: 1262228-11-4
6-[2-(2-hydroxy-acetoxy)-4,4-dimethyl-thiochroman-6-ylethynyl]-nicotinic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium periodate / water; methanol / 18.5 h / 10 - 20 °C 2: 5 h / 130 °C 3: sodium ethanolate; water / tetrahydrofuran / 12 h / 75 °C 4: triethylamine / dichloromethane / 17 h / 20 °C / Inert atmosphere 5: water; tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 20 °C View Scheme

: 118292-40-3
tazarotene

: 1262228-10-3
ethyl 6-[(2-hydroxy-4,4-dimethyl-3,4-dihydro-2-thiochromen-6-yl)ethynyl]pyridine-3-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium periodate / water; methanol / 18.5 h / 10 - 20 °C 2: 5 h / 130 °C 3: sodium ethanolate; water / tetrahydrofuran / 12 h / 75 °C View Scheme

: 118292-40-3
tazarotene

: 1262228-00-1
6-(2-(2-benzoyloxy-4,4-dimethylthiochroman-6-yl)ethynyl)nicotinic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium periodate / water; methanol / 18.5 h / 10 - 20 °C 2: 5 h / 130 °C 3: sodium ethanolate; water / tetrahydrofuran / 12 h / 75 °C 4: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere View Scheme

: 118292-40-3
tazarotene

A: 1262228-02-3
(R)-6-(2-(2-benzoyloxy-4,4-dimethylthiochroman-6-yl)ethynyl)nicotinic acid ethyl ester

B: 1262228-01-2
(S)-6-(2-(2-benzoyloxy-4,4-dimethylthiochroman-6-yl)ethynyl)nicotinic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium periodate / water; methanol / 18.5 h / 10 - 20 °C 2: 5 h / 130 °C 3: sodium ethanolate; water / tetrahydrofuran / 12 h / 75 °C 4: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 5: chiral ADH column / isopropyl alcohol; water / Resolution of racemate View Scheme

Tazarotene Specification

The Tazarotene, with the CAS register number 118292-40-3, has the systematic name of 3-Pyridinecarboxylic acid, 6-((3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl)-, ethyl ester. And it is also called as 3-pyridinecarboxylicacid,6-((3,4-dihydro-4,4-dimethyl-2h-1-benzothiopyran-6-; Tazorac; Zorac; 6-[(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran)-6-yl]nicotinic acid ethyl ester. It is a kind of white solid and is soluble in water. Tazarotene is a member of the acetylenic class of retinoids. This medication is approved for treatment of psoriasis, acne, and sun damaged skin.

Physical properties about Tazarotene are: (1)ACD/LogP: 5.987; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.99; (4)ACD/LogD (pH 7.4): 5.99; (5)ACD/BCF (pH 5.5): 20904.67; (6)ACD/BCF (pH 7.4): 20904.74; (7)ACD/KOC (pH 5.5): 43054.20; (8)ACD/KOC (pH 7.4): 43054.34; (9)#H bond acceptors: 3; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.625; (12)Molar Refractivity: 101.397 cm³; (13)Molar Volume: 286.961 cm³; (14)Polarizability: 40.197 10-24cm³; (15)Surface Tension: 57.5369987487793 dyne/cm; (16)Density: 1.225 g/cm³; (17)Flash Point: 256.053 °C; (18)Enthalpy of Vaporization: 76.823 kJ/mol; (19)Boiling Point: 499.772 °C at 760 mmHg

Uses of Tazarotene: There is limited evidence that tazarotene and isotretinoin benefit patients with moderate photodamage on the face: both are associated with skin irritation and erythema. Tazarotene is used to treat acne on the face and and to treat psoriasis.

You can still convert the following datas into molecular structure:
(1)InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3;
(2)InChIKey=OGQICQVSFDPSEI-UHFFFAOYSA-N;
(3)Smilesc12c(cc(C#Cc3ccc(C(OCC)=O)cn3)cc1)C(CCS2)(C)C

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD	oral	> 2gm/kg (2000mg/kg)		Journal of the American Academy of Dermatology. Vol. 37(Suppl), Pg. S25, 1997.

Product Name

Tazarotene

Synthetic route

Tazarotene Specification

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