3-Ethynylaniline

• CAS: 54060-30-9
• Catalog Number: ACM54060309
• Category: Alkynes
• Molecular Weight: 117.15g/mol
• Molecular Formula: C8H7N
• IUPAC Name: 3-ethynylaniline
• SMILES: C#CC1=CC(=CC=C1)N
• InChI: InChI=1S/C8H7N/c1-2-7-4-3-5-8(9)6-7/h1,3-6H,9H2
• InChI Key: NNKQLUVBPJEUOR-UHFFFAOYSA-N
• Application: The purpose of 3-Ethynylaniline, a clear yellowish to brown liquid, extends across various applications, primarily functioning as a versatile pharmaceutical intermediate. It is a key participant in click chemistry, facilitating the synthesis of complex benzoxazine monomers such as bis{4-[3-(3-ethynylphenyl)(2H,4H-benzo[3,4-e]1,3-oxazin-6-yloxy)]phenyl}phenylphosphino-1-one and related compounds. Additionally, 3-Ethynylaniline is instrumental in the synthesis of succin(m-ethynyl)dianilide and sebaco(m-ethynyl)dianilide, serves as a reagent in the multi-step production of erlotinib hydrochloride, and is vital in preparing compounds like 3-(3-ethynylphenyl)-6-methyl-2H,4H-benzo[e]1,3-oxazine and 3-[3-(4-acetylamino-benzyl)-[1,2,4]oxadiazol-5-yl]-N-(3-ethynyl-phenyl)-propionamide, showcasing its extensive utility in synthetic chemistry.
• Complexity: 131
• Covalently-Bonded Unit Count: 1
• EC Number: 258-944-6
• Exact Mass: 117.057849g/mol
• Formal Charge: 0
• Hazard Statements: H226-H304-H315-H319-H351
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Heavy Atom Count: 9
• Monoisotopic Mass: 117.057849g/mol
• RIDADR: UN 1993BE 3 / PGII
• Rotatable Bond Count: 1
• Symbol: GHS02
• XLogP3: 1.3

Synthetic Use

Downstream Synthesis Route 1

• 24424-99-5
• 54060-30-9

• 185619-66-3

Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 20, p. 4232 - 4235

Downstream Synthesis Route 2

• 54060-30-9
• 24608-52-4

• 185619-66-3

Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 15, p. 8282 - 8289

Downstream Synthesis Route 3

• 54060-30-9
• 183322-18-1

• 179688-29-0
• 183319-69-9

Reference: [1] Patent: WO2011/76813, 2011, A1, . Location in patent: Page/Page column 19

Downstream Synthesis Route 4

• 54060-30-9
• 183322-18-1

• 183319-69-9

Reference: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 2498 - 2502

Downstream Synthesis Route 5

• 24424-99-5
• 54060-30-9

• 185619-66-3

Reference: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4232 - 4235

* For details of the synthesis route, please refer to the original source to ensure accuracy.