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ChemicalBook >> CAS DataBase List >>(S)-4-Methyl-2,5-oxazolidonedione

(S)-4-Methyl-2,5-oxazolidonedione

(S)-4-Methyl-2,5-oxazolidonedione Structure
(S)-4-Methyl-2,5-oxazolidonedione structure
CAS No.
2224-52-4
Chemical Name:
(S)-4-Methyl-2,5-oxazolidonedione
Synonyms
ALA-NCA;L-Ala-NCA;N-Carboxy-L-alanine anhydride;L-Alanine N-Carbxy anhydride;(S)-4-METHYL-OXAZOLIDINE-2,5-DIONE;H-ALA-NCA;H-L-Ala-NCA;Alanine, NCA;L-Alanine NC;L-Alamine-NCA
CBNumber:
CB7180875
Molecular Formula:
C4H5NO3
Molecular Weight:
115.09
MDL Number:
MFCD03411276
MOL File:
2224-52-4.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-05-28 02:22:10
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(S)-4-Methyl-2,5-oxazolidonedione Properties

Melting point 92℃
alpha +5.13°(25/D,c=6.4,dioxane)
Density 1.296
storage temp. Inert atmosphere,Store in freezer, under -20°C
solubility DMSO (Very Slightly, Heated)
form Solid
pka 9.38±0.40(Predicted)
color White to Off-White
optical activity 5.40°(C=0.01g/mL, DCM, 20°C, 589nm)
InChI InChI=1S/C4H5NO3/c1-2-3(6)8-4(7)5-2/h2H,1H3,(H,5,7)/t2-/m0/s1
InChIKey DTETYCNJKAUROO-REOHCLBHSA-N
SMILES O1C(=O)[C@H](C)NC1=O

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H332-H335
Precautionary statements  P261-P280-P305+P351+P338
HS Code  2934999090
REACH Registrations Active

(S)-4-Methyl-2,5-oxazolidonedione price More Price(37)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TRC TRC-C177720-250MG N-Carboxyalanine Anhydride 2224-52-4 250mg $161 2026-06-03 Buy
TRC TRC-C177720-2.5G N-Carboxyalanine Anhydride 2224-52-4 2.5g $1231 2026-06-03 Buy
Biosynth FM74707 (S)-4-Methyl-2,5-oxazolidinedione 2224-52-4 0.005kg $288.24 2026-06-04 Buy
Biosynth FM74707 (S)-4-Methyl-2,5-oxazolidinedione 2224-52-4 0.01kg $382.66 2026-06-04 Buy
Biosynth FM74707 (S)-4-Methyl-2,5-oxazolidinedione 2224-52-4 0.025kg $915.06 2026-06-04 Buy
Product number Packaging Price Buy
TRC-C177720-250MG 250mg $161 Buy
TRC-C177720-2.5G 2.5g $1231 Buy
FM74707 0.005kg $288.24 Buy
FM74707 0.01kg $382.66 Buy
FM74707 0.025kg $915.06 Buy

(S)-4-Methyl-2,5-oxazolidonedione Chemical Properties, Uses, Production

Description

(S)-4-Methyl-2,5-oxazolidonedione is also known as N-Carboxy anhydrides. The Fuchs-Farthing method, reported in 1922, was the only practical method for preparing (S)-4-Methyl-2,5-oxazolidonedione[1]. N-Carboxy anhydrides (NCAs) are important as α-amino acid building blocks for the synthesis of oligopeptides and nonpeptide compounds, and for the synthesis of polypeptides[2]. The polymerization of NCAs is the main process for the preparation of polypeptides, and its purity and side chains can significantly affect the synthesized polypeptides. NCAs polymerizations have been initiated using many different nucleophiles and bases, the most common being primary amines and alkoxide anions[3].

Uses

(S)-4-Methyl-2,5-oxazolidonedione is composed of oxazolidine ring and 2,5-dione ring. It exhibits chirality, meaning it exists as two non-superimposable mirror image forms. Therefore, it can be used as an organic reagent for the synthesis of enantiomeric pure substances. (S)-4-Methyl-2,5-oxazolidonedione is a reagent used in the synthesis of poly(γ-benzyl-L-glutamate) and its block polypeptides with alanine, leucine and phenylalanine.

Production Methods

L-alanine (20.0 g, 0.224 mol) and triphosgene (53.4 g, 0.180 mol) were suspended in 400.0 mL of dry THF bubbled with nitrogen flux in a flame-dried three-neck flask. The mixture was stirred at 60 °C for 2 h before further bubbling with nitrogen flux for 30 min. After that, the solution was precipitated in 1000.0 mL of n-hexane and stored at -20 °C. The supernatant was removed, and the residues were collected and dissolved in 200.0 mL of ethyl acetate, before two washings with 100.0mL of ice-cold water and one washing with 100.0 mL of 0.5% NaHCO3 ice-cold aqueous solution. The organic phase was then dried over anhydrous MgSO4 and evaporated to obtain 15.5 g of L-Ala NCA ((S)-4-Methyl-2,5-oxazolidonedione). The yield of L-Ala NCA was 77.5%.
(S)-4-Methyl-2,5-oxazolidonedione

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 2200, 1985 DOI: 10.1021/jo00212a042

References

[1] Otake Y, et al. Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides Using Basic-to-Acidic Flash Switching in a Micro-flow Reactor. Angewandte Chemie International Edition, 2018; 57: 11389-11393.
[2] Schfer G, et al. Synthesis of Sterically Hindered N-Acylated Amino Acids from N-Carboxyanhydrides. Organic Letters, 2014; 16: 1526–1529.
[3] Imanishi Y, et al. Polymerization of α-amino acid N-carboxyanhydride in the presence of preformed poly(α-amino acid) - from chain effect to stereoselective polymerization. Pure and Applied Chemistry, 1981; 53.

(S)-4-Methyl-2,5-oxazolidonedione synthesis

56-41-7
32315-10-9
2224-52-4
Synthesis of (S)-4-Methyl-2,5-oxazolidonedione from L-Alanine and Triphosgene

(S)-4-Methyl-2,5-oxazolidonedione Preparation Products And Raw materials

Raw materials

Di-tert-butyl Tricarbonate N-(tert-Butoxycarbonyl)-L-alanine L-Alanine, N-(methoxycarbonyl)- (9CI) N-Carbobenzyloxy-L-alanine L-Alanine
Triphosgene Chloroform Diphosgene

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Preparation Products

L-Alanyl-L-proline

(S)-4-Methyl-2,5-oxazolidonedione Suppliers

Global Suppliers ( 155)
Supplier Tel Email Country ProdList Advantage
ShenZhen InnoSyn Biotech Co.,Ltd 0755-28351685 18503098468 innosyn@163.com China 602 55
Sichuan jiayinglai technology CO.,LTD 9018 15982359653 1394531348@qq.com China 2271 55
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Nanjing Chemlin Chemical Co., Ltd 025-83697070 13770331960 info@chemlin.com.cn China 16305 64
Shanghai Hanhong Scientific Co.,Ltd. 021-54306202 13764082696 info@hanhongsci.com China 42917 64
China Langchem Inc. 0086-21-58956006 China 7798 57
Shanghai Sunway Pharmaceutical Technology Co., Ltd 13761987713 hxzheng@sunwaypharm.cn China 8663 57
ZhengZhou HuaWen Chemical Co.Ltd 0370-2785118 17550508557 675141927@qq.com China 3201 55
Nanjing Norris-Pharm Technology Co., Ltd 13901585132 sales@norris-pharm.com China 8869 55
Jiangsu Aikon Biopharmaceutical R&D co.,Ltd. 025-66113011 13913916777 cfzhang@aikonchem.com China 19902 55
Supplier Advantage
ShenZhen InnoSyn Biotech Co.,Ltd 55
Sichuan jiayinglai technology CO.,LTD 55
J & K SCIENTIFIC LTD. 76
Nanjing Chemlin Chemical Co., Ltd 64
Shanghai Hanhong Scientific Co.,Ltd. 64
China Langchem Inc. 57
Shanghai Sunway Pharmaceutical Technology Co., Ltd 57
ZhengZhou HuaWen Chemical Co.Ltd 55
Nanjing Norris-Pharm Technology Co., Ltd 55
Jiangsu Aikon Biopharmaceutical R&D co.,Ltd. 55

View Latest Price from (S)-4-Methyl-2,5-oxazolidonedione manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
L-Ala-NCA pictures 2026-09-15 L-Ala-NCA
2224-52-4
 1kg 98% 1T+ Sichuan HongRi Pharma-Tech Co.,Ltd
(S)-4-Methyloxazolidine-2,5-dione pictures 2026-08-25 (S)-4-Methyloxazolidine-2,5-dione
2224-52-4
 $2.00-5.00 1kg 99% 100kg ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD
(S)-4-methyloxazolidine-2,5-dione pictures 2022-01-27 (S)-4-methyloxazolidine-2,5-dione
2224-52-4
 1KG 97.7% 100 tons Honest Joy Holdings Limited
  • L-Ala-NCA pictures
  • L-Ala-NCA
    2224-52-4
  • 98%
  • Sichuan HongRi Pharma-Tech Co.,Ltd

(S)-4-Methyl-2,5-oxazolidonedione Spectrum

(S)-4-Methyl-2,5-oxazolidonedione(2224-52-4)1HNMR

2224-52-4 ((S)-4-Methyl-2,5-oxazolidonedione) Related Search:

VINCLOZOLIN Ethyl (S)-2-[(S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutyrate Fmoc-Ala-N-carboxyanhydride 5-Methyl-2,4-oxazolidinedione Boc-Ile-N-carboxyanhydride
Boc-O-benzyl-L-serine N-carboxy anhydride Boc-Asp(OBzl)-N-carboxyanhydride Boc-L-alanine-NCA Boc-O-benzyl-L-threonine N-carboxy anhydride Fmoc-L-valine N-carboxy anhydride
NALPHA-9-Fluorenylmethoxycarbonyl-L-leucine N-carboxylic anhydride N-α-Fmoc-N-γ-trityl-L-asparagine N-carboxyanhydride N-α-Boc-N-ε-Z-L-lysine N-carboxyanhydride Fmoc-O-tert·butyl-L-threonineN-carboxyanhydride N-tert-Butoxycarbonyl-L-leucine N-carboxylic anhydride
Boc-L-glutamic acid γ-benzyl ester N-carboxyanhydride 4-[(4-Hydroxyphenyl)methyl]-2,5-oxazolidinedione 4-Methyl-2,5-oxazolidinedione

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(S)-4-METHYL-OXAZOLIDINE-2,5-DIONE (S)-4-METHYL-2,5-OXAZOLIDINEDIONE (S)-4-Methyl-2,5-oxazolidonedione H-ALA-NCA Alanine, NCA 4-methyl-1,3-oxazolidine-2,5-dione 4-methyloxazolidine-2,5-quinone N-Carboxyalanine Anhydride (4S)-4-Methyl-1,3-oxazolidine-2,5-dione L-Alanine N-Carbxy anhydride 2,5-Oxazolidinedione,4-Methyl-, (4S)- (4S)-4-Methyloxazolidine-2,5-dione ALA-NCA L-Alanine NC L-ALA-NCA(2224-52-4) L-Ala-N-Carboxyanhydride Alanine N-carboxyanhydride Creatinine Impurity 3 L-alanine-n-carboxylic intracyclic anhydride H-L-Ala-NCA Sodium Phenylbutyrate Impurity 4 L-Ala-NCA N-Carboxy-L-alanine anhydride L-Alamine-NCA 2224-52-4 AMINOACIDS DERIVATIVES