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Methyl 10-undecenoate

Name: Methyl 10-undecenoate
Brand: ALDRICH

96%

Synonym(s):

10-Undecenoic acid methyl ester, Undecylenic acid methyl ester

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About This Item

Linear Formula:

CH₂=CH(CH₂)₈CO₂CH₃

CAS Number:

111-81-9

Molecular Weight:

198.30

NACRES:

NA.22

PubChem Substance ID:

24847199

UNSPSC Code:

12352100

EC Number:

203-910-8

MDL number:

MFCD00016689

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Properties

Quality Level

100

assay

96%

refractive index

n20/D 1.437 (lit.)

bp

245 °C (lit.)

density

0.882 g/mL at 25 °C (lit.)

functional group

allyl, ester

SMILES string

COC(=O)CCCCCCCCC=C

InChI

1S/C12H22O2/c1-3-4-5-6-7-8-9-10-11-12(13)14-2/h3H,1,4-11H2,2H3

InChI key

KISVAASFGZJBCY-UHFFFAOYSA-N

Description

General description

Methyl 10-undecenoate is the chain stopper in the polymerization of long-chain aliphatic α,ω-diene through acyclic diene metathesis (ADMET). This helps in tuning the molecular weight of the resulting polyester in a range varying from 10 to 45 kDa.

Application

Methyl 10-undecenoate is an unsaturated fatty acid ester that can be used as a substrate:

To prepare bifunctional polymer precursors via hydroformylation reaction.
To synthesize α,ω-ester amides via aminocarbonylation in the presence of palladium catalyst.
To modify commercial silicone monomer, 1,3,5,7-tetramethylcyclotetrasiloxane, for the preparation of silicone hollow nano/microstructures in water by hydrosilylation reaction.

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pictograms

GHS07,GHS09

signalword

Warning

hcodes

H302 + H332,H410

pcodes

P261 - P264 - P271 - P273 - P301 + P312 - P304 + P340 + P312

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

239.0 °F - closed cup

flash_point_c

115 °C - closed cup

ppe

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Acyclic diene metathesis with a monomer from renewable resources: control of molecular weight and one-step preparation of block copolymers.

Anastasiya Rybak et al.

ChemSusChem, 1(6), 542-547 (2008-08-15)

The preparation of a long-chain aliphatic alpha,omega-diene from plant oil derivatives and its subsequent polymerization through acyclic diene metathesis (ADMET) is described. The ADMET bulk polymerization of the thus-obtained monomer, undecyl undecenoate, was investigated and optimized by applying ruthenium-based metathesis

Silicone Nano/Microstructures Obtained in Ionic Polymerization.

Kuzmicz D, et al.

Macromolecular Symposia, 308(1), 43-48 (2011)

Silicone nano/microstructures obtained in ionic polymerization