40018-26-6

Basic information

• Product Name: 2,5-Dihydroxy-1,4-dithiane
• Synonyms: 1,4-DITHIANE-2,5-DIOL;2,5-DIHYDROXY-1,4-DITHIANE;4-DITHIANE-2,5-DIOL;MERCATOACETALDEHYDE DIMER;MERCAPTOACETALDEHYDE DIMER;DITHIANE;LABOTEST-BB LT00138118;FEMA 3826
• CAS NO: 40018-26-6
• Molecular Formula: C₄H₈O₂S₂
• Molecular Weight: 152.24
• EINECS: 254-751-6
• Product Categories: Heterocyclic Compounds;aldehyde Flavor;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Others;S-Containing;2,5-Dihydroxy-1,4-Dithiane ada@tuskwei.com sky;18031153937@189.cn
• Mol File: 40018-26-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 130 °C (dec.)(lit.)
• Boiling Point: 244.73°C (rough estimate)
• Flash Point: 175.5 °C
• Appearance: White to yellow/Crystalline Powder
• Density: 1.224 (estimate)
• Vapor Pressure: 1.15E-06mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 0.39% at 20 °C
• PKA: 12.04±0.40(Predicted)
• Water Solubility: 3.9 g/L (20 ºC)
• BRN: 104402
• CAS DataBase Reference: 2,5-Dihydroxy-1,4-dithiane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dihydroxy-1,4-dithiane(40018-26-6)
• EPA Substance Registry System: 2,5-Dihydroxy-1,4-dithiane(40018-26-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-41-43-52/53-36/37/38
• Safety Statements: 26-36/37/39-61-37/39-24-36
• RIDADR: UN2811
• WGK Germany: 2
• F: 1-8-10-13
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 40018-26-6(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 40018-26-6 differently. You can refer to the following data:
1. 2,5-Dihydroxy-1,4-dithiane has a sulfurous, meaty, toasted bread-like odor
2. white to yellowish crystalline powder

Uses

Different sources of media describe the Uses of 40018-26-6 differently. You can refer to the following data:
1. 1,4-Dithiane-2,5-diol is a hydroxylated dithiane derivative with phytogrowth-inhibitory and antibacterial activities.
2. 1,4-Dithiane-2,5-diol was used in the synthesis of:substituted tetrahydrothiophene derivatives2-amino-3-(arylsulfonyl)thiophenes, potential antiviral and antitumor agents

Aroma threshold values

Aroma characteristics at 0.1% EtoH: sulfurous, grilled meaty, pungent, brothy, eggy, heavy and rich, toasted bread, tomato

Taste threshold values

Taste characteristics at 0.25 to 10 ppm: metallic, meaty savory chicken and beef, sulfurous, egg-yolk-like

Synthesis Reference(s)

Synthetic Communications, 14, p. 483, 1984 DOI: 10.1080/00397918408059569

General Description

1,4-Dithiane-2,5-diol undergoes bifunctional squaramide catalyzed sulfa-Michael/aldol cascade reaction with chalcones to afford trisubstituted tetrahydrothiophenes. It participates in diastereoselective [3+3] cycloaddition with azomethine imines catalyzed by 1,4-diazabicyclo[2.2.2]octane. It is a mercaptoacetaldehyde dimer and an efficient synthon for incorporating a thiol group to in situ generated nitroalkenes.

InChI:InChI=1/C4H8O2S2/c5-3-1-7-4(6)2-8-3/h3-6H,1-2H2/t3-,4+

Synthetic route

2-chloroethanal (107-20-0) → 1,4-dithiane-2,5-diol (40018-26-6)

Conditions	Yield
With sodium hydrogensulfide; water
With sodium hydroxide; hydrogen sulfide

2,5-diethoxy-[1,4]dithiane (408533-52-8) → 1,4-dithiane-2,5-diol (40018-26-6)

Conditions	Yield
With hydrogenchloride

2,2-diethoxy-ethanethiol (53608-94-9) → 1,4-dithiane-2,5-diol (40018-26-6)

Conditions	Yield
With hydrogenchloride

2,2-dimethyl-1,3oxathiolan-5-one (35350-46-0) → 1,4-dithiane-2,5-diol (40018-26-6) + 2-Mercaptomethyl-[1,3]oxathiolan-5-ol

Conditions	Yield
With diisobutylaluminium hydride In toluene at -78℃; for 2h;

1,4-dithiane-2,5-diol (40018-26-6) + methyl 2-diethylphosphono-4-methyl-2-pentenoate (660428-50-2) → 2-Isopropyl-2,5-dihydro-thiophene-3-carboxylic acid methyl ester (112177-95-4)

Conditions	Yield
With triethylamine In dichloromethane Heating;	100%

1,4-dithiane-2,5-diol (40018-26-6) + Benzoylacetonitrile (614-16-4) → (2-amino-thien-3-yl)phenylmethanone (21582-44-5)

Conditions	Yield
With triethylamine In 2,2,2-trifluoroethanol at 60℃; for 6.5h; Gewald Aminoheterocycles Synthesis; Microwave irradiation;	100%
Stage #1: 1,4-dithiane-2,5-diol; Benzoylacetonitrile In ethanol at 20℃; for 0.166667h; Stage #2: With N-methylpiperazine-functionalized Polyacrylonitrile Fiber In ethanol for 5h; Gewald Aminoheterocycles Synthesis; Reflux;	83%
With diethylamine In ethanol at 50℃; for 4h;	64%

1,4-dithiane-2,5-diol (40018-26-6) + cyanoacetic acid amide (107-91-5) → 2-aminothiophene-3-carboxamide (14080-51-4)

Conditions	Yield
With triethylamine In ethanol at 68℃; for 12h; Gewald Aminoheterocycles Synthesis; Inert atmosphere;	100%
With triethylamine In ethanol at 20℃; for 2.08333h; Heating / reflux;	88%
Stage #1: 1,4-dithiane-2,5-diol; cyanoacetic acid amide In ethanol at 20℃; for 0.166667h; Stage #2: With N-methylpiperazine-functionalized Polyacrylonitrile Fiber In ethanol for 4h; Gewald Aminoheterocycles Synthesis; Reflux;	87%

1,4-dithiane-2,5-diol (40018-26-6) + L-menthol glyoxylate monohydrate (111969-64-3) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate (200396-19-6)

Conditions	Yield
Stage #1: L-menthyl glyoxylate monohydrate With acetic acid In toluene at 110 - 115℃; Stage #2: 1,4-dithiane-2,5-diol In toluene Heating;	100%
Stage #1: 1,4-dithiane-2,5-diol With acetic acid In acetonitrile at 40 - 45℃; for 0.166667h; Stage #2: L-menthyl glyoxylate monohydrate In acetonitrile at 90℃; for 0.166667h;	88%
Stage #1: L-menthyl glyoxylate monohydrate With acetic acid In toluene at 110 - 111℃; for 3h; Stage #2: 1,4-dithiane-2,5-diol In toluene at 85 - 90℃; for 2h; Stage #3: With triethylamine In n-heptane at 0 - 5℃; for 6h;	80%
Stage #1: L-menthyl glyoxylate monohydrate With acetic acid In toluene at 120℃; for 2h; Dean-Stark; Stage #2: 1,4-dithiane-2,5-diol In toluene for 4h; Reflux; Stage #3: With triethylamine In hexane; toluene at 0℃; for 16h;

1,4-dithiane-2,5-diol (40018-26-6) + 3-amino-2-propanol (78-96-6, 1674-56-2) → 1-(di(thiiran-2-yl)amino)propan-2-ol

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 20℃; Reflux; Inert atmosphere;	100%

1,4-dithiane-2,5-diol (40018-26-6) + 3-amino-2-propanol (78-96-6, 1674-56-2) → C7H13NOS2

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 2h; Reagent/catalyst; Reflux;	100%

1,4-dithiane-2,5-diol (40018-26-6) + 5-(4-chlorophenyl)-1-phenylpent-2-en-4-yn-1-one → C19H15ClO2S

Conditions	Yield
With 3-{[(S)-{5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(6-methoxyquinolin-4-yl)methyl]amino}-4-[(2-fluorophenyl)amino]cyclobut-3-ene-1,2-dione In toluene at 60℃; for 6h; enantioselective reaction;	99.5%

1,4-dithiane-2,5-diol (40018-26-6) + 1-(2-thienyl)-2-nitroethene (34312-77-1) → 4-nitro-5-(thiophen-2-yl)tetrahydrothiophen-3-ol

Conditions	Yield
With triethylamine In dichloromethane at 20℃; tandem Michael-intramolecular Henry reaction; Inert atmosphere;	99%

1,4-dithiane-2,5-diol (40018-26-6) + (E)-2,4-dimethoxy-β-nitrostyrene (37630-19-6) → 5-(2,4-dimethoxyphenyl)-4-nitrotetrahydrothiophen-3-ol

Conditions	Yield
With triethylamine In dichloromethane at 20℃; tandem Michael-intramolecular Henry reaction; Inert atmosphere;	99%

1,4-dithiane-2,5-diol (40018-26-6) + (E)-1-methoxy-4-(2-nitrovinyl)benzene (3179-10-0, 5576-97-6) → 5-(4-methoxyphenyl)-4-nitrotetrahydrothiophen-3-ol

Conditions	Yield
With triethylamine In dichloromethane at 20℃; tandem Michael-intramolecular Henry reaction; Inert atmosphere;	99%

1,4-dithiane-2,5-diol (40018-26-6) + 1-[(E)-2-nitroethenyl]naphthalene (4735-49-3, 37630-26-5) → 5-naphthalen-1-yl-4-nitrotetrahydrothiophen-3-ol

Conditions	Yield
With triethylamine In dichloromethane at 20℃; tandem Michael-intramolecular Henry reaction; Inert atmosphere;	99%

1,4-dithiane-2,5-diol (40018-26-6) + trans-2,4-dichloro-β-nitrostyrene (18984-21-9, 34209-97-7) → 5-(2,4-dichlorophenyl)-4-nitrotetrahydrothiophen-3-ol

Conditions	Yield
With triethylamine In dichloromethane at 20℃; tandem Michael-intramolecular Henry reaction; Inert atmosphere;	99%

1,4-dithiane-2,5-diol (40018-26-6) + 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (959-33-1) → ((2R,3S,4S)-4-hydroxy-2-(4-methoxyphenyl)tetrahydrothiophen-3-yl)(phenyl)methanone (1357912-54-9)

Conditions	Yield
With potassium fluoride; C46H34I4O6 In dichloromethane at 20℃; for 24h; Schlenk technique; Inert atmosphere; stereoselective reaction;	99%
With C32H28F6N4O3 In toluene at 60℃; for 6h; optical yield given as %ee; enantioselective reaction;	91%
In water for 12h; Reflux;	60%

1,4-dithiane-2,5-diol (40018-26-6) + (E)-3-(4-chloro-benzylidene)-chroman-4-one (61661-20-9, 61926-52-1, 62174-08-7) → (2'SR,3SR,4'SR)-2'-(4-chlorophenyl)-4'-hydroxy-4',5'-dihydro-2'H-spiro[chromane-3,3'-thiophen]-4-one + 2'-(4-chlorophenyl)-4'-hydroxy-4',5'-dihydro-2'H-spiro[chromane-3,3'-thiophen]-4-one

Conditions	Yield
With triethylamine In toluene at 80℃; for 0.5h; diastereoselective reaction;	A n/a B 99%

1,4-dithiane-2,5-diol (40018-26-6) + (E)-3-[(pyridin-3-yl)methylene]chroman-4-one → (2'S,3S,4'S)-4'-hydroxy-2'-(pyridin-3-yl)-4',5'-dihydro-2'H-spiro[chroman-3,3'-thiophen]-4-one + C17H15NO3S + C17H15NO3S

Conditions	Yield
Stage #1: (E)-3-[(pyridin-3-yl)methylene]chroman-4-one With C31H29F3N4O3; magnesium sulfate In toluene at 20℃; for 0.25h; Stage #2: 1,4-dithiane-2,5-diol In toluene at 55℃; enantioselective reaction;	A 99% B n/a C n/a

1,4-dithiane-2,5-diol (40018-26-6) + 3-[(4-bromophenyl)methylene]-2,3-dihydro-4H-1-benzopyran-4-one (74074-04-7, 101001-05-2) → (2'S,3S,4'S)-2-(4-bromophenyl)-4'-hydroxy-4',5'-dihydro-2'H-spiro[chroman-3,3'-thiophen]-4-one + C18H15BrO3S

Conditions	Yield
Stage #1: 3-[(4-bromophenyl)methylene]-2,3-dihydro-4H-1-benzopyran-4-one With C31H29F3N4O3; magnesium sulfate In toluene at 20℃; for 0.25h; Stage #2: 1,4-dithiane-2,5-diol In toluene at 55℃; enantioselective reaction;	A 99% B n/a

1,4-dithiane-2,5-diol (40018-26-6) + 3-[(2-bromophenyl)methylene]-2,3-dihydro-4H-1-benzopyran-4-one → (2'R,3S,4'S)-2'-(2-bromophenyl)-4'-hydroxy-4',5'-dihydro-2'H-spiro[chroman-3,3'-thiophen]-4-one + C18H15BrO3S + C18H15BrO3S

Conditions	Yield
Stage #1: 3-[(2-bromophenyl)methylene]-2,3-dihydro-4H-1-benzopyran-4-one With C31H29F3N4O3; magnesium sulfate In toluene at 20℃; for 0.25h; Stage #2: 1,4-dithiane-2,5-diol In toluene at 55℃; enantioselective reaction;	A 99% B n/a C n/a

1,4-dithiane-2,5-diol (40018-26-6) + aurone (582-04-7, 37542-14-6, 75318-34-2) → (2R,2'S,4'R)-4'-hydroxy-2'-phenyl-4',5'-dihydro-2'H,3H-spiro[benzofuran-2,3'-thiophen]-3-one

Conditions	Yield
With C31H26F6N4O2 In 1,4-dioxane at 10℃; for 72h; enantioselective reaction;	99%

1,4-dithiane-2,5-diol (40018-26-6) + 3,4,5-trimethoxychalcone (127034-55-3, 60246-63-1) → ((2R,3S,4S)-4-hydroxy-2-(3,4,5-trimethoxyphenyl)tetrahydrothiophen-3-yl)(phenyl)methanone

Conditions	Yield
With potassium fluoride; C46H34I4O6 In dichloromethane at 20℃; for 24h; Schlenk technique; Inert atmosphere; stereoselective reaction;	99%

1,4-dithiane-2,5-diol (40018-26-6) + 4-fluorochalcone (1608-51-1, 22966-07-0, 102692-46-6) → ((2R,3S,4S)-2-(4-fluorophenyl)-4-hydroxytetrahydrothiophen-3-yl)(phenyl)methanone (1357912-51-6)

Conditions	Yield
With potassium fluoride; C46H34I4O6 In dichloromethane at 20℃; for 24h; Schlenk technique; Inert atmosphere; stereoselective reaction;	99%
With potassium fluoride; C46H34I4O6 In dichloromethane at 20℃; Inert atmosphere; stereoselective reaction;

1,4-dithiane-2,5-diol (40018-26-6) + 4-bromo-4'-methoxychalcone (92873-00-2) → ((2R,3S,4S)-2-(4-bromophenyl)-4-hydroxytetrahydrothiophen-3-yl)(4-methoxyphenyl)methanone

Conditions	Yield
With potassium fluoride; C46H34I4O6 In dichloromethane at 20℃; for 24h; Schlenk technique; Inert atmosphere; stereoselective reaction;	99%

1,4-dithiane-2,5-diol (40018-26-6) + 4-bromobenzal-4'-methylacetophenone (13565-40-7, 7020-14-6) → ((2R,3S,4S)-2-(4-bromophenyl)-4-hydroxytetrahydrothiophen-3-yl)(p-tolyl)methanone

Conditions	Yield
With potassium fluoride; C46H34I4O6 In dichloromethane at 20℃; for 24h; Schlenk technique; Inert atmosphere; stereoselective reaction;	99%

1,4-dithiane-2,5-diol (40018-26-6) + 4,4'-difluorochalcone (102692-35-3, 102692-49-9, 2805-56-3) → (4-fluorophenyl)((2R,3S,4S)-2-(4-fluorophenyl)-4-hydroxytetrahydrothiophen-3-yl)methanone

Conditions	Yield
With potassium fluoride; C46H34I4O6 In dichloromethane at 20℃; for 24h; Schlenk technique; Inert atmosphere; stereoselective reaction;	99%

1,4-dithiane-2,5-diol (40018-26-6) + C12H8Cl2N2O3 → 5-(3,4-dichlorophenyl)-4-(3-methyl-4-nitroisoxazol-5-yl)tetrahydrothiophen-3-ol

Conditions	Yield
In ethanol at 80℃;	99%

1,4-dithiane-2,5-diol (40018-26-6) + 3-Methyl-4-nitro-5-[(E)-2-(4-nitro-phenyl)-vinyl]-isoxazole (78080-53-2) → 4-(3-methyl-4-nitroisoxazol-5-yl)-5-(4-nitrophenyl)tetrahydrothiophen-3-ol

Conditions	Yield
In ethanol at 80℃;	99%

1,4-dithiane-2,5-diol (40018-26-6) + C12H9N3O5 → 4-(3-methyl-4-nitroisoxazol-5-yl)-5-(3-nitrophenyl)tetrahydrothiophen-3-ol

Conditions	Yield
In ethanol at 80℃;	99%

1,4-dithiane-2,5-diol (40018-26-6) + C12H9N3O5 → 4-(3-methyl-4-nitroisoxazol-5-yl)-5-(2-nitrophenyl)tetrahydrothiophen-3-ol

Conditions	Yield
In ethanol at 80℃;	99%

1,4-dithiane-2,5-diol (40018-26-6) + 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) → 2-(((3,5-bis-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)thio)acetaldehyde

Conditions	Yield
With methanol; P(p-C6H4F)3 at 20℃; for 24h;	99%

1,4-dithiane-2,5-diol (40018-26-6) + methyl vinyl ketone (78-94-4) → 3-acetyl-4-hydroxy-tetrahydrothiophene (564486-00-6)

Conditions	Yield
With 1,3-dicyclohexylimidazolium-2-carboxylate In tetrahydrofuran at 21℃; for 2h; Michael Addition;	98%
With triethylamine In dichloromethane 1.) 5 deg C, 45 min, 2.) 23 deg C, 17 h, 3.) reflux, 1 h;	48%

1,4-dithiane-2,5-diol (40018-26-6) + malononitrile (109-77-3) → 2-amino-3-cyanothiophene (4651-82-5)

Conditions	Yield
With triethylamine In methanol at 70℃; for 0.5h;	98%
Stage #1: 1,4-dithiane-2,5-diol; malononitrile In ethanol at 20℃; for 0.166667h; Stage #2: With N-methylpiperazine-functionalized Polyacrylonitrile Fiber In ethanol for 2h; Gewald Aminoheterocycles Synthesis; Reflux;	91%
With triethylamine; N,N-dimethyl-formamide In methanol at 50℃; for 0.0333333h; microwave irradiation;	81%

Upstream product

• 107-20-0 2-chloroethanal 
• 408533-52-8 2,5-diethoxy-[1,4]dithiane 
• 53608-94-9 2,2-diethoxy-ethanethiol 
• 35350-46-0 2,2-dimethyl-1,3oxathiolan-5-one 

Downstream Products

• 288-47-1 1,3-thiazole 
• 2722-34-1 2-phenylthiazoline 
• 24211-81-2 uscharin 
• 66867-06-9 2-methyl-2,5-dihydro-thiazole 
• 1534-21-0 glyoxal bis(phenylhydrazone) 
• 108284-82-8 2-ethyl-2,5-dihydro-thiazole 
• 66692-88-4 2,2-dimethyl-2,5-dihydrothiazole 
• 66867-03-6 2-Methyl-2-aethyl-thiazolin-(3) 
• 4124-63-4 mercaptoacetaldehyde 
• 55654-24-5 2-amino-3-(2-methylbenzoyl)thiophene 
• 40017-58-1 2-Amino-3-(o-chlorobenzoyl)-thiophene 
• 55865-52-6 (2-Amino-thiophen-3-yl)-(2-methoxy-phenyl)-methanone 
• 40017-77-4 2-Amino-3-(2,6-difluorbenzoyl)-thiophen 
• 76053-67-3 E-4-Mercapto-2-(o-nitrobenzoyl)-crotonsaeurenitril 

Relevant articles and documents

2-Mercaptoaldehyde dimers and 2,5-dihydrothiophenes from 1,3-oxathiolan-5-ones

Representative 1,3-oxathiolan-5-ones (6), prepared from 2-mercaptoacids, have been reduced to 2-mercaptoaldehydes 1 with diisobutylaluminum hydride.The aldehydes 1, which appear to exist in several dimeric forms, react with vinyltriphenylphosphonium bromide to give 2,5-dihydrothiophenes.