98243-47-1

Basic information

• Product Name: threo-(1-⁽²⁾H)-1-phenyl-2-dimethylaminopropane
• CAS NO: 98243-47-1
• Molecular Weight: 164.255
• Mol File: 98243-47-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: threo-(1-⁽²⁾H)-1-phenyl-2-dimethylaminopropane(CAS DataBase Reference)
• NIST Chemistry Reference: threo-(1-⁽²⁾H)-1-phenyl-2-dimethylaminopropane(98243-47-1)
• EPA Substance Registry System: threo-(1-⁽²⁾H)-1-phenyl-2-dimethylaminopropane(98243-47-1)

Safety Data

• Hazardous Substances Data: 98243-47-1(Hazardous Substances Data)

Upstream product

• 51-64-9 dexamfetamine 
• 23355-97-7 1-phenylpropylene oxide 
• 80150-96-5 C₁₆H₁₇⁽²⁾HO₃S 
• 58407-67-3 erythro-(1-(2H))-1-phenyl-2-propanol 
• 80150-91-0 C₁₂H₁₉⁽²⁾HN⁽¹⁺⁾*Cl^(1-) 
• 50-00-0 formaldehyd 
• 66432-33-5 threo-(1-⁽²⁾H)-1-phenyl-2-aminopropane 
• 873-66-5 1-propenylbenzene 
• 17279-39-9 (S)-N,N-dimethyl-α-benzylethylamine 

Downstream Products

• 80150-91-0 C₁₂H₁₉⁽²⁾HN⁽¹⁺⁾*Cl^(1-) 

Relevant articles and documents

THE HIGHLY STEREOSELECTIVE CONVERSION OF N,N-DIMETHYLAMPHETAMINE INTO N-METHYLPSEUDOEPHEDRINE; A MIMIC OF THE ENZYME MEDIATED STEREOSPECIFIC BENZYLIC HYDROXYLATION OF 2-ARYLETHYLAMINES

Treatment of (S)-(η6-N,N-dimethylamphetamine)Cr(CO)3, with n-butyllithium below -40 deg C gives a stable benzylic carbanion via loss of the pro-R-benzylic proton.Warming of this anion above -40 deg C gives (η6-E-β-methylstyrene)Cr(CO), via an ElcB type elimination wilhst trapping with an electrophile below -40 deg C gives benzylically functionalised amphetamines with overall retention of configuration.The use of oxodiperoxymolybdenum(pyridine)hexamtehylphosphoramide as the electrophile gives optically pure (1S,2S)-N-methylpseudoephedrine after decomplexation.

THE EFFECT OF PHENYL SUBSTITUENTS ON ELIMINATION STEREOCHEMISTRY: A MECHANISTIC MANIFOLD IN ALKOXIDE PROMOTED DECOMPOSITION OF 1-PHENYL-1-PROPYLTRIMETHYLAMMONIUM ION

Reactions of the positionally isomeric 1-phenyl-1-propyl (I) and 1-phenyl-2-propyltrimethylammonium (II) ions with CH3OK - CH3OH, t-C4H9OK - t-C4H9OH and t-C4H9OK - C6H6 systems have been investigated with aid of the deuterated analogues erythro-2-D-I, threo-2-D-I, 1-D-I and threo-1-D-II.At least five mechanistic components (anti-β-elimination, syn-β-elimination, α',β-elimination, Sommelet-Hauser rearrangement and SN2 substitution) have been found to participate in the reaction of the quaternary compound I, in proportions varying greatly with base-solvent combination.The corresponding reactions of the isomeric compound II proceeded in a more simple manner, withount the intervention of ylide pathways in the olefin as well as in the amine formation.The stereochemistry of β-elimination determined for the two phenyl-substituted 'onium compounds has been compared with that reported previously for structurally related aliphatic analogues.The "anomalously" low propensity for syn-elimination as well as the "anomalously" high values of trans/cis-olefin rations in anti-elimination stigmatizing the presence of phenyl substituents are proposed to originate from a lack of base-approach hindrance in the reaction.