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Basic Information
CAS No.: 13481-97-5
Name: dimethyl octadec-9-enedioate
Article Data: 97
Molecular Structure:
Molecular Structure of 13481-97-5 (dimethyl octadec-9-enedioate)
Formula: C20H36O4
Molecular Weight: 340.503
Synonyms: (E/Z)-dimethyl 9-octadecendioate;1,18-octadec-9-enedioic acid dimethyl ester;dimethyl 9-octadecene-1,18-dioate;dimethyl octadec-9-en-1,18-dioate;9-Octadecenedioic acid,dimethyl ester,(9E);dimethyl 1,18-octadec-9-enedioate;9-Octadecenedioic acid,dimethyl ester,(9Z);9-Octadecenedioic acid,dimethyl ester;
Density: 0.947g/cm3
Boiling Point: 417.8oC at 760 mmHg
Flash Point: 195.5oC
PSA: 52.60000
LogP: 5.35000
Synthetic route
25601-41-6

methyl 9-decenoate

13481-97-5

dimethyl 9-octadecen-1,18-dioate

Conditions
ConditionsYield
With Mo(N-2,6-’Pr2-C5H3)(CHCMe2Ph)(2,5-dimeth-ylpyrrolide)(O-2,6-Ph2C5H3) at 50℃; Reagent/catalyst; Temperature; Inert atmosphere; Molecular sieve; Glovebox;80.9%
With [1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene][2-isopropoxy-5-(2,2,2-trifluoroacetamido)benzylidene]ruthenium(II) dichloride In toluene at 110℃; for 2h; Inert atmosphere;63%
Grubbs catalyst first generation at 50℃; under 3.7503 Torr; for 2h;
112-62-9

octadec-9-enoic acid methyl ester

74-85-1

ethene

A

872-05-9

1-Decene

B

25601-41-6

methyl 9-decenoate

C

5557-31-3

9-octadecene

D

13481-97-5

dimethyl 9-octadecen-1,18-dioate

Conditions
ConditionsYield
With dichloro[(2-(tert-butyl)-6-propylphenoxy)(pyrrolidin-1-ium-1-ylidene)methanide](2-isopropoxyphenylmethylene)ruthenium(II) at 40℃; under 7757.43 Torr; Reagent/catalyst;A 73%
B n/a
C n/a
D n/a
With RuCl2(CN2C2H4(C6H3(CH(CH3)2)2)(C7H8(CH3)3))(CHC6H4OCH(CH3)2) In dichloromethane at 40℃; under 7757.43 Torr; for 6h; Inert atmosphere;
Stage #1: octadec-9-enoic acid methyl ester; ethene With [1 ,3-bis-(2,4,6-trimethylpheuyl)-2-imidazolidinylidene]dichloro(phenylindenylidene)(acetonitrile)ruthenium(II) at 40℃; under 8517.48 Torr; for 4h; Glovebox; Sealed tube; Inert atmosphere;
Stage #2: With tris(hydroxymethyl)phosphine In isopropyl alcohol at 70℃; for 1h; Catalytic behavior;
With Grubbs catalyst first generation In toluene for 0.333333h; Reagent/catalyst; Flow reactor;
112-62-9

Methyl oleate

74-85-1

ethene

A

872-05-9

1-Decene

B

25601-41-6

methyl 9-decenoate

C

5557-31-3

9-octadecene

D

13481-97-5

dimethyl 9-octadecen-1,18-dioate

Conditions
ConditionsYield
Cl2(PCy3)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC6H5 at 20℃; for 12h; Product distribution / selectivity;A 43%
B 46%
C 3%
D 2%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 20 - 23℃; under 11103.3 - 26618.1 Torr; Autoclave; Inert atmosphere;
With BerEt In toluene at 40℃; under 3102.97 Torr; for 1h; microfluidic reactor;
112-62-9

octadec-9-enoic acid methyl ester

74-85-1

ethene

A

872-05-9

1-Decene

B

25601-41-6

methyl 9-decenoate

C

13481-97-5

dimethyl 9-octadecen-1,18-dioate

Conditions
ConditionsYield
With C29H47Cl2OPRu In carbonic acid dimethyl ester at 20℃; under 750.075 Torr; Inert atmosphere;A 42%
B 43%
C 2%
112-62-9

Methyl oleate

A

5557-31-3

9-octadecene

B

13481-97-5

dimethyl 9-octadecen-1,18-dioate

Conditions
ConditionsYield
With [1,3-bis(2,4,5-Me3Ph)-2-imidazolidinylidene]Ru=CHPh(PCy3)Cl2 at 45℃;A n/a
B 39%
dichloro(tricyclohexylphosphino)(benzylidene)(1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)ruthenium(III) at 45℃; for 72h; Product distribution / selectivity; Neat (no solvent);A n/a
B 39%
Cl2(PCy3)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC6H5 at 20℃; for 96h; Product distribution / selectivity;A 24%
B 24%
112-62-9

octadec-9-enoic acid methyl ester

A

5557-31-3

9-octadecene

B

13481-97-5

dimethyl 9-octadecen-1,18-dioate

Conditions
ConditionsYield
With [1 ,3-bis-(2,4,6-trimethylpheuyl)-2-imidazolidinylidene]dichloro(phenylindenylidene)(acetonitrile)ruthenium(II) at 20℃; for 1h; Glovebox;A 25%
B 25%
benzylidenedichlorobis(1,3-diisopropylimidazolin-2-ylidene)ruthenium In 1,1-dichloroethane at 60℃; for 15h; Product distribution / selectivity;A 21%
B 21%
7433-78-5

cis-5-decene

112-62-9

Methyl oleate

A

19689-19-1

5-decene

B

13481-97-5

dimethyl 9-octadecen-1,18-dioate

C

9-tetradecenoic acid methyl ester

Conditions
ConditionsYield
silica supported rhenium-carbene surface at 25℃; for 3h;
[(*SiO)Re(*CtBu)(=CHtBu)(CH2tBu)] at 25℃;
112-62-9

Methyl oleate

silica supported rhenium-carbebe surface complex

silica supported rhenium-carbebe surface complex

A

5557-31-3

9-octadecene

B

13481-97-5

dimethyl 9-octadecen-1,18-dioate

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 25℃; for 1h; Product distribution; Further Variations:; Solvents;
4494-16-0

1,18-octadec-9-enedioic acid

67-56-1

methanol

13481-97-5

dimethyl 9-octadecen-1,18-dioate

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 0.5h;
sulfuric acid at 80℃; for 0.5h; Product distribution / selectivity;
With sulfuric acid Inert atmosphere;
With sulfuric acid at 65℃; for 2h; Inert atmosphere;6.65 g
67-56-1

methanol

60-33-3

linoleic acid

A

(6E,9E,12E)-Octadeca-6,9,12-triene

B

(9E,12E,15E)-Tetracosa-9,12,15-trienedioic acid dimethyl ester

C

42714-70-5

5-dodecene

D

13481-97-5

dimethyl 9-octadecen-1,18-dioate

Conditions
ConditionsYield
Stage #1: linoleic acid With [1,3-bis(2,4,5-Me3Ph)-2-imidazolidinylidene]Ru=CHPh(PCy3)Cl2 at 45℃; for 48h;
Stage #2: methanol With sulfuric acid at 80℃; for 0.5h; Further byproducts given. Title compound not separated from byproducts;
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  • 13481-97-5

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