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Safety Information

115126

Sigma-Aldrich

Methyl 10-undecenoate

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:
Molecular Weight:
198.30
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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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.

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

239.0 °F - closed cup

Flash Point(C)

115 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

115126-500ML:
115126-BULK:
115126-25ML:
115126-VAR:


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Improvement of Productivity for Aqueous Biphasic Hydroformylation of Methyl 10-Undecenoate: A Detailed Phase Investigation
Bianga J, et al.
European Journal of Lipid Science and Technology, 122(1), 1900317-1900317 (2020)
Selective formation of ?,?-ester amides from the aminocarbonylation of castor oil derived methyl 10-undecenoate and other unsaturated substrates
Jimenez-Rodriguez C, et al.
Catalysis Science & Technology, 4(8), 2332-2339 (2014)
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
Macromolecular Symposia, 308(1), 43-48 (2011)

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