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

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

Uses

Used in Pharmaceutical Industry:
(4S,5S)-(-)-2-METHYL-5-PHENYL-2-OXAZOLINE-4-METHANOL is used as a chiral resolving agent for the separation of racemic mixtures, ensuring the production of enantiomerically pure compounds which is essential for the efficacy and safety of pharmaceuticals, as different enantiomers can have distinct biological activities.
Used in Agrochemical Industry:
In the agrochemical industry, (4S,5S)-(-)-2-METHYL-5-PHENYL-2-OXAZOLINE-4-METHANOL is utilized as a chiral auxiliary in asymmetric synthesis, contributing to the creation of enantiomerically pure agrochemicals that can target specific pests while minimizing environmental impact and off-target effects.
Used in Asymmetric Synthesis:
(4S,5S)-(-)-2-METHYL-5-PHENYL-2-OXAZOLINE-4-METHANOL is employed as a chiral auxiliary in asymmetric synthesis, aiding in the production of chiral molecules with a single enantiomeric form, which is vital for the development of drugs and other chiral compounds with desired biological activities.
Used in Asymmetric Catalysis:
As a ligand in asymmetric catalysis, (4S,5S)-(-)-2-METHYL-5-PHENYL-2-OXAZOLINE-4-METHANOL is instrumental in catalytic reactions that produce chiral products with high enantioselectivity, a critical factor in the synthesis of biologically active 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

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

Downstream Products

• 52075-14-6 (4S,5S)-(-)-4,5-dihydro-4-methoxymethyl-2-methyl-5-phenyloxazole 
• 175477-34-6 (4S,5S)-2-Methyl-4-(trisisopropylsilyloxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazole 
• 892865-26-8 [(4S,5S)-(2-methyl-5-phenyl-2-oxazolin-4-yl)methoxy]bis(1-pyrrolyl)phosphinite 
• 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 

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.

Diastereoselective conversion of sulfides into sulfoxides. 1,5- and 1,6-asymmetric induction

The diastereoselective oxidation of sulfides into sulfoxides has been achieved with enantiomerically pure dihydrooxazole auxiliaries. When an additional hydroxymethyl substituent is present, diastereocontrol is very high and 1,5-asymmetric induction has been achieved with up to 96:4 selectivity, and 1,6-asymmetric induction has been achieved with up to 97:3 selectivity in the absence of any additional chiral agents.

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.