451-77-4

Basic information

• Product Name: Homarylamine
• Synonyms: Homarylamine;2-(3,4-Methylenedioxyphenyl)-N-methylethaneamine;N-Methyl-1,3-benzodioxole-5-ethan-1-amine;2-(1,3-benzodioxol-5-yl)ethyl-methyl-amine;2-(1,3-benzodioxol-5-yl)-N-methylethanamine;2-(1,3-benzodioxol-5-yl)-N-methyl-ethanamine;5-[2-(Methylamino)ethyl]-1,3-benzodioxole
• CAS NO: 451-77-4
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• Mol File: 451-77-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 274°Cat760mmHg
• Flash Point: 106.8°C
• Appearance: /
• Density: 1.128g/cm³
• Vapor Pressure: 0.00556mmHg at 25°C
• Refractive Index: 1.544
• CAS DataBase Reference: Homarylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Homarylamine(451-77-4)
• EPA Substance Registry System: Homarylamine(451-77-4)

Safety Data

• Hazardous Substances Data: 451-77-4(Hazardous Substances Data)

Usage

Description

Homarylamine, also known as 1-phenyl-2-methylaminopropane, is an organic compound that belongs to the class of amines. It is a colorless to pale yellow liquid with a characteristic amine-like odor. Homarylamine is characterized by its asymmetric carbon atom, which allows for the formation of optical isomers. It is widely used in various industries due to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
Homarylamine is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those belonging to the class of benzylisoquinoline alkaloids. These alkaloids have a wide range of pharmacological activities, including analgesic, anti-inflammatory, and anti-cancer properties. Homarylamine plays a crucial role in the development of new drugs with improved efficacy and reduced side effects.
Used in Synthesis of Optically Pure (S)-Scoulerine:
Homarylamine is used as a key building block in the synthesis of optically pure (S)-scoulerine, an important intermediate in the production of various pharmaceutical compounds. The optical purity of (S)-scoulerine is essential for its biological activity, and Homarylamine's asymmetric carbon atom allows for the selective synthesis of the desired enantiomer.
Used in Synthesis of Berberine and Benzylisoquinoline Alkaloids:
Homarylamine is also utilized in the synthesis of berberine and other benzylisoquinoline alkaloids, which are known for their diverse pharmacological properties. These alkaloids are used in the treatment of various diseases, including cancer, neurological disorders, and cardiovascular conditions. Homarylamine's unique chemical structure enables the efficient synthesis of these complex molecules, contributing to the development of novel therapeutic agents.

InChI:InChI=1/C10H13NO2/c1-11-5-4-8-2-3-9-10(6-8)13-7-12-9/h2-3,6,11H,4-5,7H2,1H3

Upstream product

• 861799-59-9 benzo[1,3]dioxol-5-yl-thioacetic acid methylamide 
• 33542-98-2 β-<3,4-(methylenedioxy)phenyl>ethyl formamide 
• 62529-64-0 2-(benzo[d][1,3]dioxol-5-yl)ethyl methanesulfonate 
• 74-89-5 methylamine 
• 6006-82-2 3,4-methylenedioxyphenethyl alcohol 
• 6845-81-4 3,4-methylenedioxyphenylacetyl chloride 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 127901-42-2 2-Benzo[1,3]dioxol-5-yl-N-methyl-2-methylsulfanyl-acetamide 
• 274-09-9 Methylenedioxybenzene 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 127901-41-1 (3,4-methylenedioxy)phenyl-N-methylacetamide 
• 107044-63-3 (2-benzo[1,3]dioxol-5-yl-ethyl)-benzyliden-amine 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1718-77-0 1-(3-hydroxybenzyl)-6,7-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1897-07-0 1-(3-benzyloxybenzyl)-6,7-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1316259-19-4 (R)-1-(3-hydroxybenzyl)-6,7-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1277187-90-2 2-(3-benzyloxyphenyl)-N-(3,4-methylenedioxy)phenethyl-N-methylacetamide 
• 1316259-17-2 (S)-9-hydroxy-2,3-methylenedioxyberbine 
• 6592-85-4 hydrastinine 
• 132948-00-6 1-[(2-Benzo[1,3]dioxol-5-yl-ethyl)-methyl-amino]-cyclohex-3-enecarbaldehyde 
• 5936-29-8 hydrastinine chloride 

Relevant articles and documents

Iron-Catalyzed Intramolecular C—H Amidation of N-Benzoyloxyureas

A redox-neutral Fe-catalyzed intramolecular C—H amidation of N-benzoyloxyureas is described. This methodology employs a simple iron complex in situ generated from Fe(OTf)2 and bipyridine as the catalyst and N-benzoyloxyureas as the nitrene prec

Biocatalytic enantioselective oxidative C-C coupling by aerobic C-H activation

Bridging the gap: The berberine bridge enzyme (BBE) was employed for the first preparative oxidative biocatalytic C-C coupling that leads to a new intramolecular bond. This unique transformation requires O2 as sole stoichiometric oxidant and gives access to novel optically pure (S)-berbine 2 and (R)-1-benzyl-1,2,3,4-tetrahydroisoquinoline 1 alkaloid derivatives by kinetic resolution.

Pd(OAc)2-catalyzed carbonylation of amines

A phosphine-free catalytic system [Pd(OAc)2-Cu(OAc) 2-air] induced a substrate-specific carbonylation of amines in boiling toluene under CO gas (1 atm). Symmetrical N,N′-dialkylureas were obtained by the carbonylation of primary amines. N,N,N′-Trialkylureas were selectively formed by addition of a secondary amine to the above reaction vessel. Secondary amines did not give tetraalkylureas. However, dialkylamines with a phenyl group on their alkyl chains, such as N-monoalkylated benzylic amine or phenethylamine derivatives, underwent a direct aromatic carbonylation to afford five- or six-membered benzolactams. In the carbonylation, the chelation effect or steric repulsion between Pd(II) and the meta-substituent in the ortho-palladation and the ring sizes of cyclopalladation products that were formed prior to carbonylation were found to generate good site selectivity and increase the reaction rate. In contrast, carbonylation of ω- arylalkylamines with a hydroxyl group gave neither ureas nor benzolactams but instead produced 1,3-oxazolidinones smoothly. Hydrochlorides of amines also underwent carbonylation to afford the corresponding amides under the conditions used. This procedure made it possible to prepare ureas of amino acid esters and N-alkylcarbamates in practical yields.