3492-47-5

Basic information

• Product Name: 1,3-bis(diethylamino)propan-2-ol
• Synonyms: 2-propanol, 1,3-bis(diethylamino)-
• CAS NO: 3492-47-5
• Molecular Formula: C₁₁H₂₆N₂O
• Molecular Weight: 202.3369
• Mol File: 3492-47-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 262.4°C at 760 mmHg
• Flash Point: 84°C
• Density: 0.909g/cm³
• Vapor Pressure: 0.00155mmHg at 25°C
• Refractive Index: 1.468
• CAS DataBase Reference: 1,3-bis(diethylamino)propan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-bis(diethylamino)propan-2-ol(3492-47-5)
• EPA Substance Registry System: 1,3-bis(diethylamino)propan-2-ol(3492-47-5)

Safety Data

• Hazardous Substances Data: 3492-47-5(Hazardous Substances Data)

Usage

Type of compound

Chemical compound, psychoactive drug

Classification

Metabolite of the antidepressant and smoking cessation aid bupropion

Structure

Tertiary amine derivative

Mechanism of action

Norepinephrine-dopamine reuptake inhibitor (NDRI)

Function

Inhibits the reuptake of norepinephrine and dopamine, increasing their levels in the brain

Additional activity

Weak inhibitor of serotonin reuptake

Therapeutic potential

Studied for treatment of depression, attention-deficit hyperactivity disorder (ADHD), and nicotine addiction

Research applications

Potential use in studying drug interactions and metabolism

Upstream product

• 109-89-7 diethylamine 
• 106-89-8 epichlorohydrin 
• 2917-91-1 glycidyldiethylamine 
• 15314-03-1 1,1’-diethyl-3-hydroxyazetidinium chloride 
• 96-21-9 1,3-dibromo-2-hydroxypropane 
• 26484-95-7 1-chloro-3-iodopropan-2-ol 
• 96-23-1 1,3-Dichloro-2-propanol 

Downstream Products

• 342045-75-4 (4-ethoxy-2-nitro-phenyl)-carbamic acid-(β,β'-bis-diethylamino-isopropyl ester) 
• 3492-54-4 1,3-Bis-N,N-diethylamino-2-chlor-propan 
• 3492-56-6 2-Benzyloxy-N,N,N',N'-tetraethyl-propane-1,3-diamine 
• 14377-48-1 4-tert.-Butyl-benzoesaeure-<1,3-bis-diethylamino-propyl-(2)-ester> 
• 14377-60-7 3,5-Di-tert.-butyl-benzoesaeure-<1,3-bis-diaethylamino-propyl-(2)-ester> 
• 102813-47-8 5-benzyl-furan-2-carboxylic acid-(β,β'-bis-diethylamino-isopropyl ester) 
• 22173-12-2 cyclohexyl-phenyl-acetic acid-(β,β'-bis-diethylamino-isopropyl ester) 
• 3579-24-6 diphenyl-acetic acid-(β,β'-bis-diethylamino-isopropyl ester) 

Relevant articles and documents

Regioselective ring opening in epoxides under the action of amines in water medium

Amino(bis-amino)derivatives of 2-propanol were synthesized by ring opening in epoxides under the action of amines in water medium using environmentally safe methods. The structure of the compounds obtained was established by elemental analysis and the IR, 1H and 13C NMR spectroscopy. It was found that these substances are effective bactericides. They suppress the growth of the sulfate-reducing bacteria and exhibit high anticorrosive properties.

Observation of stereotopic group recognition in chiral borate complexes in solution

The borate ester of 1a and 2e exhibits complete quaternization of the boron center. An equilibrium is observed between the two diastereomeric complexes 3 and 4 formed by coordination to the boron center of either amino group of 2e. At -78°C, this equilibrium is slow on the NMR timescale and a diastereomeric ratio of about 3:1 is observed. At room temperature, a rapid equilibration is observed resulting in two NMR resonances (both 1H and 13C) for the dimethylamino groups of 2e in 3/4. Comparison with the NMR characteristics of the analogous borate complexes of 1h and 1j and of 2c and 2d shows that these resonances each correspond to both methyl groups of a single dimethylamino group. The chemical shift difference occurs solely from the difference between the time fractions that the dimethylamino groups are coordinated to the boron center, and forms, therefore, a direct measure of the ratio 3/4. This ratio amounts to 63:37 at room temperature, which was confirmed by a protonation titration experiment. The elucidation of these NMR characteristics of B(1a)(2e) allowed the more rapid evaluation of the enantiotopic group recognition in many other borate complexes, which range from 57:43 to 67:33 at room temperature. The recognition of the (after complexation) diastereotopic dimethylamino groups of 2e in the borate complex B(1a)(2e) was utilized in a consecutive methylation reaction, which yielded enantiomerically enriched ammonium salt 7. The enantiomeric excess proved to be identical to the diastereomeric excess observed in the preceding recognition event. Strong evidence is presented that complex 3 is indeed the major diastereomer present in a solution of 3/4, as expected from molecular models.

Basically alkylated imides of naphthalene-1,4,5,8-tetracarboxylic acid and their chemotherapeutic effects

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