149403-05-4

Basic information

• Product Name: Benzenemethanol, a-(aminomethyl)-4-methyl-, (S)-
• Synonyms: Benzenemethanol, a-(aminomethyl)-4-methyl-, (S)-;(S)-2-amino-1-p-tolylethanol;a-(aMinoMethyl)-4-Methyl-;(1S)-2-amino-1-(4-methylphenyl)ethanol;Benzenemethanol, a-(aminomethyl)-4-methyl-, (aS)-
• CAS NO: 149403-05-4
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• Mol File: 149403-05-4.mol

Chemical Properties

• Boiling Point: 300.9°C at 760 mmHg
• Flash Point: 135.8°C
• Appearance: /
• Density: 1.076g/cm³
• Vapor Pressure: 0.000484mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: Benzenemethanol, a-(aminomethyl)-4-methyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-(aminomethyl)-4-methyl-, (S)-(149403-05-4)
• EPA Substance Registry System: Benzenemethanol, a-(aminomethyl)-4-methyl-, (S)-(149403-05-4)

Safety Data

• Hazardous Substances Data: 149403-05-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Pseudoephedrine is used as a decongestant for the treatment of nasal congestion due to allergies or the common cold. It functions by narrowing the blood vessels in the nasal passages, which helps to alleviate swelling and congestion, providing relief to the affected individual.
However, it is important to note that pseudoephedrine is also commonly used as a precursor in the illegal production of methamphetamine. As a result, its distribution and sale are heavily regulated in many countries to prevent its diversion for illicit purposes. Users should be cautious and adhere to the prescribed dosage and usage guidelines to avoid potential side effects, such as increased blood pressure and insomnia.

InChI:InChI=1/C9H13NO/c1-7-2-4-8(5-3-7)9(11)6-10/h2-5,9,11H,6,10H2,1H3/t9-/m1/s1

Upstream product

• 5467-70-9 2-amino-4'-methylacetophenone hydrochloride 
• 104-87-0 4-methyl-benzaldehyde 
• 139016-20-9 (S)-1-(4-methylphenyl)-1,2-ethanediol 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 619-41-0 4-(bromoacetyl)toluene 
• 6595-30-8 2-azido-1-(4-methylphenyl)ethan-1-one 
• 74104-57-7 α-(N-Acetylamino-)-4-methylacetophenon 
• 149342-42-7 N-Acetyl-β-hydroxy-4-methyl-phenaethylamin 
• 62968-73-4 2-nitro-1-(p-tolyl)ethan-1-one 
• 183540-43-4 (S)-(+)-1-(4-Tolyl)-2-(p-tolylsulfonyloxy)ethanol 
• 297765-46-9 (S)-2-azido-1-(4-methylphenyl)ethanol 
• 149286-03-3 Acetic acid (S)-2-acetylamino-1-p-tolyl-ethyl ester 
• 14271-73-9 4-methylbenzoyl cyanide 

Relevant articles and documents

Norepinephrine alkaloids as antiplasmodial agents: Synthesis of syncarpamide and insight into the structure-activity relationships of its analogues as antiplasmodial agents

Syncarpamide 1, a norepinephrine alkaloid isolated from the leaves of Zanthoxylum syncarpum (Rutaceae) exhibited promising antiplasmodial activities against Plasmodium falciparum with reported IC50 values of 2.04 μM (D6 clone), 3.06 μM (W2 clone) and observed by us 3.90 μM (3D7 clone) and 2.56 μM (K1 clone). In continuation of our work on naturally occurring antimalarial compounds, synthesis of syncarpamide 1 and its enantiomer, (R)-2 using Sharpless asymmetric dihydroxylation as a key step has been accomplished. In order to study structure-activity-relationship (SAR) in detail, a library of 55 compounds (3–57), which are analogues/homologues of syncarpamide 1 were synthesized by varying the substituents on the aromatic ring, by changing the stereocentre at the C-7 and/or by varying the acid groups in the ester and/or amide side chain based on the natural product lead molecule and further assayed in vitro against 3D7 and K1 strains of P. falciparum to evaluate their antiplasmodial activities. In order to study the effect of position of functional groups on antiplasmodial activity profile, a regioisomer (S)-58 of syncarpamide 1 was synthesized however, it turned out to be inactive against both the strains. Two compounds, (S)-41 and its enantiomer, (R)-42 having 3,4,5-trimethoxy cinnamoyl groups as side chains showed better antiplasmodial activity with IC50 values of 3.16, 2.28 μM (3D7) and 1.78, 2.07 μM (K1), respectively than the natural product, syncarpamide 1. Three compounds (S)-13, (S)-17, (S)-21 exhibited antiplasmodial activities with IC50 values of 6.39, 6.82, 6.41 μM against 3D7 strain, 4.27, 7.26, 2.71 μM against K1 strain and with CC50 values of 147.72, 153.0, >200 μM respectively. The in vitro antiplasmodial activity data of synthesized library suggests that the electron density and possibility of resonance in both the ester and amide side chains increases the antiplasmodial activity as compared to the parent natural product 1. The natural product syncarpamide 1 and four analogues/homologues out of the synthesized library of 55, (S)-41, (R)-42, (S)-55 and (S)-57 were assayed in vivo assay against chloroquine-resistant P. yoelii (N-67) strain of Plasmodium. However, none of the five molecules, 1, (S)-41, (R)-42, (S)-55 and (S)-57 exhibited any promising in vivo antimalarial activity against P. yoelii (N-67) strain. Compounds 4, 6, 7 and 11 showed high cytotoxicities with CC50 values of 5.87, 5.08, 6.44 and 14.04 μM, respectively. Compound 6 was found to be the most cytotoxic as compared to the standard drug, podophyllotoxin whereas compounds 4 and 7 showed comparable cytotoxicities to podophyllotoxin.

One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.

Asymmetric hydrogenation of α-primary and secondary amino ketones: Efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine

Two ss-receptor agonists (-)-denopamine and (-)-arbutamine were prepared in good yields and enantioselectivities by asymmetric hydrogenation of unprotected amino ketones for the first time by using Rh catalysts bearing electron-donating phosphine ligands. A series of α-primary and secondary amino ketones were synthesized and hydrogenated to produce various 1,2-amino alcohols in good yields and with good enantioselectivies. This Rh electron-donating phosphine-catalyzed asymmetric hyderogenation repI resents one of the most promising and convenient approaches towards the asymmetric synthesis of chiral amino alcohols.

Practical synthesis of optically active amino alcohols via asymmetric transfer hydrogenation of functionalized aromatic ketones

2-Substituted acetophenones such as 2-cyano-, 2-azido-, or 2-nitroacetophenones were effectively reduced with a mixture of HCOOH/N(C2H5)3 containing a chiral Ru(II) catalyst, RuCl[(S,S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine](p-cymene), giving the corresponding optically active alcohols, which can be converted to optically active amino alcohols with excellent ee's. Similarly, the reaction of 2-benzoylacetophenone with the same Ru catalyst gave a quantitative yield of the corresponding optically active 1,3-diol with 99% ee.

Application of optically active 1,2-diol monotosylates for synthesis of β-azido and β-amino alcohols with very high enantiomeric purity. Synthesis of enantiopure (R)-octopamine, (R)-tembamide and (R)-aegeline

A very convenient and highly efficient synthesis of near enantiopure β-azido and β-amino alcohols including biologically active substances such as (R)-octopamine, (R)-tembamide and (R)-aegeline from optically active 1,2-diol monotosylates is reported.

Baker's Yeast Reduction of α-(Acylamino)acetophenones and Lipase Catalyzed Resolution of 2-Acylamino-1-arylethanols

Enzymatic reduction of α-acylaminoacetophenones with fermenting baker's yeast afforded optically active (R)-2-acylamino-1-arylethanols.Furthermore, lipase-catalyzed resolution of the 2-acylamino-1-arylethanols using vinyl acetate as an acyl donor resulted in the formation of (S)-1-acetoxy-2-acylamino-1-arylethanols and (R)-2-acylamino-1-arylethanols.

Efficient Asymmetric Reduction of Acyl Cyanides with B-3-Pinanyl-9-BBN (Alpine-Borane)

Acyl cyanides are effectively reduced to optically active β-amino alcohols by using Alpine-Borane followed by sodium borohydride/cobaltous chloride