Phosphonic acid, P,P'-[1,4-phenylenebis(methylene)]bis-, P,P,P',P'-tetraethyl ester supplier

Name
P-XYLYLENEDIPHOSPHONIC ACID TETRAETHYL ESTER
EINECS 224-902-0
CAS No. 4546-04-7
Article Data43
CAS DataBase
Density 1.153 g/cm³
Solubility 454.7mg/L at 25℃
Melting Point 76°C
Formula C₁₆H₂₈O₆P₂
Boiling Point 490.7 °C at 760 mmHg
Molecular Weight 378.342
Flash Point 263.7 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Phosphonic acid,(p-phenylenedimethylene)di-, tetraethyl ester (7CI,8CI);Phosphonic acid,[1,4-phenylenebis(methylene)]bis-, tetraethyl ester (9CI);1,4-Bis(diethoxyphosphinylmethyl)benzene;1,4-Xylenebis(diethylphosphonate);NSC 203064;Tetraethyl [1,4-phenylenebis(methylene)]bisphosphonate;Tetraethylp-xylylenebis(phosphonate);Tetraethyl p-xylylenediphosphonate;Tetraethyl a,a'-p-xylenediphosphonate;p-Bis(diethylphosphono)xylene;p-Xylenebis(diethyl phosphonate);p-Xylylenebis(diethyl phosphonate);
PSA 90.68000
LogP 5.21880

Synthetic route

: 623-25-6
p-Xylylene dichloride

: 122-52-1
triethyl phosphite

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

Conditions

Conditions	Yield
for 24h; Reflux;	99%
Heating;	98.6%
at 147 - 159℃; Arbuzov reaction;	98%

: 623-24-5
1,4-bis(bromomethyl)benzene

: 122-52-1
triethyl phosphite

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

Conditions

Conditions	Yield
at 185℃; for 6h; Arbusov reaction;	97%
for 5h; Inert atmosphere; Reflux;	96%
for 10h; Michaelis-Arbuzov reaction; Heating;	93%

: 623-24-5
1,4-bis(bromomethyl)benzene

: 78-40-0
triethyl phosphate

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

Conditions

Conditions	Yield
for 5h; Reflux; Inert atmosphere; Schlenk technique;	96%

: 74-96-4
ethyl bromide

: 106-37-6
1.4-dibromobenzene

: 122-52-1
triethyl phosphite

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

Conditions

Conditions	Yield
at 130℃; for 2h;	89%

...Expand

: 623-25-6
p-Xylylene dichloride

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

Conditions

Conditions	Yield
With triethyl phosphite for 8h; Heating / reflux;	86.4%
With triethyl phosphite for 8h; Heating / reflux;	86.4%

: 623-24-5
1,4-bis(bromomethyl)benzene

: 122-52-1
triethyl phosphite

A: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

B: 108228-81-5
4-(diethoxyphosphorylmethyl)-1-bromomethyl-phenyl

Conditions

Conditions	Yield
at 120℃; for 3h;	A 11.8% B 48.5%

...Expand

: 106-42-3
para-xylene

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 4.33 g / N-bromosuccinimide; azoisobutyronitrile / CCl4 / Heating 2: 5.24 g / 5 h / 160 °C View Scheme
Multi-step reaction with 2 steps 1: sodium bromate; sodium hydrogensulfite / water; ethyl acetate / 5 h 2: 16 h / 150 °C View Scheme
Multi-step reaction with 2 steps 1: sodium bromate; sodium hydrogensulfite / water; ethyl acetate / 5 h 2: 16 h / 150 °C View Scheme
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 1,1'-azobis(1-cyanocyclohexanenitrile) / benzene / 8 h / Reflux 2: benzene / 6 h / 120 °C View Scheme

: 106-42-3
para-xylene

air: air

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / NBS; dibenzoyl peroxide / CCl4 / 4 h / Heating 2: 93 percent / 10 h / Heating View Scheme

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 52771-21-8
3-(trifluoromethoxy)benzaldehyde

: C24H16F6O2

Conditions

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide at 80℃; for 2h; Horner-Wadsworth-Emmons reaction;	99%

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 104-87-0
4-methyl-benzaldehyde

: 58358-54-6
(E,E)-4-methyl-4'-(4''-methylstyryl)stilbene

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;	97%
With potassium tert-butylate In tetrahydrofuran at 80℃; for 1h;	68%

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 4546-06-9
p-xylene diphosphonic acid

Conditions

Conditions	Yield
With hydrogenchloride In water for 20h; Reflux;	96%
With hydrogenchloride; water for 15h; Reflux;	81.7%
With hydrogenchloride; water for 12h; Hydrolysis; Heating;	77%
With hydrogenchloride at 150℃;
With hydrogenchloride Heating;	0.65 g

: 7342-41-8
2,2':5',2''-terthiophene-5-carboxaldehyde

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: C34H22S6

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -70℃; for 12h; Inert atmosphere;	94%

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: C11H12Br2O3

: C30H30Br4O4

Conditions

Conditions	Yield
With sodium t-butanolate In tetrahydrofuran at -78 - 20℃; Horner-Wadsworth-Emmons Olefination;	94%

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 25069-38-9
N,N-bis(4-bromophenyl)aminobenzaldehyde

: 1,4-bis(4-di(4-bromophenyl)aminostyryl)benzene

Conditions

Conditions	Yield
Stage #1: tetraethyl 1,4-xylylenediphosphonate With sodium t-butanolate In ethanol; water; N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: N,N-bis(4-bromophenyl)aminobenzaldehyde In N,N-dimethyl-formamide at 0℃; for 4.5h;	92.3%

: 785808-26-6
C38H35NO2

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 100-52-7
benzaldehyde

Reaxys ID: 11744421: Reaxys ID: 11744421

Conditions

Conditions	Yield
Stage #1: C38H35NO2; tetraethyl 1,4-xylylenediphosphonate; benzaldehyde With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Wittig-Horner reaction; Stage #2: With O,O-diethyl benzylphosphonate In tetrahydrofuran at 20℃; for 1h; Stage #3: With acetic acid In tetrahydrofuran	92%

...Expand

: 401-95-6
3,5-Bis(trifluoromethyl)benzaldehyde

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: E,E-1,4-bis(3,5-ditrifluoromethylstyryl)benzene

Conditions

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide Horner-Wadsworth-Emmons Olefination; Heating;	92%

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 123-11-5
4-methoxy-benzaldehyde

: 54842-61-4
(E,E)-1,4-bis[2-(4-methoxyphenyl)-ethenyl]benzene

Conditions

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide at 80℃; for 2h; Horner-Wadsworth-Emmons reaction;	91%
With sodium methylate

: 197513-82-9
4-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]-benzaldehyde

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 791074-81-2
E,E-1,4-bis-4,4'-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)styrylbenzene

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 0 - 20℃; for 12.75h;	91%

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 65614-70-2
1,1'-{1,4-phenylenebis[(E)-ethen-2,1-diyl]}bis(3,4-dimethoxybenzene)

Conditions

Conditions	Yield
Stage #1: tetraethyl 1,4-xylylenediphosphonate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: 3,4-dimethoxy-benzaldehyde In N,N-dimethyl-formamide at 10 - 65℃; for 26.5h; Wittig-Horner Reaction; Inert atmosphere;	91%
With sodium hydride In tetrahydrofuran at 20℃; for 13h; Horner-Wadsworth-Emmons Olefination;	44%

: 90-96-0
bis(p-methoxyphenyl)methanone

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 1,4-bis[2,2-bis(4-methoxyphenyl)ethenyl]benzene

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20 - 50℃; Horner-Wadsworth-Emmons reaction;	90%

: 5779-95-3
3,5-dimethylbenzaldehyde

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 563539-80-0
1,4-bis(3,5-dimethylstyryl)benzene

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 70℃;	89.4%

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: C13H16Br2O3

: C34H38Br4O4

Conditions

Conditions	Yield
With sodium t-butanolate In tetrahydrofuran at -78 - 20℃; Horner-Wadsworth-Emmons Olefination;	89%

: 943316-90-3
2,5-bis(octyloxy)-4-(4-[2,2′:6′,2″]terpyridin-4′-ylphenylethynyl)benzaldehyde

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 1,4-bis(4-((4-(2,2':6',2"-terpyridin-4'-yl)phenyl)ethynyl)-2,5-bis(octyloxy)styryl)benzene

Conditions

Conditions	Yield
With potassium tert-butylate In toluene for 12h; Horner-Wadsworth-Emmons olefination; Reflux;	88%

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 204905-77-1
3,4-ethylenedioxythiophene-2-carboxaldehyde

: 2,2'-(3,4-ethylenedioxy)dithienyl-ω,ω'-1,4-divinyl benzene

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 10h; Condensation; Wittig-Horner;	87%

: 4181-05-9
4-(diphenylamino)benzaldehyde

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 4,4'-((1E,1'E)-1,4-phenylenebis(ethene-2,1-diyl))bis(N,N-diphenylaniline)

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide for 0.5h; Horner-Wadsworth-Emmons reaction; Heating;	87%
With potassium tert-butylate In N,N-dimethyl-formamide at 20 - 50℃; Horner-Wadsworth-Emmons reaction;	87%
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 12h; Wittig-Horner reaction; Inert atmosphere;	86%
With sodium ethanolate In N,N-dimethyl-formamide at 60℃; for 2h; Wittig-Horner condensation;	77%
With sodium hydride In tetrahydrofuran at 66℃; for 2h; Wadsworth-Emmons condensation;	66%

pyridine-4-carbaldehyde: pyridine-4-carbaldehyde

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 110144-22-4
4-((E)-2-[4-[(E)-2-(pyridin-4-yl)vinyl]phenyl]vinyl)pyridine

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Horner olefination;	87%
Stage #1: tetraethyl 1,4-xylylenediphosphonate With potassium tert-butylate In tetrahydrofuran at -10℃; for 0.333333h; Stage #2: pyridine-4-carbaldehyde In tetrahydrofuran at 20℃; for 16h;	30%

: 1030630-68-2
4,4′-bis(9-carbazolyl)benzophenone

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 1037718-22-1
C82H54N4

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; Wittig-Horner reaction; Inert atmosphere;	87%

: bis(4-(6-(9H-carbazol-9-yl)hexyloxy)phenyl)methanone

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 1,4′-bis(2,2-bis(4-(6-(9H-carbazol-9-yl)hexyloxy)phenyl)vinyl)benzene

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 5h; Wittig-Horner Reaction; Inert atmosphere;	87%

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: C48H46OS2

: C104H98S4

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 70 - 75℃; for 24h; Inert atmosphere;	87%

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 100-10-7
4-dimethylamino-benzaldehyde

: 100675-75-0
N-4-[(E)-2-(4-(E)-2-[4-(dimethylamino)phenyl]vinylphenyl)vinyl]phenyl-N,N-dimethylamine

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20 - 50℃; Horner-Wadsworth-Emmons reaction;	86%
With sodium methylate

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 59664-42-5
2,4-bis(trifluoromethyl)benzaldehyde

: E,E-1,4-bis(2,4-ditrifluoromethylstyryl)benzene

Conditions

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide Horner-Wadsworth-Emmons Olefination; Heating;	86%

: 659-28-9
p-trifluoromethoxybenzaldehyde

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: (E,E)-1,4-Bis(4-trifluoromethoxy)styrylbenzene

Conditions

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide at 80℃; for 2h; Horner-Wadsworth-Emmons reaction;	85%

: 434-45-7
1,1,1-trifluoroacetophenone

: 4546-04-7
tetraethyl 1,4-xylylenediphosphonate

: 188997-80-0
C24H16F6

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; Inert atmosphere;	85%

Phosphonic acid, P,P'-[1,4-phenylenebis(methylene)]bis-, P,P,P',P'-tetraethyl ester Specification

This chemical is called Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl ester, and its CAS registry number is 4546-04-7. With the molecular formula of C₁₆H₂₈O₆P₂, its molecular weight is 378.34. It should be sealed in the cool and dry place, away from the light. Additionally, the product categories of this chemical are Electronic Chemicals; Horner-Emmons Reaction; Synthetic Organic Chemistry; Wittig & Horner-Emmons Reaction.

Other characteristics of the Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl ester can be summarised as followings: (1)ACD/LogP: 1.91; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.91; (4)ACD/LogD (pH 7.4): 1.91; (5)ACD/BCF (pH 5.5): 16.54; (6)ACD/BCF (pH 7.4): 16.54; (7)ACD/KOC (pH 5.5): 259.38; (8)ACD/KOC (pH 7.4): 259.38; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 90.68 Å²; (13)Index of Refraction: 1.484; (14)Molar Refractivity: 93.87 cm³; (15)Molar Volume: 327.8 cm³; (16)Polarizability: 37.21×10^-24cm³; (17)Surface Tension: 39.5 dyne/cm; (18)Density: 1.153 g/cm³; (19)Flash Point: 263.7 °C; (20)Enthalpy of Vaporization: 72.84 kJ/mol; (21)Boiling Point: 490.7 °C at 760 mmHg; (22)Vapour Pressure: 2.7E-09 mmHg at 25°C.

Production method of this chemical: The could be obtained by the reactants of 1,4-bis-chloromethyl-benzene and phosphorous acid triethyl ester. This reaction needs the heating. The yield is 98.6 %.

Uses of this chemical: The p-xylylene-bis-phosphonic acid could be obtained by the reactant of Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl ester. This reaction should be taken at the temperature of 150 °C.

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.

You can still convert the following datas into molecular structure:
1.SMILES: O=P(OCC)(OCC)Cc1ccc(cc1)CP(=O)(OCC)OCC
2.InChI: InChI=1/C16H28O6P2/c1-5-19-23(17,20-6-2)13-15-9-11-16(12-10-15)14-24(18,21-7-3)22-8-4/h9-12H,5-8,13-14H2,1-4H3
3.InChIKey: XTKQUBKFKSHRPS-UHFFFAOYAI

Product Name

P-XYLYLENEDIPHOSPHONIC ACID TETRAETHYL ESTER

Synthetic route

Phosphonic acid, P,P'-[1,4-phenylenebis(methylene)]bis-, P,P,P',P'-tetraethyl ester Specification

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