22644-28-6

Basic information

• Product Name: (R)-2-Methyl-1,4-butanediol
• Synonyms: (R)-(+)-2-METHYL-1,4-BUTANEDIOL;(R)-2-METHYL-1,4-BUTANEDIOL;(R)-2-methylbutane-1,4-diol;(R)-(+)-2-METHYL-1,4-BUTANEDIOL 98+%;2R-Methylbutan-1-ol;(2R)-2-Methylbutane-1,4-diol
• CAS NO: 22644-28-6
• Molecular Formula: C₅H₁₂O₂
• Molecular Weight: 104.15
• Product Categories: Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Chiral Building Blocks;Organic Building Blocks;Polyols
• Mol File: 22644-28-6.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 127 °C / 14mmHg
• Flash Point: 146 °C
• Appearance: /
• Density: 0.992 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.039mmHg at 25°C
• Refractive Index: n20/D 1.449
• PKA: 14.91±0.10(Predicted)
• CAS DataBase Reference: (R)-2-Methyl-1,4-butanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Methyl-1,4-butanediol(22644-28-6)
• EPA Substance Registry System: (R)-2-Methyl-1,4-butanediol(22644-28-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 22644-28-6(Hazardous Substances Data)

Usage

General Description

(R)-2-Methyl-1,4-butanediol, also known as (R)-2-Methyl-1,4-butylene glycol, is a chemical compound with the molecular formula C5H12O2. It is a colorless liquid with a faint, sweet odor. This chemical is commonly used as a solvent, as well as in the production of various chemical compounds such as pharmaceuticals, plasticizers, and agrochemicals. It is also used in the synthesis of organic compounds and as a precursor in the manufacture of polymers. Additionally, (R)-2-Methyl-1,4-butanediol has potential applications in the pharmaceutical and cosmetic industries due to its ability to act as a chiral building block for the synthesis of various drugs and cosmetics. Overall, this chemical compound has a variety of industrial and commercial uses due to its versatile properties.

InChI:InChI=1/C5H12O2/c1-5(4-7)2-3-6/h5-7H,2-4H2,1H3/t5-/m1/s1

Upstream product

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Downstream Products

• 120329-64-8 (R)-2-methylbutane-1,4-diol dibenzoate 
• 281214-26-4 (R)-2-methylbutane-1,4-diyl bis(4-methylbenzenesulfonate) 
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• 126616-47-5 (R)-(-)-4-tert-butyldiphenylsilyloxy-1-methylbutanal 
• 213740-06-8 (3Z,5R)-(-)-7-tert-butyldiphenylsilyloxy-3-hydroxymethyl-5-methylhept-3-ene 
• 213740-17-1 (3Z,5R)-(+)-3-bromomethyl-7-tert-butyldiphenylsilyloxy-5-methylhept-3-ene 
• 410523-53-4 (2'R,6'R,1E,3Z,5R)-(+)-7-tert-butyldiphenylsilyloxy-1-(5',6'-dihydro-2'H-2'-isopropoxypyran-6'-yl)-3-ethyl-5-methylhepta-1,3-diene 
• 1276031-85-6 C₄₁H₄₄O₆ 
• 620627-27-2 (S)-2-((R)-3-methylpyrrolidin-1-yl)propan-1-ol 
• 1352547-07-9 (R)-1-((S)-1-(4-(6-methoxy-2-(4-methoxyphenyl)-1H-inden-3-yl)phenoxy)propan-2-yl)-3-methylpyrrolidine 
• 1352547-08-0 (3R)-1-((2S)-1-(4-(5-methoxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-yl)phenoxy)propan-2-yl)-3-methylpyrrolidine 
• 1352546-95-2 2-(4-hydroxyphenyl)-1-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2,3-dihydro-1H-inden-5-ol 
• 1352547-09-1 2,3-bis(3-methoxyphenyl)-1-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)propan-1-one 
• 1352547-10-4 (R)-1-((S)-1-(4-(6-methoxy-2-(3-methoxyphenyl)-1H-inden-3-yl)phenoxy)propan-2-yl)-3-methylpyrrolidine 

Relevant articles and documents

Synthesis and complete structure determination of a sperm-activating and -attracting factor isolated from the ascidian ascidia sydneiensis

For the complete structure elucidation of an endogenous sperm-activating and -attracting factor isolated from eggs of the ascidian Ascidia sydneiensis (Assydn-SAAF), its two possible diastereomers with respect to C-25 were synthesized. Starting from ergosterol, the characteristic steroid backbone was constructed by using an intramolecular pinacol coupling reaction and stereoselective reduction of a hydroxy ketone as key steps, and the side chain was introduced by Julia-Kocienski olefination. Comparison of the NMR data of the two diastereomers with those of the natural product led to the elucidation of the absolute configuration as 25S; thus the complete structure was determined and the first synthesis of Assydn-SAAF was achieved.

Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (?)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.

Facile synthesis of versatile enantioenriched α-substituted hydroxy esters through a Bronsted acid catalyzed kinetic resolution

An efficient synthesis of enantioenriched α-substituted γ-hydroxy esters via a kinetic resolution event is described. Bulky racemic esters in the presence of a chiral Bronsted acid selectively lactonize to yield a recoverable enantioenriched hydroxy ester and lactone. These esters are highly versatile building blocks that can readily be converted to synthetically useful materials.