(-)-Pseudoephedrine

Base Information

• Chemical Name: (-)-Pseudoephedrine
• CAS No.: 321-97-1
• Deprecated CAS: 7009-81-6
• Molecular Formula: C10H15NO
• Molecular Weight: 165.235
• Hs Code.: 29394200
• European Community (EC) Number: 206-292-8
• UNII: S76J9U46ST
• DSSTox Substance ID: DTXSID90185895
• Nikkaji Number: J193.736G
• Wikidata: Q27288764
• Metabolomics Workbench ID: 126886
• ChEMBL ID: CHEMBL2110905
• Mol file: 321-97-1.mol

Synonyms:(-)-Pseudoephedrine;(1R,2R)-(-)-Pseudoephedrine;l-Pseudoephedrine;321-97-1;Pseudoephedrine, (-)-;(-)-threo-Ephedrine;D-(-)-Pseudoephedrine;(-)-psi-Ephedrine;(1R,2R)-Ephedrine;l-(1R,2R)-Pseudoephedrine;(-)-(1R,2R)-Pseudoephedrine;(1R,2R)-2-(methylamino)-1-phenylpropan-1-ol;CPDD 0049;EINECS 206-292-8;UNII-S76J9U46ST;S76J9U46ST;MLS000069657;Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (R-(R*,R*))-;EC 206-292-8;(R-(R*,R*))-alpha-(1-(Methylamino)ethyl)benzyl alcohol;SMR000059174;Benzenemethanol, alpha-((1R)-1-(methylamino)ethyl)-, (alphaR)-;(-)-Pseudoephedrine ((1R,2R)-Pseudoephedrine);D(-)-Pseudoephedrine;Opera_ID_462;PSEUDOEPHEDRINE, L-;SCHEMBL4786;CHEMBL2110905;CPDD-0049;(1r, 2r)-(-)-pseudoephedrine;DTXSID90185895;HMS2232I23;STR08329;PDSP1_001343;PDSP1_001346;AKOS000268842;(1R 2R)-(-)-PSEUDOEPHEDRINE;(1R,2R)-(-)-Pseudoephedrine, 98%;LS-125921;(-)-Pseudoephedrine 1.0 mg/ml in Methanol;Q27288764;(-)-Pseudoephedrine, purum, >=96.0% (sum of enantiomers, GC);Benzenemethanol, .alpha.-[1-(methylamino)ethyl]-, [R-(R*,R*)]-;(.ALPHA.R)-.ALPHA.-((1R)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL

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Chemical Property of (-)-Pseudoephedrine

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Vapor Pressure: 0.00865mmHg at 25°C
• Melting Point: 118-120 °C(lit.)
• Boiling Point: 255 °C at 760 mmHg
• PKA: 13.96±0.20(Predicted)
• Flash Point: 85.6 °C
• PSA: 32.26000
• Density: 1.015 g/cm³
• LogP: 1.71880
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 165.115364102
• Heavy Atom Count: 12
• Complexity: 121

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 20/21/22-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-37/39-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(C1=CC=CC=C1)O)NC
• Isomeric SMILES: C[C@H]([C@@H](C1=CC=CC=C1)O)NC

Technology Process of (-)-Pseudoephedrine

There total 84 articles about (-)-Pseudoephedrine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

(+/-)-erythro-methylephedrine (552-79-4,1201-56-5,14222-20-9,17605-71-9,39263-91-7,42151-56-4,51018-28-1,62560-55-8,87040-40-2) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + ephedrine (90-81-3,90-82-4,299-42-3,321-97-1,321-98-2,4125-58-0,34783-90-9,38732-95-5,53214-57-6,7009-81-6,90-83-5,6912-63-6) + benzaldehyde (100-52-7) + acetaldehyde (75-07-0,9002-91-9) + dimethyl amine (124-40-3)

Guidance literature:

With water; at 25 ℃; Product distribution; Mechanism; anodic oxidation, carbonate buffer, pH 10; effect of substituents investigated with different types of β-alkanolamines;

Reference yield: 86.0%

(2RS,3RS)-N-(2-phenyloxetan-3-yl)formamide → rac-pseudoephedrine (90-82-4,299-42-3,321-97-1,321-98-2,4125-58-0,34783-90-9,38732-95-5,53214-57-6,90-81-3,7009-81-6,90-83-5,6912-63-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 25 ℃;

DOI:10.1016/S0040-4039(97)00721-1

Reference yield: 79.0%

(+/-)-erythro-methoxyephedrine (2226-33-7,46288-71-5,79297-94-2,79297-97-5,82950-54-7,133161-06-5) → methanol (67-56-1) + ephedrine (90-81-3,90-82-4,299-42-3,321-97-1,321-98-2,4125-58-0,34783-90-9,38732-95-5,53214-57-6,7009-81-6,90-83-5,6912-63-6) + benzaldehyde (100-52-7) + acetaldehyde (75-07-0,9002-91-9) + dimethyl amine (124-40-3) + methylamine (74-89-5)

Guidance literature:

With water; at 25 ℃; Product distribution; Mechanism; anodic oxidation, carbonate buffer, pH 10; effect of substituents investigated with different types of β-alkanolamines;

upstream raw materials:

D-tartaric acid

rac-pseudoephedrine

(1S,2R)-(+)-ephedrine

(4R,5R)-4-methyl-5-phenyl-1,3-oxazolidin-2-one

Downstream raw materials:

3,4r-dimethyl-5t-phenyl-oxazolidin-2-ylideneamine

(1R,2R)-pseudoephedrine

pseudoephedrine

(+/-)-2ξ-heptyl-3,4r-dimethyl-5t-phenyl-oxazolidine

Refernces

• 1、 Ottenbacher, Roman V.,Talsi, Evgenii P.,Bryliakov, Konstantin P.. "Chiral Manganese Aminopyridine Complexes: the Versatile Catalysts of Chemo- and Stereoselective Oxidations with H2O2". . p. 78 - 90. Retrieved 2017/10/06.
• 2、 Schulze, Matthias. "Synthesis of 2-Arylethylamines by the Curtius Rearrangement". experimental part. p. 1461 - 1476. Retrieved 2010/07/08.