27763-54-8

Basic information

• Product Name: (S)-2-Methylbutanoyl chloride
• Synonyms: (S)-2-METHYLBUTANOYL CHLORIDE;(S)-2-Methylbutyryl chloride
• CAS NO: 27763-54-8
• Molecular Formula: C₅H₉ClO
• Molecular Weight: 120.58
• Mol File: 27763-54-8.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 116 °C
• Flash Point: 25 °C
• Appearance: /
• Density: 1.005
• Vapor Pressure: 18.2mmHg at 25°C
• Refractive Index: 1.415
• CAS DataBase Reference: (S)-2-Methylbutanoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Methylbutanoyl chloride(27763-54-8)
• EPA Substance Registry System: (S)-2-Methylbutanoyl chloride(27763-54-8)

Safety Data

• Hazardous Substances Data: 27763-54-8(Hazardous Substances Data)

Usage

Uses

(2S)-2-Methylbutanoyl chloride is an intermediate in the synthesis 4a,5-Dihydro Lovastatin (Lovastatin EP Impurity E; Lovastatin USP Related Compound A, D448570), an impurity in Lovastatin (L472225) bulk drug.

InChI:InChI=1/C5H9ClO/c1-3-4(2)5(6)7/h4H,3H2,1-2H3/t4-/m0/s1

Upstream product

• 1565-80-6 (2S)-2-methyl-1-butanol 
• 79-37-8 oxalyl dichloride 
• 1730-91-2 (S)-2-Methylbutyric acid 

Downstream Products

• 1607-30-3 bis-((S)-2-methyl-butyryl)-peroxide 
• 101737-97-7 1-((S)-2-methyl-butyryl)-5-oxo-L-proline-phenethylamide 
• 27763-95-7 (S)-2,5-dimethylheptan-4-one 
• 63157-98-2 (S)-(-)-N-1-phenylethyl-(S)-(+)-2-methylbutyramide 
• 130610-52-5 4-Decyloxy-benzoic acid 4-[(S)-cyano-((S)-2-methyl-butyryloxy)-methyl]-phenyl ester 
• 130565-74-1 4-Decyloxy-benzoic acid 4-[(R)-cyano-((S)-2-methyl-butyryloxy)-methyl]-phenyl ester 
• 79691-11-5 6(R)-<2-<1,2,6,7,8,8a(R)-Hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutyryl>oxy>-1(S)-naphtyl>ethyl>-3,4,5,6-tetrahydro-4(R)-<(tert-butyldimethylsilyl)oxy>-2H-pyran-2-one 
• 122587-83-1 ajugamarin G1 
• 54394-78-4 (+)-(S)-N-(2-methylbutanoyl)aniline 
• 120836-99-9 (S)-4-(2-methylbutanoyl)phenol 
• 910658-45-6 (2R,3R)-2,3,4-trihydroxybutyl (S)-2-methylbutanoate 
• 193340-33-9 (S)-N-(2-methylbutyl)-N-phenylamine 
• 193340-34-0 (+)-(S)-N-(2-hydroxyethyl)-N-(2-methylbutyl)aniline 
• 1333469-53-6 (S)-1-(2,4-bis((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)-2-methylbutan-1-one 

Relevant articles and documents

Enantioselective synthesis of the female sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus

The pink hibiscus mealybug, Maconellicoccus hirsutus (Green), is an exotic insect pest and recently invaded Southern California and Florida. The female M. hirsutus releases the 2-methylbutanoate of a novel cyclobutanoid monoterpene alcohol (maconelliol) that together with lavandulyl 2-methylbutanoate constitutes the sex pheromone to attract males from a distance. Enantioselective syntheses of four different stereoisomers of the major component, maconelliyl 2-methylbutanoate 1, from α-pinene are reported. Absolute configurations of both naturally occurring maconelliyl 2-methylbutanoate 1 and the minor component, lavandulyl 2-methylbutanoate 2, have been established. Comparison of the analytical data of naturally occurring compounds with those of optically active synthetic isomers proved that both esters show the (R)-configuration at the alcohol and the (S)-configuration at acid moieties.

Total synthesis of (S)-(+)-ent-phomapyrones B and surugapyrone B

Phomapyrone B (1), the 2-pyrones isolated from the phytopathogenic fungus Leptosphaeria maculans, has been synthesized as the enantiomeric form starting from (S)-2-methylbutanol (4). Surugapyrone B (3) isolated from Streptmyces sp. USF-6280 as an antioxidant has also been synthesized as a natural form. The absolute configuration of phomapyrone B (1) was estimated to be the (R)-form and that of surugapyrone B (3) being the (S)-form. A series of 2-pyrone derivatives 17 have been synthesized through the established procedure and their DPPH radical-scavenging activities have also been evaluated.

dM-Dim for carboxylic acid protection

The 1,3-dithian-2-yl-methyl (Dim) and its analogous groups including dimethyl-Dim (dM-Dim) can provide a new dimension of orthogonality for carboxylic acid protection. They can be deprotected under nearly neutral oxidative conditions. In this paper, the protection of carboxylic acid with dM-Dim, deprotection of dM-Dim ester with sodium periodate, stability of dM-Dim protected carboxylic acid under acidic and basic conditions, and selective deprotection of dM-Dim protected carboxylic acids in the presence of tertiary butyl and methyl esters are presented.

Stereocontrol in Preparation of Cyclopalladated Alkylaromatic Oximes and Evaluation of Their Stereoselective Esterase-Type Catalytic Activity

The stereochemistry of 2′-methylbutyrophenone oxime, the rates of ortho-palladation of its E- and Z-isomers, and catalytic activity of the respective Pd complexes were studied. The full stereoisomeric composition of oximes was established for the first time by means of supercritical fluid chromatography on chiral polysaccharide column. It was shown that enantiomeric excesses of both E/Z-isomers of (S)-2′-methylbutyrophenone oxime (1S) and (R)-2′-methylbutyrophenone oxime (1R) were equal to 92 ± 2. The cyclopalladation study revealed that while E-isomer is ortho-palladated very quickly its Z-counterpart does not enter this reaction. However, upon coordination to Pd(II), Z-oxime slowly isomerizes into E-form with fast subsequent cyclopalladation, so it was possible to perform ortho-palladation of E-oxime in kinetic resolution mode with removal of unreacted Z-oxime. Comparatively rare cis-structure of cyclopalladated oxime dimer was proved by means of single-crystal X-ray study. For the first time, it was shown that ortho-palladated chiral oximes behave as enantioselective catalyst in the hydrolysis of chiral esters.