N-Thionylaniline (also known as N-sulfinylaniline or phenylthionyl imide) is an organosulfur compound characterized by a sulfinyl group (S=O) directly attached to the nitrogen atom of an aniline ring, and this electrophilic S=O–N motif, with its ambiphilic reactivity and ability to act as both a dienophile and a source of sulfur-functionalized anions, serves as a versatile linchpin for constructing heterocycles, introducing sulfur functionality into aromatic scaffolds, and enabling nucleophilic aromatic substitution in complex organic synthesis.
N-Thionylaniline (CAS 1122-83-4), also referred to as N-sulfinylaniline, is an organosulfur compound with the molecular formula C₆H₅NOS and a molecular weight of 139.18 g/mol. It appears as a light yellow to orange clear liquid, sometimes described as a straw‑colored or very strongly colored liquid, with a density of 1.236 g/mL at 25 °C, a boiling point of 200 °C at standard pressure (or 83 °C at 15 mmHg), and a flash point of 84 °C.
In organic synthesis, N-thionylaniline is a highly valued reagent and building block. Its sulfinyl group can act as both an electrophile and a nucleophile, facilitating a wide range of chemical transformations. As a source of the N‑sulfinyl group, N-thionylaniline enables the introduction of sulfur-containing fragments into organic molecules through nucleophilic aromatic substitution, where it acts as a source of a reactive sulfur‑containing anionic species. This capability makes N-thionylaniline a versatile synthetic intermediate for preparing sulfur-containing organic compounds, including biologically active intermediates, agrochemicals, and functional materials.
In materials science and medicinal chemistry, N-thionylaniline has been employed in the synthesis of novel low‑band‑gap donor–acceptor copolymers for organic electronics and as a precursor for fluorescent probes used in cancer imaging, showing applications ranging from materials science to pharmaceutical development. The compound also serves as a dienophile in Diels‑Alder cycloaddition reactions, a reactivity that has been exploited to generate 1,2-thiazine derivatives and other heterocyclic scaffolds. Additionally, N-thionylaniline participates in organometallic ligand‑exchange reactions and has been used in the synthesis of narrow‑bandgap polymers.
Product Parameters
Parameter
Specification
CAS Number
1122-83-4
MDL Number
MFCD00002084
EINECS Number
214-362-4
Molecular Formula
C₆H₅NOS
Molecular Weight
139.18 g/mol
Purity
≥98.0% (GC) as standard
Appearance
Light yellow to orange clear liquid; straw-colored or very strongly colored liquid
Density
1.236 g/mL at 25 °C
Boiling Point
200 °C at 760 mmHg; 83 °C at 15 mmHg
Flash Point
84 °C (closed cup)
Refractive Index
n20/D 1.627
Solubility
Partly miscible in water
Canonical SMILES
O=S=NC1=CC=CC=C1
Storage Condition
Store under inert gas (nitrogen or argon), refrigerated at 2–8°C, in a cool dry place away from light and heat
DOT/IATA Transport
UN 1993, Combustible Liquid, Packing Group III
Hazard Class
Flammable liquid (Class 3)
GHS Signal Word
Danger
Hazard Statements
H315 (skin irritation), H319 (serious eye irritation), H334 (may cause allergy or asthma symptoms), H335 (may cause respiratory irritation)
Storage Class
3 – flammable liquid
GHS Hazard Classification:
● Causes skin irritation
● Causes serious eye irritation
● May cause allergy or asthma symptoms or breathing difficulties if inhaled
● In case of inadequate ventilation, wear respiratory protection
● IF ON SKIN: Wash with plenty of water
● IF INHALED: Remove person to fresh air and keep comfortable for breathing
● IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing
● IF EXPERIENCING RESPIRATORY SYMPTOMS: Call a POISON CENTER/doctor
● Store in a well‑ventilated place. Keep container tightly closed
● Store locked up
● Dispose of contents/container in accordance with local regulations
First aid measures:
● If inhaled: Move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
● In case of skin contact: Wash off with soap and plenty of water. Consult a physician if skin irritation persists.
● In case of eye contact: Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. Continue rinsing during transport to hospital.
● If swallowed: Rinse mouth with water. Never give anything by mouth to an unconscious person. Consult a physician.
Frequently Asked Questions (FAQ)
Q1:Is N-Thionylaniline a hazardous material?
A: Yes. N-Thionylaniline is classified as a dangerous good (UN 1993, Combustible Liquid, Packing Group III). It has GHS signal word “Danger” with hazard statements H315 (skin irritation), H319 (serious eye irritation), H334 (may cause allergy or asthma symptoms or breathing difficulties if inhaled), and H335 (may cause respiratory irritation).
Q2:Can Cosperpharm supply this compound on a kilogram scale?
A: Yes. With our large‑scale reactors (20 L–5000 L), we support production from gram‑scale R&D samples to multi‑kilogram commercial batches. Please contact us for a custom quote.
Contact Us
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