3-Maleimidopropionic acid

Base Information

• Chemical Name: 3-Maleimidopropionic acid
• CAS No.: 7423-55-4
• Molecular Formula: C7H7NO4
• Molecular Weight: 169.137
• Hs Code.: 29252900
• UNII: Q5C4V9T6GU
• DSSTox Substance ID: DTXSID00341526
• Nikkaji Number: J814.755H
• Wikidata: Q69756856
• Mol file: 7423-55-4.mol

Synonyms:3-Maleimidopropionic acid;7423-55-4;3-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoic acid;N-Maleoyl-beta-alanine;3-(2,5-dioxopyrrol-1-yl)propanoic acid;BMPA Protein Modifier;1h-pyrrole-1-propanoic acid, 2,5-dihydro-2,5-dioxo-;Maleimide-(CH2)2-COOH;MFCD00043030;N-Maleoyl-.beta.-alanine;3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-propionic acid;2,5-DIHYDRO-2,5-DIOXO-1H-PYRROLE-1-PROPANOIC ACID;3-maleimido-propionic acid;N-carboxyethylmaleimide;3-Maleimdepropionicacid;3-Maleimidopropanoic acid;Mal-(CH2)2-COOH;Q5C4V9T6GU;N-(2-Carboxyethyl)maleimide;SCHEMBL34464;N-Maleoyl-beta-alanine, 97%;DTXSID00341526;BCP13655;BBL027986;s1127;STK934575;.BETA.-MALEIMIDOPROPIONIC ACID;AKOS000143815;AC-5036;CS-W019611;GS-6614;BP-20452;HY-42145;SY021699;AM20100720;BB 0218381;FT-0604091;FT-0608194;M1962;N-Maleoyl-beta-alanine, >=98.0% (HPLC);EN300-227402;J-512738;F1265-0534;Z245319606;3-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoic acid #;MPA-OH;Maleoyl-beta-Ala-OH

Chemical Property of 3-Maleimidopropionic acid

Chemical Property:

• Appearance/Colour: white to pale yellow solid
• Vapor Pressure: 6.53E-07mmHg at 25°C
• Melting Point: 103-106 °C(lit.)
• Refractive Index: 1.565
• Boiling Point: 382.5 °C at 760 mmHg
• PKA: 4.18±0.10(Predicted)
• Flash Point: 185.1 °C
• PSA: 74.68000
• Density: 1.473 g/cm³
• LogP: -0.67600
• Storage Temp.: -15°C
• Sensitive.: Moisture Sensitive
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in methanol, dimethyl formamide, alcohol and dimethyl sulfoxide. Slightly soluble in water.
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 169.03750770
• Heavy Atom Count: 12
• Complexity: 251

Purity/Quality:

99% ^*data from raw suppliers

3-Maleimidopropionic 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)CCC(=O)O
• Description: 3-Maleimidopropionic 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: 3-Maleimidopropionic acid is a sulfhydryl reactive heterobifunctional crosslinking reagent. A sulfhydryl reactive heterobifunctional crosslinking reagent.

Technology Process of 3-Maleimidopropionic acid

There total 4 articles about 3-Maleimidopropionic 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:

3-(1-methyl-3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.0(2,6)]dec-8-en-4-yl)propanoic acid → 2-methylfuran (534-22-5) + 3-maleimidepropionic acid (7423-55-4)

Guidance literature:

In methanol; water; at 90 ℃; for 0.333333h; Microwave irradiation;

DOI:10.1021/ol201690b

Reference yield:

3-(1,7-dimethyl-3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.0(2,6)]dec-8-en-4-yl)propanoic acid → 2,5-dimethylfuran (625-86-5) + 3-maleimidepropionic acid (7423-55-4)

Guidance literature:

In methanol; water; at 80 ℃; for 0.333333h; Microwave irradiation;

DOI:10.1021/ol201690b

Reference yield:

3-((3aR,4S,7R,7aS)-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-epoxyisoindol-2-yl)propanoic acid → furan (110-00-9) + 3-maleimidepropionic acid (7423-55-4)

Guidance literature:

In methanol; water; at 120 ℃; for 0.333333h; Microwave irradiation;

DOI:10.1021/ol201690b

Downstream raw materials:

C₁₆H₁₅NO₇

C₆₅H₇₅N₉O₁₃

O-(paclitaxel-2'-yl) 3-maleimidopropionate

Refernces

• 1、 Bennes, Raphael M.,Philp, Douglas. "Probing selectivity in recognition-mediated dynamic covalent processes". . p. 3651 - 3654. Retrieved 2007/10/03.