Decanedioyl dichloride
[CAS 111-19-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Halogenated aliphatic hydrocarbon
• Name: Decanedioyl dichloride
• Synonyms: Decanedioic acid dichloride; Decanedioic dichloride; Decanedioyl chloride; NSC 56763; Sebacic acid chloride; Sebacic acid dichloride; Sebacic dichloride; Sebacoyl dichloride; Sebacyl chloride
• Molecular Formula: C₁₀H₁₆Cl₂O₂
• Molecular Weight: 239.14
• CAS Registry Number: 111-19-3
• EC Number: 203-843-4
• SMILES: C(CCCCC(=O)Cl)CCCC(=O)Cl

Properties

• Solubility: Very slightly soluble (0.41 g/L) (25 °C), Calc.^*
• Density: 1.1±0.1 g/cm³ Calc.^*, 1.121 g/mL (Expl.)
• Melting point: -5 - -3 °C (Expl.)
• Boiling point: 306.1 °C 760 mmHg (Calc.)^*, 337.2 °C (Expl.)
• Flash point: 151.4±21.2 °C (Calc.)^*, 113 °C (Expl.)
• Index of refraction: 1.464 (Calc.)^*, 1.468 (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314
• Safety Statements: P260-P264-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P330-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	2	H310
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1A	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Acute toxicity	Acute Tox.	1	H310

chemBlink Chemical Story

Sebacoyl chloride is one of the reagents behind the classic “nylon rope trick.” It has a reactive acyl chloride at each end of an eight-carbon chain. When a solution of sebacoyl chloride contacts an aqueous diamine solution, polyamide forms rapidly at the interface.

Each acyl chloride reacts with an amine to form an amide bond. Because both monomers are difunctional, the sequence repeats to produce nylon 6,10. Pulling the interfacial polymer film away exposes fresh boundary, allowing a continuous strand to form.

The demonstration is memorable because polymerization becomes visible, but it also illustrates an industrial principle: interfacial polymerization can organize fast reactions by keeping monomers in separate phases and letting them meet only at a boundary.

References:
PubChem. Sebacoyl chloride, CAS 111-19-3.
Sigma-Aldrich application information and polymer literature on nylon 6,10 interfacial polymerization.

Read more stories