3-Ethynylaniline

Base Information

• Chemical Name: 3-Ethynylaniline
• CAS No.: 54060-30-9
• Molecular Formula: C8H7N
• Molecular Weight: 117.15
• Hs Code.: 29214990
• European Community (EC) Number: 258-944-6
• UNII: DU8GFZ5KGE
• DSSTox Substance ID: DTXSID30885746
• Nikkaji Number: J207.976C
• Wikidata: Q72440425
• ChEMBL ID: CHEMBL4212090
• Mol file: 54060-30-9.mol

Synonyms:3-Ethynylaniline;3-Aminophenylacetylene;54060-30-9;Benzenamine, 3-ethynyl-;3-ethynylbenzenamine;m-Aminophenylacetylene;DU8GFZ5KGE;EINECS 258-944-6;m-ethynylaniline;3-ethynylphenylamine;3 - Ethynylaniline;(m-Aminophenyl)acetylene;MFCD00014779;isooctylnitrate;3-ethynyl-aniline;3-Ethynyl aniline;3-ethynyl-benzenamin;3-Ethynylaniline #;3-ethynyl-phenylamine;m-aminophenyl acetylene;3-amino-phenylacetylene;3-aminophenyl acetylene;(3-Ethynylphenyl)amine;3-Amino phenylacetylene;UNII-DU8GFZ5KGE;Bencenamina, 3-etinil-;3-amino-phenyl acetylene;(3-Aminophenyl)acetylene;1-Amino-3-ethynylbenzene;3-Ethynylaniline, >=98%;SCHEMBL107461;CHEMBL4212090;DTXSID30885746;BCP26724;STR05978;AC-068;AKOS009116045;CS-W007423;BP-21433;A1122;A7863;AM20050517;FT-0615662;EN300-26967;F11443;A830615;Q-101339;F5608-0061;Z235485474

Chemical Property of 3-Ethynylaniline

Chemical Property:

• Appearance/Colour: clear yellowish to brown liquid
• Vapor Pressure: 0.0379mmHg at 25°C
• Melting Point: 27 ºC
• Refractive Index: 1.614-1.616
• Boiling Point: 240.5 ºC at 760 mmHg
• PKA: 3.67±0.10(Predicted)
• Flash Point: 59 ºC
• PSA: 26.02000
• Density: 1.05 g/cm³
• LogP: 1.83130
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (
• Water Solubility.: Insoluble in water.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 117.057849228
• Heavy Atom Count: 9
• Complexity: 131

Purity/Quality:

99% ^*data from raw suppliers

3-Ethynylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 26-36-37/39-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CC(=CC=C1)N
• Chemical Composition and Structure: 3-Ethynylaniline has the molecular formula C₈H₇N and consists of an aniline ring with an ethynyl group (-C≡CH) attached at the 3-position.
• Categories and Type: 3-Ethynylaniline is classified as an aromatic amine compound.
• Uses: 3-Ethynylaniline is used as an intermediate in the synthesis of various compounds, including epoxide derivatives and liquid crystal thermosets (LCTs). It is involved in the synthesis of erlotinib, a drug used in the treatment of non-small cell lung cancer and other types of cancer.^[1],[2]
• References: [1] Method Development and Validation Study for Quantitative Determination of 3-Ethynylaniline Content in Erlotinib by Liquid Chromatography Tandem Mass Spectrometry; [2] Retracted: Design and synthesis of two epoxide derivatives from 3-ethynylaniline

Technology Process of 3-Ethynylaniline

There total 34 articles about 3-Ethynylaniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-methyl-4-(3-aminophenyl)-3-butyn-2-ol (69088-96-6) → 3-acetylenephenylamine (54060-30-9)

Guidance literature:

With sodium hydroxide; In toluene; at 105 - 110 ℃; for 4h; Inert atmosphere;

Reference yield: 95.0%

N‐(3‐ethynylphenyl)formamide (1364394-80-8) → 3-acetylenephenylamine (54060-30-9)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 70 - 75 ℃; for 2.5h;

Reference yield: 90.0%

N-(3-ethynylphenyl)acetamide (70933-58-3) → 3-acetylenephenylamine (54060-30-9)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 70 ℃; for 2h;

upstream raw materials:

3-nitrophenylacetylene

2-methyl-4-(3-aminophenyl)-3-butyn-2-ol

3-Iodoaniline

7-Benzenesulfonyl-4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

Downstream raw materials:

erlotinib hydrochloride

(3-ethynyl-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine

(3-ethynyl-phenyl)-carbamic acid tert-butyl ester

3-benzyloxycarbonylaminophenylacetylene

Refernces

• 1、 -. "Preparation method of acetenyl aniline". Paragraph 0055; 0058-0059; 0062-0063; 0066-0067; 0070-0071. . Retrieved 2021/04/14.
• 2、 Gu, Xianmo,Pei, Linjuan,Wang, Jie,Zhang, Jin,Zheng, Zhanfeng,Zhu, Pengqi. "Differences in the selective reduction mechanism of 4-nitroacetophenone catalysed by rutile- And anatase-supported ruthenium catalysts". . p. 1518 - 1528. Retrieved 2020/03/26.