2338-18-3

Basic information

• Product Name: 1H-Inden-2-amine,2,3-dihydro-, hydrochloride (1:1)
• Synonyms: 1H-Inden-2-amine,2,3-dihydro-, hydrochloride (9CI);2-Indanamine, hydrochloride (8CI);(2,3-Dihydro-1H-inden-2-yl)amine hydrochloride;2,3-Dihydro-1H-inden-2-aminehydrochloride;2-Amino-2,3-dihydro-1H-indene hydrochloride;2-Aminoindanhydrochloride;2-Aminoindan monohydrochloride;Indan-2-ylamine hydrochloride;SU 8629 hydrochloride
• CAS NO: 2338-18-3
• Molecular Formula: C₉H₁₁N*ClH
• Molecular Weight: 169.6513
• EINECS: 219-048-0
• Mol File: 2338-18-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 245-247℃
• Boiling Point: 226.2 °C at 760 mmHg
• Flash Point: 96.8 °C
• Appearance: white solid
• Density: 1.056 g/cm³
• Vapor Pressure: 0.0831mmHg at 25°C
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• BRN: 3913700
• CAS DataBase Reference: 1H-Inden-2-amine,2,3-dihydro-, hydrochloride (1:1)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Inden-2-amine,2,3-dihydro-, hydrochloride (1:1)(2338-18-3)
• EPA Substance Registry System: 1H-Inden-2-amine,2,3-dihydro-, hydrochloride (1:1)(2338-18-3)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:
• Safety Statements: S22:; S24/25:
• WGK Germany: 3
• RTECS: NK4050000
• Hazardous Substances Data: 2338-18-3(Hazardous Substances Data)

Usage

Description

1H-Inden-2-amine,2,3-dihydro-, hydrochloride (1:1), also known as 2-AI, is a white powder substance that belongs to the aminoindan class. It is a semi-rigid congener of phenylethylamines, which are psychoactive alkaloids. 2-AI serves as the starting point for the synthesis of various psychoactive compounds, such as 5,6-methylenedioxy-2-aminoindane. It is prepared from 2-indanols via azide displacement and subsequent hydrogenation. This product is primarily intended for forensic applications due to its potential use in the synthesis of psychoactive substances.

Uses

Used in Forensic Applications:
1H-Inden-2-amine,2,3-dihydro-, hydrochloride (1:1) is used as a starting material for the synthesis of psychoactive compounds in forensic applications. Its role in the production of these compounds makes it a valuable tool for the analysis and identification of such substances in criminal investigations and toxicological studies.
Used in Pharmaceutical Research:
1H-Inden-2-amine,2,3-dihydro-, hydrochloride (1:1) is used as a key intermediate in the development of new pharmaceutical compounds. Its unique chemical structure allows for the exploration of its potential therapeutic properties, such as its modest analgesic and stimulatory effects, which could be further investigated and optimized for medical use.
Used in Chemical Synthesis:
1H-Inden-2-amine,2,3-dihydro-, hydrochloride (1:1) is used as a versatile building block in the synthesis of various organic compounds. Its chemical properties make it suitable for use in the creation of new molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C9H11N.ClH/c10-9-5-7-3-1-2-4-8(7)6-9;/h1-4,9H,5-6,10H2;1H

Upstream product

• 485-47-2 indan-1,2,3-trione hydrate 
• 15028-10-1 indan-1,2-dione-2-oxime 
• 83-33-0 inden-1-one 
• 4254-29-9 indan-2-ol 
• 180260-72-4 2-azido-2,3-dihydro-1H-indene 
• 3349-63-1 indan-2-one oxime 
• 24446-27-3 indan-2-yl-carbamic acid ethyl ester 

Downstream Products

• 73536-88-6 5-bromo-2-aminoindane 
• 2975-41-9 2,3-dihydro-1H-inden-2-amine 
• 39169-92-1 4-(N-acetyl-N-methylamino)benzenesulfonyl chloride 
• 162140-97-8 4-Chloro-2-(indan-2-yl)amino-1-nitrobenzene 
• 83402-63-5 tert-butyl N-(2,3-dihydro-1H-inden-2-yl)glycinate 
• 439933-30-9 2-[1-(3,4-Dimethoxy-benzyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-N-indan-2-yl-2-phenyl-acetamide 
• 889362-93-0 (S)-benzyl 5-bromo-2,3-dihydro-1H-inden-2-ylcarbamate 
• 1199827-76-3 (R)-benzyl 5-bromo-2,3-dihydro-1H-inden-2-ylcarbamate 
• 1199828-07-3 (S)-benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-ylcarbamate 
• 1199827-80-9 (R)-benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-ylcarbamate 
• 1251457-90-5 C₁₈H₁₈ClNO₂ 
• 1199827-78-5 (R)-methyl 2-(benzyloxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate 
• 1199828-05-1 (S)-methyl 2-(benzyloxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate 
• 1199827-82-1 (R)-benzyl-5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-ylcarbamate 

Relevant articles and documents

Preparation method of 2-aminoindan derivative

The invention discloses a preparation method of a 2-aminoindan derivative. The preparation method comprises the following steps: with a 1-indanone derivative as a starting raw material, carrying out oximation reaction, and synchronously reducing carbonyl and hydroxyl oxime under the catalysis of Lewis acid such as aluminum chloride in the presence of a boron metal reducing agent, so as to obtain the 2-aminoindan derivative. The invention further provides the 2-aminoindan derivative prepared by virtue of a synthetic method and a corresponding intermediate derivative. Compared with a synthetic method of the 2-aminoindan derivative in the prior art, the synthetic method disclosed by the invention has the beneficial effects that (1) only two reaction steps are adopted, and the reaction steps are obviously less than the reaction steps in the prior art; (2) the cost is relatively low, the operation is simple and convenient, and the yield is high; and (3) the preparation method is suitable for large-scale industrial production and has relatively good application prospects.

Concise syntheses of 2-aminoindans via indan-2-ol

2-Amino-5,6-dimethoxyindan hydrochloride was synthesized in seven steps and with an overall yield of 48%. Indan-2-ol was converted to 5,6-dibromo-indan-2- ol in three steps by acetylation, electrophilic bromination and deacetylation. Dimethoxylation of 5,6-dibromoindan-2-ol with NaOCH3 in the presence of CuI gave 5,6-dimethoxy-indan-2-ol, which was converted to 2-amino-5,6-dimethoxyindan hydrochloride by azidation, followed by Pd-C catalyzed hydrogenation. Similarly, 2-amino-5-bromoindan was synthesized in five steps and with an overall yield of 50%. Indan-2-ol was converted to 2-aminoindan by azidation followed by Pd-C catalyzed hydrogenation. The reaction of 2-aminoindan with 2.5 equiv Br2 afforded 2-amino-5,6- dibromoindan.

Amino-benzocycloalkane derivatives

Compounds of the formula I wherein R2—C, R3—C, R4—C or R5—C may be replaced by N; and wherein n is 1, 2 or 3; R1is aryl, cycloalkyl or heterocyclyl; R2, R3, R4and R5are independently hydrogen, optionally substituted alkyl, halo, amino, substituted amino, trifluoromethyl, cyano, carboxyl, alkoxycarbonyl, aralkoxycarbonyl, (alkyl, aryl or aralkyl)-thio, (alkyl, aryl or aralkyl)-oxy, acyloxy, (alkyl, aryl or aralkyl)-aminocarbonyloxy; or any two of R2, R3, R4and R5at adjacent positions are alkylenedioxy; R6is hydrogen, optionally substituted alkyl, amino, substituted amino, acylamino, wherein Rais hydrogen or optionally substituted alkyl, Rband Rcare independently hydrogen, optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl; or Rband Rctogether represent lower alkylene or lower alkylene interrupted by O, S, or N—(H, alkyl or aralkyl); Rdis optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl; and Reis optionally substituted alkyl, aryl, heterocyclyl, cycloalkyl, amino or substituted amino; and pharmaceutically acceptable salts thereof; and enantiomers thereof; which are useful as inhibitors of microsomal triglyceride transfer protein (MTP) and of apolipoprotein B (ApoB) secretion.