| Identification | More | [Name]
4-MALEIMIDOBUTYRIC ACID | [CAS]
57078-98-5 | [Synonyms]
4-(2,5-DIOXO-2,5-DIHYDRO-1H-PYRROL-1-YL)BUTANOIC ACID
4-(2,5-DIOXO-2,5-DIHYDRO-PYRROL-1-YL)-BUTYRIC ACID
4-MALEIMIDOBUTANOIC ACID
4-MALEIMIDOBUTYRIC ACID
GAMMA-MALEIMIDOBUTYRIC ACID
MALEIMIDOPROPIONIC ACID
MBA
N-(3-CARBOXYPROPYL)MALEIMIDE
N-MALEOYL-4-AMINOBUTYRIC ACID
N-MALEOYL-GABA
RARECHEM AL CD 0913
4-MALEIMIDOBUTANOIC ACID DIHYDRATE
γ-Maleimidobutyric acid, 4-Maleimidobutanoic acid, N-(3-Carboxypropyl)maleimide, N-Maleoyl-4-aminobutyric acid, N-Maleoyl-GABA | [EINECS(EC#)]
611-461-8 | [Molecular Formula]
C8H9NO4 | [MDL Number]
MFCD00043139 | [Molecular Weight]
183.16 | [MOL File]
57078-98-5.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
95-98 °C
| [Boiling point ]
400.1±28.0 °C(Predicted) | [density ]
1.395±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly) | [form ]
Solid | [pka]
4.59±0.10(Predicted) | [color ]
White to Pale Yellow | [Usage]
A short crosslinking reagent. | [BRN ]
1455876 | [InChI]
InChI=1S/C8H9NO4/c10-6-3-4-7(11)9(6)5-1-2-8(12)13/h3-4H,1-2,5H2,(H,12,13) | [InChIKey]
NCPQROHLJFARLL-UHFFFAOYSA-N | [SMILES]
N1(CCCC(O)=O)C(=O)C=CC1=O | [CAS DataBase Reference]
57078-98-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10-21 | [HS Code ]
29251900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
4-(2,5-dioxo-2H-pyrrol-1(5H)-yl)butanoic acid contains a maleimide group and a terminal carboxylic acid. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol. | [Chemical Properties]
White Solid | [Synthesis]
General procedure for the synthesis of 4-maleimidobutyric acid from the compound (CAS: 15938-22-4): compound (II) (191 g, 0.95 mol, X = 3) and 600 mL of acetonitrile were added to a 1000 mL three-necked flask, followed by the addition of diisopropylethylamine (363 g, 2.8 mol) and a solution of phenyl 4-nitro trifluoroacetate. Phenyl 4-nitrilotrifluoroacetate (353.4 g, 1.5 mol) dissolved in 300 mL of acetonitrile was added dropwise to the reaction system and the reaction temperature was controlled to be between -5 and 10 °C. After completion of the reaction, the mixture was dried, 400 mL of water was added and the pH was adjusted to 3-4 with concentrated hydrochloric acid. 4-nitrophenol was removed by filtration and the filtrate was extracted three times with dichloromethane, the organic phases were combined, washed with water and dried with anhydrous magnesium sulfate. After concentration and drying, 129 g of light yellow solid was obtained. 111 g of white solid was obtained by recrystallization from mixed solvent of ethyl acetate and petroleum ether, 99 g was weighed after drying, and the purity was 98.4% by HPLC, and the yield was 57.0%. | [IC 50]
Alkyl-Chain | [References]
[1] Patent: CN105037237, 2017, B. Location in patent: Paragraph 0063-0066
[2] Organic and Biomolecular Chemistry, 2009, vol. 7, # 17, p. 3400 - 3406 |
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J & K SCIENTIFIC LTD.
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Energy Chemical
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www.energy-chemical.com |
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Aemon Chemical
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www.aemonchem.com |
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