22314-94-9

Basic information

• Product Name: 3-methylharman
• Synonyms: 3-methylharman;1,3-Dimethyl-9H-pyrido[3,4-b]indole;1,3-Dimethyl-β-carboline
• CAS NO: 22314-94-9
• Molecular Formula: C13H12 N2
• Molecular Weight: 196.25
• Mol File: 22314-94-9.mol

Chemical Properties

• Boiling Point: 385.9°Cat760mmHg
• Flash Point: 172.4°C
• Appearance: /
• Density: 1.213g/cm³
• Vapor Pressure: 8.18E-06mmHg at 25°C
• Refractive Index: 1.723
• CAS DataBase Reference: 3-methylharman(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methylharman(22314-94-9)
• EPA Substance Registry System: 3-methylharman(22314-94-9)

Safety Data

• Hazardous Substances Data: 22314-94-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H12N2/c1-8-7-11-10-5-3-4-6-12(10)15-13(11)9(2)14-8/h3-7,15H,1-2H3

Upstream product

• 1201-26-9 3-(1H-indolyl)acetone 
• 87-51-4 indole-3-acetic acid 
• 132922-37-3 2-(1H-indol-3-yl)-N-methoxy-N-methyl-acetamide 
• 1132804-51-3 C₉H₁₁IN₂O 
• 1298035-42-3 tert-butyl 1-(2-iodophenylamino)-1-oxopropan-2-ylcarbamate 
• 1298035-44-5 2-acetamido-N-(2-iodophenyl)propanamide 
• 1298035-46-7 N-(2-iodophenyl)-2,4-dimethyloxazol-5-amine 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 615-43-0 2-iodophenylamine 
• 151721-32-3 N-benzenesulfonyl-o-aminobenzaldehyde 
• 1015760-82-3 (E)-N-(2-(3-oxobut-1-en-1-yl)phenyl)benzenesulfonamide 
• 738608-55-4 1-(2-acetyl-1H-indol-3-yl)-propan-2-one 

Relevant articles and documents

A short divergent approach to highly substituted carbazoles and β-carbolines via in situ-generated diketoindoles

Based on an aza-alkylation/Michael addition cascade reaction developed by Kim and co-workers we have developed divergent cascade reactions leading to either highly substituted 1-hydroxycarbazoles, 3-hydroxycarbazoles or β-carbolines, starting from readily

β-Carbolines: synthesis of harmane, harmine alkaloids and their structural analogs by thermolysis of 4-aryl-3-azidopyridines and investigation of their optical properties

[Figure not available: see fulltext.] Interest in β-carbolines is caused by the biological activity of these compounds and the use of their fluorescent properties in the study of their interaction with DNA and other biological targets, as well as with drug delivery vehicles. A new general method for the synthesis of harmane, harmine, and their structural analogs by thermolysis of substituted 4-aryl-3-azidopyridines was developed, and their optical properties were studied.

A Br?nsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α-(3-Indolyl) Ketones by Using 2-Benzyloxy Aldehydes

A Br?nsted acid catalyzed, operationally simple, scalable route to several functionalized α-(3-indolyl) ketones has been developed and the long-standing regioisomeric issue has been eliminated by choosing appropriate carbonyls. A readily available and cheap bottle reagent was used as the catalyst. This protocol was also applicable to the synthesis of densely functionalized α-(3-pyrrolyl) ketones. A detailed mechanistic study confirmed the involvement of enolether as a reaction intermediate. Several postsynthetic modifications along with easy access to β-carboline, tryptamines, tryptophols, and spiro-indolenine proclaim the synthetic utility of this powerful building block. On the basis of this concept, functionalized carbazoles were constructed by a cascade annulation strategy.

SUBSTITUTED PYRIDO[3,4-B]INDOLES FOR THE TREATMENT OF CARTILAGE DISORDERS

Substituted pyrido[3,4-b]indoles and their use as pharmaceuticals The present invention relates to 8-aryl-substituted and 8-heteroaryl-substituted 9H-pyrido[3,4-b]indoles of the formula I, in which A, E, G, R1 to R6 and R10 are as defined in the claims, which stimulate chondrogenesis and cartilage matrix synthesis and can be used in the treatment of cartilage disorders and conditions in which a regeneration of damaged cartilage is desired, for example joint diseases such as osteoarthritis. The invention furthermore relates to processes for the synthesis of the compounds of the formula I, their use as pharmaceuticals, and pharmaceutical compositions comprising them.

Intramolecular [4+2]-cycloaddition of 5-amino-substituted oxazoles as an approach toward the left-hand segment of haplophytine

The [4+2]-cycloaddition chemistry of several 5-amino-substituted oxazoles has been examined as an approach toward the construction of the left-half segment of the aspidosperma alkaloid haplophytine. Georg Thieme Verlag Stuttgart.

Synthesis of substituted carbazoles and β-carbolines by cyclization of diketoindole derivatives

A new route to substituted β-carbolines and carbazoles is described. Diketoindole intermediates, prepared by Friedel-Crafts acylations of 3-substituted indoles, have been converted to 3-hydroxycarbazoles and β-carbolines in good yields, 51-96% and 82-97%, respectively. This method also allows for the formation of 4-substituted β-carbolines. The application of this methodology to the synthesis of the natural products hyellazole and 6-chlorohyellazole is also described.