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

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

Uses

Used in Pharmaceutical Industry:
4-Benzyloxy-3-methylbutyric acid is used as a key intermediate in the synthesis of various drugs and pharmaceuticals for its ability to contribute to the development of medications with diverse therapeutic applications.
Used in Cholesterol-Lowering Medications:
In the pharmaceutical industry, 4-Benzyloxy-3-methylbutyric acid is used as a building block for the production of cholesterol-lowering compounds such as atorvastatin and cerivastatin, which help in managing and reducing high cholesterol levels in the body.
Used in Medical Research:
4-Benzyloxy-3-methylbutyric acid is utilized in medical research for its potential anti-inflammatory and anti-cancer properties, making it a promising candidate for the development of new therapeutic agents to combat inflammation and cancer.

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.