Tetraisopropyl (dichloromethylene)diphosphonate supplier

Name
TETRAISOPROPYL DICHLOROMETHYLENE DIPHOSPHONATE
EINECS
CAS No. 10596-22-2
Article Data9
CAS DataBase
Density 1.211 g/cm³
Solubility
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
Appearance colourless liquid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Phosphonicacid, (dichloromethylene)di-, tetraisopropyl ester (7CI,8CI);Dichloromethylenebisphosphonatetetraisopropyl ester;Tetraisopropyl (dichloromethylene)bisphosphonate;Tetraisopropyl (dichloromethylene)diphosphonate;
PSA 90.68000
LogP 6.16150

Synthetic route

: 1660-95-3
Tetraisopropyl methylenediphosphonate

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

Conditions

Conditions	Yield
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 hypochlorite	82%

: 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

Conditions	Yield
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;

...Expand

: 1660-95-3
Tetraisopropyl methylenediphosphonate

A: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

B: 161063-26-9
tetraisopropyl carbonylbisphosphonate

Conditions

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 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

Conditions	Yield
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;

...Expand

: 116-17-6
triisopropyl phosphite

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

Conditions

Conditions	Yield
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

Conditions	Yield
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-butyllithium	71%

: 102-82-9
tributyl-amine

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

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

Conditions

Conditions	Yield
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

Conditions	Yield
at 110℃; for 0.5h;	83%

: 110-86-1
pyridine

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: <dichloromethyl>phosphonic acid mono(1-methylethyl) ester N-isopropyl pyridinium salt

Conditions

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

: 1660-95-3
Tetraisopropyl methylenediphosphonate

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 20107-67-9
tetraisopropyl esters of monochloromethylene bisphosphonic acid

Conditions

Conditions	Yield
With methyllithium In hexane	75%

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 1660-95-3
Tetraisopropyl methylenediphosphonate

Conditions

Conditions	Yield
With potassium fluoride; 18-crown-6 ether In acetonitrile at 60℃; for 168h;	60%

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 28845-76-3
[[Bis-(diisopropoxy-phosphoryl)-methyldisulfanyl]-(diisopropoxy-phosphoryl)-methyl]-phosphonic acid diisopropyl ester

Conditions

Conditions	Yield
With sodium sulfide In methanol

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: (dichloromethylene) bisphosphonic acid monoisopropyl ester trisodium salt

Conditions

Conditions	Yield
With sodium hydroxide; water 1.) reflux, 10 h, 2.) MeOH; Yield given. Multistep reaction;
Yield given. Multistep reaction;

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

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

Conditions

Conditions	Yield
With sodium hydroxide; water 1.) reflux, 8 h, 2.) MeOH; Yield given. Multistep reaction;

: 110-86-1
pyridine

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 124-63-0
methanesulfonyl chloride

: N-(1-methylethyl)pyridinium O-methylsulphonyl[(di-1-methylethoxyphosphoryl)dichloromethyl]phosphonate

Conditions

Conditions	Yield
1.) reflux, 3.5 h, 2.) CH3CN, reflux, 30 min; Multistep reaction;

...Expand

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: C7H14Cl2O6P2(2-)*2Na(1+)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) reflux, 3.5 h, 2.) CH3CN, reflux, 30 min 2: 2M NaOH / H2O; acetone / 0.5 h / Ambient temperature View Scheme

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 101194-30-3
[1-Chloro-1-(diisopropoxy-phosphoryl)-ethyl]-phosphonic acid diisopropyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / n-butyllithium 2: 80 percent / thallium(I) ethoxide / tetrahydrofuran / 2 h / Heating View Scheme

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 101194-31-4
[1-Chloro-1-(diisopropoxy-phosphoryl)-propyl]-phosphonic acid diisopropyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / n-butyllithium 2: 81 percent / thallium(I) ethoxide / tetrahydrofuran / 2 h / Heating View Scheme

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 101194-37-0
[1-Chloro-1-(diisopropoxy-phosphoryl)-2-methyl-propyl]-phosphonic acid diisopropyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / n-butyllithium 2: 15 percent Spectr. / thallium(I) ethoxide / tetrahydrofuran / 2 h / Heating View Scheme

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 101194-32-5
[1-Chloro-1-(diisopropoxy-phosphoryl)-butyl]-phosphonic acid diisopropyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / n-butyllithium 2: 78 percent / thallium(I) ethoxide / tetrahydrofuran / 2 h / Heating; in dark View Scheme

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 101194-33-6
[1-Chloro-1-(diisopropoxy-phosphoryl)-heptyl]-phosphonic acid diisopropyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / n-butyllithium 2: 79 percent / thallium(I) ethoxide / tetrahydrofuran / 2 h / Heating View Scheme

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 101194-34-7
[1-Chloro-1-(diisopropoxy-phosphoryl)-2-phenyl-ethyl]-phosphonic acid diisopropyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / n-butyllithium 2: 82 percent / NaI, thallium(I) ethoxide / tetrahydrofuran / 2 h / Heating View Scheme

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 51258-88-9
[1-Chloro-1-(diisopropoxy-phosphoryl)-pentyl]-phosphonic acid diisopropyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / n-butyllithium 2: 78 percent / thallium(I) ethoxide / tetrahydrofuran / 2 h / Heating; in dark View Scheme

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

tetraisopropyl bromochloromethanediphosphonate: tetraisopropyl bromochloromethanediphosphonate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / sodium sulfite / ethanol; H2O / 1 h / Ambient temperature 2: 94 percent / bromine, NaOH / H2O / 0 deg C, 10 min; RT, 40 min View Scheme
Multi-step reaction with 2 steps 1: sodium sulfite / water; ethanol / 1 h / 20 °C 2: bromine; sodium hydroxide / 0.17 h / 0 - 20 °C / Inert atmosphere View Scheme

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 7757-83-7
sodium sulfite

: 20107-67-9
tetraisopropyl esters of monochloromethylene bisphosphonic acid

Conditions

Conditions	Yield
In ethanol; water

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: <dichloromethyl>phosphonic acid mono(1-methylethyl) ester monosodium salt

: 134757-53-2
(dichloromethylene)bisphosphonic acid, triisopropyl ester

Conditions

Conditions	Yield
In methanol

: 10596-22-2
tetraisopropyl dichloromethylenebisphosphonate

: 10596-23-3
clodronate

Conditions

Conditions	Yield
With hydrogenchloride In water Reflux;
With hydrogenchloride In water for 3h; Reflux; Inert atmosphere;

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

Product Name

TETRAISOPROPYL DICHLOROMETHYLENE DIPHOSPHONATE

Synthetic route

Tetraisopropyl (dichloromethylene)diphosphonate Specification

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