Dimethyl sebacate supplier

Name
Dimethyl sebacate
EINECS 203-431-4
CAS No. 106-79-6
Article Data104
CAS DataBase
Density 0.985 g/cm³
Solubility Insoluble in water.
Melting Point 29-31 °C(lit.)
Formula C₁₂H₂₂O₄
Boiling Point 299 °C at 760 mmHg
Molecular Weight 230.304
Flash Point 145 °C
Transport Information
Appearance colourless melt or liquid
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Decanedioicacid, dimethyl ester (9CI);Sebacic acid, dimethyl ester (6CI,8CI);Dimethyldecane-1,10-dioate;Dimethyl octane-1,8-dicarboxylate;Dimethyldecanedioate;NSC 9415;Decanedioic acid,1,10-dimethyl ester;
PSA 52.60000
LogP 2.45320

Synthetic route

: 67-56-1
methanol

: 111-81-9
Methyl 10-undecenoate

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
Stage #1: methanol; Methyl 10-undecenoate With ozone In methanol at 0℃; Stage #2: With semicarbazide hydrochloride at 0 - 20℃; Reagent/catalyst; Inert atmosphere;	95%

: 67-56-1
methanol

: 111-20-6
1,10-decanedioic acid

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With boron trifluoride at 65℃; for 0.333333h;	100%
With modification of hypercrosslinked supermicroporous polymer (HMP-1) via sulfonation (HMP-1-SO3H) at 24.84℃; for 12h; Green chemistry;	97%
With Fe3O4 immobilized thiol functionalized mesoporous silica at 24.84℃; for 20h;	96%

: 111-20-6
1,10-decanedioic acid

: 616-38-6
carbonic acid dimethyl ester

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With triethylamine at 160℃; for 5h; Autoclave; Green chemistry;	99%

: 274251-02-4
prop-2-enyl 4-quinolylmethyl decanedioate

: 74-88-4
methyl iodide

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
Stage #1: prop-2-enyl 4-quinolylmethyl decanedioate With ammonium formate; 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 50℃; for 12h; Reduction; Deprotection; Stage #2: methyl iodide With sodium carbonate In water; dimethyl sulfoxide at 20℃; for 12h; Methylation;	92%

: 274251-03-5
di(4-quinolylmethyl) decanedioate

: 74-88-4
methyl iodide

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
Stage #1: di(4-quinolylmethyl) decanedioate With ammonium formate; 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 50℃; for 12h; Reduction; Deprotection; Stage #2: methyl iodide With sodium carbonate In water; dimethyl sulfoxide at 20℃; for 12h; Methylation;	95%

: 627-91-8
adipic acid monomethyl ester

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With piperidine; silica gel In methanol; acetonitrile Kolbe electrolytic synthesis; Electrolysis; cooling;	88%
With sodium In pyridine; methanol at 20℃; electrolysis, Pt-anode, other anodes;	73%
With methanol; sodium bei der Elektrolyse;
With potassium hydroxide In methanol at 30℃; electrolysis, Pt-electrodes, 150 mA/cm-2;

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 20731-23-1
methyl non-8-enoate

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With P(p-CH3OC6H4)3; lithium chloride; tin(ll) chloride; palladium dichloride In 1,2-dimethoxyethane at 110℃; under 18100.7 Torr; for 22h; Autoclave; regioselective reaction;	91%

...Expand

: 111-20-6
1,10-decanedioic acid

: 124-38-9
carbon dioxide

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With hydrogen; C51H53ClOP3Ru(1+)*ClO4(1-) In 1,2-dimethoxyethane at 160℃; under 60006 Torr; for 24h; Autoclave;

: 67-56-1
methanol

: 1002-33-1
octa-1,3-diene

: 201230-82-2
carbon monoxide

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With palladium(II) trifluoroacetate; toluene-4-sulfonic acid; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In toluene at 120℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;	73%

...Expand

: 67-56-1
methanol

: 13643-08-8
2,4-Octadiene

: 201230-82-2
carbon monoxide

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With palladium(II) trifluoroacetate; toluene-4-sulfonic acid; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In toluene at 120℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;	73%

...Expand

: 67-56-1
methanol

: 1072-19-1
octa-1,2-diene

: 201230-82-2
carbon monoxide

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With palladium(II) trifluoroacetate; toluene-4-sulfonic acid; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In toluene at 120℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;	73%

...Expand

: 67-56-1
methanol

: 112-39-0
hexadecanoic acid methyl ester

A: 627-93-0
hexanedioic acid dimethyl ester

B: 1732-10-1
Dimethyl azelate

C: 1731-84-6
nonanoic acid methyl ester

D: 110-42-9
Methyl decanoate

E: 1731-86-8
methyl undecanoate

F: 111-82-0
methyl n-dodecanoate

G: 1731-88-0
methyl tridecanoate

H: 124-10-7
methyl myristoate

I: 1732-08-7
dimethyl 1,7-heptanedioate

J: 1732-09-8
dimethyl subarate

K: 106-79-6
dimethyl sebacate

L: 4567-98-0
dimethyl undecanedioate

M: 1731-79-9
dodecanedioic acid dimethyl ester

N: 1472-87-3
dimethyl 1,11-undecanedicarboxylate

O: 5024-21-5
dimethyl tetradecanedioate

P: 36575-82-3
dimethyl pentadecanedioate

Conditions

Conditions	Yield
With cobalt(II) acetate; manganese(II) acetate; zirconium(IV) chloride; acetic acid; potassium bromide at 150℃; under 30003 Torr; for 2h; Autoclave;

...Expand

: 67-56-1
methanol

: 124-04-9
Adipic acid

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With Fe3O4 immobilized thiol functionalized mesoporous silica at 24.84℃; for 20h;	95%

: 627-91-8
adipic acid monomethyl ester

: 124-41-4
sodium methylate

A: 627-93-0
hexanedioic acid dimethyl ester

B: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With pyridine In methanol at 60 - 65℃; for 26.5h; Electrolysis;	A n/a B 71%

...Expand

: 67-56-1
methanol

: 13154-30-8
α-nitrocyclodecanone

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; sulfuric acid at 80℃; for 3h;	81%

: 67-56-1
methanol

: 112-47-0
1,10-Decanediol

A: 2640-94-0
methyl 10-hydroxydecanoate

B: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With (2-hydroxyethyl)(methyl)amine; potassium phosphate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In acetone at 25℃; for 24h; Inert atmosphere;	A 48% B 39%

...Expand

: 67-56-1
methanol

: 112-38-9
10-undecenoic acid

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
Stage #1: methanol; 10-undecenoic acid With ozone at 0℃; Inert atmosphere; Stage #2: With semicarbazide hydrochloride at 0 - 20℃; for 48h; Reagent/catalyst; Inert atmosphere;	97%

: 67-56-1
methanol

: 112-38-9
10-undecenoic acid

A: 53663-26-6
9-cyanononanoic acid methyl ester

B: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
Stage #1: methanol; 10-undecenoic acid With ozone at 0 - 20℃; Inert atmosphere; Stage #2: With hydroxylamine hydrochloride Inert atmosphere;	A 10% B 85%

...Expand

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 35329-51-2
methyl (E)-non-4-enoate

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With methanesulfonic acid; 1,2-bis[(2,2,6,6-tetramethylphosphinan-4-onyl)methyl]benzene; palladium diacetate at 105℃; under 15001.5 - 37503.8 Torr; for 12h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;

...Expand

: 627-91-8
adipic acid monomethyl ester

A: 106-79-6
dimethyl sebacate

B: 120167-83-1
7-(Acetyl-octadecyl-amino)-heptanoic acid methyl ester

C: 120167-85-3
N-[4-(Acetyl-octadecyl-amino)-butyl]-N-octadecyl-acetamide

Conditions

Conditions	Yield
With acide (N-octadecyl acetamido)-3 propanoique; sodium In pyridine; methanol at 30℃; coelectrolysis;	A 56% B 57% C 30%

...Expand

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 20731-23-1
methyl non-8-enoate

A: 106-79-6
dimethyl sebacate

B: α-Methyl nonanedioic acid, dimethyl ester

Conditions

Conditions	Yield
With lithium chloride; tin(ll) chloride; palladium dichloride; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In 1,2-dimethoxyethane at 110℃; under 18100.7 Torr; for 22h; Autoclave; Overall yield = 86 %; regioselective reaction;	A 91 %Spectr. B 9 %Spectr.

...Expand

: 627-91-8
adipic acid monomethyl ester

: 120167-80-8
acide (N-dodecyl acetamido)-3 propanoique

A: 106-79-6
dimethyl sebacate

B: 120167-82-0
7-(Acetyl-dodecyl-amino)-heptanoic acid methyl ester

C: 120167-84-2
bis (N-dodecyl acetamido)-1,4 butane

Conditions

Conditions	Yield
With sodium In pyridine; methanol at 30℃; coelectrolysis;	A 44% B 60% C 32%

...Expand

: 627-91-8
adipic acid monomethyl ester

: 13052-21-6
acide (N-octadecyl acetamido)-3 propanoique

A: 106-79-6
dimethyl sebacate

B: 120167-83-1
7-(Acetyl-octadecyl-amino)-heptanoic acid methyl ester

C: 120167-85-3
N-[4-(Acetyl-octadecyl-amino)-butyl]-N-octadecyl-acetamide

Conditions

Conditions	Yield
With sodium In pyridine; methanol at 30℃; coelectrolysis;	A 56% B 57% C 30%

...Expand

: 114050-32-7
Hexanedioic acid methyl ester 2-thioxo-2H-pyridin-1-yl ester

A: 106-79-6
dimethyl sebacate

B: 114050-40-7
5-(Pyridin-2-ylsulfanyl)-pentanoic acid methyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at -64℃; for 2h; Irradiation;	A 24% B 35%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 3710-30-3
1,7-Octadiene

A: 39590-02-8
dimethyl ester of/the/ hihger-melting 2,7-dimethyl-suberic acid

B: 106-79-6
dimethyl sebacate

C: α-Methyl nonanedioic acid, dimethyl ester

Conditions

Conditions	Yield
With palladium(II) acetylacetonate; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; toluene-4-sulfonic acid at 120℃; under 30003 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Inert atmosphere; Autoclave; Overall yield = 94 %;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 112-38-9
10-undecenoic acid

: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
Stage #1: 10-undecenoic acid With aluminum oxide; potassium permanganate; water for 0.166667h; Stage #2: diazomethane In diethyl ether	23 % Chromat.

: 627-91-8
adipic acid monomethyl ester

: 2834-05-1
11-bromoundecanoic acid

A: 14296-16-3
1,20-dibromoeicosane

B: 41240-56-6
15-bromopentadecanoic acid methyl ester

C: 106-79-6
dimethyl sebacate

Conditions

Conditions	Yield
With sodium In methanol; water at 45 - 50℃; for 42h; (electrolysis);

...Expand

: 627-91-8
adipic acid monomethyl ester

: 73367-80-3
12-bromododecanoic acid

A: 34540-49-3
1,22-dibromodocosane

B: 106-79-6
dimethyl sebacate

C: 26825-89-8
methyl 16-bromohexadecanoate

Conditions

Conditions	Yield
With sodium In methanol at 50 - 54℃; for 21h; (electrolysis);

...Expand

: 76469-08-4
5-octynolic acid

: 627-91-8
adipic acid monomethyl ester

A: 106-79-6
dimethyl sebacate

B: 76470-06-9
Dodec-9-ynoic acid methyl ester

Conditions

Conditions	Yield
With potassium hydroxide In methanol at 30℃; electrolysis, Pt-electrodes, 150 mA/cm-2; Title compound not separated from byproducts;

...Expand

: 627-91-8
adipic acid monomethyl ester

: 55182-79-1
5-Decinsaeure

A: 106-79-6
dimethyl sebacate

B: 55538-60-8
9-Tetradecynoic acid methyl ester

Conditions

Conditions	Yield
With potassium hydroxide In methanol at 30℃; electrolysis, Pt-electrodes, 150 mA/cm-2; Title compound not separated from byproducts;

...Expand

: 7031-93-8
2,2,6,6-tetramethylpiperidin-1-ol

: 106-79-6
dimethyl sebacate

: bis(2,2,6,6-tetramethylpiperidinyl)sebacate

Conditions

Conditions	Yield
Stage #1: 2,2,6,6-tetramethylpiperidin-1-ol; dimethyl sebacate In water-d2 at 120℃; Inert atmosphere; Stage #2: With titanium(IV)isopropoxide In water-d2 at 150℃; Solvent;	99.62%

: 106-79-6
dimethyl sebacate

: 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol

: bis-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate

Conditions

Conditions	Yield
With tetrakis(2,4-pentanedionato) hafnium(IV) In n-heptane at 90 - 105℃; for 12h; Reagent/catalyst; Solvent; Dean-Stark;	99%

: 106-79-6
dimethyl sebacate

: 456-56-4
phenyl trifluoromethylsulfide

: 1,1,1,12,12,12-hexafluorododecan-2,11-dione

Conditions

Conditions	Yield
With Triethylgermyl-natrium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -60℃; for 1.5h;	97%

: 106-79-6
dimethyl sebacate

: N-cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidinol

: bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate

Conditions

Conditions	Yield
With titanium(IV) isopropylate; tetrabutylammomium bromide Reagent/catalyst;	92%

: 1271-55-2
acetylferrocene

: 106-79-6
dimethyl sebacate

: 256955-97-2
[(C5H5FeC5H4)CO(CH2)CO(CH2)8COCH2CO(C5H4FeC5H5)]

Conditions

Conditions	Yield
With KH In tetrahydrofuran stirring (room temp., 4 d); concn. (vac.), suspending (H2O), extraction (conc. HCl/CH2Cl2), drying (MgSO4, several h), evapn., washing (pentane), drying (vac.); elem. anal.;	91%

: 106-79-6
dimethyl sebacate

: 5578-84-7
N1,N10-dihydroxydecanediamide

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; potassium hydroxide In methanol for 24h; Reflux;	86%

: 112-92-5
1-octadecanol

: 106-79-6
dimethyl sebacate

: 3072-03-5
Di-n-octadecyl sebacate

Conditions

Conditions	Yield
With 1-hexadecyl-3-sulfo-1H-imidazol-3-ium chloride In neat (no solvent) at 110℃; for 16h; Green chemistry;	84%

: 239792-70-2
1-n-propoxy-4-hydroxy-2,2,6,6-tetramethylpiperidine

: 106-79-6
dimethyl sebacate

A: bis(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate

B: (1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacic acid monomethyl ester

Conditions

Conditions	Yield
With tetrabutylammomium bromide; lithium hydroxide In n-heptane at 0.98℃; for 0.5h;	A 80.4% B n/a

...Expand

: 87018-00-6
1-cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidine

: 106-79-6
dimethyl sebacate

A: bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate

B: (1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacic acid monomethyl ester

Conditions

Conditions	Yield
With tetrabutylammomium bromide; lithium hydroxide In n-heptane at 0.98℃; for 0.5h;	A 80.26% B n/a

...Expand

: 1001080-97-2
i-propyl-4-hydroxy-2,2,6,6-tetramethylpiperidinyl-1-oxyl

: 106-79-6
dimethyl sebacate

A: bis(1-isopropoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate

B: (1-isopropoxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacic acid monomethyl ester

Conditions

Conditions	Yield
With tetrabutylammomium bromide; lithium hydroxide In n-heptane at 0.98℃; for 0.5h;	A 79.74% B n/a

...Expand

: 64-17-5
ethanol

: 106-79-6
dimethyl sebacate

: 693-55-0
monoethyl sebacate

Conditions

Conditions	Yield
With potassium hydroxide at 0℃; for 12h;	75%

: 122586-72-5
1-methoxy-2,2,6,6-tetramethylpiperidin-4-ol

: 106-79-6
dimethyl sebacate

A: 122586-50-9
bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate

B: (1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacic acid monomethyl ester

Conditions

Conditions	Yield
With tetrabutylammomium bromide; lithium hydroxide In n-heptane at 0.98℃; for 0.5h;	A 74.31% B n/a

...Expand

: 1-ethoxy-4-hydroxy-2,2,6,6-tetramethylpiperidine

: 106-79-6
dimethyl sebacate

A: 122586-65-6
bis(1-ethoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate

B: (1-ethoxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacic acid monomethyl ester

Conditions

Conditions	Yield
With tetrabutylammomium bromide; lithium hydroxide In n-heptane at 0.98℃; for 0.5h;	A 74.21% B n/a

...Expand

Dimethyl sebacate Specification

The CAS register number of Dimethyl sebacate is 106-79-6. It also can be called as Decanedioic acid dimethyl ester and the IUPAC name about this chemical is dimethyl decanedioate. The molecular formula about this chemical is C₁₂H₂₂O₄and the molecular weight is 230.30. It belongs to the following product categories which include Fatty Acid Esters (Plasticizer); Functional Materials; Plasticizer and so on. When you are using it, please avoid contact with skin and eyes.

Physical properties about Dimethyl sebacate are: (1)ACD/LogP: 2.79; (2)ACD/LogD (pH 5.5): 2.79; (3)ACD/LogD (pH 7.4): 2.79; (4)ACD/BCF (pH 5.5): 77.24; (5)ACD/BCF (pH 7.4): 77.24; (6)ACD/KOC (pH 5.5): 781.48; (7)ACD/KOC (pH 7.4): 781.48; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 11; (10)Polar Surface Area: 52.6Å²; (11)Index of Refraction: 1.436; (12)Molar Refractivity: 61.19 cm³; (13)Molar Volume: 233.5 cm³; (14)Polarizability: 24.25x10^-24cm³; (15)Surface Tension: 32.8 dyne/cm; (16)Flash Point: 145 °C; (17)Enthalpy of Vaporization: 53.89 kJ/mol; (18)Boiling Point: 299 °C at 760 mmHg; (19)Vapour Pressure: 0.00123 mmHg at 25°C.

Preparation: this chemical can be prepared by decanedioic acid and methanol at heating. This reaction will need reagent H₂SO₄.

Uses of Dimethyl sebacate: it can be used to produce decanedioic acid at heating. This reaction will need reagent KOH and solvent methanol with reaction time of 24 hours.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)CCCCCCCCC(=O)OC
(2)InChI: InChI=1/C12H22O4/c1-15-11(13)9-7-5-3-4-6-8-10-12(14)16-2/h3-10H2,1-2H3
(3)InChIKey: ALOUNLDAKADEEB-UHFFFAOYAX
(4)Std. InChI: InChI=1S/C12H22O4/c1-15-11(13)9-7-5-3-4-6-8-10-12(14)16-2/h3-10H2,1-2H3
(5)Std. InChIKey: ALOUNLDAKADEEB-UHFFFAOYSA-N

Product Name

Dimethyl sebacate

Synthetic route

Dimethyl sebacate Specification

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