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413364

Sigma-Aldrich

3-(Triethoxysilyl)propyl isocyanate

95%

Synonym(s):

Triethoxy(3-isocyanatopropyl)silane, (3-Isocyanatopropyl)triethoxysilane

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About This Item

Linear Formula:
(C2H5O)3Si(CH2)3NCO
CAS Number:
24801-88-5
Molecular Weight:
247.36
Beilstein:
4404652
EC Number:
246-467-6
MDL number:
MFCD00051459
UNSPSC Code:
12352103
PubChem Substance ID:
24865861
NACRES:
NA.22

Quality Level

200

Assay

95%

form

liquid

refractive index

n20/D 1.42 (lit.)

bp

283 °C (lit.)

density

0.999 g/mL at 25 °C (lit.)

SMILES string

CCO[Si](CCCN=C=O)(OCC)OCC

InChI

1S/C10H21NO4Si/c1-4-13-16(14-5-2,15-6-3)9-7-8-11-10-12/h4-9H2,1-3H3

InChI key

FRGPKMWIYVTFIQ-UHFFFAOYSA-N

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Application

3-(Triethoxysilyl)propyl isocyanate can be used:
  • As a bifunctional reagent (isocyanate and ethoxysilyl groups) for the immobilization of cellulose derivatives onto silica matrix to generate bonded type of chiral stationary phases (CSPs).
  • To convert 5-amino-1,10-phenanthroline into 5-(N,N-bis-3-(triethoxysilyl)propyl)-ureyl-1,10-phenanthroline, a hydrolysable sol–gel precursor.
  • To synthesize ruthenium bipyridyl tethered porous organosilica(Ru-POS) for organo-photocatalysis.
  • To synthesize nanoparticle-supported oxime palladacycle catalyst for Suzuki-Miyaura cross-coupling reaction.

3-(triethoxysilyl)propyl isocyanate (TEPI) was used as a spacer reagent to prepare cellulose based chiral stationary phases (CSPs). TEPI may be used to modify 2-hydroxynicotinic acid to prepare luminescent hybrid materials.2 Luminescent inorganic-organic hybrid materials were prepared by grafting the isocynate with the ortho aminobenzoic acid derivative. TEPI may also be used to prepare 5-(N,N-bis-3-(triethoxysilyl)propyl)ureyl-1,10- phenanthroline (phen-Si).

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

223.7 °F - closed cup

Flash Point(C)

106.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Magnetic nanoparticles supported oxime palladacycle as a highly efficient and separable catalyst for room temperature Suzuki?Miyaura coupling reaction in aqueous media.
Gholinejad M, et al.
Royal Society of Chemistry Advances, 5(61), 49568-49576 (2015)
Synthesis of covalently bonded cellulose derivative chiral stationary phases with a bifunctional reagent of 3-(triethoxysilyl) propyl isocyanate.
Chen X, et al.
Journal of Chromatography A, 1010(2), 185-194 (2003)
A luminescent tris (2-thenoyltrifluoroacetonato) europium (III) complex covalently linked to a 1, 10-phenanthroline-functionalised sol?gel glass.
Journal of Materials Chemistry, 14(2), 191-195 (2004)
Designing a family of luminescent hybrid materials by 3-(triethoxysilyl)-propyl isocyanate grafted 2-hydroxynicotinic acid bridge molecules
Journal of Organometallic Chemistry, 691(17), 3567-3573 (2006)
Synthesis of covalently bonded cellulose derivative chiral stationary phases with a bifunctional reagent of 3-(triethoxysilyl) propyl isocyanate
Journal of Chromatography A, 1010(2), 185-194 (2003)
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