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Dibutyl phosphate

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Name

Dibutyl phosphate

EINECS 203-509-8
CAS No. 107-66-4 Density 1.078 g/cm3
PSA 65.57000 LogP 2.72020
Solubility insoluble in water Melting Point -13 °C
Formula C8H19O4P Boiling Point 275.3 °C at 760 mmHg
Molecular Weight 210.21 Flash Point 120.3 °C
Transport Information UN 3261 Appearance clear liquid
Safety 26-39-45-36/37/39-25 Risk Codes 37/38-41-38-34
Molecular Structure Molecular Structure of 107-66-4 (Dibutyl phosphate) Hazard Symbols IrritantXi, CorrosiveC
Synonyms

Butylphosphate, (BuO)2(HO)PO (6CI);DP 4;DP 4 (coupling agent);Di-n-Butylphosphate;Dibutyl acid phosphate;Dibutyl hydrogen phosphate;HDBP;NSC 203039;NSC 22313;

Article Data 44

Dibutyl phosphate Synthetic route

126-73-8

phosphoric acid tributyl ester

107-66-4

dibutyl phosphate

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water for 2.5h; Heating;97%
With sodium hydroxide
With hydrogenchloride In hydrogenchloride byproducts: C4H9Cl; hydrolysis of TBP in concd. HCl;; hydrolytic decompn. of 18.5 % TBP in 6 days at ambient temp.;;
With HCl In hydrogenchloride byproducts: C4H9Cl; hydrolysis of TBP in concd. HCl;; hydrolytic decompn. of 18.5 % TBP in 6 days at ambient temp.;;
71-36-3

butan-1-ol

A

1623-15-0

n-butyl phosphoric acid

B

126-73-8

phosphoric acid tributyl ester

C

107-66-4

dibutyl phosphate

Conditions
ConditionsYield
With phosphorus; tetraethylammonium iodide In water; acetonitrile electrolysis;A n/a
B 87%
C n/a
71-36-3

butan-1-ol

A

126-73-8

phosphoric acid tributyl ester

B

107-66-4

dibutyl phosphate

Conditions
ConditionsYield
With sodium bromate; phosphan at 80℃; Kinetics; Condensation;A 20%
B 80%
With sodium hypophosphite; copper dichloride at 24.9℃; for 4h;A 22.2%
B 77.8%
With phosphorous; air; ruthenium hydroxide trichloride; copper dichloride at 80℃; oxidative alkoxylation;A 33.7%
B 11.3%
38257-85-1

Di-n-butyl-(o-hydroxy-phenyl)-phosphat

107-66-4

dibutyl phosphate

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; water In acetonitrile at 20℃; for 1h; oxidative cleavage;72%
71-36-3

butan-1-ol

A

107-66-4

dibutyl phosphate

B

16456-56-7

Phosphoric acid mono-n-butylester

Conditions
ConditionsYield
With oxygen; hypophosphorous acid; copper dichloride at 50℃; for 6h;A 4%
B 48%
819-43-2

dibutyl chlorophosphate

107-66-4

dibutyl phosphate

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 0℃;46%
With water beim Erhitzen;
With water In toluene for 1h; Reflux;29.5 g
121252-83-3

N-prolyl>proline

A

121252-84-4

(R)-1-[(R)-1-(Dibutoxy-phosphoryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid butyl ester

B

107-66-4

dibutyl phosphate

C

19943-27-2

rac-octahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione

Conditions
ConditionsYield
With butan-1-ol at 105 - 110℃; for 6h;A 28.6%
B 25%
C 42%
121252-83-3

N-prolyl>proline

71-36-3

butan-1-ol

A

121252-84-4

(R)-1-[(R)-1-(Dibutoxy-phosphoryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid butyl ester

B

107-66-4

dibutyl phosphate

C

19943-27-2

rac-octahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione

Conditions
ConditionsYield
at 105 - 110℃; for 6h;A 28.6%
B 25%
C 42%
2528-36-1

dibutyl phenyl phosphate

107-66-4

dibutyl phosphate

Conditions
ConditionsYield
With ethanol Hydrogenation.an Platin;
71-36-3

butan-1-ol

107-66-4

dibutyl phosphate

Conditions
ConditionsYield
With water; trichlorophosphate
With triethylamine; trichlorophosphate In toluene at 60℃; for 1h;

Dibutyl phosphate Consensus Reports

Reported in EPA TSCA Inventory.

Dibutyl phosphate Standards and Recommendations

OSHA PEL: TWA 1 ppm; STEL 2 ppm
ACGIH TLV: TWA 1 ppm; STEL 2 ppm

Dibutyl phosphate Analytical Methods

For occupational chemical analysis use NIOSH: Dibutyl Phosphate, 5017.

Dibutyl phosphate Specification

The Dibutyl phosphate is an organic compound with the formula C8H19O4P. The IUPAC name of this chemical is dibutyl hydrogen phosphate. With the CAS registry number 107-66-4 and EINECS 203-509-8, it is also named as Di-n-butyl hydrogen phosphate. It is clear liquid which is insoluble in water and soluble in diethyl ether, carbon tetrachloride and other organic solvents. What's more, it is toxic and flammable. When heated to decomposition it emits toxic fumes of POx. So the storage environment should be well-ventilated, low-temperature and dry. Keep Dibutyl phosphate separate from raw materials of food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.20; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.17; (4)ACD/LogD (pH 7.4): -1.3; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 54.57 Å2; (13)Index of Refraction: 1.436; (14)Molar Refractivity: 51.01 cm3; (15)Molar Volume: 194.9 cm3; (16)Polarizability: 20.22×10-24 cm3; (17)Surface Tension: 36.3 dyne/cm; (18)Density: 1.078 g/cm3; (19)Flash Point: 120.3 °C; (20)Enthalpy of Vaporization: 56.54 kJ/mol; (21)Boiling Point: 275.3 °C at 760 mmHg; (22)Vapour Pressure: 0.00141 mmHg at 25°C.

Uses of Dibutyl phosphate: It is used as extraction agent of uranium and thorium. It also can react with 2-iodo-propane to get phosphoric acid dibutyl ester isopropyl ester. This reaction needs reagent CsF and solvent acetonitrile at ambient temperature. The reaction time is 6 hours. The yield is 96%.

Dibutyl phosphate can react with 2-iodo-propane to get phosphoric acid dibutyl ester isopropyl ester

When you are using this chemical, please be cautious about it as the following:
It can cause burns and is irritating to respiratory system and skin. It also has risk of serious damage to the eyes, so people should avoid contact with eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure. 
1. SMILES:O=P(OCCCC)(OCCCC)O
2. InChI:InChI=1/C8H19O4P/c1-3-5-7-11-13(9,10)12-8-6-4-2/h3-8H2,1-2H3,(H,9,10)
3. InChIKey:JYFHYPJRHGVZDY-UHFFFAOYAZ

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 3200mg/kg (3200mg/kg)   National Technical Information Service. Vol. OTS0528344

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