111-19-3

Basic information

• Product Name: Sebacoyl chloride
• Synonyms: DECANEDIOYL CHLORIDE;SEBACOYL CHLORIDE, TECH., 92%;SEBACOYL DICHLORIDE 99+%;n-Octane-1,8-dicarboxylic acid dichloride;octane-1,8-dicarbonyl chloride;SEBACOYLCHLORIDE,REAGENT;SEBACRYL CHLORIDE;Sebacoyl chloride,92%, tech.
• CAS NO: 111-19-3
• Molecular Formula: C₁₀H₁₆Cl₂O₂
• Molecular Weight: 239.14
• EINECS: 203-843-4
• Product Categories: ACID CHLORIDES
• Mol File: 111-19-3.mol
• Article Data: 37

Chemical Properties

• Melting Point: -2.5 °C
• Boiling Point: 220 °C
• Flash Point: >230 °F
• Appearance: yellow/liquid
• Density: 1.121 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000787mmHg at 25°C
• Refractive Index: n20/D 1.468(lit.)
• Storage Temp.: 2-8°C
• Solubility: Miscible with hydrocarbons and ethers.
• Sensitive: Moisture Sensitive
• Stability: Reacts violently with water liberating toxic gas. Incompatible with water, oxidizing agents, amines, alcohols.
• BRN: 1365665
• CAS DataBase Reference: Sebacoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Sebacoyl chloride(111-19-3)
• EPA Substance Registry System: Sebacoyl chloride(111-19-3)

Safety Data

• Hazard Codes: T,C
• Statements: 22-24-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• RTECS: HD8454250
• F: 10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 111-19-3(Hazardous Substances Data)

Usage

Chemical Properties

colourless to light yellow liquid with a pungent odour

Uses

Sebacoyl Chloride can be used for cosmetic use that involves excellent activities of absorption and skin protection.

General Description

Sebacoyl chloride is a light yellow, pungent odored di-acryl chloride. It is soluble in hydrocarbons and ethers.It hydrolyzes in water, releasing hydrogen chloride.

InChI:InChI=1/C10H16Cl2O2/c11-9(13)7-5-3-1-2-4-6-8-10(12)14/h1-8H2

Synthetic route

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%

sebacoyl chloride (111-19-3) + 4-hydroxy-benzaldehyde (123-08-0) → bis(4-formylphenyl)decanedioate (118702-75-3)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 5h;	100%
With pyridine; N,N-dimethyl-formamide	67%
With pyridine Ambient temperature;

sebacoyl chloride (111-19-3) + Dimethyl phosphite (868-85-9) + phosphorous acid trimethyl ester (121-45-9) → [10-(Dimethoxy-phosphoryl)-1,10-bis-(dimethoxy-phosphoryloxy)-decyl]-phosphonic acid dimethyl ester

Conditions	Yield
at 130 - 135℃; for 6h;	100%

sebacoyl chloride (111-19-3) + 4-(1,3-dioxolan-2-yl)-N1-hydroxybenzenecarboximidamide (852691-00-0) → bis{(4-[1,3]-dioxolan-2-yl)-O-carboxybenzamidoximo}-1,8-octane (1003867-90-0)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 16h;	100%

sebacoyl chloride (111-19-3) + glycine ethyl ester hydrochloride (623-33-6) → [9-(Ethoxycarbonylmethyl-carbamoyl)-nonanoylamino]-acetic acid ethyl ester (105172-45-0)

Conditions	Yield
With triethylamine In chloroform at 0 - 20℃; for 13h;	99%

sebacoyl chloride (111-19-3) + 2-mercaptopyridine N-oxide (1121-31-9) → C20H24N2O4S2

Conditions	Yield
With pyridine In chloroform at -78 - 0℃;	99%

sebacoyl chloride (111-19-3) + 1-phenoxyhexane (1132-66-7) → 1,10-Bis-(4-hexyloxy-phenyl)-decane-1,10-dione (104192-36-1)

Conditions	Yield
With aluminium trichloride In Petroleum ether for 3h;	98.5%

sebacoyl chloride (111-19-3) + thiophenol (108-98-5) → S-phenyl decenedithioate (47510-31-6)

Conditions	Yield
With triethylamine In toluene	98%
With triethylamine In toluene for 0.666667h;	98%

sebacoyl chloride (111-19-3) + 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + terephthaloyl chloride (100-20-9) → 4-(4-{4-[4-(9-{4-[9-(4-Hydroperoxy-1,1,4-trimethyl-pentylperoxycarbonyl)-nonanoylperoxy]-1,1,4-trimethyl-pentylperoxycarbonyl}-nonanoylperoxy)-1,1,4-trimethyl-pentylperoxycarbonyl]-benzoylperoxy}-1,1,4-trimethyl-pentylperoxycarbonyl)-benzoic acid

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1.5h;	98%

sebacoyl chloride (111-19-3) + 12-(p-aminophenyl)-9,9-dimethyl-8,9,10,11-tetrahydrobenzacridin-11-one (159146-73-3) → decanedioic acid bis-{[4-(9,9-dimethyl-11-oxo-8,9,10,11-tetrahydro-benzo[a]acridin-12-yl)-phenyl]-amide}

Conditions	Yield
In acetone at 5℃; for 0.25h;	98%

sebacoyl chloride (111-19-3) + 4-acetamidosalicylic acid (50-86-2) → 1,10-bis-4-acetamidosalicyl-sebacate (537048-78-5)

Conditions	Yield
Stage #1: sebacoyl chloride; 4-acetamidosalicylic acid With pyridine In N,N-dimethyl-formamide at 0 - 20℃; for 6.08333h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide pH=2;	98%

sebacoyl chloride (111-19-3) + 2-Amino-5-nitrophenol (121-88-0) → C22H26N4O8

Conditions	Yield
With lithium chloride In 1-methyl-pyrrolidin-2-one; isopropyl alcohol at 20℃; for 1h; Inert atmosphere; Cooling with ice;	98%

sebacoyl chloride (111-19-3) + 4-methoxybenzonitrile (874-90-8) → 1,8-bis<4,6-bis(4-methoxyphenyl)-1,3,5-oxadiazin-2-yl-1-ium>octane bis hexachloroantimonate

Conditions	Yield
With antimonypentachloride In dichloromethane 1) -40 to 25 deg C, 2) 25 deg C, 3 h;	97%

sebacoyl chloride (111-19-3) + Nε-lauroyl-L-lysine ethyl ester (292140-08-0) → Nα,Nα'-sebacoyl-bis(Nε-lauroyl-L-lysine ethyl ester)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 24h;	97%

sebacoyl chloride (111-19-3) + salicylic acid (69-72-7) → salicylic acid-C10-salicylic acid (74134-03-5)

Conditions	Yield
With pyridine In tetrahydrofuran for 0.75h;	97%
With pyridine In tetrahydrofuran at 20℃;	91%
Stage #1: sebacoyl chloride; salicylic acid With pyridine In tetrahydrofuran at 0 - 20℃; for 2.08333h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=2;	91%
With pyridine In tetrahydrofuran at 70℃; for 5h;

sebacoyl chloride (111-19-3) + 3-phenyl-2H-chromen-2-imine (67231-69-0) → C40H36N2O4 (1367368-24-8)

Conditions	Yield
With pyridine In chloroform at 0 - 20℃; for 5h;	97%

1,2-dimethoxybenzene (91-16-7) + sebacoyl chloride (111-19-3) → 1,10-bis(3,4-dimethoxyphenyl)-1,10-decanedione (859742-49-7)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at -10 - 0℃; for 6h; Friedel Crafts acylation;	96%
With aluminium trichloride; 1,1,2,2-tetrachloroethane

sebacoyl chloride (111-19-3) + 2-amino-N-(2',5'-dimethoxyphenyl)acetamide (138778-05-9) → N,N'-bis<2'-(2",5"-dimethoxyphenylamino)-2'-oxoethyl>decanediamide (138778-06-0)

Conditions	Yield
With triethylamine In chloroform for 5h; Ambient temperature;	96%

sebacoyl chloride (111-19-3) + 7-(p-Aminophenyl)-10,10-dimethyl-8,9,10,11-tetrahydrobenz[c]acridin-8-one (117358-75-5) → decanedioic acid bis-{[4-(10,10-dimethyl-8-oxo-8,9,10,11-tetrahydro-benzo[c]acridin-7-yl)-phenyl]-amide}

Conditions	Yield
In acetone at 5℃; for 0.25h;	96%

sebacoyl chloride (111-19-3) + N-Acetyl-5-aminosalicylic acid (51-59-2) → 1,10-bis-5-acetamidosalicyl-sebacate (377064-84-1)

Conditions	Yield
Stage #1: sebacoyl chloride; N-Acetyl-5-aminosalicylic acid With pyridine In tetrahydrofuran at 0℃; for 6.16667h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=2;	96%

sebacoyl chloride (111-19-3) + 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid (22494-42-4) → 1,10-bis-5-(2,4-difluorophenyl)salicyl-sebacate (537048-80-9)

Conditions	Yield
Stage #1: sebacoyl chloride; 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid With pyridine In tetrahydrofuran at 0℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=2;	96%

sebacoyl chloride (111-19-3) + phosphorous acid trimethyl ester (121-45-9) → [10-(Dimethoxy-phosphoryl)-10-oxo-decanoyl]-phosphonic acid dimethyl ester

Conditions	Yield
for 2h; Ambient temperature;	95%

sebacoyl chloride (111-19-3) + 4,4-bis(p-tert-butylphenyl)-4-phenylbutanol (135273-20-0) → di<4,4-bis(p-tert-butylphenyl)-4-phenylbutyl> sebacate

Conditions	Yield
In diethylene glycol dimethyl ether at 100℃; for 24h;	95%

sebacoyl chloride (111-19-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → bis(N,N-dimethyl)nonanamide (13424-83-4)

Conditions	Yield
for 12h; amination; Heating;	95%

N-p-toluenesulfonylpyrrole (17639-64-4) + sebacoyl chloride (111-19-3) → 1,10-bis(N-tosyl-3-pyrrole)decane-1,10-dione (939881-12-6)

Conditions	Yield
aluminium trichloride In dichloromethane at 0℃; for 2h; Friedel-Crafts acylation;	95%

sebacoyl chloride (111-19-3) + tetrabutylammonium (1,7-dihydroxy)decahydro-closo-dodecaborate → 2N(C4H9)4(1+)*[(B12H10)](OOC(CH2)8COO)(2-)=[N(C4H9)4]2[(B12H10)](OOC(CH2)8COO)

Conditions	Yield
In pyridine; acetonitrile equimolar ratio, stirring (12 h); filtn., evapn. (vac.);	95%

sebacoyl chloride (111-19-3) + 5-chloro-2-hydroxybenzoic acid (321-14-2) → 1,10-bis-4-chlorosalicyl-sebacate

Conditions	Yield
Stage #1: sebacoyl chloride; 5-chloro-2-hydroxybenzoic acid With pyridine In tetrahydrofuran for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=2;	95%

sebacoyl chloride (111-19-3) + 1,3-dimethylbarbituric acid (769-42-6) → C18H22N4O8

Conditions	Yield
With pyridine at 0 - 25℃;	95%

sebacoyl chloride (111-19-3) + di-poly(Ε-caprolactone5400)-L-lysine-poly(ethyleneglycol); PDI = 1.49 → Nα-[carbonylnonanoyloxy-poly(ε-caprolactone5400)]-Nε-poly(ε-caprolactone)-L-lysine-polyethylene glycol; PDI = 1.82

Conditions	Yield
In chloroform at 70℃; for 4h;	94%

sebacoyl chloride (111-19-3) + Nε-monooctanoyl-L-lysine → bis(Nε-octanoyl-L-lysine)sebacoylamide monosodium salt

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 24h;	94%

Upstream product

• 111-20-6 1,10-decanedioic acid 

Downstream Products

• 14065-32-8 methyl 10-chloro-10-oxodecanoate 
• 113455-26-8 1,10-bis-(4-bromo-phenyl)-decane-1,10-dione 
• 13018-50-3 N,N'-bis-(1-methyl-4-phenyl-[4]piperidylmethyl)-decanediamide 
• 2525-88-4 1,10-bis-(4-methoxy-phenyl)-decane-1,10-dione 
• 550372-19-5 decanedioic acid bis-(4-chloro-phenyl ester) 
• 13424-83-4 bis(N,N-dimethyl)nonanamide 
• 17329-53-2 1,10-dithio-decanedioic acid S,S'-di-p-tolyl ester 
• 10365-10-3 1.8-Bis(2.5-dimethoxybenzoyl)octane 
• 143050-66-2 decanedioic acid di-tert-butyl ester 
• 109-43-3 dibutyl sebacate 
• 6268-61-7 1,10-diphenyl-decane-1,10-dione 
• 4355-07-1 10-cyclohexyl-decanoic acid 
• 2918-18-5 diphenyl sebacate 
• 22537-96-8 di-tert-butyl bisperoxysebacate 

Related news

Polymerization of reactive fluoroaliphatic diamines with Sebacoyl chloride (cas 111-19-3) to give fluorinated aliphatic polyamides (Nylons)08/22/2019

Both aminoacylated fluoroaliphatic diamines (‘reactive’ diamines) [H2N(CH2)3- C(O)NHCH2CH2(CF2)nCH2CH2NHC(O)(CH2)3NH2; n=4,8] and their tetrahydrobromide salts have been polymerized interfacially with sebacoyl chloride to give fluoroaliphatic polyamides. The polymers have been characterize...detailed

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