261930-06-7

Basic information

• Product Name: 1-(4-Methoxyphenyl)-2-methylpropane-1,2-diol.
• Synonyms: 1-(4-Methoxyphenyl)-2-methylpropane-1,2-diol.;1,2-Propanediol, 1-(4-methoxyphenyl)-2-methyl-
• CAS NO: 261930-06-7
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.24
• Product Categories: Aryl;Catalysts-Ligands
• Mol File: 261930-06-7.mol

Chemical Properties

• Boiling Point: 345.5±32.0 °C(Predicted)
• Appearance: /
• Density: 1.120±0.06 g/cm3(Predicted)
• PKA: 14.22±0.20(Predicted)
• CAS DataBase Reference: 1-(4-Methoxyphenyl)-2-methylpropane-1,2-diol.(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Methoxyphenyl)-2-methylpropane-1,2-diol.(261930-06-7)
• EPA Substance Registry System: 1-(4-Methoxyphenyl)-2-methylpropane-1,2-diol.(261930-06-7)

Safety Data

• Hazardous Substances Data: 261930-06-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-Methoxyphenyl)-2-methylpropane-1,2-diol, or guaifenesin, is used as an expectorant medication for treating coughs and chest congestion caused by respiratory illnesses such as the common cold and bronchitis. It works by thinning and loosening mucus in the airways, making it easier to cough up.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 877-99-6 1-methoxy-4-(2-methyl-1-propenyl)benzene 
• 121-98-2 methyl 4-methoxybenzoate 
• 67-63-0 isopropyl alcohol 
• 261929-95-7 β,β-dimethyl-4-methoxystyrene oxide 
• 917-64-6 methyl magnesium iodide 
• 36141-66-9 ethyl 2-hydroxy-2-(4-methoxyphenyl)acetate 

Downstream Products

• 15482-17-4 2-hydroxy-1-(4-methoxyphenyl)-2-methyl-1-propanone 
• 7074-12-6 3-(4-methoxyphenyl)butan-2-one 

Relevant articles and documents

Electrically addressable cell immobilization using phenylboronic acid diazonium salts

(Chemical Equation Presented) Holding cells: Individual gold electrodes can be activated by phenylboronic acid diazonium salts for the facile and reversible immobilization of eukaryotic cells (see scheme). This platform provides a simple method for on-demand release of captured cells (yeast and macrophage) and can be used in single-cell or array-based studies.

A novel redox-sensitive protecting group for boronic acids, MPMP-diol

A new boronic acid protecting group, 1-(4-methoxyphenyl)-2-methylpropane-1, 2-diol (MPMP-diol), has been developed. Both protection and deprotection can be accomplished under mild conditions with quantitative conversions. The deprotection can be carried out using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

Unusual head-to-tail coupling of alkyl benzoates by electroreduction

The electroreduction of alkyl benzoates in an alcoholic solvent gave unusual head-to-tail coupled products. Usual head-to-head coupled products derived from acyloin condensation could not be detected. The best result (73% yield) was obtained from methyl benzoate using an undivided cell with an Sn cathode in i-PrOH containing tetraalkylammonium salt as a supporting electrolyte. Using an undivided cell, the products cross-coupled with a solvent molecule were obtained as byproducts. The substitution at the para position of methyl benzoate considerably decreased the yields of the head-to-tail coupled products and increased those of the cross-coupled products. The possible mechanism of the head-to-tail coupling is the attack of anion radical, generated from methyl benzoate by one-electron transfer, to another methyl benzoate. The cross-coupled products were formed by the reaction with carbonyl compound anodically produced from a solvent molecule. The cross-coupling between methyl benzoate and aromatic aldehydes was also effected by the mixed electroreduction under the same conditions.

Spontaneous Hydrolysis Reactions of cis- and trans-β-Methyl-4-methoxystyrene Oxides (Anethole Oxides): Buildup of frans-Anethole Oxide as an Intermediate in the Spontaneous Reaction of cis-Anethole Oxide

Rates and products of the reactions of trans- and cis-β-methyl-4-methoxystyrene oxides (1 and 2) (anethole oxides) and β,β-dimethyl-4-methoxystyrene oxide (3) in water solutions in the pH range 4-12 have been determined. In the pH range ca. 8-12, each of these epoxides reacts by a spontaneous reaction. The spontaneous reaction of trans-anethole oxide (1) yields ca. 40% of (4-methoxyphenyl)acetone and 60% of 1-(4-methoxyphenyl)-1,2-propanediols (erythro:threo ratio ca. 3:1). The spontaneous reaction of cis-anethole oxide is more complicated. The yields of diol and ketone products vary with pH in the pH range 8-11, even though there is not a corresponding change in rate. These results are interpreted by a mechanism in which 2 undergoes isomerization in part to the more reactive trans-anethole oxide (1), which subsequently reacts by acid-catalyzed and/or spontaneous reactions, depending on the pH, to yield diol and ketone products. The buildup of the intermediate trans-anethole oxide in the spontaneous reaction of cis-anethole oxide was detected by 1H NMR analysis of the reaction mixture. Other primary products of the spontaneous reaction of 2 are (4-methoxyphenyl)acetone (73%) and theo-1-(4-methoxyphenyl)-1,2-propanediol (ca. 3%). The rates and products of the spontaneous reaction of 2 and its β-deuterium-labeled derivative were determined, and the lack of significant kinetic and partitioning deuterium isotope effects indicates that the isomerization of 2 to ketone and to trans-anethole oxide must occur primarily by nonintersecting reaction pathways.