53732-41-5

Basic information

• Product Name: (4S,5S)-(-)-2-METHYL-5-PHENYL-2-OXAZOLINE-4-METHANOL
• Synonyms: 4-HYDROXYMETHYL-2-METHYL-5-PHENYL-2-OXAZOLINE;(4S,5S)-(-)-4-HYDROXYMETHYL-2-METHYL-5-PHENYL-2-OXAZOLINE;(4S,5S)-(-)-2-METHYL-5-PHENYL-2-OXAZOLINE-4-METHANOL;(4S,5S)-(-)-4-Hydroxymethyl-2-methyl-5-phenyl-2-oxazoline = (4S,5S)-(-)-2-Methyl-5-phenyl-2-oxazol;4-Oxazolemethanol, 4,5-dihydro-2-methyl-5-phenyl-, (4S,5S)-;(4s,5s)-(-)-4-hydroxymethyl-2-methyl-5-phenyloxazoline;(4S)-2-Methyl-4β-(hydroxymethyl)-5α-phenyl-2-oxazoline;(4S)-2-Methyl-5α-phenyl-2-oxazoline-4β-methanol
• CAS NO: 53732-41-5
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.23
• EINECS: 258-730-2
• Mol File: 53732-41-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 61-65 °C(lit.)
• Boiling Point: 322.2°Cat760mmHg
• Flash Point: 148.7°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 0.000117mmHg at 25°C
• Refractive Index: 1.578
• BRN: 1212843
• CAS DataBase Reference: (4S,5S)-(-)-2-METHYL-5-PHENYL-2-OXAZOLINE-4-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-(-)-2-METHYL-5-PHENYL-2-OXAZOLINE-4-METHANOL(53732-41-5)
• EPA Substance Registry System: (4S,5S)-(-)-2-METHYL-5-PHENYL-2-OXAZOLINE-4-METHANOL(53732-41-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 53732-41-5(Hazardous Substances Data)

Usage

General Description

(4S,5S)-(-)-2-Methyl-5-phenyl-2-oxazoline-4-methanol is a chiral compound with a stereocenter at the 4th and 5th carbon atoms. It is a crystalline solid that is commonly used as a chiral resolving agent in the separation of racemic mixtures. (4S,5S)-(-)-2-METHYL-5-PHENYL-2-OXAZOLINE-4-METHANOL is also used as a chiral auxiliary in asymmetric synthesis and as a ligand in asymmetric catalysis. Its chiral nature and ability to form diastereomers make it an important tool in the synthesis of various chiral molecules. The compound has potential applications in the pharmaceutical and agrochemical industries, particularly in the production of enantiomerically pure compounds.

InChI:InChI=1/C11H13NO2/c1-8-12-10(7-13)11(14-8)9-5-3-2-4-6-9/h2-6,10-11,13H,7H2,1H3/t10-,11+/m1/s1

Upstream product

• 926-67-0 O-Ethyl thioacetate 
• 3306-06-7 (+/-)-threo-2-amino-1-phenyl-1,3-propanediol 
• 3313-19-7 (1RS,2RS)-2-acetylamino-1-phenyl-propane-1,3-diol 
• 3313-19-7 (1RS,2SR)-2-acetylamino-1-phenyl-propane-1,3-diol 
• 3306-06-7 (1RS,2SR)-2-amino-1-phenyl-propane-1,3-diol 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 78-39-7 Triethyl orthoacetate 
• 14777-29-8 methyl acetimidate 
• 14777-27-6 methyl acetimidate hydrochloride 
• 2208-07-3 ethyl acetimidate hydrochloride 
• 74104-28-2 α-acetamido-β-hydroxypropiophenone 
• 15917-28-9 (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester 
• 106270-15-9 (+/-)-2-methyl-5t-phenyl-4,5-dihydro-oxazole-4r-carboxylic acid ethyl ester 
• 42267-16-3 (2S,3R)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester; hydrochloride 

Downstream Products

• 57403-86-8 4-methoxymethyl-5-phenyl-2-(2-phenyl-propyl)-4,5-dihydro-oxazole 
• 52230-95-2 4-methoxymethyl-2-(2-methyl-octyl)-5-phenyl-4,5-dihydro-oxazole 
• 59614-90-3 2-(2-ethyl-heptyl)-4-methoxymethyl-5-phenyl-4,5-dihydro-oxazole 
• 57403-87-9 2-(2-ethyl-hexyl)-4-methoxymethyl-5-phenyl-4,5-dihydro-oxazole 
• 57403-85-7 4-methoxymethyl-2-(2-methyl-hexyl)-5-phenyl-4,5-dihydro-oxazole 
• 59620-84-7 2-(2-ethyl-pentyl)-4-methoxymethyl-5-phenyl-4,5-dihydro-oxazole 
• 52230-94-1 4-methoxymethyl-2-(2-methyl-pentyl)-5-phenyl-4,5-dihydro-oxazole 
• 52230-93-0 4-methoxymethyl-2-(2-methyl-butyl)-5-phenyl-4,5-dihydro-oxazole 
• 5668-19-9 (2R)-2-Benzylhexanoic acid 
• 51594-34-4 (1S,2S)-2-amino-3-methoxy-1-phenyl-1-propanol 
• 58635-82-8 (S,S)-2-benzyl-4-methoxymethyl-5-phenyl-2-oxazoline 
• 51594-38-8 (4S)-4r-methoxymethyl-2-phenethyl-5t-phenyl-4,5-dihydro-oxazole 
• 73713-17-4 (4S,5S)-2-n-Pentyl-4-(methoxymethyl)-5-phenyl-2-oxazoline 
• 58635-80-6 (4S)-2-butyl-4r-methoxymethyl-5t-phenyl-4,5-dihydro-oxazole 

Relevant articles and documents

Effect of chain length on radical to carbanion cyclo-coupling of bromoaryl alkyl-linked oxazolines: 1,3-Areneotropic migration of oxazolines

(Chemical Equation Presented) 2-Halophenylalkyl-2-oxazolines with alkyl chain spacers of two to six C atoms (n = 0-4) were prepared and their S RN1-type reactions with several base systems examined. The best conditions to promote cyclocoupling to the corresponding benzocycloalkane derivatives involved use of LDA in THF. The precursors with 3-C-atom and 4-C-atom spacers gave good yields of 2-(1′-phenylindan-1′-yl)-2- oxazolines and 2-(1-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)-2-oxazoline, respectively. The major products from the precursor with a 5-C-atom spacer were derivatives of benzocycloheptane in which the oxazoline group had undergone a novel areneotropic migration from the end of the spacer to the benzo ring. The product from reaction of the corresponding 2-C-atom precursor was a 9-oxazolinophenanthrene derivative. EPR spectroscopy showed the intermediates of the LDA-promoted reactions to be radical anions of the product benzocycloalkanes. This supported an SRN1-type chain mechanism involving initial production of aryl radicals connected to azaenolate ions via the spacer groups. Intramolecular radical to carbanion coupling then generated ring-closed benzocycloalkane radical anions that transferred an electron to more precursor. Diastereoselective radical to carbanion cyclo-coupling reactions were carried out with 2-bromophenylpropyl precursors containing chiral 2-oxazolines. The diastereoselectivity achievable was modest, but the product diastereoisomeric Indane derivatives were easily separable by chromatography.

Enantiomerically pure oxazolines tethered to alcohols. Preparation and use in asymmetric catalysis

A series of enantiomerically pure oxazolines tethered to alcohols have been prepared. The use of these oxazolines has been demonstrated in the catalysed addition of diethylzine to aromatic aldehydes to afford the corresponding secondary alcohols with modest levels of asymmetric induction.