1073-05-8

Basic information

• Product Name: 1,3,2-DIOXATHIANE 2,2-DIOXIDE
• Synonyms: 1,3-Propanediol, cyclic sulphate;1,3-Propylene sulfate;1,3-Propylenesulfate;Trimethylene sulfate;trimethylenesulfate;1,3,2-DIOXATHIANE 2,2-DIOXIDE;1,3-PROPANEDIOL CYCLIC SULFATE;1,3-PROPYLENESULPHATE
• CAS NO: 1073-05-8
• Molecular Formula: C₃H₆O₄S
• Molecular Weight: 138.14
• EINECS: 214-022-5
• Product Categories: Heterocyclic Compounds;Fine Chemical&Pharmaceutical
• Mol File: 1073-05-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 58-62 °C(lit.)
• Boiling Point: 153℃ (14 Torr)
• Flash Point: 99.2ºC
• Appearance: /solid
• Density: 1.332 (estimate)
• Vapor Pressure: 0.0589mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• CAS DataBase Reference: 1,3,2-DIOXATHIANE 2,2-DIOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-DIOXATHIANE 2,2-DIOXIDE(1073-05-8)
• EPA Substance Registry System: 1,3,2-DIOXATHIANE 2,2-DIOXIDE(1073-05-8)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36
• WGK Germany: 3
• RTECS: TY4560000
• Hazardous Substances Data: 1073-05-8(Hazardous Substances Data)

Usage

Uses

1,3,2-Dioxathiane 2,2-Dioxide is a reagent used in the synthesis of deoxy salacinols via coupling reaction.

General Description

Bacillus sp. CCZU11-1 catalyzed biotransformation of 1,3-propanediol cyclic sulfate (1,3-PDS) and its derivatives has been proposed. It can undergo biocatalyzed transformation to diols by Rhodococcus sp.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C3H6O4S/c4-8(5)6-2-1-3-7-8/h1-3H2

Synthetic route

sulfuric acid mono-(3-hydroxy-propyl) ester → 1,3,2-dioxathiane 2,2-dioxide (1073-05-8)

Conditions	Yield
With modified ZSM-5 molecular sieve catalyst In toluene at 105 - 115℃; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube;	92%

2-oxo-1,3,2-dioxathiane (4176-55-0) → 1,3,2-dioxathiane 2,2-dioxide (1073-05-8)

Conditions	Yield
With ruthenium tetroxide In chloroform; water at 0℃; for 0.0125h;	87%
With potassium permanganate In acetic acid for 1h; Ambient temperature;	20%
With ruthenium trichloride; sodium periodate; sodium hydrogencarbonate In tetrachloromethane; water; acetonitrile at 20℃; for 0.5h;	890 mg

trimethyleneglycol (504-63-2) → 1,3,2-dioxathiane 2,2-dioxide (1073-05-8)

Conditions	Yield
Stage #1: trimethyleneglycol With thionyl chloride In tetrachloromethane for 1.5h; Heating; Stage #2: With ruthenium trichloride; sodium periodate In water; acetonitrile at 20℃; for 1.5h; Further stages.;	87%
Stage #1: trimethyleneglycol With sodium methylate In toluene for 15h; Reflux; Stage #2: With fluorosulfonyl fluoride In dichloromethane; toluene at -10 - 0℃; for 2h; Autoclave; Inert atmosphere;	82.7%
Stage #1: trimethyleneglycol With fluorosulfonyl fluoride; sodium sulfate; cetyltrimethylammonim bromide; N-ethyl-N,N-diisopropylamine In acetonitrile at 5 - 10℃; for 1.5h; Inert atmosphere; Stage #2: With 15-crown-5; 18-crown-6 ether Reflux;	68%
With ruthenium trichloride; sodium periodate; thionyl chloride 1) CCl4, 45 min, reflux, 2) H2O, CCl4, acetonitrile, RT, 2 h; Yield given. Multistep reaction;
With sodium periodate; thionyl chloride; ruthenium trichloride Yield given. Multistep reaction;

ruthenium (III) chloride hydrate + trimethyleneglycol (504-63-2) → 1,3,2-dioxathiane 2,2-dioxide (1073-05-8)

Conditions	Yield
With sodium periodate; thionyl chloride In carbon tetrachloride (CCl4); diethyl ether; water	87%

1,3-diacetoxypropane (628-66-0) + dimethyl sulfate (77-78-1) → 1,3,2-dioxathiane 2,2-dioxide (1073-05-8)

Conditions	Yield
130 deg C oil bath;	56%

1,3-bis-sulfooxy-propane; barium compound → 1,3,2-dioxathiane 2,2-dioxide (1073-05-8)

Conditions	Yield
at 180 - 190℃; under 4 Torr;

1,3-dibromo-propane (109-64-8) → 1,3,2-dioxathiane 2,2-dioxide (1073-05-8)

Conditions	Yield
With silver sulfate; xylene
With silver sulfate In xylene

barium salt of/the/ trimethylenedisulfuric acid → 1,3,2-dioxathiane 2,2-dioxide (1073-05-8)

Conditions	Yield
at 180 - 190℃; under 4 Torr;

trimethyleneglycol (504-63-2) + oleum → 1,3-bis-sulfooxy-propane (79431-21-3) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8)

Conditions	Yield
With chloroform at 60℃;

sodium salt of 1,3-propane-diol (37480-93-6, 54481-30-0, 59571-05-0) → 1,3,2-dioxathiane 2,2-dioxide (1073-05-8)

Conditions	Yield
Stage #1: sodium salt of 1,3-propane-diol With sodium methylate In toluene at -10 - 10℃; for 2h; Inert atmosphere; Stage #2: With 15-crown-5 In toluene at 20℃; for 1h;	41.5 g

1,3,2-dioxathiane 2,2-dioxide (1073-05-8) + sodium pyrrolidine-N-carbodithioate (872-71-9) → C13H20NO7S3(1-)*Na(1+)

Conditions	Yield
In methanol at 20℃;	99%

sodium N,N-diethyldithiocarbamate (148-18-5) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → C13H22NO7S3(1-)*Na(1+)

Conditions	Yield
In methanol at 20℃;	97%

pent-1-yn-5-ol (5390-04-5) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → sodium 3-[4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl]propyl sulfate (1383982-25-9)

Conditions	Yield
With sodium azide In water; tert-butyl alcohol at 60℃; for 0.25h; Microwave irradiation; regioselective reaction;	96%

sodium N,N-diethyldithiocarbamate (148-18-5) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → Na(1+)*C8H16NO4S3(1-)

Conditions	Yield
In methanol at 20℃;	96%

1,3,2-dioxathiane 2,2-dioxide (1073-05-8) + sodium pyrrolidine-N-carbodithioate (872-71-9) → C15H24NO8S3(1-)*Na(1+)

Conditions	Yield
In methanol at 20℃;	95%

sodium N,N-diethyldithiocarbamate (148-18-5) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → C15H26NO8S3(1-)*Na(1+)

Conditions	Yield
In methanol at 20℃;	92%

benzylamine (100-46-9) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → 3-(benzylammonio)propyl sulfate (1198271-81-6)

Conditions	Yield
In acetonitrile at 80℃;	91%

C5H10NS2(1-)*Na(1+) (65279-33-6) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → C13H22NO7S3(1-)*Na(1+)

Conditions	Yield
In methanol at 20℃;	91%

C5H10NS2(1-)*Na(1+) (65279-33-6) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → C15H26NO8S3(1-)*Na(1+)

Conditions	Yield
In methanol at 20℃;	91%

3-Ethynylpyridine (2510-23-8) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → sodium 3-[4-(pyridin-3-yl)-1H-1,2,3-triazol-1-yl]propyl sulfate (1383982-26-0)

Conditions	Yield
With sodium azide In water; tert-butyl alcohol at 60℃; for 0.25h; Microwave irradiation; regioselective reaction;	90%

1,3,2-dioxathiane 2,2-dioxide (1073-05-8) + propynoic acid ethyl ester (623-47-2) → sodium 3-[4-(ethoxycarbonyl)-1H-1,2,3-triazol-1-yl]propyl sulfate (1383982-27-1)

Conditions	Yield
With sodium azide In water; tert-butyl alcohol at 60℃; for 0.25h; Microwave irradiation; regioselective reaction;	90%

C5H9NO2S2 (1135256-40-4) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → Na(1+)*C8H14NO6S3(1-)

Conditions	Yield
With sodium hydrogencarbonate In methanol at 20℃;	90%

tert-butylamine (75-64-9) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → 3-(tert-butylammonio)propyl sulfate (1198271-85-0)

Conditions	Yield
In acetonitrile at 80℃;	89%

2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → 3-((3-methacrylamidopropyl)dimethylammonio)propyl sulfate

Conditions	Yield
With nitrobenzene In acetonitrile at 50℃; for 24h; Schlenk technique; Inert atmosphere;	88.8%

n-Dodecylamine (124-22-1) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → 3-(dodecylammonio)propyl sulfate (1198271-83-8)

Conditions	Yield
In acetonitrile at 80℃;	88%

C5H9NO2S2 (1135256-40-4) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → C15H24NO10S3(1-)*Na(1+)

Conditions	Yield
With sodium hydrogencarbonate In methanol at 20℃;	88%

4-(3,4,5-trimethoxybenzyl)morpholine (34274-05-0) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → C17H27NO8S (1529658-14-7)

Conditions	Yield
In acetonitrile at 40℃; for 49h;	88%

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (83476-52-2) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → sodium 3-[4-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyloxymethyl)-1H-1,2,3-traizol-1-yl]propyl sulfate (1383982-28-2)

Conditions	Yield
With sodium azide In water; tert-butyl alcohol at 60℃; for 0.25h; Microwave irradiation; regioselective reaction;	87%

cyclohexylamine (108-91-8) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → 3-(cyclohexylammonio)propyl sulfate (747374-68-1)

Conditions	Yield
In acetonitrile at 80℃;	86%

C5H9NO2S2 (1135256-40-4) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → C13H20NO9S3(1-)*Na(1+)

Conditions	Yield
With sodium hydrogencarbonate In methanol at 20℃;	85%

lithium diphenylphosphide (65567-06-8, 4541-02-0) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → C15H16O4PS(1-)*Li(1+)

Conditions	Yield
In tetrahydrofuran at 0 - 5℃;	84%

carbon disulfide (75-15-0) + diethylamine (109-89-7) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → Na(1+)*C8H16NO4S3(1-)

Conditions	Yield
With β‐cyclodextrin; sodium hydroxide In water at 35 - 65℃; Microwave irradiation;	84%

Cyclopentamine (1003-03-8) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → 3-(cyclopentylammonio)propyl sulfate (1198271-86-1)

Conditions	Yield
In acetonitrile at 80℃;	83%

1,3,2-dioxathiane 2,2-dioxide (1073-05-8) + sodium pyrrolidine-N-carbodithioate (872-71-9) → Na(1+)*C8H14NO4S3(1-)

Conditions	Yield
In methanol at 20℃;	82%

pyrrolidine (123-75-1) + carbon disulfide (75-15-0) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → Na(1+)*C8H14NO4S3(1-)

Conditions	Yield
With β‐cyclodextrin; sodium hydroxide In water at 35 - 65℃; Microwave irradiation;	80%

Upstream product

• 109-64-8 1,3-dibromo-propane 
• 504-63-2 trimethyleneglycol 
• 37480-93-6 sodium salt of 1,3-propane-diol 
• 628-66-0 1,3-diacetoxypropane 
• 77-78-1 dimethyl sulfate 
• 4176-55-0 2-oxo-1,3,2-dioxathiane 

Downstream Products

• 16133-83-8 tetrahydro-2-phenylfuran 
• 92764-21-1 3-(nonyldimethylammonio)propyl sulfate 
• 92764-22-2 3-(decyldimethylammonio)propyl sulfate 
• 107-18-6 allyl alcohol 
• 937798-40-8 3-{3-benzyloxy-4-[3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}propyl ammonium sulfate 
• 747374-68-1 3-(cyclohexylammonio)propyl sulfate 
• 1198271-87-2 3-(phenylammonio)propyl sulfate 
• 1198271-81-6 3-(benzylammonio)propyl sulfate 
• 1529658-14-7 C₁₇H₂₇NO₈S 
• 1004735-86-7 5'-(methyloxy)-4'-{[3-(4-morpholinyl)propyl]oxy}acetophenone 
• 30684-07-2 N-methyl-3-phenylpropylamine hydrochloride 
• 313681-30-0 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-{4-[3-(sulfoxy)propoxy]benzyl}propylcarbamate potassium salt 
• 213999-54-3 3-[(1S,2R)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2-isoquinolinio]propyl-1-sulfate 
• 213999-55-4 3-{(1R,2S)-6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-2-isoquinolinio}propyl-1-sulfate 

Relevant articles and documents

Concentration of hydrophobic organic compounds and extraction of protein using alkylammoniosulfate zwitterionic surfactant mediated phase separations (cloud point extractions)

The zwitterionic surfactants 3-[nonyl- (or decyl-) dimethylammonio]propyl sulfate, (C9-APSO4 or C10-APSO4) were synthesized using Nilsson's procedure, and their phase separation behavior under different experimental conditions was evaluated. The results indicate that such zwitterionic surfactants can be utilized for the extraction/preconcentration of hydrophobic species in a manner akin to that previously reported for nonionic surfactants. This was demonstrated for several practical applications including the extraction/preconcentration of some steroidal hormones and vitamin E prior to high-performance liquid chromatography analysis. The zwitterionic surfactant mediated phase separation was also applied to the extraction of the hydrophobic membrane protein, bacterio-rhodopsin, from the hydrophilic cytochrome c protein, both originally present In an aqueous phase. The concentration factors for this aqueous two-phase extraction technique using C10-APSO4 ranged from 26 to 35 with recoveries In the range 88 to > 96%. Some comparative studies Indicate that the use of zwittterionic surfactants In lieu of nonionic surfactants (e.g. polyoxyethylene(7.5) nonyl phenyl ether PONPE-7.5) In such an extraction method offers some significant advantages such as purer, homogeneous surfactant preparation, minimum background absorbance at UV detection wavelengths, the two-phase region occurring at lower temperatures, and greater extraction efficiencies/concentration factors among others.

METHOD OF OXIDIZING USING CALCIUM HYPOCHLORIDE AND MANUFACTURING FOR SULFONE OR SULFIDE

Is a process for preparing a sulphone or sulfate compound using calcium hypochlorite, and, wherein the method comprises introducing, sulfoxide or sulfite compound in an organic solvent and adding calcium hypochlorite in a solid state to an organic solvent in which the compound is introduced to oxidize the compound. (by machine translation)

Sulfate preparation method

The invention relates to the field of organic synthesis, and especially relates to a sulfate preparation method. The invention provides a sulfate preparation method. According to the preparation method, a compound represented by a formula (II) reacts with sulfuryl fluoride in the presence of a reaction solvent to prepare a compound represented by a formula (I). During the sulfate preparation process, the introduction of water and chlorine ions is avoided effectively, the situation that the product is degraded and the chlorine ion content is high is avoided therefore; moreover, the steps of thepreparation method are simple and short, the raw material are common chemical products on the market, the kinds of raw materials and the side reactions are few, and the yield is high. The manufacturing cost is low, only recyclable organic solvents are used, the reaction byproduct is a single inorganic salt solid and can be easily recovered, no wastewater is generated, the environment is better protected, and the sulfate preparation method is green and environmentally friendly and is suitable for industrial large scale production.