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Tetraisopropyl (dichloromethylene)diphosphonate

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Name

Tetraisopropyl (dichloromethylene)diphosphonate

EINECS N/A
CAS No. 10596-22-2 Density 1.211 g/cm3
PSA 90.68000 LogP 6.16150
Solubility N/A Melting Point 50-51 °C
Formula C13H28Cl2O6P2 Boiling Point 405.3 °C at 760 mmHg
Molecular Weight 413.215 Flash Point 310.3 °C
Transport Information N/A Appearance colourless liquid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 10596-22-2 (TETRAISOPROPYL DICHLOROMETHYLENE DIPHOSPHONATE) Hazard Symbols N/A
Synonyms

Phosphonicacid, (dichloromethylene)di-, tetraisopropyl ester (7CI,8CI);Dichloromethylenebisphosphonatetetraisopropyl ester;Tetraisopropyl (dichloromethylene)bisphosphonate;Tetraisopropyl (dichloromethylene)diphosphonate;

Article Data 9

Tetraisopropyl (dichloromethylene)diphosphonate Synthetic route

1660-95-3

Tetraisopropyl methylenediphosphonate

10596-22-2

tetraisopropyl dichloromethylenebisphosphonate

Conditions
ConditionsYield
With sodium hypochlorite In water at 25℃; for 1h; Inert atmosphere; Schlenk technique;95%
With sodium hypochlorite for 0.333333h; Ambient temperature;88%
With sodium hypochlorite82%
1660-95-3

Tetraisopropyl methylenediphosphonate

A

10596-22-2

tetraisopropyl dichloromethylenebisphosphonate

B

20107-67-9

tetraisopropyl esters of monochloromethylene bisphosphonic acid

C

102786-81-2

[(Chloro-difluoro-methylsulfanyl)-(diisopropoxy-phosphoryl)-methyl]-phosphonic acid diisopropyl ester

D

102786-83-4

[(Dichloro-fluoro-methylsulfanyl)-(diisopropoxy-phosphoryl)-methyl]-phosphonic acid diisopropyl ester

Conditions
ConditionsYield
With n-butyllithium; aluminium trichloride; dichlorofluoromethanesulphenyl chloride 1.) ether, hexane, below 25 deg C 2.) ether, 4 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;
1660-95-3

Tetraisopropyl methylenediphosphonate

A

10596-22-2

tetraisopropyl dichloromethylenebisphosphonate

B

161063-26-9

tetraisopropyl carbonylbisphosphonate

Conditions
ConditionsYield
With formic acid; tert-butylhypochlorite for 2h; Heating;
1660-95-3

Tetraisopropyl methylenediphosphonate

2712-93-8

dichlorofluoromethanesulphenyl chloride

A

10596-22-2

tetraisopropyl dichloromethylenebisphosphonate

B

20107-67-9

tetraisopropyl esters of monochloromethylene bisphosphonic acid

C

102786-79-8

[(Diisopropoxy-phosphoryl)-trifluoromethylsulfanyl-methyl]-phosphonic acid diisopropyl ester

D

102786-83-4

[(Dichloro-fluoro-methylsulfanyl)-(diisopropoxy-phosphoryl)-methyl]-phosphonic acid diisopropyl ester

Conditions
ConditionsYield
With n-butyllithium; aluminium trichloride 1.) ether, hexane, below 25 deg C 2.) ether, 4 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;
1660-95-3

Tetraisopropyl methylenediphosphonate

2712-93-8

dichlorofluoromethanesulphenyl chloride

A

10596-22-2

tetraisopropyl dichloromethylenebisphosphonate

B

20107-67-9

tetraisopropyl esters of monochloromethylene bisphosphonic acid

C

102786-81-2

[(Chloro-difluoro-methylsulfanyl)-(diisopropoxy-phosphoryl)-methyl]-phosphonic acid diisopropyl ester

D

102786-83-4

[(Dichloro-fluoro-methylsulfanyl)-(diisopropoxy-phosphoryl)-methyl]-phosphonic acid diisopropyl ester

Conditions
ConditionsYield
With n-butyllithium; aluminium trichloride 1.) ether, hexane, below 25 deg C 2.) ether, 4 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;
116-17-6

triisopropyl phosphite

10596-22-2

tetraisopropyl dichloromethylenebisphosphonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: aq. NaOCl, NaCl
View Scheme
10596-22-2

tetraisopropyl dichloromethylenebisphosphonate

20107-67-9

tetraisopropyl esters of monochloromethylene bisphosphonic acid

Conditions
ConditionsYield
With sodium sulfite In ethanol; water for 1h; Ambient temperature;96%
With sodium sulfite In ethanol; water at 25℃; for 1h; Inert atmosphere; Schlenk technique;80%
With n-butyllithium71%
102-82-9

tributyl-amine

10596-22-2

tetraisopropyl dichloromethylenebisphosphonate

dichloromethylenebis(phosphonic acid) mono(tri-n-butylammonium) salt

Conditions
ConditionsYield
Stage #1: tetraisopropyl dichloromethylenebisphosphonate With hydrogenchloride In water at 85℃; for 2h;
Stage #2: tributyl-amine In n-butanol; ethanol
89%
110-91-8

morpholine

10596-22-2

tetraisopropyl dichloromethylenebisphosphonate

(dichloromethylene)bisphosphonic acid P,P'-bis(1-methylethyl) ester dimorpholinium salt

Conditions
ConditionsYield
at 110℃; for 0.5h;83%
110-86-1

pyridine

10596-22-2

tetraisopropyl dichloromethylenebisphosphonate

phosphonic acid mono(1-methylethyl) ester N-isopropyl pyridinium salt

Conditions
ConditionsYield
at 115℃; for 3.5h;80%

Tetraisopropyl (dichloromethylene)diphosphonate Specification

This chemical is called Phosphonic acid,(dichloromethylene)bis-, tetrakis(1-methylethyl) ester (9CI), and its IUPAC name is 2-[[dichloro-di(propan-2-yloxy)phosphorylmethyl]-propan-2-yloxyphosphoryl]oxypropane. With the molecular formula of C13H28Cl2O6P2, its product categories are Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. The CAS registry number of this chemical is 10596-22-2. It's an intermediate in the sythesis of clodronic acid, disodium salt, tetrahydrate, a biphosphonate bone resorption inhibitor.

Other characteristics of the Phosphonic acid,(dichloromethylene)bis-, tetrakis(1-methylethyl) ester (9CI) can be summarised as followings: (1)ACD/LogP: 3.62; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.62; (4)ACD/LogD (pH 7.4): 3.62; (5)ACD/BCF (pH 5.5): 330.91; (6)ACD/BCF (pH 7.4): 330.91; (7)ACD/KOC (pH 5.5): 2214.19; (8)ACD/KOC (pH 7.4): 2214.19; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 90.68 Å2; (13)Index of Refraction: 1.454; (14)Molar Refractivity: 92.5 cm3; (15)Molar Volume: 341.1 cm3; (16)Polarizability: 36.67×10-24cm3; (17)Surface Tension: 35.6 dyne/cm; (18)Density: 1.211 g/cm3; (19)Flash Point: 310.3 °C; (20)Enthalpy of Vaporization: 63.14 kJ/mol; (21)Boiling Point: 405.3 °C at 760 mmHg; (22)Vapour Pressure: 2.07E-06 mmHg at 25°C.

Production method of this chemical: The Phosphonic acid,(dichloromethylene)bis-, tetrakis(1-methylethyl) ester (9CI) could be obtained by the reactant of P,P'-methanediyl-bis-phosphonic acid tetraisopropyl ester. This reaction needs the reagents of aq. NaOCl, NaCl.

The Phosphonic acid,(dichloromethylene)bis-, tetrakis(1-methylethyl) ester (9CI) could be obtained by the reactant of P,P'-methanediyl-bis-phosphonic acid tetraisopropyl ester

Uses of this chemical: The Phosphonic acid,(dichloromethylene)bis-, tetrakis(1-methylethyl) ester (9CI) could react with pyridine to obtain the [(bis(1-methylethoxy)phosphino)dichloromethyl]phosphonic acid mono(1-methylethyl) ester N-isopropyl pyridinium salt. This reaction should be taken for 3.5 hours at the temperature of 115 °C. The yield is 80 %.

The Phosphonic acid,(dichloromethylene)bis-, tetrakis(1-methylethyl) ester (9CI) could react with pyridine to obtain the [(bis(1-methylethoxy)phosphino)dichloromethyl]phosphonic acid mono(1-methylethyl) ester N-isopropyl pyridinium salt.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. As it's flammable, keep it away from the sources of ignition.

You can still convert the following datas into molecular structure: 
1.SMILES: O=P(OC(C)C)(OC(C)C)C(Cl)(Cl)P(=O)(OC(C)C)OC(C)C
2.InChI: InChI=1/C13H28Cl2O6P2/c1-9(2)18-22(16,19-10(3)4)13(14,15)23(17,20-11(5)6)21-12(7)8/h9-12H,1-8H3
3.InChIKey: OMTPMIYCEZYHFY-UHFFFAOYAY

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