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68572

Sigma-Aldrich

Dibutyl phosphate

≥97.0% (T)

Synonym(s):

Phosphoric acid dibutyl ester

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About This Item

Linear Formula:
(CH3CH2CH2CH2O)2P(O)OH
CAS Number:
107-66-4
Molecular Weight:
210.21
Beilstein:
607224
EC Number:
203-509-8
MDL number:
MFCD00015245
UNSPSC Code:
12352100
PubChem Substance ID:
329760992
NACRES:
NA.22

Assay

≥97.0% (T)

form

liquid

density

1.06 g/mL at 20 °C (lit.)

SMILES string

CCCCOP(O)(=O)OCCCC

InChI

1S/C8H19O4P/c1-3-5-7-11-13(9,10)12-8-6-4-2/h3-8H2,1-2H3,(H,9,10)

InChI key

JYFHYPJRHGVZDY-UHFFFAOYSA-N

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General description

Dibutyl phosphate, also known as Phosphoric acid dibutyl ester, is an organophosphate compound with a long alkyl chain that is commonly used as an organocatalyst for polymer synthesis via ring-opening polymerization of cyclic esters and to catalyzed transesterification reactions.

Application

Dibutyl phosphate can be used as a reactant to synthesize:
  • Glycosyl phosphates by using 1,2-orthoesters.
  • 2-Aminophosphatesvia catalyst-free regioselective and enantiospecific SN2-type ring opening reaction with aziridines.
It can also be used as a catalyst to synthesize polyesters via ring-opening polymerization.

Features and Benefits

  • Inherently biodegradable
  • Stable in neutral, acidic, or alkaline solutions

Pictograms

Health hazardCorrosion
GHS08,GHS05

Signal Word

Danger

Hazard Statements

H314,H351

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

352.4 °F - closed cup

Flash Point(C)

178 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Neal B Gallagher et al.
Applied spectroscopy, 60(7), 713-722 (2006-07-21)
Multivariate curve resolution (MCR) is a powerful technique for extracting chemical information from measured spectra of complex mixtures. A modified MCR technique that utilized both measured and second-derivative spectra to account for observed sample-to-sample variability attributable to changes in soil
Y Nishimura et al.
Journal of biochemistry, 118(1), 46-55 (1995-07-01)
Organophosphate compounds are known to cause a selective increase of beta-glucuronidase activity in rat serum. Previous data suggested that increase of serum beta-glucuronidase activity was well correlated with decrease of that activity in rat liver microsomal fraction, thereby, suggesting a
S Maji et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 64(4), 972-976 (2006-02-21)
The fluorescence of Tb(3+) is sensitized by complexation with dibutylphosphate (DBP) and tri-n-butylphosphate (TBP). The excitation maximum for the Tb(3+)-DBP complex occurs at 218.5 nm, while that for the Tb(3+)-TBP complex is observed at 228.0 nm. Both complexes yield Tb(3+)
Effects of added dibutyl phosphate on the luminescent properties of europium tetrakis dibenzoylmethide triethylammonium
Ross F S, et al.
Journal of Luminescence, 158, 428-434 (2015)
G K Hemakanthi De Alwis et al.
Journal of analytical toxicology, 32(9), 721-727 (2008-11-22)
Organophosphorus (OP) pesticides are highly toxic but used commonly worldwide, nevertheless. Their urinary dialkylphosphate (DAP) metabolites are widely used for exposure assessment of OP pesticides in humans. We previously developed an analytical method to measure urinary DAPs utilizing solid-phase extraction
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