6-Ethynyl-4,4-dimethylthiochroman supplier

Name
6-Ethynyl-4,4-dimethylthiochroman
EINECS
CAS No. 118292-06-1
Article Data12
CAS DataBase
Density 1.095 g/cm³
Solubility
Melting Point 69-72 °C
Formula C₁₃H₁₄S
Boiling Point 299.19 °C at 760 mmHg
Molecular Weight 202.32
Flash Point 127.846 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4,4-Dimethyl-6-ethynylthiochroman;6-Ethynyl-4,4-dimethyl-1,2,3,4-tetrahydro[1]benzthiothiopyran;
PSA 25.30000
LogP 3.44130

Synthetic route

: 1187617-88-4
6-(1,1-dichloroethyl)-4,4-dimethylthiochroman

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

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -5 - 35℃; Product distribution / selectivity;	90%

: 3-[4,4-dimethylthiochroman-6-yl]-3-chloro-2-propene-1-al

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

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 80 - 90℃; for 2h; Vilsmeier Hack reaction;	87.68%
With sodium hydroxide In 1,4-dioxane; water at 80 - 90℃; for 2h;	87.68%
With sodium hydroxide In 1,4-dioxane; water at 80 - 90℃; for 2h;	87.68%

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

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

Conditions

Conditions	Yield
With N,N-dimethyl-formamide; phosphorus trichloride at -20℃; for 1h;	85%
With phosphorus trichloride In N,N-dimethyl-formamide at -20℃; for 1h;	85%

: C13H18N2S

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

Conditions

Conditions	Yield
Stage #1: C13H18N2S With iodine; triethylamine In tetrahydrofuran at 20℃; for 2h; Stage #2: With potassium hydroxide In ethanol for 8h; Heating / reflux;

conc. hydrogen chloride: conc. hydrogen chloride

: 814-49-3
diethyl chlorophosphate

: 88579-23-1
3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl methyl ketone

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

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane; water; ethyl acetate
With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane; water; ethyl acetate

...Expand

: 2,2-dibromo-1-(4,4-dimethylthiochroman-6-yl)ethylene

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

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane

: 814-49-3
diethyl chlorophosphate

: 88579-23-1
3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl methyl ketone

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

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane
With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane

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

: 57362-77-3
ethyl 4-iodo-3-nitrobenzoate

: ethyl 3-nitro-4-((4,4-dimethylthiochroman-6-yl)ethynyl)benzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 70℃; for 8h; Inert atmosphere;	97%

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

: ethyl 2-chloro-4-iodobenzoate

: ethyl 2-chloro-4-((4,4-dimethylthiochroman-6-yl)ethynyl)benzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 80℃; for 8h; Inert atmosphere;	95%

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

: 2622-74-4
2-(4-bromophenyl)-1H-benzimidazole

: 1038865-98-3
C26H22N2S

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; triphenylphosphine; palladium dichloride In dimethyl sulfoxide at 90℃; Sonogashira coupling;	90%

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

: 205750-82-9
ethyl 2-fluoro-4-iodobenzoate

: ethyl 2-fluoro-4-((4,4-dimethylthiochroman-6-yl)ethynyl)benzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere;	86%

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

: 20776-54-9
2-amino-4-iodobenzoic acid

: 2-amino-4-((4,4-dimethylthiochroman-6-yl)ethynyl)benzoic acid

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 75℃; for 12h; Inert atmosphere;	85%

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

: 745783-97-5
triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

: (Z)-(2-(4,4-dimethylthiochroman-6-yl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)triethylsilane

Conditions

Conditions	Yield
With potassium hexamethylsilazane at 70℃; for 12h; stereoselective reaction;	84%

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

: ethyl 2,3-difluoro-4-iodobenzoate

: ethyl 2,3-difluoro-4-((4,4-dimethylthiochroman-6-yl)ethynyl)benzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 75℃; for 8h; Inert atmosphere;	82%

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

: 148490-97-5
4-iodo-2-methoxybenzoic acid-methyl ester

: C22H22O3S

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; isopropylamine In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere;	82%

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

: 730977-57-8
ethyl 2-hydroxy-4-iodobenzoate

: ethyl 4-((4,4-dimethylthiochroman-6-yl)ethynyl)-2-hydroxybenzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; isopropylamine In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere;	82%

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

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

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

Conditions

Conditions	Yield
Stage #1: (4,4-dimethylthiochroman-6-yl)acetylene; 6-chloro-3-pyridinecarboxylic acid ethyl ester With copper(l) iodide; triethanolamine; bis-triphenylphosphine-palladium(II) chloride In dimethyl sulfoxide at 20 - 98℃; for 3h; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 2.25h;	81%

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

: 18179-39-0
methyl 4-iodosalicylate

: methyl 4-((4,4-dimethylthiochroman-6-yl)ethynyl)-2-hydroxybenzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; isopropylamine In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere;	81%

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

: C10H11IO3

: C23H24O3S

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; isopropylamine In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere;	77%

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

: 51411-83-7
methyl 3-acetamido-4-iodobenzoate

: methyl 3-acetamido-4-((4,4-dimethylthiochroman-6-yl)ethynyl)benzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 70℃; for 8h; Inert atmosphere;	76%

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

: 121-69-7
N,N-dimethyl-aniline

: N-(3-(4,4-dimethylthiochroman-6-yl)prop-2-yn-1-yl)-N-methylaniline

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper(I) bromide In decane at 100℃; for 3.25h; Inert atmosphere;	76%

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

: 35387-92-9
methyl 4-iodo-3-methoxybenzoate

: C22H22O3S

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; isopropylamine In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere;	75%

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

: 257887-58-4
(3-bromo-3, 3-difluoroprop-1-yn-1-yl)triisopropylsilane

: C25H34F2SSi

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; caesium carbonate; tris-(o-tolyl)phosphine In toluene at 100℃; for 24h;	74%

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

: 89793-12-4
ethyl 2-chloropyrimidine-5-carboxylate

: ethyl 2-((4,4-dimethylthiochroman-6-yl)ethynyl)pyrimidin-5-carboxylate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 75℃; for 22h; Inert atmosphere;	73%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide for 22h; Inert atmosphere;	73%

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

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

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 3h;	72%

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

: trifluoroacetaldehyde N-triftosylhydrazone

: 5-(4,4-dimethylthiochroman-6-yl)-3-(trifluoromethyl)-1H-pyrazole

Conditions

Conditions	Yield
With potassium hydroxide In 1,4-dioxane at 100℃; for 10h; Schlenk technique; Glovebox; Inert atmosphere;	72%

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

: 36070-83-4
ethyl 5-bromopyrazine-2-carboxylate

: ethyl 5-((4,4-dimethylthiochroman-6-yl)ethynyl)pyrazin-2-carboxylate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 80℃; for 8h; Inert atmosphere;	71.5%

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

: 157942-12-6
methyl 3-hydroxy-4-iodobenzoate

: methyl 4-((4,4-dimethylthiochroman-6-yl)ethynyl)-3-hydroxybenzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; isopropylamine In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere;	71%

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

: 1027513-43-4
ethyl 3-fluoro-4-iodobenzoate

: ethyl 3-fluoro-4-((4,4-dimethylthiochroman-6-yl)ethynyl)benzoate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 70℃; for 8h; Inert atmosphere;	68%

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

: 38275-56-8
5-chloropyrimidine-2-carbonitrile

: 2-cyano-5-((4,4-dimethylthiochroman-6-yl)ethynyl)pyrimidine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; for 22h; Inert atmosphere;	65%

: 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

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

: 88284-48-4
2-(trimethylsilyl)phenyl trifluoromethanesulfonate

: 6-((2-iodophenyl)ethynyl)-4,4-dimethylthiochromane

Conditions

Conditions	Yield
With N-iodo-succinimide; chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]copper(I); caesium carbonate; cesium fluoride In acetonitrile at 60℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;	54%

: 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;

6-Ethynyl-4,4-dimethylthiochroman Chemical Properties

Empirical Formula of 6-Ethynyl-4,4-dimethylthiochroman (CAS NO.118292-06-1): C₁₃H₁₄S
Molecular Weight: 202.3153
Nominal Mass: 202 Da
Average Mass: 202.3153 Da
Monoisotopic Mass: 202.08162 Da
Index of Refraction: 1.597
Molar Refractivity: 62.935 cm³
Molar Volume: 184.789 cm³
Surface Tension: 45.195 dyne/cm
Density: 1.095 g/cm³
Flash Point: 127.846 °C
Enthalpy of Vaporization: 51.76 kJ/mol
Boiling Point: 299.19 °C at 760 mmHg
Vapour Pressure: 0.002 mmHg at 25 °C
Melting point: 69-72 °C
Structure of 6-Ethynyl-4,4-dimethylthiochroman (CAS NO.118292-06-1):

IUPAC Name: 4-(1-Ethoxyethenyl)-3,3,5,5-tetramethylcyclohexan-1-one
Canonical SMILES: CCOC(=C)C1C(CC(=O)CC1(C)C)(C)C
InChI: InChI=1S/C14H24O2/c1-7-16-10(2)12-13(3,4)8-11(15)9-14(12,5)6/h12H,2,7-9H2,1,3-6H3
InChIKey: YLNYLLVKHRZLGO-UHFFFAOYSA-N

6-Ethynyl-4,4-dimethylthiochroman Specification

6-Ethynyl-4,4-dimethylthiochroman , its cas register number is 118292-06-1. It also can be called 4,4-Dimethyl-6-ethynylthiochroman ; 6-Ethynyl-3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran ; and Kephalis .

Product Name

6-Ethynyl-4,4-dimethylthiochroman

Synthetic route

6-Ethynyl-4,4-dimethylthiochroman Chemical Properties

6-Ethynyl-4,4-dimethylthiochroman Specification

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