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Basic Information
CAS No.: 298-07-7
Name: Bis(2-ethylhexyl) phosphate
Article Data: 18
Molecular Structure:
Molecular Structure of 298-07-7 (Bis(2-ethylhexyl) phosphate)
Formula: C16H35O4P
Molecular Weight: 322.425
Synonyms: 1-Hexanol,2-ethyl-, hydrogen phosphate (7CI);2-Ethyl-1-hexanol hydrogen phosphate;A208;A 208 (phosphate);Bis(2-ethylhexyl) hydrogen phosphate;Bis(2-ethylhexyl)orthophosphate;D 2EHPA;Dehpa extractant;DP 8;DP 8R;Di(2-ethylhexyl) phosphate;Di(2-ethylhexyl)phosphoric acid;O,O-Di(2-ethylhexyl)phosphoric acid;Phosphoric acid di(2-ethylhexyl) ester;Di-(2-ethylhexyl) phosphoric acid;
EINECS: 206-056-4
Density: 0.983 g/cm3
Melting Point: -60 °C(lit.)
Boiling Point: 393.4 °C at 760 mmHg
Flash Point: 191.7 °C
Solubility: slightly soluble in water
Appearance: clear colorless to light yellow liquid
Hazard Symbols: CorrosiveC
Risk Codes: 21-34
Safety: 26-36/37/39-45-25
Transport Information: UN 1902 8/PG 3
PSA: 65.57000
LogP: 5.55280
Synthetic route
104-76-7

2-Ethylhexyl alcohol

A

298-07-7

Bis(2-ethylhexyl)phosphoric acid

B

78-42-2

tris(2-ethylhexyl) phosphate

Conditions
ConditionsYield
With pyridine; trichlorophosphate In neat (no solvent) at 88℃; for 0.0208333h; Microwave irradiation;A n/a
B 75%
104-76-7

2-Ethylhexyl alcohol

A

298-07-7

Bis(2-ethylhexyl)phosphoric acid

B

78-42-2

tris(2-ethylhexyl) phosphate

C

1070-03-7

2-ethylhexylphosphoric acid

Conditions
ConditionsYield
With phosphorus pentoxide at 21℃; for 0.616667h; Product distribution; Mechanism; var.temps. and time;A 21.9%
B 25%
C 15.6%
3658-48-8

bis(2-ethylhexyl)phosphite

298-07-7

Bis(2-ethylhexyl)phosphoric acid

Conditions
ConditionsYield
With Nitrogen dioxide
Multi-step reaction with 2 steps
1: sulfuryl chloride
2: aqueous NaOH-solution
View Scheme
Multi-step reaction with 2 steps
1: chlorine
2: aqueous NaOH-solution
View Scheme
With Nitrogen dioxide at 35℃; Cooling;
63449-80-9

bis(2-ethylhexyl) phosphorochloridate

298-07-7

Bis(2-ethylhexyl)phosphoric acid

Conditions
ConditionsYield
With sodium hydroxide
With sodium hydroxide
With water In toluene for 1h; Reflux;49.3 g
104-76-7

2-Ethylhexyl alcohol

A

298-07-7

Bis(2-ethylhexyl)phosphoric acid

B

1070-03-7

2-ethylhexylphosphoric acid

Conditions
ConditionsYield
With phosphorus pentaoxide microwave irradiation;
78-42-2

tris(2-ethylhexyl) phosphate

A

298-07-7

Bis(2-ethylhexyl)phosphoric acid

B

1070-03-7

2-ethylhexylphosphoric acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 100℃; for 2h; Title compound not separated from byproducts.;
104-76-7

2-Ethylhexyl alcohol

298-07-7

Bis(2-ethylhexyl)phosphoric acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium / 160 °C
2: nitrogen dioxide
View Scheme
Multi-step reaction with 3 steps
1: sodium / 160 °C
2: sulfuryl chloride
3: aqueous NaOH-solution
View Scheme
Multi-step reaction with 2 steps
1: sodium / 160 °C
2: nitrogen dioxide
View Scheme
685498-13-9

di-2-ethylhexyl phosphite

298-07-7

Bis(2-ethylhexyl)phosphoric acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (chlorination)
2: aq. NaOH
View Scheme

copper(II) di(2-ethylhexyl)phosphate

144-62-7

oxalic acid

A

298-07-7

Bis(2-ethylhexyl)phosphoric acid

B

814-91-5

copper(II) oxalate

Conditions
ConditionsYield
In tetrachloromethane; water at 29.2℃; for 0.388889h; Kinetics; Further Variations:; reaction times, electrostatic field effects;
1369964-84-0

(1,1-dioxido-4-oxo-3-phenyl-4H-thiochromen-2-yl)methyl bis(2-ethylhexyl) phosphate

298-07-7

Bis(2-ethylhexyl)phosphoric acid

Conditions
ConditionsYield
In chloroform-d1 for 0.216667h; Irradiation;> 99 %Spectr.
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13340-46-0
141-65-1
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Reported in EPA TSCA Inventory.

Specification

The Bis(2-ethylhexyl) phosphate, with the CAS registry number 298-07-7 and EINECS registry number 206-056-4, has the systematic name and IUPAC name of bis(2-ethylhexyl) hydrogen phosphate. It is a kind of clear colorless to light yellow liquid, and belongs to the following product categories of Industrial/Fine Chemicals and Organics. And the molecular formula of this chemical is C16H35O4P. What's more, it is usually used as plasticizer and solvent in the synthesis of plastic.

The physical properties of Bis(2-ethylhexyl) phosphate are as followings: (1)ACD/LogP: 6.09; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.7; (4)ACD/LogD (pH 7.4): 2.59; (5)ACD/BCF (pH 5.5): 10.17; (6)ACD/BCF (pH 7.4): 7.87; (7)ACD/KOC (pH 5.5): 19.95; (8)ACD/KOC (pH 7.4): 15.44; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 14; (12)Polar Surface Area: 54.57 Å2; (13)Index of Refraction: 1.449; (14)Molar Refractivity: 87.99 cm3; (15)Molar Volume: 327.7 cm3; (16)Polarizability: 34.88×10-24cm3; (17)Surface Tension: 34 dyne/cm; (18)Density: 0.983 g/cm3; (19)Flash Point: 191.7 °C; (20)Enthalpy of Vaporization: 70.61 kJ/mol; (21)Boiling Point: 393.4 °C at 760 mmHg; (22)Vapour Pressure: 2.75E-07 mmHg at 25°C.

Preparation: First, 2-Ethylhexyl alcohol react with phosphorus to produce iso-octyl phosphate chloride, and it is a esterification reaction. Second, dissove the iso-octyl phosphate chloride with lye. Third, acidified it with sulfuric acid.
2C8H17OH+POCl3→(C8H17)2POCl+2HCl 
C8H17)2POCl+NaOH→(C8H17)2POONa+HCl 
(C8H17)2POONa+H2SO4→(C8H17)2POOH+Na2SO4

You should be cautious while dealing with this chemical. It is harmful in contact with skin, and may cause burns. Therefore, you had better take the following instructions: Avoid contact with eyes; Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=P(OCC(CC)CCCC)(OCC(CCCC)CC)O
(2)InChI: InChI=1/C16H35O4P/c1-5-9-11-15(7-3)13-19-21(17,18)20-14-16(8-4)12-10-6-2/h15-16H,5-14H2,1-4H3,(H,17,18)
(3)InChIKey: SEGLCEQVOFDUPX-UHFFFAOYAP

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intraperitoneal 62500ug/kg (62.5mg/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 9, Pg. 132, 1957.
rabbit LD50 skin 1250uL/kg (1.25mL/kg)   Union Carbide Data Sheet. Vol. 5/18/1972,
rat LD50 intraperitoneal 50mg/kg (50mg/kg) LIVER: OTHER CHANGES Hydrometallurgy. Vol. 3, Pg. 201, 1978.
rat LD50 oral 4940uL/kg (4.94mL/kg)   Union Carbide Data Sheet. Vol. 5/18/1972,