3-Ethynylaniline CAS 54060-30-9

Introduction：Basic information about 3-Ethynylaniline CAS 54060-30-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

3-Ethynylaniline Basic information

• Product Name: 3-Ethynylaniline
• Synonyms: M-ETHYNYLANILINE;M-AMINOPHENYL ACETYLENE;3-AMINOPHENYLACETYLENE;3-ETHYNYLBENZENEAMINE;3-ETHYNYL-PHENYLAMINE;3-ETHYNYLANILINE;Benzenamine, 3-ethynyl-;3-ethynyl-benzenamin
• CAS: 54060-30-9
• MF: C8H7N
• MW: 117.15
• EINECS: 258-944-6
• Product Categories: Alkynes and Other Reagents;Building Blocks;Chemical Biology;Chemical Synthesis;Conjugation Chemistry: Azides;Functionalized Alkynes;Organic Building Blocks;Intermediate of erlotinib hydrochloride;Alkynes;Organic Building Blocks;Terminal;Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research;Reagents for Conducting Polymer Research;Amines and Anilines;Acid Anhydrides, etc. (Reagents for Conducting Polymer Research);Functionalized Acetylenes;Acetylenes;54060-30-9
• Mol File: 54060-30-9.mol

3-Ethynylaniline Chemical Properties

• Melting point: 27°C
• Boiling point: 92-93 °C (2 mmHg)
• density: 1.04
• refractive index: 1.614-1.616
• Fp: 138 °F
• storage temp.: 2-8°C
• solubility: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly)
• form: Liquid
• pka: 3.67±0.10(Predicted)
• color: Clear yellow to brown
• Specific Gravity: 1.12
• Water Solubility: Insoluble in water.
• BRN: 2935417
• Stability: Light Sensitive
• InChI: 1S/C8H7N/c1-2-7-4-3-5-8(9)6-7/h1,3-6H,9H2
• InChIKey: NNKQLUVBPJEUOR-UHFFFAOYSA-N
• SMILES: Nc1cccc(c1)C#C
• CAS DataBase Reference: 54060-30-9(CAS DataBase Reference)
• NIST Chemistry Reference: M-aminophenylacetylene(54060-30-9)
• EPA Substance Registry System: Benzenamine, 3-ethynyl- (54060-30-9)

Safety Information

• Hazard Codes: Xi,F
• Risk Statements: 36/37/38
• Safety Statements: 26-36-37/39-36/37
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: TSCA listed
• HazardClass: 3
• PackingGroup: Ⅲ
• HS Code: 29214990
• Storage Class: 3 - Flammable liquids
• Hazard Classifications: Eye Irrit. 2 Flam. Liq. 3 Skin Irrit. 2 STOT SE 3

3-Ethynylaniline Usage And Synthesis

Chemical Properties

Clear yellowish to brown liquid

Uses

Reagent in the preparation of a labelled metabolite of Erlotinib (E625000).

Uses

3-Aminophenylacetylene is used as a pharmaceutical intermediate.

Application

3-Ethynylaniline may be used in the synthesis of the following benzoxazine monomers: bis{4-[3-(3-ethynylphenyl)(2H,4Hbenzo[3,4-e]1,3-oxazin-6-yloxy)]phenyl}phenylphosphino-1-one, [3-(3-ethynylphenyl)(2H,4Hbenzo[3,4-e]1,3-oxazaperhydroin-6-yl)][3-(3-ethynylphenyl)(2H,4H-benzo[3,4-e]1,3-oxazin-6-yl)]phenylphosphino-1-one, and bis[3-(3-ethynylphenyl)(2H,4Hbenzo[3,4-e]1,3-oxazin-6-yl)oxy]phenylphosphino-1-one.
It may be used:To synthesize succin(m-ethynyl)dianilide and sebaco(m-ethynyl)dianilide. As a reagent in the multi-step synthesis of erlotinib hydrochloride. To prepare 3-(3-ethynylphenyl)-6-methyl-2H, 4H-benzo[e]1,3-oxazine. To prepare 3-[3-(4-acetylamino-benzyl)-[1,2,4]oxadiazol-5- yl]-N-(3-ethynyl-phenyl)-propionamide.

General Description

3-Ethynylaniline is a terminal alkyne that can be prepared by the reduction of 3-ethylnylnitrobenzene.

reaction suitability

reaction type: click chemistry

Synthesis

Starting with m-nitrocinnamic acid: First, it undergoes an addition reaction with liquid bromine in glacial acetic acid to generate 3-(3-nitro)phenyl-2,3-dibromopropionic acid; subsequently, it undergoes dehydrobromination and decarboxylation reactions under the action of an organic base (such as DBU) to generate the key intermediate m-nitrophenylacetylene; finally, the nitro group is reduced to an amino group using iron powder in an acidic aqueous ethanol solution to obtain the target product 3-Ethynylaniline.

3-Ethynylaniline Preparation Products And Raw materials

• Raw materials: Ethanol-->Hydrazinium hydroxide solution-->Stannous chloride dihydrate-->Activated carbon-->Iron chloride hexahydrate-->3-NITROPHENYLACETYLENE
• Preparation Products: Erlotinib-->(3aR,6aR)-N-(4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-yl)-1-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxamide-->3-Vinylaniline-->Benzenamine, 3-ethynyl-N-methyl- (9CI)-->3-(2H-1,2,3-triazol-4-yl)aniline