16958-25-1

Basic information

• Product Name: (R)-3-METHYL-PENTANOIC ACID
• Synonyms: 3R-Methyl-pentanoic acid;(3R)-3-methylpentanoic acid
• CAS NO: 16958-25-1
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16
• Mol File: 16958-25-1.mol

Chemical Properties

• Boiling Point: 199 °C at 760 mmHg
• Flash Point: 88.4 °C
• Appearance: /
• Density: 0.947 g/cm³
• Vapor Pressure: 0.147mmHg at 25°C
• Refractive Index: 1.425
• Storage Temp.: 2-8°C
• PKA: 4.80±0.10(Predicted)
• CAS DataBase Reference: (R)-3-METHYL-PENTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-METHYL-PENTANOIC ACID(16958-25-1)
• EPA Substance Registry System: (R)-3-METHYL-PENTANOIC ACID(16958-25-1)

Safety Data

• Hazardous Substances Data: 16958-25-1(Hazardous Substances Data)

Usage

Uses

Used in the Food Industry:
(R)-3-METHYL-PENTANOIC ACID is used as a flavoring agent for its strong odor that resembles the smell of cheese, enhancing the taste and aroma of various food products.
Used in the Perfume Industry:
(R)-3-METHYL-PENTANOIC ACID is used as a component in the production of perfumes, where its unique and pungent odor contributes to the creation of distinct fragrances.
Used in the Pharmaceutical Industry:
(R)-3-METHYL-PENTANOIC ACID is used in the manufacturing process of various pharmaceuticals, potentially due to its chemical properties and reactivity in the synthesis of medicinal compounds.
Safety Considerations:
(R)-3-METHYL-PENTANOIC ACID is considered a potentially hazardous substance. It is used with caution to prevent irritation to the skin, eyes, and respiratory system, ensuring proper handling and safety measures are in place during its use in various applications.

InChI:InChI=1/C6H12O2/c1-3-5(2)4-6(7)8/h5H,3-4H2,1-2H3,(H,7,8)/t5-/m1/s1

Upstream product

• 105-43-1 3-methylvaleric acid 
• 104651-15-2 N-[3(R)-methylpentanoyl]-(1S,2R)-bornane-2,10-sultam 
• 74-96-4 ethyl bromide 
• 199006-79-6 (R)-(+)-N-(1-ethyl-2-hydroxy)ethyl-N-(2-fluorobenzyl) crotonamide 
• 250229-60-8 (R)-3-methylpentanenitrile 
• 104637-16-3 (E)-3-methylpent-2-enoyl chloride 
• 13991-37-2 trans-2-pentenoic acid 
• 935473-81-7 (R)-1-diazo-3-methyl-pentan-2-one 
• 137-32-6 (-)-2-Methylbutan-1-ol 
• 137-32-6 (+/-)-2-methyl-1-butanol 
• 124-38-9 carbon dioxide 
• 534-00-9 (+)-1-bromo-2-methylbutane 
• 534-00-9 (S)-2-methylbutyl bromide 
• 1417724-91-4 (1S,7S,8S,9S)-11-acetoxy-10-chloro-1-isovaleroxy-7-[(R)-3-methylvaleroxy]-valtrate chlorohydrin 

Downstream Products

• 18893-65-7 (R)-3-methyl-valeric acid-(4-nitro-phenyl ester) 
• 70200-36-1 (R)-3-methylpentan-1-ol tosyl ester 
• 250229-74-4 (2R,6R,10R)-1-tert-butyldiphenylsilyloxy-2,6,10-trimethyldodecane 
• 28959-00-4 1,1-Dibenzyl-3-methyl-pentanol-⁽¹⁾ 
• 28958-99-8 1,1-Diphenyl-3-methyl-pentanol-⁽¹⁾ 
• 20659-68-1 (+)-3-methylpentanoyl benzene 
• 589-35-5 (S)-3-methyl-pentan-1-ol 
• 28977-69-7 α(+)-2-Methylvalerylchlorid 
• 5870-68-8 (S)-3-methyl-pentanoic acid ethyl ester 
• 1449396-56-8 C₁₉H₃₁NO₂ 
• 1061728-08-2 (3R,1'R,2'R)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-3-methylpentanamide 
• 87106-30-7 (3R,7R)-3,7-dimethylnonyl tosylate 
• 87106-27-2 (R)-2-methyl-1-phenylsulfonylbutane 
• 87106-26-1 (R)-(-)-2-methylbutyl phenyl sulfide 

Relevant articles and documents

Cu-catalyzed enantioselective conjugate additions of alkyl zinc reagents to unsaturated N-acyloxazolidinones promoted by a chiral triamide phosphane

A chiral triamide phosphane promotes highly efficient and enantioselective Cu-catalyzed conjugate additions of alkyl zinc compounds to unsaturated oxazolidinones (see scheme). The resulting β-alkyl chiral oxazolidinones are readily converted into synthetically useful carbonyl compounds not accessible by alternative catalytic methods.

Asymmetric hydrogenation of prochiral carboxylic acids catalyzed by the five-coordinate ruthenium(II)-hydride complex PF6 (binap = (R)- or (S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)

The five-coordinate complex PF6 (1, binap = (R)- or (S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) has been found to have sufficient catalytic activity for asymmetric hydrogenation of itaconic acid and other prochiral carboxylic acids under mild conditions.The catalytic hydrogenation of itaconic acid by I was examined under a variety of conditions, and the addition of triethylamine was found to effect high enantioselectivities (above 90percent ee). 1H and 31 P NMR examinations of reaction mixtures of I and itaconic acid under conditions similar to the hydrogenation suggested the formation of ruthenium species containing one binap chelate.

A Concise Synthesis of (-)-Dihydroprotolichesterinic Acid via Consecutive Stereocontrolled 1,4-Conjugate Addition and syn-Aldol Condensation Reactions

(-)-Dihydroprotolichesterinic acid 1a is synthesised in 6 steps and 57percent overall yield by a strategy employing the camphene-derived chiral auxiliary 2 to construct the three contiguous stereogenic centres in consecutive stereocontrolled 1,4-conjugate addition and syn-aldol reactions.

Characterization of chlorinated valepotriates from Valeriana jatamansi

HPLC-PDA-MS and TLC analysis were used to look for minor cytotoxic chlorinated valepotriates from whole plants of Valeriana jatamansi (syn. Valeriana wallichii DC.). This resulted in isolation of 15 chlorinated valepotriates, designated as chlorovaltrates A-O, together with six known analogues, (1S,3R,5R,7S,8S,9S)-3,8-epoxy-1,5-dihydroxyvalechlorine, volvaltrate B, chlorovaltrate, rupesin B, (1S,3R,5R,7S,8S,9S)-3,8-epoxy-1-O-ethyl-5- hydroxyvalechlorine, and (1R,3R,5R,7S,8S,9S)-3,8-epoxy-1-O-ethyl-5- hydroxyvalechlorine. Their structures were elucidated by spectroscopic methods including homo- and heteronuclear two-dimensional NMR experiments. Chlorovaltrates K-N, chlorovaltrate and rupesin B showed moderate cytotoxicity against lung adenocarcinoma (A 549), metastatic prostate cancer (PC-3M), colon cancer (HCT-8) and hepatoma (Bel 7402) cell lines with IC50 values of 0.89-9.76 μM.

Novel iridium complex of spirophosphine-carboxylic acid, preparation method and application thereof

The invention relates to an iridium complex of spirophosphine-carboxylic acid, a preparation method and application thereof. The iridium complex of spirophosphine-carboxylic acid is a compound with a structure shown as formula (I), wherein n=0-3; and the values of R1, R2, R3, R4, R5, R6 and R7 are defined as claim 1. Substituted 7-carboxyl-7'-diarylphosphino-1, 1'-spirobiindane is taken as the ligand to from carboxylic acid anion under the action of alkali, and then complexation with an iridium precursor is carried out to obtain different iridium/spirophosphine-carboxylic acid complexes. The iridium complex of spirophosphine-carboxylic acid provided by the invention can catalyze the asymmetric hydrogenation reaction of a variety of unsaturated carboxylic acids, and show high activity and enantioselectivity, thus having good industrialization prospects. (formula (I)).

Neutral iridium catalysts with chiral phosphine-carboxy ligands for asymmetric hydrogenation of unsaturated carboxylic acids

We developed neutral iridium catalysts with chiral spiro phosphine-carboxy ligands (SpiroCAP) for asymmetric hydrogenation of unsaturated carboxylic acids. Different from the cationic Crabtree-type catalysts, the iridium catalysts with chiral spiro phosphine-carboxy ligands are neutral and do not require the use of a tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (BArF?) counterion, which is necessary for stabilizing cationic Crabtree-type catalysts. Another advantage of the neutral iridium catalysts is that they have high stability and have a long lifetime in air. The new iridium catalysts with chiral spiro phosphine-carboxy ligands exhibit unprecedented high enantioselectivity (up to 99.4% ee) in the asymmetric hydrogenations of various unsaturated carboxylic acids, particularly for 3-alkyl-3-methylenepropionic acids, which are challenging substrates for other chiral catalysts.

Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to α′-oxy enones

The copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to α'-oxy enones was investigated. Cu(OTf)2, ligand, and toluene were placed in a flame-dried Schlenk tube. the resulting mixture was stirred at room temperature f

Highly enantioselective copper-phosphoramidite-catalyzed conjugate addition of dialkylzinc reagents to acyclic α,β-unsaturated imides

A new and practical way to introduce an alkyl fragment in the β-position of aliphatic carboxylic acid derivatives with high enantioselectivities by the use of a commercially available chiral ligand is reported. N-Acylpyrrolidinones, as simple derivatives

Syntheses of new chiral bicyclic sultams and their use as auxiliaries in asymmetric conjugate addition of Grignard reagents

Starting from L-aminoacids, 5-N-unsubstituted isothiazolo[4,5-c]isoxazole 4,4-dioxides have been synthesized and used as chiral auxiliaries in asymmetric conjugated additions of Grignard reagents to α,β-unsaturated carboxylic acids.

Practical synthesis of (+)-alloisoleucine

Subsequent treatment of N-crotoyl-(1S,2R)-bornane-10,2-sultam with EtMgCl, recrystallization of the product and saponification, afforded R-(-)- 3-methylpenthanoic acid which was used for acylation of (1R,2S)-bornane-10,2- sultam. The product was converted into N-[(2S,3R)-2-amino-3- methylpentanoyl](1R,2S)-bornane-10,2-sultam by hydroxyamination with 1- chloro-1-nitrosocyclohexane, followed by reduction of the hydroxylamine grouping. Saponification of the sultam imide provided (+)-alloisoleucine.