69088-96-6

Basic information

• Product Name: 4-(3-AMINOPHENYL)-2-METHYL-3-BUTYN-2-OL
• Synonyms: 2-METHYL-4-(3-AMINOPHENYL)-3-BUTYN-2-OL;3-(3-HYDROXY-3-METHYL-1-BUTYN-1-YL)ANILINE;4-(3-AMINOPHENYL)-2-METHYL-3-BUTYN-2-OL;4-(3-AMINOPHENYL)-2-METHYLBUT-3-YN-2-OL;3-(3-Hydroxy-3-methylbutyn-1-yl)aniline;M-APACB
• CAS NO: 69088-96-6
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.23
• EINECS: 1312995-182-4
• Product Categories: Acetylenic Alcohols & Their Derivatives;Acetylenes
• Mol File: 69088-96-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 120 °C
• Boiling Point: 340.2 °C at 760 mmHg
• Flash Point: 159.5 °C
• Appearance: /
• Density: 1.11
• Vapor Pressure: 3.38E-05mmHg at 25°C
• Refractive Index: 1.591
• Solubility: soluble in Methanol
• PKA: 12.99±0.29(Predicted)
• CAS DataBase Reference: 4-(3-AMINOPHENYL)-2-METHYL-3-BUTYN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-AMINOPHENYL)-2-METHYL-3-BUTYN-2-OL(69088-96-6)
• EPA Substance Registry System: 4-(3-AMINOPHENYL)-2-METHYL-3-BUTYN-2-OL(69088-96-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 69088-96-6(Hazardous Substances Data)

Usage

Uses

4-(3-Aminophenyl)-2-methyl-3-butyn-2-ol is used as a reactant in the cross-coupling reaction of aromatics and heteroaromatics with alkynes.

InChI:InChI=1/C11H13NO/c1-11(2,13)7-6-9-4-3-5-10(12)8-9/h3-5,8,13H,12H2,1-2H3

Upstream product

• 115-19-5 2-methyl-but-3-yn-2-ol 
• 591-19-5 m-Bromoaniline 
• 33432-52-9 2-methyl-4-(3-nitrophenyl)-3-butyn-2-ol 
• 50624-25-4 4-hydroxy-4-methyl-2-pentynoic acid 
• 585-79-5 m-nitrobromobenzene 
• 108-42-9 3-chloro-aniline 
• 626-01-7 3-Iodoaniline 

Downstream Products

• 54060-30-9 3-acetylenephenylamine 
• 183319-69-9 erlotinib hydrochloride 
• 248594-19-6 N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine, methanesulfonic acid salt 
• 31661-59-3 3-(4-(3-aminophenyl)buta-1,3-diynyl)benzeneamine 
• 299912-59-7 3-butyn-2-ol, 4-[3-[[6,7-bis(2-methoxyethoxy)-4-quinazolinyl]amine]phenyl]-2-methyl, hydrochloride 
• 1611477-69-0 3-(3-aminophenyl)-5,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxaborol-2(5H)-ol 
• 67-64-1 acetone 

Relevant articles and documents

Fast heck-cassar-sonogashira (hcs) reactions in green solvents

The replacement of toxic solvents with greener alternatives in Heck-Cassar-Sonogashira (HCS) cross-couplings was investigated. The fine-tuning of the HCS protocol allowed to achieve complete conversions and high speed under mild conditions. N-Hydroxyethylpyrrolidone (HEP) gave the best results. Moreover, the methodology was successfully applied to the synthesis of an intermediate of the anticancer drug Erlotinib, demonstrating the versatility of the new green protocol.

New method for the preparation of erlotinib

The present invention refers to an alternative method for the preparation of Erlotinib through a new chemical reaction for the preparation of the 4-(3-aminophenyl)-2-methyl-3-butyn-2-ol key intermediate of formula (IV) according to the following scheme.

Process for preparing 3-aminophenylacetylenes

A process for preparing a 3-aminophenylacetylene compound of formula (5), including: a) reacting a 3-haloaniline compound of formula (1) with an acetylene compound of formula (2) in the presence of a palladium compound, a copper compound, and an amine compound of formula (3) to form an aniline compound of formula (4); b) precipitating the aniline compound of formula (4) in the form of a crystal, and isolating it by solid/liquid separation; and c) reacting the aniline compound of formula (4) with a base to obtain 3-aminophenylacetylene.