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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:
Molecular Weight:
210.21
Beilstein/REAXYS Number:
607224
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥97.0% (T)

form

liquid

density

1.06 g/mL at 20 °C (lit.)

functional group

phosphate

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

signalword

Danger

hcodes

Hazard Classifications

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

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

352.4 °F - closed cup

flash_point_c

178 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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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
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
Anticorrosive and antimicrobial efficiency of photopolymerizable phosphorus (meth) acrylate oligomers-based coating materials
Agata K, et al.
Progress in Organic Coatings, 187, 108141-108141 (2024)
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)
Dibutyl phosphate catalyzed commercial relevant ring-opening polymerizations to bio-based polyesters
Jingjing L, et al.
European Polymer Journal, 113, 197-207 (2019)

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