62999-73-9

Basic information

• Product Name: Diethyl (1,3-Dithian-2-yl)phosphonate
• Synonyms: Diethyl (1,3-Dithian-2-yl)phosphonate;(1,3-Dithian-2-yl)phosphonic Acid Diethyl Ester;Phosphonic acid, 1,3-dithian-2-yl-, diethyl ester
• CAS NO: 62999-73-9
• Molecular Formula: C₈H₁₇O₃PS₂
• Molecular Weight: 256.322541
• Mol File: 62999-73-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 35 °C
• Boiling Point: 134°C/0.1mmHg(lit.)
• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Diethyl (1,3-Dithian-2-yl)phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl (1,3-Dithian-2-yl)phosphonate(62999-73-9)
• EPA Substance Registry System: Diethyl (1,3-Dithian-2-yl)phosphonate(62999-73-9)

Safety Data

• Hazardous Substances Data: 62999-73-9(Hazardous Substances Data)

Upstream product

• 505-23-7 1,3 dithiane 
• 122-52-1 triethyl phosphite 
• 814-49-3 diethyl chlorophosphate 
• 57529-04-1 2-chloro-1,3-dithiane 
• 183791-52-8 C₈H₁₆LiO₃PS₂ 

Downstream Products

• 1226497-30-8 2-((3R,4R)-4-(benzyloxymethoxy)-5-methyl-3-vinylhexylidene)-1,3-dithiane 
• 1107648-79-2 2-[(S)-3-(1-methyl-1-nitroethyl)cyclohexylidene]-[1,3]dithiane 
• 13504-37-5 diethyl phenylacetylphosphonate 
• 1523-68-8 diethyl (1-oxopropyl)phosphonate 
• 145547-33-7 diethyl 1,1-(1,3-propylenedithio)-2-phenyl-4-oxo-pentanephosphonate 
• 145547-47-3 2-(1-methyl-3-phenyl-2-propenylidene)-1,3-dithiane 
• 17590-61-3 2-(3-phenyl-2-propenylidene)-1,3-dithiane 
• 145547-32-6 diethyl 1,1-(1,3-propylenedithio)-2,4-diphenyl-4-oxo-3-butanephosphonate 
• 145547-46-2 2-(1,3-diphenyl-2-propenylidene)-1,3-dithiane 
• 103563-39-9 (Z)-(3S,4S,5R)-8-Benzyloxymethoxy-1-[1,3]dithian-2-ylidene-3,5-dimethyl-6-trimethylsilanyl-oct-6-en-4-ol 
• 83268-74-0 (E)-(3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(2,4-dichloro-phenyl)-7-[1,3]dithian-2-ylidene-hept-1-en-3-ol 
• 103563-41-3 (E)-(3S,4S,5S)-8-Benzyloxymethoxy-1-[1,3]dithian-2-ylidene-3,5-dimethyl-oct-6-en-4-ol 
• 83268-77-3 6-phenyl-2,2-(trimethylenedithio)tetrahydropyran 

Relevant articles and documents

A new synthesis of α-ketophosphonates

α-Ketophosphonates are prepared from 2-alkyl-2-phosphonyl-1,3-dithianes.

Oxidative cyclization based on reversing the polarity of enol ethers and ketene dithioacetals. Construction of a tetrahydrofuran ring and application to the synthesis of (+)-nemorensic acid

The utility of oxidative cyclization reactions for the construction of tetrahydrofuran rings has been examined. In these experiments, alcohol nucleophiles were found to be effective traps for radical cation intermediates generated from both enol ether and ketene dithioacetal groups, The reactivity of the alcohol trapping group appeared to lie between that of an enol ether and an allylsilane trapping group. The stereochemical outcome of cyclization reactions originating from the oxidation of an enol ether was found to be controlled by stereoelectronic factors. The utility of these cyclization reactions was illustrated with the synthesis of a key tetrahydrofuran building block for the synthesis of linalool oxide and rotundisine. Cyclization reactions triggered by the oxidation of a ketene dithioacetal led to far greater levels of stereoselectivity. The stereochemical outcome of these reactions was shown to arise from steric factors involving the larger ketene acetal group. The synthetic utility of cyclizations utilizing ketene dithioacetal derived radical cations was demonstrated by completing an asymmetric synthesis of (+)-nemorensic acid. Finally, the reactions were shown to be compatible with the use of an amide nucleophile and the direct formation of a lactone product.

Carbanionic displacement reactions at phosphorus: Synthesis and reactivity of 5,5-dimethyl-2-oxo-2-(1,3-dithian-2-yl)-1,3,2-dioxaphosphorinane

We describe the formation and reactivity of the lithiated carbanion of 5,5-dimethyl-2-oxo-2-(1,3-dithian-2-yl)-1,3,2-dioxaphosphorinane 3b.The derived carbanion 2b is prepared in quantitative yield by internal quench condensation of 1,3-dithiane and 2-chl