149-95-1

Basic information

• Product Name: (S)-4-(2-amino-1-hydroxyethyl)pyrocatechol
• Synonyms: (S)-4-(2-amino-1-hydroxyethyl)pyrocatechol;-L-NoradrenalineHCl;(S)-Noradrenaline;(S)-Norepinephrine;1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (S)-;1,2-Benzenediol, 4-[(1S)-2-amino-1-hydroxyethyl]- (9CI);d-Norepinephrine;S-(+)-Norepinephrine
• CAS NO: 149-95-1
• Molecular Formula: C₈H₁₁NO₃
• Molecular Weight: 169.17784
• EINECS: 205-750-4
• Mol File: 149-95-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 216°C (rough estimate)
• Boiling Point: 298.46°C (rough estimate)
• Flash Point: 221.5°C
• Appearance: /
• Density: 1.2435 (rough estimate)
• Vapor Pressure: 1.3E-08mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• CAS DataBase Reference: (S)-4-(2-amino-1-hydroxyethyl)pyrocatechol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(2-amino-1-hydroxyethyl)pyrocatechol(149-95-1)
• EPA Substance Registry System: (S)-4-(2-amino-1-hydroxyethyl)pyrocatechol(149-95-1)

Safety Data

• Hazardous Substances Data: 149-95-1(Hazardous Substances Data)

Usage

Health Hazard

Blood circulation: increase blood pressure; peripheral vasoconstrictor without change or slight decrease in output and heart rate. No flow increase in brain, liver, or muscle Central nervous system effects: adrenergic transmitter agent at synapses; no brain excitation Kidney: decreases glomerular filtration rate Lung, intestine, genital system: inhibited Metabolic effects: weak epinephrine effect

InChI:InChI=1/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m1/s1

Upstream product

• 138-65-8 Norepinephrine 
• 104819-55-8 S-(-)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-oxo-2-amido-ethan 
• 5090-29-9 1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid 
• 56-40-6 glycine 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 104819-57-0 S-(-)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan 
• 26164-26-1 (S)-2-methoxy-2-phenylacetic acid 

Relevant articles and documents

Synthesis of aromatic 1,2-amino alcohols utilizing a bienzymatic dynamic kinetic asymmetric transformation

The applicability of the recent published bienzymatic protocol for the synthesis of (R)-2-amino-1-phenylethanol was tested using L-threonine aldolase from Pseudomonas putida and L-tyrosine decarboxylase from either Enterococcus faecalis (Efa) or two genes from Enterococcus faecium (Efil, Efi2). In all 21 benzaldehyde derivatives were applied for an initial TLC screening. On a small scale, octopamine and noradrenaline were obtained as (S)-enantiomers using Efil. Three protocols were upscaled yielding enantioenriched (S)-octopamine (yield 99%, ee 81%), (R)-2-amino-1-phenylethanol (yield 61%, ee 62%) and (S)-noradrenaline (yield 76%, ee 79%).

Enantiomers of 2,2'-dinitrobiphenyl-6,6'-dicarboxylic acid as stereoselective reversible protective groups. I. Stereospecificity of syntheses of S-(+)- and R-(-)-noradrenalin and adrenalin

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