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4546-04-7

Basic Information
CAS No.: 4546-04-7
Name: P-XYLYLENEDIPHOSPHONIC ACID TETRAETHYL ESTER
Article Data: 43
Molecular Structure:
Molecular Structure of 4546-04-7 (P-XYLYLENEDIPHOSPHONIC ACID TETRAETHYL ESTER)
Formula: C16H28O6P2
Molecular Weight: 378.342
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);
EINECS: 224-902-0
Density: 1.153 g/cm3
Melting Point: 76°C
Boiling Point: 490.7 °C at 760 mmHg
Flash Point: 263.7 °C
Solubility: 454.7mg/L at 25℃
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37/39
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
at 130℃; for 2h;89%
623-25-6

p-Xylylene dichloride

4546-04-7

tetraethyl 1,4-xylylenediphosphonate

Conditions
ConditionsYield
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
ConditionsYield
at 120℃; for 3h;A 11.8%
B 48.5%
106-42-3

para-xylene

4546-04-7

tetraethyl 1,4-xylylenediphosphonate

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