Thiochroman-4-one supplier | CasNO.3528-17-4

Name
Thiochroman-4-one
EINECS 222-548-1
CAS No. 3528-17-4
Article Data41
CAS DataBase
Density 1.241 g/cm³
Solubility
Melting Point 28-30 °C(lit.)
Formula C₉H₈OS
Boiling Point 293.7 °C at 760 mmHg
Molecular Weight 164.228
Flash Point 154.9 °C
Transport Information
Appearance
Safety S24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Thiochroman-4-one(6CI,7CI,8CI);1-Thiochroman-4-one;2,3-Dihydro-4-benzothiopyranone;2,3-Dihydro-4H-1-benzothiopyran-4-one;2,3-Dihydro-4H-thiochromen-4-one;Thiachroman-4-one;Thiochromanone;
PSA 42.37000
LogP 2.36510

Synthetic route

: 40316-60-7
thiochroman-4-ol

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

Conditions

Conditions	Yield
With dimethyl sulfoxide; triethylamine In dichloromethane at -40 - 20℃; for 8h;	93%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 24h; Ambient temperature;	92%
With ammonium nitrate; hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In water; acetonitrile at 60℃; for 18h; Green chemistry;	85%

: 93622-03-8
thiochroman-4-one semicarbazone

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

Conditions

Conditions	Yield
With potassium permanganate; silica gel In water at 20℃; for 0.416667h;	91%

: 5219-65-8
acide phenylthio-3 propanoique

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

Conditions

Conditions	Yield
With PPA for 0.0166667h; microwave irradiation;	80%
With sulfuric acid at 110℃; for 4h;	80%
With PPA at 60℃; for 96h;	66%

: 55454-08-5
4-(trimethylsilyloxy)thiochrom-3-ene

: 108-94-1
cyclohexanone

A: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

B: 94445-51-9
3-cyclohexylidene-4-thiochromanone

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane 1.) -78 deg C; 2.) 25 deg C, 18 h;	A 63% B 32%

...Expand

: 55454-08-5
4-(trimethylsilyloxy)thiochrom-3-ene

: 120-92-3
cyclopentanone

A: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

B: 491-39-4
thiochromen-4-one

C: 94445-49-5
3-cyclopentylidene-4-thiochromanone

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane 1.) -78 deg C; 2.) 25 deg C, 18 h;	A 24% B 20% C 22%

...Expand

: 7664-93-9
sulfuric acid

: 5219-65-8
acide phenylthio-3 propanoique

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 930-69-8
sodium thiophenolate

cyclooctatetraene 1,2-trans-dihalide: cyclooctatetraene 1,2-trans-dihalide

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / 0.06 h / microwave irradiation 2: 80 percent / polyphosphoric acid / 0.02 h / microwave irradiation View Scheme

: 882-33-7
diphenyldisulfane

1-(4-(biphenyl-4-yl)thiazol-2-yl)piperazine bound to Wang resin: 1-(4-(biphenyl-4-yl)thiazol-2-yl)piperazine bound to Wang resin

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / Heating 2: various solvent(s) / 1 h / 100 °C / Heating View Scheme

: 108-98-5
thiophenol

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH-solution 2: concentrated sulfuric acid / 20 °C View Scheme
Multi-step reaction with 2 steps 1: NaOH-solution 2: concentrated sulfuric acid / 60 °C View Scheme
Multi-step reaction with 2 steps 1: ethanol; water / 2 h / Reflux 2: sulfuric acid / 0 - 20 °C View Scheme

: 107-94-8
chloropropionic acid

: 108-98-5
thiophenol

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

Conditions

Conditions	Yield
With sodium hydroxide

: 60805-64-3
ethyl 3-(phenylthio)propionate

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol; water / Reflux 2: polyphosphoric acid / 100 °C View Scheme

: 66303-55-7
2-(phenylthio)acetaldehyde

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: zinc; iodine / diethyl ether; benzene / 20 °C / Inert atmosphere 1.2: 24 h / Inert atmosphere 2.1: sodium hydroxide / methanol; water / Reflux 3.1: polyphosphoric acid / 100 °C View Scheme

: 103-04-8
(phenylthio)acetic acid

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: polyphosphoric acid / 100 °C 2.1: zinc; iodine / diethyl ether; benzene / 20 °C / Inert atmosphere 2.2: 24 h / Inert atmosphere 3.1: sodium hydroxide / methanol; water / Reflux 4.1: polyphosphoric acid / 100 °C View Scheme

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 104-87-0
4-methyl-benzaldehyde

: 69964-53-0, 135521-92-5, 101001-08-5
(Z)-3-(4-methylbenzylidene)thiochroman-4-one

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 3h;	100%
With sulfuric acid In acetic acid at 20℃; for 0.333333h;	89%
With hydrogenchloride In ethanol for 0.0833333h; Ambient temperature;	64.1%
With piperidine In chloroform for 5h; Reflux;
With sodium hydroxide In ethanol; water at 0℃; for 0.5h;

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 100-52-7
benzaldehyde

: 74074-09-2
Z-3-benzylidene-1-thiochromanone

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 3h;	100%
With hydrogenchloride In ethanol	79.6%
With piperidine In chloroform for 5h; Reflux;
With sodium hydroxide In ethanol; water at 0℃; for 0.5h;

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 95-92-1
oxalic acid diethyl ester

: 56876-58-5
3-ethoxalyl-2,3-dihydro-1-benzothiopyran-4-one

Conditions

Conditions	Yield
With sodium ethanolate In ethanol at 40℃; for 2h;	100%
With sodium In ethanol Claisen Condensation;

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 26524-91-4
1-thiochroman-4-one 1-oxide

Conditions

Conditions	Yield
With water; silica gel; magnesium monoperoxyphthalate hexahydrate In dichloromethane at 40℃; for 1h;	100%
With phthaloyl peroxide In dichloromethane at 25℃; for 8h; Schlenk technique; chemoselective reaction;	99%
With sodium bromate; ammonium cerium(IV) nitrate; silica gel In dichloromethane at 20℃; for 0.566667h;	96%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 378-75-6
perfluoropropionic acid methyl ester

: lithium 3-(pentafluoropropanoyl)thiochromanonate

Conditions

Conditions	Yield
With methanol; lithium hydride In benzene Reflux; Inert atmosphere;	100%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 40316-60-7, 135711-13-6, 135818-63-2, 120466-74-2
(R)-3,4-dihydro-2H-thiochromen-4-ol

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C49H64FeNOP; hydrogen; sodium t-butanolate In isopropyl alcohol at 25 - 30℃; under 38002.6 Torr; for 12h; Autoclave; enantioselective reaction;	99%
With (S)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine; dimethylsulfide borane complex In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	92%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium formate In water at 30℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction;	79%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 19446-96-9
1,1-dioxo-1-thiochroman-4-one

Conditions

Conditions	Yield
With dihydrogen peroxide In acetonitrile at 40℃; for 0.333333h;	99%
With 3,3-dimethyldioxirane In dichloromethane; acetone at 0 - 5℃;	96%
With silica gel; magnesium monoperoxyphthalate hexahydrate In dichloromethane for 1.41667h; Heating;	84%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 40316-60-7, 120466-74-2, 135818-63-2, 135711-13-6
(S)-3,4-dihydro-2H-thiochromen-4-ol

Conditions

Conditions	Yield
With formic acid; [RuCl2(hexamethylbenzene)]2; (S)-2-piperidinemethanethiol hydrochloride; triethylamine at 30℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%
With Cp*Ir(OTf)(Msdpen); hydrogen In methanol at 60℃; under 11400.8 Torr; for 24h; optical yield given as %ee; enantioselective reaction;	99%
With formic acid; [RuCl2(hexamethylbenzene)]2; (S)-2-piperidinemethanethiol hydrochloride; triethylamine at 30℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 540-63-6
ethane-1,2-dithiol

: spiro[thiochromane-4,2’-[1,3]dithiolane]

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Inert atmosphere;	99%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 2054-35-5
thiochromane

Conditions

Conditions	Yield
With hydrogenchloride; mercury dichloride; zinc In toluene for 72h; Heating;	98%
With hydrogenchloride; amalgamated zinc In toluene for 72h; Heating;	98%
With molybdenum trisulfide; hydrogen In octane at 240℃; under 75006 Torr; for 1.5h;	95%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 40316-60-7
thiochroman-4-ol

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; Inert atmosphere;	98%
With methanol; sodium tetrahydroborate at 0 - 20℃; for 0.666667h; Inert atmosphere;	84%
With potassium hydroxide; Cr(L-Ala)2 In water; N,N-dimethyl-formamide for 18h; Ambient temperature; pH=9.9;	74%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 151-50-8
potassium cyanide

: 506-87-6
ammonium carbonate

: 66892-42-0
spiro(hydantoin-5,4'-thiochromane)

Conditions

Conditions	Yield
In ethanol; water at 55 - 60℃; Bucherer-Bergs reaction;	98%

...Expand

: 75-77-4
chloro-trimethyl-silane

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 55454-08-5
4-(trimethylsilyloxy)thiochrom-3-ene

Conditions

Conditions	Yield
With triethylamine; potassium iodide In chloroform 1.) chloroform, 0 deg C; 2.) reflux, 16 h;	97%
With triethylamine; potassium iodide In chloroform for 16h; Heating;	94%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 100-63-0
phenylhydrazine

: 4079-26-9
6,11-Dihydro-5-thia-11-aza-benzo[a]fluorene

Conditions

Conditions	Yield
With chloro-trimethyl-silane In ethanol for 4h; Reflux;	96%
With chloro-trimethyl-silane In ethanol for 4h; Reflux;	72%
(i) AcOH, (ii) HCl; Multistep reaction;
With hydrogenchloride In 1,4-dioxane; ethanol for 4h; Fischer indole reaction; Heating;

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 383-63-1
ethyl trifluoroacetate,

: 3-trifluoroacetyl-thiochroman-4-one

Conditions

Conditions	Yield
Stage #1: ethyl trifluoroacetate, With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2,3-dihydro-4H-[1]benzothiopyran-4-one In tetrahydrofuran for 2h; Reflux;	96%
With sodium methylate In methanol; diethyl ether for 16h;

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3
manganese triacetate

: 55444-15-0
4-oxo-3,4-dihydro-2H-thiochromen-3-yl acetate

Conditions

Conditions	Yield
With acetic acid In benzene for 5h; Heating;	96%
In benzene Heating;	89%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 15857-68-8
thiochroman-4-one oxime

Conditions

Conditions	Yield
With pyridine; hydroxylamine hydrochloride at 20℃; for 1.5h;	96%
With hydroxylamine hydrochloride; sodium acetate In methanol at 20℃; for 12h;	90%
With pyridine; hydroxylamine hydrochloride at 20℃; for 3h;	87%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 100-52-7
benzaldehyde

: 70-55-3
toluene-4-sulfonamide

: rac-(R)-3-[(S)-phenyl(tosylamino)methyl]thiochroman-4-one

Conditions

Conditions	Yield
With N,N,N',N'-tetramethylguanidine In toluene at 20℃; for 5h; Mannich reaction; Molecular sieve; optical yield given as %de; diastereoselective reaction;	96%

...Expand

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 109-94-4
formic acid ethyl ester

: 55390-63-1
3-(hydroxymethylene)thiochroman-4-one

Conditions

Conditions	Yield
With sodium hydride In toluene	95%
With sodium methylate In pyridine for 18h; Ambient temperature;

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 828-73-9
pentafluorophenyl hydrazine

: N-pentafluorophenyl-N'-thiochroman-4-ylidene-hydrazine

Conditions

Conditions	Yield
With acetic acid In ethanol for 3h; Condensation; Heating;	95%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

A: 26524-91-4
1-thiochroman-4-one 1-oxide

B: 19446-96-9
1,1-dioxo-1-thiochroman-4-one

Conditions

Conditions	Yield
With 3,3-dimethyldioxirane In dichloromethane; acetone at 0 - 5℃;	A 93% B 4.8%
With dihydrogen peroxide; titanium(IV) isopropylate; L-Tartaric acid; silica gel In methanol; water at 25℃; for 24h; Title compound not separated from byproducts;	A 92 % Spectr. B 3%
With sodium periodate Yield given. Yields of byproduct given;

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 5329-12-4
(2,4,6-trichlorophenyl)hydrazine

: N-thiochroman-4-ylidene-N'-(2,4,6-trichloro-phenyl)-hydrazine

Conditions

Conditions	Yield
With acetic acid In ethanol for 3h; Condensation; Heating;	93%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 100-52-7
benzaldehyde

: 17356-08-0
thiourea

: 116924-21-1
4-phenyl-(5H)-(1-benzthiopyrano)-(4,3-d)-1,2,3,4-tetrahydropyrimidine-2-thione

Conditions

Conditions	Yield
With 1-butyl-3-methylimidazolium hydrogen sulfate at 70℃; for 1h; Reagent/catalyst; Temperature; Green chemistry;	92%
With hydrogenchloride In butan-1-ol Heating;	53.23%

...Expand

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 4114-31-2
ethylhydrazine carboxylate

: 464201-58-9
thiochroman-4-one ethoxy carbonylhydrazone

Conditions

Conditions	Yield
With acetic acid In ethanol for 3h; Heating;	92%

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 100-52-7
benzaldehyde

: 17356-08-0
thiourea

: 536-38-9
4-chlorobenzoylmethyl bromide

: 9-(4-chlorophenyl)-7-phenyl-6,7-dihydrothiazolo[3,2-a]thiochromeno[4,3 d] pyrimidine

Conditions

Conditions	Yield
Stage #1: 2,3-dihydro-4H-[1]benzothiopyran-4-one; benzaldehyde; thiourea at 80℃; for 0.333333h; Ionic liquid; Stage #2: 4-chlorobenzoylmethyl bromide at 80℃; for 1h; Ionic liquid;	92%

...Expand

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 100-52-7
benzaldehyde

: 17356-08-0
thiourea

: 619-41-0
4-(bromoacetyl)toluene

: 7-phenyl-9-(p-tolyl)-6,7-dihydrothiazolo[3,2-a]thiochromeno[4,3-d]pyrimidine

Conditions

Conditions	Yield
Stage #1: 2,3-dihydro-4H-[1]benzothiopyran-4-one; benzaldehyde; thiourea at 80℃; for 0.333333h; Ionic liquid; Stage #2: 4-(bromoacetyl)toluene at 80℃; for 1h; Ionic liquid;	92%

...Expand

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 104-87-0
4-methyl-benzaldehyde

: 17356-08-0
thiourea

: 99-73-0
para-bromophenacyl bromide

: 9-(4-bromophenyl)-7-(p-tolyl)-6,7-dihydrothiazolo[3,2-a]thiochromeno[4,3-d]pyrimidine

Conditions

Conditions	Yield
Stage #1: 2,3-dihydro-4H-[1]benzothiopyran-4-one; 4-methyl-benzaldehyde; thiourea at 80℃; for 0.333333h; Ionic liquid; Stage #2: para-bromophenacyl bromide at 80℃; for 1h; Ionic liquid;	92%

...Expand

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 104-88-1
4-chlorobenzaldehyde

: 99-81-0
4-Nitrophenacyl bromide

: 17356-08-0
thiourea

: 7-(4-chlorophenyl)-9-(4-nitrophenyl)-6,7-dihydrothiazolo[3,2-a]thiochromeno[4,3-d]pyrimidine

Conditions

Conditions	Yield
Stage #1: 2,3-dihydro-4H-[1]benzothiopyran-4-one; 4-chlorobenzaldehyde; thiourea at 80℃; for 0.333333h; Ionic liquid; Stage #2: 4-Nitrophenacyl bromide at 80℃; for 1h; Ionic liquid;	92%

...Expand

: 3528-17-4
2,3-dihydro-4H-[1]benzothiopyran-4-one

: 123-11-5
4-methoxy-benzaldehyde

: 17356-08-0
thiourea

: 137985-64-9
4-(4-methoxyphenyl)-3,4-dihydro-1H-thiochromeno[4,3-d]pyrimidine-2(5H)-thione

Conditions

Conditions	Yield
With 1-butyl-3-methylimidazolium hydrogen sulfate at 70℃; for 1h; Green chemistry;	92%

...Expand

Thiochroman-4-one Chemical Properties

Molecular Structure of Thiochroman-4-one (CAS NO.3528-17-4):

IUPAC Name: 2,3-dihydrothiochromen-4-one
Empirical Formula: C₉H₈OS
Molecular Weight: 164.2242
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 42.37 Å²
Index of Refraction: 1.624
Molar Refractivity: 46.71 cm³
Molar Volume: 132.2 cm³
Surface Tension: 49.1 dyne/cm
Density: 1.241 g/cm³
Flash Point: 154.9 °C
Enthalpy of Vaporization: 53.33 kJ/mol
Boiling Point: 293.7 °C at 760 mmHg
Vapour Pressure: 0.0017 mmHg at 25°C
Melting point: 28-30 °C(lit.)
InChI
InChI=1/C9H8OS/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-4H,5-6H2
Smiles
c12c(C(CCS1)=O)cccc2
EINECS: 222-548-1
Product Categories: Heterocyclic Compounds; Heterocyclic Building Blocks; Others; S-Containing

Thiochroman-4-one Safety Profile

Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3

Thiochroman-4-one Specification

Thiochroman-4-one , with CAS number of 3528-17-4, can be called 1-Thiochroman-4-one ; 2,3-Dihydro-4-benzothiopyranone ; 2,3-Dihydro-4H-1-benzothiopyran-4-one ; 2,3-Dihydro-4H-thiochromen-4-one . It is an orange low melting solid.

Product Name

Thiochroman-4-one

Synthetic route

Thiochroman-4-one Chemical Properties

Thiochroman-4-one Safety Profile

Thiochroman-4-one Specification

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