112211-92-4

Basic information

• Product Name: (R)-2-ISOPROPYLAMINO-2-PHENYLETHANOL
• Synonyms: (R)-2-ISOPROPYLAMINO-2-PHENYLETHANOL;(R)-2-ISOPROPYLAMINO-2;(R)-2-ISOPROPYLAMINO-2-PHENYLETHANOL 98+%;(betaR)-beta-[(1-Methylethyl)amino]benzeneethanol;Benzeneethanol, b-[(1-methylethyl)amino]-, (bR)-;(2R)-2-(Isopropylamino)-2-phenylethanol;(R)-2-Isopropylamino-2-phenylethanol
• CAS NO: 112211-92-4
• Molecular Formula: C₁₁H₁₇NO
• Molecular Weight: 179.26
• Product Categories: Asymmetric Synthesis;Synthetic Organic Chemistry
• Mol File: 112211-92-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 75-76.5℃ (hexane )
• Boiling Point: 294.8°C at 760 mmHg
• Flash Point: 104.1°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 0.000721mmHg at 25°C
• Refractive Index: 1.523
• PKA: 14.48±0.10(Predicted)
• CAS DataBase Reference: (R)-2-ISOPROPYLAMINO-2-PHENYLETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-ISOPROPYLAMINO-2-PHENYLETHANOL(112211-92-4)
• EPA Substance Registry System: (R)-2-ISOPROPYLAMINO-2-PHENYLETHANOL(112211-92-4)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-43-22
• Safety Statements: 26-36/37/39-36/37
• Hazardous Substances Data: 112211-92-4(Hazardous Substances Data)

Usage

General Description

(R)-2-Isopropylamino-2-phenylethanol, also known as propylhexedrine, is a chemical compound with a molecular structure containing an isopropylamino group and a phenylethanol group. It is a chiral compound, meaning it has two possible stereoisomers, and the (R)-enantiomer is the active form that is used as a nasal decongestant. Propylhexedrine works by constricting blood vessels in the nasal passages, reducing swelling and congestion. It is often found in over-the-counter nasal inhalers and has a stimulant effect due to its similarity to amphetamine. However, it can be addictive and abuse of propylhexedrine can lead to harmful side effects such as elevated blood pressure, rapid heart rate, and CNS toxicity.

InChI:InChI=1/C11H17NO/c1-9(2)12-11(8-13)10-6-4-3-5-7-10/h3-7,9,11-13H,8H2,1-2H3/t11-/m0/s1

Upstream product

• 112211-91-3 N-isopropyl (R)-phenylglycine 
• 245443-16-7 N-isopropylidene-D-phenylglycinol 
• 56613-80-0 D-2-phenylglycinol 
• 67-64-1 acetone 
• 875-74-1 (R)-phenylglycine 

Downstream Products

• 132273-73-5 (1R,1'R)-N-isopropyl-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine 
• 132273-96-2 (1S,1'R)-N-isopropyl-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine 
• 132273-86-0 (2R,4R)-N-isopropyl-2,4-diphenyl-1,3-oxazolidine 
• 132273-86-0 (2S,4R)-N-isopropyl-2,4-diphenyl-1,3-oxazolidine 
• 132273-89-3 (2R,4R)-N-isopropyl-2-methyl-4-phenyl-1,3-oxazolidine 
• 143490-18-0 (2R,4R)-2-(2-bromophenyl)-3-isopropyl-4-phenyl-1,3-oxazolidine 
• 143490-18-0 (2S,4R)-2-(2-bromophenyl)-3-isopropyl-4-phenyl-1,3-oxazolidine 
• 112211-94-6 (R)-1-t-butoxy-2-isopropylamino-2-phenylethane 
• 112211-93-5 (R)-2-isopropylamino-1-methoxy-2-phenylethane 
• 135324-38-8 (R)-N-(2-Hydroxy-1-phenylethyl)-N-isopropylhydrazine 
• 135324-40-2 7-Isopropyl-6-phenyl-4-oxa-7,7a-diazaperhydroindan 
• 135324-62-8 (1'R,2S)-1--2-methylpyrrolidine 
• 135324-63-9 (1'R,2S)-2-Ethyl-1-pyrrolidine 
• 135324-64-0 (1'R,2R)-2-Benzyl-1-pyrrolidine 

Relevant articles and documents

Influence of steric factors on chiral lithium amide aggregates

The solution structures of three mixed aggregates dissolved in toluene-d8 consisting of the lithiated amides derived from (S)-N-isopropyl-1-((triisopropylsilyl)oxy)propan-2-amine, (R)-N-(1-phenyl-2- ((triisopropylsilyl)oxy)ethyl)propan-2-amine, or (S)-N-isobutyl-3-methyl-1- ((triisopropylsilyl)oxy)butan-2-amine and n-butyllithium are characterized by various NMR experiments including diffusion-ordered NMR spectroscopy with diffusion coefficient-formula weight correlation analyses (D-FW) and other one- and two-dimensional NMR techniques. We report that steric hindrance of R 1 and R2 groups of the chiral lithium amide controls the aggregation state of the mixed aggregates. With a less hindered R2 group, lithium (S)-N-isopropyl-1-((triisopropylsilyl)oxy)propan-2-amide forms mostly a 2:2 ladder-type mixed aggregate with n-butyllithium. Increase of steric hindrance of the R1 and R2 groups suppresses the formation of the 2:2 mixed aggregate and promotes formation of a 2:1 mixed aggregate. We observe that lithium (S)-N-isobutyl-3-methyl-1- ((triisopropylsilyl)oxy)butan-2-amide forms both a 2:2 mixed aggregate and a 2:1 mixed trimer with n-butyllithium. Further increase in the steric hindrance of R1 and R2 groups results in the formation of only 2:1 mixed aggregate as observed with lithium (R)-N-(1-phenyl-2-((triisopropylsilyl) oxy)ethyl)propan-2-amide.

Rational design of chiral lithium amides for asymmetric alkylation reactions - NMR spectroscopic studies of mixed lithium amide/alkyllithium complexes

Treatment of solutions of chiral lithium amides, containing internally coordinating groups, in diethyl ether (DEE) with alkyllithiums results in the formation of chiral lithium amide/alkyllithium mixed dimers. We report the use of eight different chiral l

Asymmetric Synthesis using Chiral Bases: Enantioselective α-Alkylation of Carboxylic Acids

Enantioselective alkylation of carboxylic acids (1) and (2) at the α-position can be performed using the chiral lithium isopropylamides (3) or (4), which function as both a strong base and a chiral auxiliary.