146725-34-0

Basic information

• Product Name: dichloropane
• Synonyms: dichloropane;8-Azabicyclo[3.2.1]octane-2-carboxylicacid, 3-(3,4-dichlorophenyl)-, Methyl ester, (1R,2S,3S,5S)-;RTI-4229-111,O-401;Dichloropane lila@tuskwei.com;O-401
• CAS NO: 146725-34-0
• Molecular Formula: C₁₅H₁₇Cl₂NO₂
• Molecular Weight: 314.20698
• Product Categories: Dichloropane;pharmaceutical intermediate;use for pharmaceutical intermediate and medicine grade
• Mol File: 146725-34-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 407.6 °C at 760 mmHg
• Flash Point: 200.3 °C
• Appearance: /
• Density: 1.284 g/cm³
• Vapor Pressure: 7.46E-07mmHg at 25°C
• Refractive Index: 1.557
• PKA: 9.70±0.60(Predicted)
• CAS DataBase Reference: dichloropane(CAS DataBase Reference)
• NIST Chemistry Reference: dichloropane(146725-34-0)
• EPA Substance Registry System: dichloropane(146725-34-0)

Safety Data

• Hazardous Substances Data: 146725-34-0(Hazardous Substances Data)

Usage

Uses

Dichloropane is an analog of Cocaine (C633500), a compound that inhibits the dopamine, norepinephrine, and serotonin transporters. Unlike amphetamines, it has no effect on catecholamine release.

InChI:InChI=1/C15H17Cl2NO2/c1-20-15(19)14-10(7-9-3-5-13(14)18-9)8-2-4-11(16)12(17)6-8/h2,4,6,9-10,13-14,18H,3,5,7H2,1H3/t9-,10+,13+,14-/m0/s1

Upstream product

• 211046-98-9 O-1109 
• 168143-65-5 methyl (1R,5S)-8-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate 
• 85506-18-9 (1R)-(-)-2-carbomethoxy-3-tropinone 
• 151169-75-4 3,4-dichlophenylboronic acid 
• 532-24-1 tropinone 
• 50-36-2 Cocaine 
• 484-93-5 ecgonidine 
• 50373-10-9 methyl ecgonidine 
• 481-37-8 ecgonine 
• 72393-99-8 anhydroecgonine acid chloride 
• 53-21-4 (-)-cocaine hydrochloride 
• 79175-35-2 3,4-dichlorophenylmagnesium bromide 
• 143965-99-5 dicholoropane 

Downstream Products

• 190719-16-5 N-[2-((3'-N'-propyl-(1R-3β-(3,4-dichlorophenyl)-2β-methoxycarbonyltropane))(2-mercaptoethyl)amino)acetyl]-2-aminoethanethiol 
• 872460-79-2 8-(2-aminoethyl)-3β-(3,4-dichlorophenyl)-8-aza-bicyclo[3.2.1]octane-2β-carboxylic acid methyl ester 
• 872460-78-1 3β-(3,4-dichlorophenyl)-8-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethyl]-8-aza-bicyclo[3.2.1]octane-2β-carboxylic acid methyl ester 
• 196295-98-4 (1R,2S,3S,5S)-3-(3,4-Dichloro-phenyl)-8-prop-2-ynyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 

Relevant articles and documents

[3H]MFZ 2-12: A novel radioligand for the dopamine transporter

In an effort to develop a tritiated dopamine transporter radioligand with higher affinity than the widely used [3H]WIN 35,428, we have synthesized [3H]2β-carbomethoxy-3β-(3′,4′- dichlorophenyl)tropane ([3H]MFZ 2-12). Unlabeled MFZ 2-12 and the N-demethylated intermediate (MFZ 2-13) inhibited dopamine uptake by the human dopamine transporter with IC50's of 1.1 and 1.4 nM, respectively. The N-nor-intermediate (MFZ 2-13) was treated with CT3I resulting in [3H]MFZ 2-12; S.A. = 80 Ci/mmol). [3H]MFZ 2-12 reversibly bound with a KD of 2.8 nM to human dopamine transporter expressed heterologously in EM4 cells.

Rhodamine-labeled 2β-carbomethoxy-3β-(3,4-dichlorophenyl)tropane analogues as high-affinity fluorescent probes for the dopamine transporter

Novel fluorescent ligands were synthesized to identify a high-affinity probe that would enable visualization of the dopamine transporter (DAT) in living cells. Fluorescent tags were extended from the N- or 2-position of 2β-carbomethoxy-3β-(3,4-dichlorophenyl)tropane, using an ethylamino linker. The resulting 2-substituted (5) and N-substituted (9) rhodamine-labeled ligands provided the highest DAT binding affinities expressed in COS-7 cells (Ki = 27 and 18 nM, respectively) in the series. Visualization of the DAT with 5 and 9 was demonstrated by confocal fluorescence laser scanning microscopy in stably transfected HEK293 cells.

Substituted 3-Phenyltropane Analogs of Cocaine: Synthesis, Inhibition of Binding at Cocaine Recognition Sites, and Positron Emission Tomography Imaging

It is now accepted that (-)-cocaine binds to specific recognition sites associated with monoamine transporters in the mammalian brain. In this study, several analogs of 3β-phenyltropane-2β-carboxylic acid methyl ester were prepared and their potency for inhibiting the binding of -3β-(4-fluorophenyl)tropane-2β-carboxylic acid methyl ester to primate caudate-putamen was evaluated. The synthesis and binding affinity of 3β-(3,4-dichlorophenyl)tropane-2β-carboxylic acid methyl ester, one of the most potent cocaine congeners yet reported, is presented. The feasibility of synthesizing high-affinity ligands for cocaine recognition sites and their suitability as PET imaging ligands for cocaine receptors in vivo is demonstrated.