73494-49-2

Basic information

• Product Name: (R)-alpha-methylbenzenebutanol
• Synonyms: (R)-alpha-methylbenzenebutanol;(R)-α-Methylbenzene-1-butanol;(R)-5-phenylpentan-2-ol
• CAS NO: 73494-49-2
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.24414
• EINECS: 277-482-6
• Mol File: 73494-49-2.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-alpha-methylbenzenebutanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-alpha-methylbenzenebutanol(73494-49-2)
• EPA Substance Registry System: (R)-alpha-methylbenzenebutanol(73494-49-2)

Safety Data

• Hazardous Substances Data: 73494-49-2(Hazardous Substances Data)

Usage

General Description

(R)-alpha-Methylbenzenebutanol, also known as 2-Methyl-1-phenyl-1-propanol, is a chiral alcohol compound with the chemical formula C10H14O. It is commonly used in the synthesis of pharmaceuticals and fragrances due to its unique chemical structure and stereochemistry. (R)-alpha-Methylbenzenebutanol exhibits a slight floral aroma and is often used as a fragrance in cosmetics and personal care products. Additionally, it has been studied for its potential therapeutic properties, including its ability to act as a chiral auxiliary in asymmetric synthesis reactions. Despite its potential applications, (R)-alpha-Methylbenzenebutanol is considered to be a low-toxicity compound and generally safe for use in various consumer products.

Upstream product

• 2344-71-0 5-phenylpentan-2-ol 
• 927385-39-5 (S)-5-phenylpent-4-yn-2-ol 
• 66820-55-1 (E)-5-phenylpent-4-ene-2,3-diol 
• 2235-83-8 5-phenyl-2-pentanone 
• 538-68-1 pentylbenzene 
• 1075-74-7 5-phenylpent-1-ene 
• 611-71-2 MANDELIC ACID 
• 67470-74-0 (2S,3R,E)-5-phenylpent-4-ene-2,3-diol 
• 14371-10-9 (E)-3-phenylpropenal 
• 73444-35-6 (2S,3R)-5-Phenylpentane-2,3-diol 
• 98-59-9 p-toluenesulfonyl chloride 
• 87118-98-7 4S-Benzyloxy-1-phenyl-1-pentanone 
• 108-05-4 vinyl acetate 
• 2344-70-9 1-phenyl-3-butanol 

Downstream Products

• 1429484-72-9 (S)-5-hydroxy-2-methyl-7-[(R)-5-phenyl-2-pentyloxy]-2,3-dihydroquinolin-4(1H)-one 
• 1429484-73-0 (2S)-1-formyl-5-hydroxy-2-methyl-4-oxo-3-(3-oxobutyl)-7-[(R)-5-phenyl-2-pentyloxy]-2,3-dihydroquinoline 
• 78513-72-1 (6S,6aR)-5,6,6a,7-tetrahydro-1-hydroxy-6-methyl-3-[(R)-5-phenyl-2-pentyloxy]benzo[c]quinoline-9(8H)-one 
• 1429484-74-1 (6S,6aR,10aR)-5,6,6a,7,10,10a-hexahydro-1-acetoxy-6-methyl-3-[(R)-5-phenyl-2-pentyloxy]benzo[c]quinoline-9(8H)-one 
• 77209-75-7 (6S,6aR,9R,10aR)-5,6,6a,7,8,9,10,10a-octahydro-1-acetoxy-9-hydroxy-6-methyl-3-[(R)-5-phenyl-2-pentyloxy]benzo[c]quinoline hydrochloride 
• 1429391-71-8 1-(4-chloropentyl)benzene 
• 63790-07-8 1-methyl-4-phenylbutyl methanesulphonate 
• 158514-49-9 (R)-(+)-4-[4-methoxy-3-(5-phenylpent-2-yloxy)phenyl]benzoic acid 
• 158514-50-2 (S)-(-)-4-[4-methoxy-3-(5-phenylpent-2-yloxy)phenyl]benzoic acid 

Relevant articles and documents

The biogenic amine transporter activity of vinylogous amphetamine analogs

A series of vinylogous amphetamine analogs was synthesized and examined for their activity at biogenic amine transporters and serotonin-2 receptor (5-HT2) subtypes. (1S,3E)-1-Methyl-4-phenyl-but-3-enylamine (S-6) is a potent dual dopamine/serotonin (DA/5-HT) releaser with no activity at 5-HT2 receptors. This unique profile of actions suggests that analog S-6 is a viable lead compound for identifying new structural classes of DA/5-HT releasers with therapeutic benefit and reduced abuse liability.

Enantio- and diastereoselective synthesis of 1,2-hydroxyboronates through Cu-Catalyzed additions of alkylboronates to aldehydes

The first catalytic enantio- and diastereoselective synthesis of 1,2-hydroxyboronates is reported. Reactions are promoted by a readily available chiral monodentate phosphoramidite-copper complex in the presence of an alkyl 1,1-diboron reagent. Products contain two contiguous stereogenic centers and are obtained in up to 91% yield, >98:2 d.r., and 98:2 e.r. The reaction is tolerant of aryl and vinyl aldehydes, and the 1,2-hydroxyboronate products can be transformed into versatile derivatives. Mechanistic experiments indicate control of absolute stereochemistry of the α-boryl component.

Copper(I)-catalyzed boryl substitution of unactivated alkyl halides

Borylation of alkyl halides with diboron proceeded in the presence of a copper(I)/Xantphos catalyst and a stoichiometric amount of K(O-t-Bu) base. The boryl substitution proceeded with normal and secondary alkyl chlorides, bromides, and iodides, but alkyl sulfonates did not react. Menthyl halides afforded the corresponding borylation product with excellent diastereoselectivity, whereas (R)-2-bromo-5-phenylpentane gave a racemic product. Reaction with cyclopropylmethyl bromide resulted in ring-opening products, suggesting the reaction involves a radical pathway.