111-20-6

Basic information

• Product Name: Sebacic acid
• Synonyms: Sebacic acids;1, 10-Decanedioic acid;Sebacicacid;1,10-decanedioic acid;Sebacinsaeure;Decanedioic acid;Usaf hc-1;Decanedicarboxylic acid;1,8-Octanedicarboxylic acid
• CAS NO: 111-20-6
• Molecular Formula: C₁₀H₁₈O₄
• Molecular Weight: 202.28
• EINECS: 203-845-5
• Mol File: 111-20-6.mol
• Article Data: 221

Chemical Properties

• Melting Point: 131-134℃
• Boiling Point: 374.3 °C at 760 mmHg
• Flash Point: 198.3 °C
• Appearance: white powder
• Density: 1.106 g/cm³
• Vapor Pressure: 1.24E-06mmHg at 25°C
• Water Solubility: 1 g/L (20℃)
• CAS DataBase Reference: Sebacic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Sebacic acid(111-20-6)
• EPA Substance Registry System: Sebacic acid(111-20-6)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S36:
• Hazardous Substances Data: 111-20-6(Hazardous Substances Data)

Usage

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)/p-2

Synthetic route

10-undecenoic acid (112-38-9) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
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%

sebaconitrile (1871-96-1) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
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%

4,7-dioxo-1,10-decanedioic acid (5169-82-4) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
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;

1,10-Decanediol (112-47-0) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
With periodic acid; pyridinium chlorochromate In acetonitrile	98%
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 → 1,10-decanedioic acid (111-20-6)

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

C28H58O4Si2 → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
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 → 1,10-decanedioic acid (111-20-6)

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

Decanedioic acid bis-(3-methyl-but-2-enyl) ester → 1,10-decanedioic acid (111-20-6)

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

10-acetoxydecane-1-ol (59694-62-1) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
With palladium 10% on activated carbon; water; sodium hydroxide at 80℃; under 600.06 Torr; for 6h;	90%

Cyclodecene (3618-12-0) → 1,10-decanedioic acid (111-20-6)

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

1,3-Dioxa-cyclotridecane-4,13-dione → 1,10-decanedioic acid (111-20-6) + 1,10-Decanediol (112-47-0) + 10-hydroxydecanoic acid (1679-53-4)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 6h;	A n/a B 10% C 82%

methyl ricinoleate (141-24-2) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
With sodium hydroxide; sodium nitrate In water	81.7%

10-undecenoic acid (112-38-9) → 1,10-decanedioic acid (111-20-6) + 10-(hydroxyimino)decanoic acid (91017-32-2)

Conditions	Yield
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%

Ricinoleic acid (141-22-0) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
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

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 (247599-44-6) → 1,10-decanedioic acid (111-20-6) + C18H22O6

Conditions	Yield
With sulfuric acid at 130℃; for 0.25h; Hydrolysis;	A 68% B 41%

carbon monoxide (201230-82-2) + 2-octenol (22104-78-5) → 1,10-decanedioic acid (111-20-6)

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

C30H54O12 (74515-86-9) → 1,10-decanedioic acid (111-20-6) + ethene (74-85-1) + 10-oxo-dodecanoic acid (673-85-8) + carbon monooxide, carbon dioxide, oxygen

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

cyclooctanol (696-71-9) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
With Oxone In water; acetonitrile for 36h; Reflux;	60%

cyclodecane (293-96-9) → 1,10-decanedioic acid (111-20-6)

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

10-undecenoic acid (112-38-9) → 1,10-decanedioic acid (111-20-6) + ω-oxydecanocarboxylic acid (5578-80-3)

Conditions	Yield
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.

dimethyl sebacate (106-79-6) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
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 → 1,10-decanedioic acid (111-20-6) + rac-octan-2-ol (4128-31-8) + hexyl-methyl-ketone (111-13-7)

Conditions	Yield
at 240℃; for 7h;	A 12% B 49% C 24%

1,4-dibromo-butane (110-52-1) → Adipic acid (124-04-9) + 1,10-decanedioic acid (111-20-6)

Conditions	Yield
With magnesium durch Einw. von CO2 auf das Gemisch von Magnesiumverbindungen;

1,4-dibromo-butane (110-52-1) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
With magnesium Behandeln des entstehenden Gemisches von Magnesiumverbindungen mit Kohlendioxyd;

peracetic acid (79-21-0) + undec-10-ynoic acid (2777-65-3) → 1,10-decanedioic acid (111-20-6)

1 ,6-dibromohexane (629-03-8) + acetic acid tert-butyl ester (540-88-5) → 1,10-decanedioic acid (111-20-6)

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

cyclodecanone (1502-06-3) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
With chromium(VI) oxide; acetic acid

1,10-Decanediol (112-47-0) → 1,10-decanedioic acid (111-20-6) + 10-hydroxydecanoic acid (1679-53-4)

Conditions	Yield
With copper oxide-chromium oxide; hydrogen at 250℃; under 7355.08 Torr;

methanol (67-56-1) + 1,10-decanedioic acid (111-20-6) → dimethyl sebacate (106-79-6)

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%

1,10-decanedioic acid (111-20-6) → sebacoyl chloride (111-19-3)

Conditions	Yield
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%

1,10-decanedioic acid (111-20-6) + vinyl propionate (105-38-4) → divinyl sebacate (10355-50-7)

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

1,10-decanedioic acid (111-20-6) + 2-Ethylhexyl alcohol (104-76-7) → bis(2-ethylhexyl)sebacate (122-62-3)

Conditions	Yield
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%

1,10-decanedioic acid (111-20-6) → decanedial (45037-67-0)

Conditions	Yield
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;

1,10-decanedioic acid (111-20-6) + 1,1'-bis(4-pyridinyl)ferrocene (459142-93-9) → [(Fe(η5-C5H4-1-(4-C5H4N))2)2(1-sebastic acid)2]

Conditions	Yield
In methanol 1:1 mixt. ground for 5 min, dissolved in methanol; crystd.;	99%

1,10-decanedioic acid (111-20-6) + dyanol 22 (901-44-0) → C106H138O22

Conditions	Yield
In melt at 150 - 200℃; for 24h; Inert atmosphere;	99%

1,10-decanedioic acid (111-20-6) + 2-pentanol (584-02-1) → 1,10-di-3-pentyl 2,9-dibromodecanedioate

Conditions	Yield
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%

1,10-decanedioic acid (111-20-6) → sebacic acid-d16 (73351-71-0)

Conditions	Yield
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%

1,10-decanedioic acid (111-20-6) + carbonic acid dimethyl ester (616-38-6) → dimethyl sebacate (106-79-6)

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

1,10-decanedioic acid (111-20-6) + ethanol (64-17-5) → diethyl sebacate (110-40-7)

Conditions	Yield
for 2h; Reflux; Acidic conditions;	98%
With sulfuric acid In benzene for 4h; Reflux;	88.4%
With sulfuric acid Reflux;	75%

1,10-decanedioic acid (111-20-6) → 1,10-Decanediol (112-47-0)

Conditions	Yield
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%

1,10-decanedioic acid (111-20-6) + (+)-O-Demethyltramadol (144830-14-8) → (+)-(1R,2R)-3-[2-(dimethylamino)-methyl-1-hydroxycyclohexyl]phenol hemi-sebacate

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

1,10-decanedioic acid (111-20-6) + dyanol 22 (901-44-0) → C77H100O16

Conditions	Yield
In melt at 160 - 180℃; for 20h; Inert atmosphere;	98%

tapentadol (175591-23-8) + 1,10-decanedioic acid (111-20-6) → (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol sebacinate (1356394-20-1)

Conditions	Yield
In ethyl acetate at 20℃; for 15h;	97.37%
In ethyl acetate for 15h;	97.37%

1,10-decanedioic acid (111-20-6) + n-Pent-4-enyl alcohol (821-09-0) → C20H34O4

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

methanol (67-56-1) + 1,10-decanedioic acid (111-20-6) → sebacic acid mono methyl ester (818-88-2)

Conditions	Yield
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℃;

1,10-decanedioic acid (111-20-6) + 1,1,1-tri(hydroxymethyl)propane (77-99-6) + hydrogenated castor oil → polymer, product of polycondensation of 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, sebacic acid, and hydrogenated castor oil

Conditions	Yield
With dibutyltin(II) dilaurate at 180 - 200℃;	96.4%

1,10-decanedioic acid (111-20-6) + butan-1-ol (71-36-3) → dibutyl sebacate (109-43-3)

Conditions	Yield
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

1,10-decanedioic acid (111-20-6) + C15H16O4 → C40H46O10

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane	96%

1,10-decanedioic acid (111-20-6) + 1,4-diaminobutane (110-60-1) → butanediyldiamine; decanedioate (81062-09-1)

Conditions	Yield
In ethanol at 50 - 80℃; for 2h;	95%

1,10-decanedioic acid (111-20-6) + n-butyl formate (592-84-7) → Decanedioic acid monobutyl ester (5278-98-8) + dibutyl sebacate (109-43-3)

Conditions	Yield
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%

1,10-decanedioic acid (111-20-6) + 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	Yield
With dmap In tetrahydrofuran for 6h; Ambient temperature;	93%

1,10-decanedioic acid (111-20-6) + 4-hydroxymethyldibenzo-24-crown-8 ether (221002-03-5) → C35H50O12 (1245792-14-6)

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

1,6-Hexanediamine (124-09-4) + 1,10-decanedioic acid (111-20-6) → 1,6-hexamethylenediamine sebacic acid (6422-99-7)

Conditions	Yield
In ethanol at 50 - 80℃; for 2h;	93%

Upstream product

• 56-23-5 Carbon tetrachloride 
• 120-92-3 Cyclopentanone 
• 68153-81-1 Grease 
• 8001-79-4 Castor oil 
• 8013-06-7 SODIUM CASTORATE 
• 142-29-0 Cyclopentene 
• 124-18-5 Decane 

Downstream Products

• 4128-31-8 2-Octanol 
• 64701-47-9 1-PYRENEDECANOIC ACID 
• 27214-90-0 Diisooctyl sebacate 
• 1871-96-1 Sebaconitrile 
• 131-15-7 Dicapryl Phthalate 
• 110-40-7 Diethyl sebacate 
• 112-47-0 1,10-Decanediol 
• 106-79-6 Dimethyl sebacate 
• 109-43-3 Dibutyl sebacate 
• 122-62-3 Dioctyl sebacate 
• 2432-87-3 SEBACIC ACID DI-N-OCTYL ESTER 
• 4669-02-7 14-METHYLPENTADECANOIC ACID 
• 506-48-9 OCTACOSANOIC ACID 

Recommend Products

• 106-79-6  dimethyl sebacate 
• 186581-53-3  diazomethane 
• 111-20-6  1,10-decanedioic acid 
• 4629-03-2  1,10-di(piperidin-1-yl)decane-1,10-dione 
• 110-89-4  piperidine 
• 4650-79-7  decanedioic acid bis-tetrahydrofurfuryl ester 
• 97-99-4  Tetrahydrofurfuryl alcohol 
• 767-08-8  3-(tetrahydrofuran-2-yl)propan-1-ol 
• 124-04-9  Adipic acid 
• 110-52-1  1,4-dibromo-butane 
• 818-88-2  sebacic acid mono methyl ester 
• 67-56-1  methanol 
• 15419-91-7  bis(propyl) sebacate 
• 71-23-8  propan-1-ol 

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