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

Description

2,5-Dihydroxy-1,4-dithiane, also known as 1,4-dithiane-2,5-diol, is a hydroxylated dithiane derivative characterized by its sulfurous, meaty, and toasted bread-like odor. It is a white to yellowish crystalline powder that is a mercaptoacetaldehyde dimer and serves as an efficient synthon for incorporating a thiol group into in situ generated nitroalkenes. 2,5-Dihydroxy-1,4-dithiane is known for its phytogrowth-inhibitory and antibacterial activities, making it a versatile chemical with potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
2,5-Dihydroxy-1,4-dithiane is used as a key intermediate in the synthesis of various pharmaceutical compounds, including substituted tetrahydrothiophene derivatives and 2-amino-3-(arylsulfonyl)thiophenes. These compounds have potential applications as antiviral and antitumor agents, contributing to the development of new treatments for various diseases.
Used in Flavor and Fragrance Industry:
Due to its unique aroma characteristics, 2,5-Dihydroxy-1,4-dithiane is used as a flavoring agent in the food and beverage industry. It imparts a sulfurous, grilled meaty, pungent, brothy, eggy, heavy and rich, and toasted bread-like aroma to products, enhancing their taste and overall sensory experience.
Used in Chemical Synthesis:
2,5-Dihydroxy-1,4-dithiane is used as a versatile building block in organic synthesis, particularly in the preparation of complex organic molecules. Its ability to participate in bifunctional squaramide catalyzed sulfa-Michael/aldol cascade reactions and diastereoselective [3+3] cycloaddition with azomethine imines catalyzed by 1,4-diazabicyclo[2.2.2]octane makes it a valuable compound for the synthesis of various organic compounds with potential applications in different industries.
Used in Agriculture:
2,5-Dihydroxy-1,4-dithiane is used as a phytogrowth-inhibitory agent in the agricultural industry. Its ability to inhibit plant growth can be utilized to control the growth of unwanted plants and improve crop yield, contributing to more efficient and sustainable agricultural practices.

Synthesis Reference(s)

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

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

Downstream Products

• 78389-10-3 2-Amino-3-(2,6-dichlorbenzoyl)-thiophen 
• 78389-11-4 2-(2,6-Dichlorbenzoyl)-4-mercapto-crotonsaeurenitril 
• 168542-30-1 (2-aminothiophen-3-yl)(4-fluorophenyl)methanone 
• 21582-44-5 (2-amino-thien-3-yl)phenylmethanone 
• 55865-51-5 (2-aminothiophen-3-yl)(4-chlorophenyl)methanone 
• 143446-73-5 5-acetoxy-2-(n-butyryloxy)methyl-1,3-oxathiolane 
• 4688-16-8 5-Nitrobenzothiophene-2-carboxaldehyde 
• 436093-36-6 (2-aminothiophen-3-yl)(4-methoxyphenyl)methanone 
• 21582-46-7 2-amino-3-(2-thiophenoyl)thiophene 

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.