3067-19-4

Basic information

• Product Name: N-Acetyl-DL-valine
• Synonyms: AC-DL-VAL-OH;ACETYL-DL-VALINE;ACETYL-DL-VALINE, N-;N-ACETYL-L(DL)-VALINE;N-ACETYL VALINE;N-ACETYL-DL-VALINE;N-A-ACETYL-DL-VALINE;Valine, N-acetyl-
• CAS NO: 3067-19-4
• Molecular Formula: C₇H₁₃NO₃
• Molecular Weight: 159.18
• EINECS: 221-321-4
• Product Categories: Amino Acids;Amino Acid Derivatives;Ac-Amino Acids;Amino Acids (N-Protected);Biochemistry;Amino Acid Derivatives;Peptide Synthesis;Valine;amino acid;amino
• Mol File: 3067-19-4.mol

Chemical Properties

• Melting Point: 148°C
• Boiling Point: 362.2 °C at 760 mmHg
• Flash Point: 172.8 °C
• Appearance: COA
• Density: 1.094 g/cm³
• Vapor Pressure: 3.14E-06mmHg at 25°C
• Refractive Index: 1.456
• Storage Temp.: Store at 0
• Solubility: 37g/l (experimental)
• PKA: 3.62±0.10(Predicted)
• BRN: 1723835
• CAS DataBase Reference: N-Acetyl-DL-valine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-DL-valine(3067-19-4)
• EPA Substance Registry System: N-Acetyl-DL-valine(3067-19-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: WGK 3 highly water endangering
• Hazardous Substances Data: 3067-19-4(Hazardous Substances Data)

Usage

Uses

N-Acetyl-DL-Valine is an amino acid.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 2829, 1987 DOI: 10.1016/S0040-4039(00)96220-8

InChI:InChI=1/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)/t6-/m0/s1

Upstream product

• 64724-68-1 diethyl 2-N-acetylamino-2-isopropylmalonate 
• 6642-21-3 2-acetylamino-3-methyl-crotonic acid 
• 108-24-7 acetic anhydride 
• 516-06-3 D,L-valine 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 830-03-5 4-nitrophenol acetate 
• 60-35-5 acetamide 
• 201230-82-2 carbon monoxide 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 78-84-2 isobutyraldehyde 
• 72-18-4 L-valine 
• 759-05-7 3-methyl-2-ketobutanoic acid 

Downstream Products

• 17623-72-2 2-methyl-4-iso-propyl-4H-oxazolin-5-one 
• 52152-47-3 N-acetyl-DL-valine methyl ester 
• 91077-78-0 3-Acetyl-4-isopropyl-5-oxazolidinone 
• 109924-94-9 Ac-(R,S)-Val-(R,S)-PhSer-OMe 
• 114285-08-4 C₇H₁₂NO₃ 
• 72-18-4 L-valine 
• 17916-88-0 N-acetyl-D-valine 
• 923954-52-3 N-acetyl-ambo-valyl-ambo-alanine methyl ester 
• 251988-77-9 N-[2-methyl-1-(4-methyl-benzoyl)-propyl]-acetamide 
• 96-81-1 N-acetyl-L-valine 
• 96574-46-8 N²-<(R)-N²-acetylvalyl>-L-phenylalanine dimethylamide 
• 96574-45-7 N²-<(S)-N²-acetylvalyl>-L-phenylalanine dimethylamide 
• 109924-97-2 racemic Ac-Val-ΔPhe-azlactone 
• 109924-99-4 racemic Ac-Val-ΔPhe-OMe 

Relevant articles and documents

Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media

The kinetics of the reaction of a series of α-amino acids with 4-nitrophenyl acetate, 4-nitrophenyl benzoate, and 2,4,6-trinitrophenyl benzoate in aqueous 1,4-dioxane medium has been studied. Kinetics of the reactions involving 4-nitrophenyl acetate and 2,4,6-trinitrophenyl benzoate has complied with the Br?nsted dependence and revealed linear correlation between rate constant logarithm and the energy difference of the frontier orbitals of α-amino acids anions.

Microwave-assisted synthesis of amide under solvent-free conditions

An efficient and environmentally friendly synthetic method for the synthesis of primary amides under microwave irradiation was described, in which the primary amine was directly reacted with acid without any catalytic agents. The reaction took place in 8-12-min, which was much shorter than the traditional synthetic methods, with almost quantitative yields. The influential factor of the reaction was discussed. The tautomerization between the carboxylic acid group and the H atom in α-carbon of L-amino acid was observed, presumably a dehydrated intermediate forming from this tautomerized isomer. Copyright Taylor & Francis Group, LLC.

Amidoearbonylation of aldehydes utilizing cobalt oxide-supported gold nanoparticles as a heterogeneous catalyst

Cobalt oxide-supported gold-nanoparticles-catalyzed transformation of aldehydes and their equivalents to N-acyl-α-arnino acids was achieved. The desired products were obtained in moderate to excellent yields under milder reaction conditions than previous reports employing octacarbonyldicobalt as a catalyst. Copyright

METHOD OF AMIDOCARBONYLATION REACTION

A novel method of an amidocarbonylation reaction among an aldehyde compound, an amide compound, and carbon monoxide, which comprises using a palladium-supporting crosslinked-polymer composition containing palladium clusters having a major-axis length of 20 nm or shorter to conduct the amidocarbonylation reaction. Thus, an N-acyl-±-amino acid can be more efficiently and selectively synthesized in a clean reaction system. Also provided is a catalyst for use in the method.

Palladium-catalyzed amidocarbonylation improved by recyclable ionic liquids

Two types of ionic liquids (halide anion ionic liquids and Brensted acidic ionic liquids) were first applied to improve the palladium-catalyzed amidocarbonylation. Both the palladium catalyst and the ionic liquids could be recycled at least five times without significant loss in catalytic activity. Georg Thieme Verlag Stuttgart.

A study of amidocarbonylation reactions catalyzed by Pd/HZSM-5

A HZSM-5-supported palladium catalyst, which was prepared by the conventional impregnation method, was utilized in amidocarbonylation reactions. Several important parameters were optimized to give moderate to excellent yields. The catalyst recycling of Pd/HZSM-5, for the first time, was achieved for at least four run times without depreciation of catalytic activity. The studies of TEM images revealed that agglomeration of the palladium species of Pd/ HZSM-5 catalyst was avoided after reaction, which was quite different from the case of Pd/C catalyst.

Efficient synthesis of N-acyl-α-amino acids via polymer incarcerated palladium-catalyzed amidocarbonylation

A novel polymer incarcerated Pd catalyst (PI Pd 7c) was synthesized from amide-containing polymer 6b, and this catalyst was shown to be effective in amidocarbonylation, which is a versatile one-pot method for the preparation of N-acyl-α-amino acids. The reactions proceeded smoothly with a wide variety of substrates, and no leaching of the Pd metal to the reaction mixture was detected.

Platinum-catalyzed amidocarbonylation

The first example of platinum-catalyzed amidocarbonylation of aldehydes with amides and carbon monoxide is described. In contrast to precedent palladium catalysis, a remarkable ligand acceleration by phosphines was observed. Furthermore, an optically active N-acetyl amino acid was partially epimerized under the platinum-catalyzed conditions, while faster racemization was observed under the palladium catalysis.

Efficient Asymmetric Hydrogenations of (Z)-2-Acetamidoacrylic Acid Derivatives with the Cationic Rhodium Complex of (2S,4S)-MOD-BPPM

The preparation of (2S,4S)-MOD-BPPM ((2S,4S)-N-(t-butoxycarbonyl)-4-phosphino>-2-phosphino>methyl>pyrrolidine) and its application to highly effective asymmetric hydrogenations of (Z)-2-acetamidoacrylic acid derivatives are described.

A general and accurate nmr determination of the enantiomeric purity of α-aminoacids and α-aminoacid derivatives

Derivatization of α-aminoacids, α-aminoesters and α-aminolactones as N-acetyl derivatives allow the accurate NMR determination of the enantiomeric purity. In these conditions the major coordination site with a chiral shift reagent will correspond to the NMR observation site. Experimental factors leading to the highest ΔΔδ values are ascertained. No straightforward correlation with absolute configurations can be established.