132437-90-2

Basic information

• Product Name: 4-BENZYLOXY-3-METHYLBUTYRIC ACID
• Synonyms: RARECHEM AH CK 0031;4-BENZYLOXY-3-METHYLBUTYRIC ACID;4-BENZYLOXY-3-METHYLBUTANOIC ACID
• CAS NO: 132437-90-2
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25
• Mol File: 132437-90-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 345.2°Cat760mmHg
• Flash Point: 130.2°C
• Appearance: /
• Density: 1.098g/cm³
• Vapor Pressure: 2.38E-05mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: 4-BENZYLOXY-3-METHYLBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXY-3-METHYLBUTYRIC ACID(132437-90-2)
• EPA Substance Registry System: 4-BENZYLOXY-3-METHYLBUTYRIC ACID(132437-90-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 132437-90-2(Hazardous Substances Data)

Usage

General Description

4-Benzyloxy-3-methylbutyric acid is a chemical compound with the molecular formula C14H18O3. It is a white crystalline solid that is commonly used in the pharmaceutical industry as a key intermediate in the synthesis of various drugs and pharmaceuticals. 4-BENZYLOXY-3-METHYLBUTYRIC ACID is known for its role as an important building block for the production of compounds such as atorvastatin and cerivastatin, which are both used to lower cholesterol levels in the body. Additionally, 4-Benzyloxy-3-methylbutyric acid has been studied for its potential anti-inflammatory and anti-cancer properties, making it a valuable compound for further research and development in the medical field.

InChI:InChI=1/C12H16O3/c1-10(7-12(13)14)8-15-9-11-5-3-2-4-6-11/h2-6,10H,7-9H2,1H3,(H,13,14)

Upstream product

• 64809-19-4 (RS)-4-(Benzyloxy)-3-methylbutanal 
• 1838-94-4 isoprene epoxide 
• 132437-89-9 (1E,3RS)-4-(Benzyloxy)-N,N-diethyl-3-methylbut-1-enylamine 
• 132364-34-2 (E)-4-(Diethylamino)-2-methylbut-2-en-1-ol 
• 90809-13-5 (E)-4-(Benzyloxy)-N,N-diethyl-3-methylbut-2-enylamine 

Downstream Products

• 132364-40-0 (3RS)-4-(Benzyloxy)-3-methyl-N-<(R)-α-methyl-4-nitrobenzyl>butanamide 

Relevant articles and documents

Synthesis of Optically Active Bifunctional Isoprenoid Building Blocks by Rhodium(I)-Catalyzed Asymmetric Allylamine to Enamine Isomerization

The application of the known asymmetric allylamine to enamine isomerization methodology to bifunctional C5-isoprenoid allylic amines of types IId and IIe (Scheme 1) is described.It is shown that a number of such substrates can be isomerized with enantioselectivities of >90percent ee using cationic RhI complexes containing (6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine) (BIPHEMP; 9) as asymmetry-inducing ligand (Scheme 2, Tables 1 and 2).Synthetically most useful is the isomerization of the benzyloxy derivative 10a into the (E)-enamine 11a.This isomerization proceeds with very high enantioselectivity (98-99percent ee) and affords, after enamine hydrolysis, the optically active 4-(benzyloxy)-3-methylbutanals ((R)- or (S)-12) in chemical yields of ca. 90percent.In conjunction, a short synthetic route to the starting material 10a has been developed which has a Pd-catalyzed amination of isoprene epoxide (30) as the key step.Thus, convenient and practical access to the optically active aldehydes (R)- and (S)-12 is now at hand.These aldehydes are useful optically active bifunctional building blocks for isoprenoid homologation.