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111-20-6

Basic Information
CAS No.: 111-20-6
Name: Sebacic acid
Molecular Structure:
Molecular Structure of 111-20-6 (Sebacic acid)
Formula: C10H18O4
Molecular Weight: 202.28
Synonyms: Sebacic acids;1, 10-Decanedioic acid;Sebacicacid;1,10-decanedioic acid;Sebacinsaeure;Decanedioic acid;Usaf hc-1;Decanedicarboxylic acid;1,8-Octanedicarboxylic acid;
EINECS: 203-845-5
Density: 1.106 g/cm3
Melting Point: 131–134.5 °C
Boiling Point: 374.3 °C at 760 mmHg
Flash Point: 198.3 °C
Solubility: 1 g/L in water
Appearance: white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information:
PSA: 74.60000
LogP: 2.27640
Synthetic route
112-38-9

10-undecenoic acid

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With ozone; sodium hydroxide In methanol; dichloromethane at -78 - 20℃; for 6h;100%
With sodium periodate; RuCl3*2.9H2O In water at 20℃; for 0.75h; Sonication;85%
Stage #1: 10-undecenoic acid With ozone; acetic acid In dichloromethane Inert atmosphere;
Stage #2: With semicarbazide hydrochloride at 0 - 20℃; for 48h; Inert atmosphere;
83%
1871-96-1

sebaconitrile

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
enzyme from Synechocystis sp. PCC 6803 In phosphate buffer at 30℃; for 2h;99%
With water for 48h; Rhodococcus rhodochrous AJ270;89%
With potassium phosphate buffer; Rhodococcus sp. AJ270 at 30℃; for 48h;89%
5169-82-4

4,7-dioxo-1,10-decanedioic acid

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; W(OTf)6; hydrogen; acetic acid at 20 - 180℃; under 22801.5 Torr; for 10.5h; Reagent/catalyst; Pressure; Temperature;98%
With palladium 10% on activated carbon; W(OTf)6; hydrogen; acetic acid at 180℃; under 22502.3 Torr; for 10h; Autoclave;88%
With sodium carbonate anschliessend Hydrierung an Raney-Nickel bei 250grad/150at;
112-47-0

1,10-Decanediol

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With periodic acid; pyridinium chlorochromate In acetonitrile98%
With Oxone; 2-Iodobenzoic acid In water; acetonitrile at 70℃; for 6h;97%
With periodic acid; tripropylammonium fluorochromate (VI) In acetonitrile at 0℃;96%

C42H54O4Si2

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With water; N,N-dimethyl-formamide at 70℃; for 1.5h; Green chemistry; chemoselective reaction;93%

C28H58O4Si2

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With water; N,N-dimethyl-formamide at 70℃; for 1.5h; Green chemistry; chemoselective reaction;91%

Decanedioic acid mono-(3-methyl-but-2-enyl) ester

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With iodine In cyclohexane for 24h; Ambient temperature;90%

Decanedioic acid bis-(3-methyl-but-2-enyl) ester

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With iodine In cyclohexane for 24h; Ambient temperature;90%
59694-62-1

10-acetoxydecane-1-ol

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; water; sodium hydroxide at 80℃; under 600.06 Torr; for 6h;90%
3618-12-0

Cyclodecene

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With periodic acid; ruthenium trichloride In tetrachloromethane; water; acetonitrile at 20℃; for 2h; Ring cleavage; oxidation;87%

1,3-Dioxa-cyclotridecane-4,13-dione

A

111-20-6

1,10-decanedioic acid

B

112-47-0

1,10-Decanediol

C

1679-53-4

10-hydroxydecanoic acid

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 6h;A n/a
B 10%
C 82%
141-24-2

methyl ricinoleate

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium nitrate In water81.7%
112-38-9

10-undecenoic acid

A

111-20-6

1,10-decanedioic acid

B

91017-32-2

10-(hydroxyimino)decanoic acid

Conditions
ConditionsYield
Stage #1: 10-undecenoic acid With ozone; acetic acid In dichloromethane Inert atmosphere;
Stage #2: With hydroxylamine hydrochloride at 0 - 20℃; for 48h; Inert atmosphere;
A 77%
B 9%
Stage #1: 10-undecenoic acid With ozone; acetic acid In dichloromethane Inert atmosphere;
Stage #2: With hydroxylamine hydrochloride at 0 - 20℃; for 48h; Inert atmosphere;
A 26%
B 55%
141-22-0

Ricinoleic acid

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With 3-n-Pentadecylphenol; water; sodium hydroxide at 230 - 250℃; for 8h; Time; Dean-Stark;73%
With sodium hydroxide; phenol In water at 250 - 290℃; for 8.5h; Dean-Stark;70%
With alkali
247599-44-6

28,29-dihydroxy-11,26-dioxa-tricyclo[22.2.2.210,13]triaconta-1(27),10(30),13(29),24(28)-tetraene-12,14,23,25-tetraone

A

111-20-6

1,10-decanedioic acid

B

C18H22O6

Conditions
ConditionsYield
With sulfuric acid at 130℃; for 0.25h; Hydrolysis;A 68%
B 41%
201230-82-2

carbon monoxide

22104-78-5

2-octenol

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;65%
74515-86-9

C30H54O12

A

111-20-6

1,10-decanedioic acid

B

74-85-1

ethene

C

673-85-8

10-oxo-dodecanoic acid

D

carbon monooxide, carbon dioxide, oxygen

carbon monooxide, carbon dioxide, oxygen

Conditions
ConditionsYield
In n-heptane at 100℃; Product distribution;A 60%
B n/a
C 10%
D n/a
696-71-9

cyclooctanol

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With Oxone In water; acetonitrile for 36h; Reflux;60%
293-96-9

cyclodecane

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With N-hydroxyphthalimide; bis(acetylacetonato)manganese(II); oxygen; acetic acid at 100℃; under 760.051 Torr; for 14h;55%
With nitric acid
112-38-9

10-undecenoic acid

A

111-20-6

1,10-decanedioic acid

B

5578-80-3

ω-oxydecanocarboxylic acid

Conditions
ConditionsYield
Stage #1: 10-undecenoic acid With ozone In dichloromethane Inert atmosphere;
Stage #2: With semicarbazide hydrochloride at 0 - 20℃; for 48h; Inert atmosphere;
A 51%
B 37%
Stage #1: 10-undecenoic acid With oxygen; Sudan III In dichloromethane at -78℃; for 0.666667h; Inert atmosphere;
Stage #2: With dimethylsulfide In dichloromethane at 20 - 45℃; for 36h;
A n/a
B 89 %Spectr.
106-79-6

dimethyl sebacate

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With porcine liver esterase; sodium hydroxide; phosphate buffer for 6h;49%
With porcine liver esterase; sodium hydroxide; phosphate buffer for 6h; Product distribution; chain length dependence;49%
With potassium hydroxide In methanol for 24h; Heating;
castor soap

castor soap

A

111-20-6

1,10-decanedioic acid

B

4128-31-8

rac-octan-2-ol

C

111-13-7

hexyl-methyl-ketone

Conditions
ConditionsYield
at 240℃; for 7h;A 12%
B 49%
C 24%
110-52-1

1,4-dibromo-butane

A

124-04-9

Adipic acid

B

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With magnesium durch Einw. von CO2 auf das Gemisch von Magnesiumverbindungen;
110-52-1

1,4-dibromo-butane

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With magnesium Behandeln des entstehenden Gemisches von Magnesiumverbindungen mit Kohlendioxyd;
79-21-0

peracetic acid

2777-65-3

undec-10-ynoic acid

111-20-6

1,10-decanedioic acid

629-03-8

1 ,6-dibromohexane

540-88-5

acetic acid tert-butyl ester

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With lithium amide; ammonia at -40℃; Erwaermen einer Loesung des Reaktiosprodukts in Dioxan mit konz.wss.Salzsaeure;
1502-06-3

cyclodecanone

111-20-6

1,10-decanedioic acid

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
112-47-0

1,10-Decanediol

A

111-20-6

1,10-decanedioic acid

B

1679-53-4

10-hydroxydecanoic acid

Conditions
ConditionsYield
With copper oxide-chromium oxide; hydrogen at 250℃; under 7355.08 Torr;
67-56-1

methanol

111-20-6

1,10-decanedioic acid

106-79-6

dimethyl sebacate

Conditions
ConditionsYield
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

111-19-3

sebacoyl chloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide for 1.5h; Reflux;100%
With oxalyl dichloride In dichloromethane at 20℃; for 24h; Inert atmosphere;92%
With phosgene at 160℃; Green chemistry;67.65%
111-20-6

1,10-decanedioic acid

105-38-4

vinyl propionate

10355-50-7

divinyl sebacate

Conditions
ConditionsYield
With sulfuric acid; mercury(II) diacetate at 20 - 50℃; for 4h;100%
111-20-6

1,10-decanedioic acid

104-76-7

2-Ethylhexyl alcohol

122-62-3

bis(2-ethylhexyl)sebacate

Conditions
ConditionsYield
With choline chloride; zinc(II) chloride at 110℃; for 16h;99%
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 2h; Time; Temperature; Concentration;99%
With titanium(IV) isopropylate at 150 - 215℃; for 3.5h; Reagent/catalyst; Temperature; Large scale;97.23%
111-20-6

1,10-decanedioic acid

45037-67-0

decanedial

Conditions
ConditionsYield
With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h;99%
With thexylchloroborane-Me2SO4 In dichloromethane for 0.25h; Ambient temperature;97%
With 9-borabicyclo[3.3.1]nonane dimer; tert.-butyl lithium 1.) THF, room temp.; 2.) THF, pentane, -20 deg C, 10 min and room temp., 1 h; Yield given. Multistep reaction;
111-20-6

1,10-decanedioic acid

459142-93-9

1,1'-bis(4-pyridinyl)ferrocene

[(Fe(η5-C5H4-1-(4-C5H4N))2)2(1-sebastic acid)2]

Conditions
ConditionsYield
In methanol 1:1 mixt. ground for 5 min, dissolved in methanol; crystd.;99%
111-20-6

1,10-decanedioic acid

901-44-0

dyanol 22

C106H138O22

Conditions
ConditionsYield
In melt at 150 - 200℃; for 24h; Inert atmosphere;99%
111-20-6

1,10-decanedioic acid

584-02-1

2-pentanol

1,10-di-3-pentyl 2,9-dibromodecanedioate

Conditions
ConditionsYield
Stage #1: 1,10-decanedioic acid With thionyl chloride at 75℃; for 1.5h; Sealed tube;
Stage #2: With bromine for 12h; Irradiation;
Stage #3: 2-pentanol for 1.5h; Cooling with ice;
99%
111-20-6

1,10-decanedioic acid

73351-71-0

sebacic acid-d16

Conditions
ConditionsYield
Stage #1: 1,10-decanedioic acid With d8-isopropanol; 10% Pt/activated carbon; water-d2 at 120℃; for 24h;
Stage #2: With water; sodium hydroxide at 70℃; for 24h; Reagent/catalyst;
99%
111-20-6

1,10-decanedioic acid

616-38-6

carbonic acid dimethyl ester

106-79-6

dimethyl sebacate

Conditions
ConditionsYield
With triethylamine at 160℃; for 5h; Autoclave; Green chemistry;99%
111-20-6

1,10-decanedioic acid

64-17-5

ethanol

110-40-7

diethyl sebacate

Conditions
ConditionsYield
for 2h; Reflux; Acidic conditions;98%
With sulfuric acid In benzene for 4h; Reflux;88.4%
With sulfuric acid Reflux;75%
111-20-6

1,10-decanedioic acid

112-47-0

1,10-Decanediol

Conditions
ConditionsYield
Stage #1: 1,10-decanedioic acid With sodium aminodiboranate In tetrahydrofuran at 20℃;
Stage #2: With water
98%
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane for 4h; Ambient temperature;88%
With sodium tetrahydroborate; benzene-1,2-diol; trifluoroacetic acid In tetrahydrofuran at 25℃; for 4h;68%
111-20-6

1,10-decanedioic acid

144830-14-8

(+)-O-Demethyltramadol

(+)-(1R,2R)-3-[2-(dimethylamino)-methyl-1-hydroxycyclohexyl]phenol hemi-sebacate

Conditions
ConditionsYield
In tert-butyl methyl ether at 30℃; for 17h; Product distribution / selectivity;98%
111-20-6

1,10-decanedioic acid

901-44-0

dyanol 22

C77H100O16

Conditions
ConditionsYield
In melt at 160 - 180℃; for 20h; Inert atmosphere;98%
175591-23-8

tapentadol

111-20-6

1,10-decanedioic acid

1356394-20-1

(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol sebacinate

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 15h;97.37%
In ethyl acetate for 15h;97.37%
111-20-6

1,10-decanedioic acid

821-09-0

n-Pent-4-enyl alcohol

C20H34O4

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 48h; Inert atmosphere;97.3%
67-56-1

methanol

111-20-6

1,10-decanedioic acid

818-88-2

sebacic acid mono methyl ester

Conditions
ConditionsYield
With sulfonated poly-divinylbenzene-co-triallylamine at 24.84℃; for 12h;97%
With hydrogenchloride at 170℃; for 12h;38%
With sulfuric acid at 75 - 80℃;
111-20-6

1,10-decanedioic acid

77-99-6

1,1,1-tri(hydroxymethyl)propane

hydrogenated castor oil

hydrogenated castor oil

polymer, product of polycondensation of 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, sebacic acid, and hydrogenated castor oil

polymer, product of polycondensation of 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, sebacic acid, and hydrogenated castor oil

Conditions
ConditionsYield
With dibutyltin(II) dilaurate at 180 - 200℃;96.4%
111-20-6

1,10-decanedioic acid

71-36-3

butan-1-ol

109-43-3

dibutyl sebacate

Conditions
ConditionsYield
With triflic acid on silica-encapsulated superparamagnetic iron oxide nanoparticles In neat (no solvent) at 90℃; for 0.25h; Catalytic behavior; Time; Reagent/catalyst; Flow reactor; Green chemistry;96%
With Candida antarctica lipase B In cyclohexane at 45℃; for 6h;80%
With hydrogenchloride; benzene
111-20-6

1,10-decanedioic acid

C15H16O4

C40H46O10

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane96%
111-20-6

1,10-decanedioic acid

110-60-1

1,4-diaminobutane

81062-09-1

butanediyldiamine; decanedioate

Conditions
ConditionsYield
In ethanol at 50 - 80℃; for 2h;95%
111-20-6

1,10-decanedioic acid

592-84-7

n-butyl formate

A

5278-98-8

Decanedioic acid monobutyl ester

B

109-43-3

dibutyl sebacate

Conditions
ConditionsYield
With Dowex 50W-X2 (50-100 mesh) In octane at 100℃; for 4.33333h;A 93%
B 4%
With Dowex 50Wx2 In octane at 100℃; for 4.33333h; Esterification;A 93%
B 4%
111-20-6

1,10-decanedioic acid

Carbonic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (E)-7-hydroxy-hept-2-enyl ester

Decanedioic acid mono-{(E)-7-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxycarbonyloxy]-hept-5-enyl} ester

Conditions
ConditionsYield
With dmap In tetrahydrofuran for 6h; Ambient temperature;93%
111-20-6

1,10-decanedioic acid

221002-03-5

4-hydroxymethyldibenzo-24-crown-8 ether

1245792-14-6

C35H50O12

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;93%
124-09-4

1,6-Hexanediamine

111-20-6

1,10-decanedioic acid

6422-99-7

1,6-hexamethylenediamine sebacic acid

Conditions
ConditionsYield
In ethanol at 50 - 80℃; for 2h;93%
  • CHemwill --   Sebacic acid

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Chemistry

Molecular Structure of Sebacic acid (CAS NO.111-20-6):

IUPAC Name: decanedioic acid 
Empirical Formula: C10H18O4
Molecular Weight: 202.2475
H bond acceptors: 4
H bond donors: 2
Freely Rotating Bonds: 9
Index of Refraction: 1.475
Molar Refractivity: 51.5 cm3
Molar Volume: 182.8 cm3
Surface Tension: 44.9 dyne/cm
Density: 1.106 g/cm3
Flash Point: 198.3 °C
Enthalpy of Vaporization: 68.26 kJ/mol
Boiling Point: 374.3 °C at 760 mmHg
Vapour Pressure: 1.24E-06 mmHg at 25°C
Water Solubility: 1 g/L (20 ºC)
Merck: 14,8415
BRN: 1210591
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, bases, reducing agents
Melting point: 131–134.5 °C
Solubility in water: 0.25 g/L
InChI
InChI=1/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)
Smiles
C(CCCCCCCCC(O)=O)(O)=O
EINECS: 203-845-5
Product Categories: Intermediates; alpha,omega-Alkanedicarboxylic Acids; alpha,omega-Bifunctional Alkanes; Monofunctional & alpha,omega-Bifunctional Alkanes; Organic Chemicals

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LC inhalation > 900mg/m3 (900mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: EXCITEMENT
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 24(5), Pg. 48, 1980.
mammal (species unspecified) LD50 intraperitoneal 1175mg/kg (1175mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 24(5), Pg. 48, 1980.
mammal (species unspecified) LD50 oral > 11gm/kg (11000mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(9), Pg. 72, 1983.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 oral 6gm/kg (6000mg/kg)   Biochemical Journal. Vol. 34, Pg. 1196, 1940.
rat LC50 inhalation > 4500mg/m3 (4500mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(2), Pg. 17, 1992.
rat LD50 oral 14375mg/kg (14375mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(2), Pg. 17, 1992.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S25:Avoid contact with eyes. 
S36:Wear suitable protective clothing.
WGK Germany: 1
RTECS: VS0875000
HS Code: 29171310

Specification

 Sebacic acid , with CAS number of 111-20-6, can be called decanedioic acid ; Sebacic acid ; 1, 10-Decanedioic acid ; 1,10-decanedioic acid ; Decanedioic acid ; 1,8-Octanedicarboxylic acid ; decanedioate . It is a white powder,  Sebacic acid (CAS NO.111-20-6) is also used as an intermediate for antiseptics,aromatics and painting materials. Sebacic acid (CAS NO.111-20-6) is a low toxic substance, with flammability, burning will produce toxic fumes, so it should be stored in cool and dry environment, dry powder, foam, sand, carbon dioxide, water mist can be used if something urgent happened.

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