113522-45-5

Basic information

• Product Name: 2-Butanol, 4-(triphenylmethoxy)-, (R)-
• CAS NO: 113522-45-5
• Molecular Formula: C23H24O2
• Molecular Weight: 332.442
• Mol File: 113522-45-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Butanol, 4-(triphenylmethoxy)-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butanol, 4-(triphenylmethoxy)-, (R)-(113522-45-5)
• EPA Substance Registry System: 2-Butanol, 4-(triphenylmethoxy)-, (R)-(113522-45-5)

Safety Data

• Hazardous Substances Data: 113522-45-5(Hazardous Substances Data)

Upstream product

• 108-22-5 Isopropenyl acetate 
• 7386-50-7 4-((triphenylmethyl)oxy)butan-2-ol 
• 6290-03-5 (R)-butane-1,3-diol 
• 76-83-5 trityl chloride 

Downstream Products

• 116838-26-7 (R)-3-O-benzyl-1-O-trityl-1,3-butanediol 
• 113522-46-6 (R)-3(2-methyl-2-propenyloxy)-1-trityloxybutane 

Relevant articles and documents

Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB

The hydrolytic dehalogenation of rac-1,3-dibromobutane catalyzed by the haloalkane dehalogenase LinB from Sphingobium japonicum UT26 proceeds in a sequential fashion: initial formation of intermediate haloalcohols followed by a second hydrolytic step to produce the final diol. Detailed investigation of the course of the reaction revealed favored nucleophilic displacement of the sec-halogen in the first hydrolytic event with pronounced R enantioselectivity. The second hydrolysis step proceeded with a regioselectivity switch at the primary position, with preference for the S enantiomer. Because of complex competition between all eight possible reactions, intermediate haloalcohols formed with moderate to good ee ((S)-4-bromobutan-2-ol: up to 87 %). Similarly, (S)-butane-1,3-diol was formed at a maximum ee of 35 % before full hydrolysis furnished the racemic diol product.

Aminocyclopentadienyl Ruthenium Complexes as Racemization Catalysts for Dynamic Kinetic Resolution of Secondary Alcohols at Ambient Temperature

Aminocyclopentadienyl ruthenium complexes, which can be used as room-temperature racemization catalysts with lipases in the dynamic kinetic resolution (DKR) of secondary alcohols, were synthesized from cyclopenta-2,4-dienimines, Ru3(CO)12, and CHCl 3: [2,3,4,5-Ph4(η5-C 4CNHR)]Ru-(CO)2Cl (4: R = i-Pr; 5: R = n-Pr; 6: R = t-Bu), [2,5-Me2-3,4-Ph2(η5-C 4CNHR)]Ru(CO)2Cl (7: R = i-Pr; 8: R = Ph), and [2,3,4,5-Ph4(η5-C4CNHAr)]Ru(CO) 2Cl (9: Ar =p-NO2C6H4; 10: Ar = p-ClC6H4; 11: Ar = Ph; 12: Ar = p-OMeC6H 4; 13: Ar = p-NMe2C6H4). The tests in the racemization of (S)-4-phenyl-2-butanol showed that 7 is the most active catalyst, although the difference decreased in the DKR. Complex 4 was used in the DKR of various alcohols; at room temperature, not only simple alcohols but also functionalized ones such as allylic alcohols, alkynyl alcohols, diols, hydroxyl esters, and chlorohydrins were successfully transformed to chiral acetates. In mechanistic studies for the catalytic racemization, ruthenium hydride 14 appeared to be a key species. It was the major organometallic species in the racemization of (S)-1-phenylethanol with 4 and potassium tert-butoxide. In a separate experiment, (S)-1-phenylethanol was racemized catalytically by 14 in the presence of acetophenone.

A NEW SYNTHESIS OF BOTH THE ENANTIOMERS OF GRANDISOL, THE BOLL WEEVIL PHEROMONE

The pure enantiomers of grandisol (2-isopropenyl-1-methylcyclobutane-ethanol), the pheromone component of Anthonomus grandis Boheman, were synthesized employing ethyl (R)-3-hydroxybutanoate as the single chiral source.