552-79-4

Basic information

• Product Name: (-)-N-METHYLEPHEDRINE
• Synonyms: METHYLEPHEDRINE, (-)-1R,2S-;METHYLEPHEDRINE, (-)-1R,2S N-;L-N-METHYLEPHEDRINE;(-)-ALPHA-[1-(DIMETHYLAMINO)ETHYL]BENZENEMETHANOL;(-)-1R,2S N-METHYLEPHEDRINE;(1R,2S)-(-)-N-METHYLEPHEDRINE;(-)-1R,2S-METHYLEPHEDRINE;(-)-(1R,2S)-2-DIMETHYLAMINO-1-PHENYL-1-PROPANOL
• CAS NO: 552-79-4
• Molecular Formula: C₁₁H₁₇NO
• Molecular Weight: 179.26
• EINECS: 209-022-7
• Product Categories: Pharmaceutical Raw Materials
• Mol File: 552-79-4.mol
• Article Data: 30

Chemical Properties

• Melting Point: 86-88 °C(lit.)
• Boiling Point: 311.8°C (rough estimate)
• Flash Point: 9℃
• Appearance: White crystals or adhering crystalline powder
• Density: 1.0020 (rough estimate)
• Vapor Pressure: 0.0108mmHg at 25°C
• Refractive Index: 1.5065 (estimate)
• Storage Temp.: Refrigerator (+4°C)
• PKA: pKa 9.257(H2O,t =25,I=0.00) (Uncertain)
• Sensitive: Moisture Sensitive
• Merck: 14,6068
• CAS DataBase Reference: (-)-N-METHYLEPHEDRINE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-N-METHYLEPHEDRINE(552-79-4)
• EPA Substance Registry System: (-)-N-METHYLEPHEDRINE(552-79-4)

Safety Data

• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-36-45-36/37-16-7
• RIDADR: 1544
• WGK Germany: 3
• F: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 552-79-4(Hazardous Substances Data)

Usage

Description

The Chinese plant 'Ma-Huang' contains this alkaloid, first isolated by Smith. According to Read, the name 'Ma-Huang' is the name for various Ephedra species but the material principally used in China is E. sinica Stapf. (Syn. E. j7ava Porter Smith, E. Mahuang Liu). It has subsequently been discovered in European species, notably E. helvetica C. A. Meyer and E. distachya Linn. The alkaloid crystallizes in stout, colourless needles and has [α]D - 29.2° (MeOH). It yields several crystalline salts and derivatives: hydrochloride, m.p. 188-9°C; [α]20D - 29.8° (H20); oxalate, m.p. 187°C; aurichloride, m.p. 128-9°C; picrate, m.p. 144°C and the methiodide, m.p. 212-3°C; [α]D - 21.8° (H20).

Chemical Properties

White crystals or adhering crystalline powder

Uses

Different sources of media describe the Uses of 552-79-4 differently. You can refer to the following data:
1. adrenergic agonist, analeptic
2. Used in conjunction with LiAlH4 for chiral reductions

References

Smith., J. Chern. Soc., 2056 (1927) Smith., ibid, 51 (1928) Smith., ibid, 2755 (1929) Wolfes., Arch. Pharrn., 268,327 (1930) Preparation: Nagai., J. Pharrn. Soc., Japan, No. 120, 109 (1892) Nagai, Kanao., ibid, 48, 145 (1928)

InChI:InChI=1/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/p+1/t9-,11+/m0/s1

Upstream product

• 492-41-1 (1R,2S)-norephedrine 
• 541-41-3 chloroformic acid ethyl ester 
• 50-00-0 formaldehyd 
• 50-98-6 ephedrine hydrochloride 
• 124-38-9 carbon dioxide 
• 299-42-3 ephedrine 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 
• 6084-17-9 2-chloro-1-phenylpropan-1-one 
• 130459-53-9 (1R,2S)-2-(tert-butoxycarbonyl(methyl)amino)-1-phenyl-1-propanol 
• 90-82-4 pseudoephedrine 
• 74-88-4 methyl iodide 
• 16251-47-1 (4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one 
• 66574-19-4 (4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidine 
• 35026-77-8 (S)-2-(dimethylamino)propiophenone 

Downstream Products

• 129216-60-0 lithium N-methylpseudoephedrate 
• 139528-46-4 (1R,2S)-α-<1-(dimethylamino)ethyl>-N-butylbenzylamine 
• 60999-91-9 (-)-(1R,2S)-N-hexadecyl-N,N-dimethylephedrinium bromide 
• 479253-11-7 (1'R,2'S)-2-(2'-dimethylamino-1'-phenyl-propoxy)dinaphtho[2,1-d:1',2'-f](1,3,2) dioxaphosphepine 
• 445298-98-6 (S,S)-N-methylpseudoephedrine α-bromo-α-ethylacetate 
• 445298-99-7 (S,S)-N-methylpseudoephedrine α-bromo-α-n-butylacetate 
• 1017295-11-2 (R(p))-1,2-ferrocenediyl(BMe(OMe))(SnMe₂Cl) 

Relevant articles and documents

Asymmetric Sulfinylations of N-Methylephedrine-Modified Tri- or Tetraalkyl Zincates by Symmetric Diaryl Sulfoxides

Diethylzinc was treated with 1 or 2 equiv. of AlkMgCl or PhMgBr (preferably) or with 1 equiv. of nBuLi (less efficiently) for forming species – plausibly zincates – which were sulfinylated by diaryl sulfoxides to give racemic alkyl aryl sulfoxides in yields reaching 100 %. Dialkylzinc reagents were also activated by treatments with 1 or 2 equiv. of an enantiomerically pure alkylmagnesium β-aminoalkoxide. This worked best when the alkoxide stemmed from a dialkylmagnesium reagent and an equimolar amount of N-methyl-(–)-ephedrine. This second activation mode allowed sulfinylations of what was originally the dialkylzinc reagent with diaryl sulfoxides. This generated alkyl aryl sulfoxides with enantiomeric ratios up to 93:7 in up to 100 % yield.

Efficient ruthenium-catalyzed N-methylation of amines using methanol

An in situ-generated complex from [RuCpCl2]2 and dpePhos ligand is reported as an efficient catalyst in the presence of 5 mol % of LiOtBu for the N-methylation of amines using methanol as the methylating agent at moderate conditions, following hydrogen borrowing strategy. This simple catalyst system provides selective N-monomethylation of substituted primary anilines and sulfonamides as well as N,N dimethylation of primary aliphatic amines in excellent yields at 40-100 °C with good tolerance to reducible functional groups. The catalytic intermediate CpRu(dpePhos)H was isolated and was shown to be active for methylation in the absence of base.

Ephedrine-based diselenide: A promiscuous catalyst suitable to mimic the enzyme glutathione peroxidase (GPx) and to promote enantioselective C-C coupling reactions

The ephedrine-based diselenide appears as a new promiscuous catalyst, able to generate optically active alcohols by addition of organozinc to aldehydes (up to 97% ee), and shows powerful GPx like activity, reducing H2O 2 to water in only 16.33 min (eleven times faster than PhSeSePh).