Product Name

  • Name

    Diethyl (tosyloxy)methylphosphonate

  • EINECS 608-653-9
  • CAS No. 31618-90-3
  • Article Data41
  • CAS DataBase
  • Density 1.255 g/cm3
  • Solubility
  • Melting Point
  • Formula C12H19O6PS
  • Boiling Point 441.7 °C at 760 mmHg
  • Molecular Weight 322.319
  • Flash Point 220.9 °C
  • Transport Information
  • Appearance Pale yellow oil
  • Safety 36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 31618-90-3 (Diethyl (tosyloxy)methylphosphonate)
  • Hazard Symbols
  • Synonyms Phosphonicacid, (hydroxymethyl)-, diethyl ester, p-toluenesulfonate (8CI);Phosphonicacid, [[[(4-methylphenyl)sulfonyl]oxy]methyl]-, diethyl ester (9CI);Diethyl[[(p-toluenesulfonyl)oxy]methyl]phosphonate;Diethyl[[[(4-tolyl)sulfonyl]oxy]methyl]phosphonate;Diethylp-tosyloxymethylphosphonate;Tosyloxymethyl diethyl phosphonate;[[[(4-Tolyl)sulfonyl]oxy]methyl]phosphonic acid diethyl ester;
  • PSA 97.09000
  • LogP 4.00470

Synthetic route

diethyl (1-hydroxymethyl)phosphonate
3084-40-0

diethyl (1-hydroxymethyl)phosphonate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

Conditions
ConditionsYield
With triethylamine In diethyl ether97%
In water at 3 - 35℃; for 14.5h; Temperature;95.4%
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;92%
diethyl (1-hydroxymethyl)phosphonate
3084-40-0

diethyl (1-hydroxymethyl)phosphonate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

A

magnesium para-toluenesulfonate

magnesium para-toluenesulfonate

B

diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

Conditions
ConditionsYield
With magnesium carbonate In water at 65℃; for 20h;A n/a
B 91%
...Expand
hydroxymethyl-phosphonic acid dimethyl ester
24630-67-9

hydroxymethyl-phosphonic acid dimethyl ester

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane at 5 - 10℃; for 3h;86.5%
formaldehyd
50-00-0

formaldehyd

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

Conditions
ConditionsYield
Stage #1: formaldehyd; phosphonic acid diethyl ester With triethylamine In toluene at 85 - 90℃; for 3h; Heating / reflux;
Stage #2: p-toluenesulfonyl chloride With triethylamine at 4 - 20℃; for 14.75h;		77.6%
Stage #1: formaldehyd; phosphonic acid diethyl ester With triethylamine In toluene at 90 - 125℃; for 5h; Inert atmosphere;
Stage #2: p-toluenesulfonyl chloride With triethylamine In toluene at 0 - 20℃;		47%
Stage #1: formaldehyd; phosphonic acid diethyl ester With triethylamine In toluene at 70℃; Inert atmosphere; Reflux;
Stage #2: p-toluenesulfonyl chloride With triethylamine In toluene at 5 - 20℃; Inert atmosphere;
Stage #1: formaldehyd; phosphonic acid diethyl ester With triethylamine In toluene at 87℃; for 2h;
Stage #2: p-toluenesulfonyl chloride In toluene
Stage #1: formaldehyd; phosphonic acid diethyl ester With triethylamine In toluene at 87℃; for 3h; Inert atmosphere; Reflux;
Stage #2: p-toluenesulfonyl chloride With triethylamine In toluene at -2 - 22℃; Inert atmosphere;
...Expand
formaldehyd
50-00-0

formaldehyd

Diethyl phosphonate
762-04-9, 123-22-8

Diethyl phosphonate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

Conditions
ConditionsYield
Stage #1: formaldehyd; Diethyl phosphonate With triethylamine In toluene at 85 - 90℃; for 3h; Heating / reflux;
Stage #2: p-toluenesulfonyl chloride In toluene at 4 - 20℃; for 14.75h;		77.6%
Stage #1: formaldehyd; Diethyl phosphonate With triethylamine In toluene at 85 - 90℃; for 3h; Heating / reflux;
Stage #2: p-toluenesulfonyl chloride With triethylamine In toluene at 4 - 20℃; for 14.75h;		77.6%
...Expand
diethyl (1-hydroxymethyl)phosphonate
3084-40-0

diethyl (1-hydroxymethyl)phosphonate

diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

Conditions
ConditionsYield
With triethylamine In diethyl ether at -10 - 20℃; for 17h;75%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

(R)-9-[3-trityloxy-2-hydroxypropyl]-N6-(4-monomethoxytrityl)adenine
1338605-36-9

(R)-9-[3-trityloxy-2-hydroxypropyl]-N6-(4-monomethoxytrityl)adenine

diethyl (R)-9-[3-trityloxy-2-(phosphonomethoxy)propyl]-N6-(4-monomethoxytrityl)adenine
1338605-37-0

diethyl (R)-9-[3-trityloxy-2-(phosphonomethoxy)propyl]-N6-(4-monomethoxytrityl)adenine

Conditions
ConditionsYield
With sodium t-butanolate In N,N-dimethyl-formamide at 80℃;99%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

3-trifluoromethyl-2-mercaptopyridine
104040-74-6

3-trifluoromethyl-2-mercaptopyridine

diethyl (((3-(trifluoromethyl)pyridin-2-yl)thio)methyl)phosphonate

diethyl (((3-(trifluoromethyl)pyridin-2-yl)thio)methyl)phosphonate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;99%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

4-benzyloxybutanal
5470-84-8

4-benzyloxybutanal

(E)-p-tolyl 5-(benzyloxy)pent-1-en-1-yl sulfone

(E)-p-tolyl 5-(benzyloxy)pent-1-en-1-yl sulfone

Conditions
ConditionsYield
With triethylamine; lithium chloride In acetonitrile at 20℃; for 18h; Horner-Wadsworth-Emmons Olefination;98%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

{[(4-methylbenzenesulfonyl)oxy]methyl}phosphonic acid
161760-09-4

{[(4-methylbenzenesulfonyl)oxy]methyl}phosphonic acid

Conditions
ConditionsYield
With trimethylsilyl bromide In acetonitrile at 30℃; for 24h; Solvent; Reagent/catalyst; Temperature; Cooling with ice;98%
With trimethylsilyl bromide In dichloromethane at 20℃; for 12h;97%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

3,5-bis(trifluoromethyl)thiophenol
130783-02-7

3,5-bis(trifluoromethyl)thiophenol

(2-ethyl)bistrifluoromethyl thiophenolmethylphosphoric acid ethyl ester
934177-56-7

(2-ethyl)bistrifluoromethyl thiophenolmethylphosphoric acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h;94%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;89%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

S-(((3aS,4S,6R,6aR)-6-(6-chloro-5-cyano-4-(((1S,3S)-3-fluorocyclobutyl)amino)-1H-pyrrolo[2,3-b]pyridin-1-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl) ethanethioate

S-(((3aS,4S,6R,6aR)-6-(6-chloro-5-cyano-4-(((1S,3S)-3-fluorocyclobutyl)amino)-1H-pyrrolo[2,3-b]pyridin-1-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl) ethanethioate

diethyl (((((3aS,4S,6R,6aR)-6-(6-chloro-5-cyano-4-(((1S,3S)-3-fluorocyclobutyl)amino)-1H-pyrrolo[2,3-b]pyridin-1-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)thio)methyl)phosphonate

diethyl (((((3aS,4S,6R,6aR)-6-(6-chloro-5-cyano-4-(((1S,3S)-3-fluorocyclobutyl)amino)-1H-pyrrolo[2,3-b]pyridin-1-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)thio)methyl)phosphonate

Conditions
ConditionsYield
Stage #1: S-(((3aS,4S,6R,6aR)-6-(6-chloro-5-cyano-4-(((1S,3S)-3-fluorocyclobutyl)amino)-1H-pyrrolo[2,3-b]pyridin-1-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl) ethanethioate With sodium ethanolate In ethanol at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: diethyl (p-toluenesulfonyloxymethane)phosphonate In ethanol at 56℃; for 2h; Inert atmosphere;		90%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

bis-(diethoxy)phosphorylmethyl disulfide
70660-09-2

bis-(diethoxy)phosphorylmethyl disulfide

Conditions
ConditionsYield
With sulfur; sodium sulfide In ethanol Heating;89%
4-Fluorothiophenol
371-42-6

4-Fluorothiophenol

diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

diethyl (4-fluorophenylthio)methylphosphonate

diethyl (4-fluorophenylthio)methylphosphonate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;88%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;63%
With caesium carbonate In N,N-dimethyl-formamide at 70℃;
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

2-mercapto-5-(trifluoromethyl)benzothiazole
23420-87-3

2-mercapto-5-(trifluoromethyl)benzothiazole

(2-ethyl)-5-trifluoromethyl-thiophenethiol-methylphosphoric acid ethyl ester

(2-ethyl)-5-trifluoromethyl-thiophenethiol-methylphosphoric acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;88%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

(±)-2-fluoro-4-(6-methoxy-9H-purin-9-yl)-2-cyclopenten-1-ol

(±)-2-fluoro-4-(6-methoxy-9H-purin-9-yl)-2-cyclopenten-1-ol

(±)-diethyl {[-2-fluoro-4-(6-methoxy-9H-purin-9-yl)-2-cyclopenten-1-yl]oxy}methylphosphonate

(±)-diethyl {[-2-fluoro-4-(6-methoxy-9H-purin-9-yl)-2-cyclopenten-1-yl]oxy}methylphosphonate

Conditions
ConditionsYield
Stage #1: (±)-2-fluoro-4-(6-methoxy-9H-purin-9-yl)-2-cyclopenten-1-ol With lithium tert-butoxide In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: diethyl (p-toluenesulfonyloxymethane)phosphonate In tetrahydrofuran at 30℃; for 192h; Inert atmosphere;		88%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

(S)-9-(2-phosphonylmethoxypropyl)adenine
147127-19-3

(S)-9-(2-phosphonylmethoxypropyl)adenine

Conditions
ConditionsYield
Stage #1: (R)-9-(2-hydroxypropyl)adenine With bis(isopropoxy) magnesium In N,N-dimethyl-formamide at 65℃; for 1h; Inert atmosphere;
Stage #2: diethyl (p-toluenesulfonyloxymethane)phosphonate In N,N-dimethyl-formamide at 45 - 55℃; for 10h;
Stage #3: With hydrogenchloride In water at 90℃; for 10h;		88%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

1-((diphenylmethylamino)methyl)cyclopropan-1-ol
428855-17-8

1-((diphenylmethylamino)methyl)cyclopropan-1-ol

diethyl ({1-[(dibenzylamino)methyl]cyclopropoxy}methyl)phosphonate

diethyl ({1-[(dibenzylamino)methyl]cyclopropoxy}methyl)phosphonate

Conditions
ConditionsYield
With lithium tert-butoxide In tetrahydrofuran at 60℃; Inert atmosphere;87.5%
3-mercaptophenol
40248-84-8

3-mercaptophenol

diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

diethyl (((3-hydroxyphenyl)thio)methyl)phosphonate

diethyl (((3-hydroxyphenyl)thio)methyl)phosphonate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;87%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

1-(6-chloro-9H-purin-9-yl)propan-2-ol
75166-59-5

1-(6-chloro-9H-purin-9-yl)propan-2-ol

diethyl (((1-(6-chloro-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

diethyl (((1-(6-chloro-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

Conditions
ConditionsYield
Stage #1: 1-(6-chloro-9H-purin-9-yl)propan-2-ol With magnesium 2-methylpropan-2-olate In N,N-dimethyl-formamide at 70℃; for 0.5h;
Stage #2: diethyl (p-toluenesulfonyloxymethane)phosphonate In N,N-dimethyl-formamide at 70℃; for 7h; Inert atmosphere;		87%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

fluconazole
86386-73-4

fluconazole

C18H23F2N6O4P

C18H23F2N6O4P

Conditions
ConditionsYield
Stage #1: fluconazole With sodium hydride In tetrahydrofuran at 20℃; for 1.08333h; Inert atmosphere;
Stage #2: diethyl (p-toluenesulfonyloxymethane)phosphonate In tetrahydrofuran at 50℃; for 4h; Inert atmosphere;		86.5%
3-methoxybenzenethiol
15570-12-4

3-methoxybenzenethiol

diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

diethyl (((3-methoxyphenyl)thio)methyl)phosphonate
1478586-07-0

diethyl (((3-methoxyphenyl)thio)methyl)phosphonate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;86%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;86%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

4(5)-(3-bromophenyl)-1H-imidazole

4(5)-(3-bromophenyl)-1H-imidazole

C14H18BrN2O3P

C14H18BrN2O3P

Conditions
ConditionsYield
Stage #1: 4(5)-(3-bromophenyl)-1H-imidazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; pH=1; Inert atmosphere;
Stage #2: diethyl (p-toluenesulfonyloxymethane)phosphonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;		86%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

(R)-diethyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate
180587-75-1

(R)-diethyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

Conditions
ConditionsYield
With magnesium 2-methylpropan-2-olate In N,N-dimethyl-formamide at 80℃; for 5h; Solvent;85%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;44%
Stage #1: (R)-9-(2-hydroxypropyl)adenine With sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: diethyl (p-toluenesulfonyloxymethane)phosphonate In N,N-dimethyl-formamide for 64h;		29%
2-chlorothiphenol
6320-03-2

2-chlorothiphenol

diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

diethyl (((2-chlorophenyl)thio)methyl)phosphonate

diethyl (((2-chlorophenyl)thio)methyl)phosphonate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;85%
With caesium carbonate In N,N-dimethyl-formamide at 70℃;

Diethyl (tosyloxy)methylphosphonate Specification

The Diethyl (tosyloxy)methylphosphonate is an organic compound with the formula C12H19O6PS. The systematic name of this chemical is (diethoxyphosphoryl)methyl 4-methylbenzenesulfonate. With the CAS registry number 31618-90-3, it is also named as [[[(4-Tolyl)sulfonyl]oxy]methyl]phosphonic acid diethyl ester. The product's categories are Phospholipids - 13C & 2H; Phosphorylating and Phosphitylating Agents. Besides, it is a useful synthetic intermediate.

Physical properties about Diethyl (tosyloxy)methylphosphonate are: (1)ACD/LogP: 1.51; (2)ACD/LogD (pH 5.5): 1.51; (3)ACD/LogD (pH 7.4): 1.51; (4)ACD/BCF (pH 5.5): 8.23; (5)ACD/BCF (pH 7.4): 8.23; (6)ACD/KOC (pH 5.5): 157.39; (7)ACD/KOC (pH 7.4): 157.39; (8)#H bond acceptors: 6; (9)#Freely Rotating Bonds: 8; (10)Polar Surface Area: 97.09 Å2; (11)Index of Refraction: 1.498; (12)Molar Refractivity: 75.3 cm3; (13)Molar Volume: 256.7 cm3; (14)Polarizability: 29.85×10-24cm3; (15)Surface Tension: 42.1 dyne/cm; (16)Density: 1.255 g/cm3; (17)Flash Point: 220.9 °C; (18)Enthalpy of Vaporization: 67.21 kJ/mol; (19)Boiling Point: 441.7 °C at 760 mmHg; (20)Vapour Pressure: 1.39E-07 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=P(OCC)(OCC)COS(=O)(=O)c1ccc(cc1)C
(2)InChI: InChI=1/C12H19O6PS/c1-4-16-19(13,17-5-2)10-18-20(14,15)12-8-6-11(3)7-9-12/h6-9H,4-5,10H2,1-3H3
(3)InChIKey: UOEFFQWLRUBDME-UHFFFAOYAT
(4)Std. InChI: InChI=1S/C12H19O6PS/c1-4-16-19(13,17-5-2)10-18-20(14,15)12-8-6-11(3)7-9-12/h6-9H,4-5,10H2,1-3H3
(5)Std. InChIKey: UOEFFQWLRUBDME-UHFFFAOYSA-N

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