13100-00-0

Basic information

• Product Name: 2-methyltryptoline
• Synonyms: 2-methyltryptoline;N-METHYL-1,2,3,4-TETRAHYDRO-BETA-CARBOLINE;2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole
• CAS NO: 13100-00-0
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.25
• Mol File: 13100-00-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 216-217 °C
• Boiling Point: 326.4°Cat760mmHg
• Flash Point: 151.2°C
• Appearance: /
• Density: 1.165g/cm³
• Vapor Pressure: 0.000217mmHg at 25°C
• Refractive Index: 1.66
• PKA: 17.28±0.20(Predicted)
• CAS DataBase Reference: 2-methyltryptoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyltryptoline(13100-00-0)
• EPA Substance Registry System: 2-methyltryptoline(13100-00-0)

Safety Data

• Hazardous Substances Data: 13100-00-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H14N2/c1-14-7-6-10-9-4-2-3-5-11(9)13-12(10)8-14/h2-5,13H,6-8H2,1H3

Upstream product

• 61-49-4 [2-(1H-indol-3-yl)-ethyl]-methylamine 
• 16502-01-5 tetrahydrobetacarboline 
• 214834-26-1 2-formyl-2,3,4,9-tetrahydro-1H-β-carboline 
• 5667-11-8 2-methyl-β-carboline-2-ium iodide 
• 89759-47-7 methyl 1,3,4,9‐tetrahydro‐2H‐pyrido[3,4‐b]indole‐2‐carboxylate 
• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 50-00-0 formaldehyd 
• 1147830-51-0 N-(4-chlorophenyl)sulfonyl-2-ethynylaniline 
• 61-54-1 tryptamine 
• 120-72-9 indole 
• 615-36-1 2-bromoaniline 
• 106047-18-1 2-(pyridin-4-yl)phenylamine 
• 1692-15-5 4-pyridylboronic acid 
• 1296771-21-5 2-methyl-9H-pyrido[3,4-b]indolium triflate 

Downstream Products

• 81375-36-2 Toluene-4-sulfonate2-methyl-2-methylamino-2,3,4,9-tetrahydro-1H-β-carbolin-2-ium; 
• 82820-65-3 Toluene-4-sulfonate2-ethylamino-2-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-2-ium; 
• 1239034-71-9 4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzoic acid methyl ester 
• 1239034-62-8 N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt 

Relevant articles and documents

Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement

Tetrahydro-β-carboline (THBC) is a tricyclic ring system that can be found in a large number of bioactive alkaloids. Herein, we report a simple and efficient method for the synthesis of enantiopure THBCs through a chiral thiosquaramide (11b) catalyzed imine reduction of dihydro-β-carbolines (17a-f). The in situ generated Pd-H employed as hydride source in the reaction of differently substituted chiral THBCs (18a-f) afforded high selectivities (R isomers, up to 96% ee) and good isolated yields (up to 88%). Moreover, the chiral thiosquaramide used also afforded exceptional catalyst activity in the syntheses of (-)-coerulescine (5) and (-)-horsfiline (6) with excellent enantioselectivities up to 98% and 93% ee, respectively, via an enantioselective oxidative rearrangement approach.

RhII2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides

Approaching all isomers: A range of α-, β- and δ-carbolinium ions are readily available from ortho-substituted aryl azides using a rhodium(II) carboxylate catalyst (see scheme). The carbolinium ions are readily reduced to afford tryptolines or deprotonated to access pyridoindoles. This [RhII2]-catalyzed C-H bond amination was used in the synthesis of (±)-horsfiline and neocryptolepine. esp=α,α,α',α'- tetramethyl-1,3-benzenedipropionate. Copyright

Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; Synthesis of dimebolin

A range of γ-carbolines were produced stereoselectively from ruthenium(III)-catalyzed reactions of 3-pyridyl substituted aryl azides. Other catalysts and conditions were neither as selective nor as high-yielding. This method was used to synthesize dimebolin in a concise and efficient manner.