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Merck

68572

Sigma-Aldrich

Dibutyl phosphate

≥97.0% (T)

Sinónimos:

Phosphoric acid dibutyl ester

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About This Item

Fórmula lineal:
(CH3CH2CH2CH2O)2P(O)OH
Número de CAS:
Peso molecular:
210.21
Beilstein/REAXYS Number:
607224
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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

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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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
Dibutyl phosphate catalyzed commercial relevant ring-opening polymerizations to bio-based polyesters
Jingjing L, et al.
European Polymer Journal, 113, 197-207 (2019)
Liqin Hu et al.
Chemosphere, 233, 724-732 (2019-06-15)
Organophosphate flame retardants and plasticizers (OPFRs) are widely additives in consumer products and building materials. They are frequently detected in environmental media, including indoor air, water, soil, and dust. To provide a low-cost and multi-target tool for monitoring individual exposure
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)
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

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