4-Maleimidobutyric acid

Base Information

• Chemical Name: 4-Maleimidobutyric acid
• CAS No.: 57078-98-5
• Molecular Formula: C8H9NO4
• Molecular Weight: 183.164
• Hs Code.: 29251900
• UNII: PJ96MF9P4Q
• DSSTox Substance ID: DTXSID90392183
• Nikkaji Number: J578.952D
• Wikidata: Q82190185
• Mol file: 57078-98-5.mol

Synonyms:4-Maleimidobutyric acid;57078-98-5;4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid;4-(2,5-dioxo-2H-pyrrol-1(5H)-yl)butanoic acid;gamma-Maleimidobutyric acid;Maleimide-(CH2)3-COOH;1H-Pyrrole-1-butanoic acid, 2,5-dihydro-2,5-dioxo-;N-(3-Carboxypropyl)maleimide;MFCD00043139;4-(2,5-dioxopyrrol-1-yl)butanoic Acid;Mal-(CH2)3-COOH;omega-maleimidobutyric acid;PJ96MF9P4Q;SCHEMBL155346;4-Maleimidobutyric acid, 98%;AMY4562;DTXSID90392183;NCPQROHLJFARLL-UHFFFAOYSA-N;BBL027988;FD6069;STK929546;AKOS000150996;GS-6122;HY-W037355;2,5-Dioxo-3-pyrroline-1-butyric acid;AC-30052;BP-21999;SY057251;(N-Maleoyl-GABA);4-Maleimidobutyric acid, >=98.0% (T);A8148;BB 0218442;CS-0093528;FT-0604088;M2337;4-Maleimidobutyric acid, >=98% (titration);EN300-1653626;2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-butanoic acid;4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-butanoic acid;Z245319624;4-Maleimidobutyric Acid

Chemical Property of 4-Maleimidobutyric acid

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 1.61E-07mmHg at 25°C
• Melting Point: 95-98 °C
• Refractive Index: 1.553
• Boiling Point: 400.1 °C at 760 mmHg
• PKA: 4.59±0.10(Predicted)
• Flash Point: 195.8 °C
• PSA: 74.68000
• Density: 1.395 g/cm³
• LogP: -0.28590
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 183.05315777
• Heavy Atom Count: 13
• Complexity: 264

Purity/Quality:

97% ^*data from raw suppliers

4-Maleimidobutyric Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)N(C1=O)CCCC(=O)O
• 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.
• Uses: A short crosslinking reagent Modification reagent for thiol groups in proteins Maleimide Derivatives MTS & Sulfhydryl Active Reagents 4-Maleimidobutyric Acid is a short crosslinking reagent. Modification reagent for thiol groups in proteins

Technology Process of 4-Maleimidobutyric acid

There total 4 articles about 4-Maleimidobutyric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

maleic anhydride (108-31-6) + 4-amino-n-butyric acid (56-12-2) → 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid (57078-98-5)

Guidance literature:

With acetic acid; at 20 ℃; for 2h; Reflux;

Reference yield: 57.0%

C8H11NO5 (15938-22-4) → 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid (57078-98-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; 1-nitro-4-trifluoroacetoxy-benzene; In acetonitrile; at -5 - -2 ℃; for 3h;

Reference yield:

4-{(1S,2R,6S,7R)-1-[3-(6-Methyl-pyridin-2-ylcarbamoyl)-phenyl]-3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl}-butyric acid → 3-furan-2-yl-N-(6-methyl-pyridin-2-yl)-benzamide (247046-50-0) + 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid (57078-98-5)

Guidance literature:

In chloroform-d1; at 49.85 ℃; Kinetics; Equilibrium constant;

DOI:10.1021/ol061177m

upstream raw materials:

maleic anhydride

4-amino-n-butyric acid

C₈H₁₁NO₅

Downstream raw materials:

N-benzyloxycarbonyl-3-(N-maleimidobutyryloxymethyl)-2,2,4,4-tetramethylpyrrolidine

4-maleimidobutyric acid N-hydroxysuccinimide ester

urea