3-Maleimidopropionic acid
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3-Maleimidopropionic acid
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CAS No:
7423-55-4
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Formula:
C7H7NO4
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Chemical Name:
3-Maleimidopropionic acid
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Synonyms:
1H-Pyrrole-1-propanoic acid,2,5-dihydro-2,5-dioxo-;3-Pyrroline-1-propionic acid,2,5-dioxo-;2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-propanoic acid;N-(2-Carboxyethyl)maleimide;3-Maleimidopropionic acid;β-Maleimidopropionic acid;N-Maleoyl-β-alanine;3-(Maleimido)propanoic acid;3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-propionic acid;BMPA;BMPA (imide);3-(2,5-Dioxo-2H-pyrrol-1(5H)-yl)propanoic acid;2,5-Dioxopyrrole-1-propanoic acid
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CAS No:
Description
3-Maleimidopropionic acid is an alkyl chain-based PROTAC linker that can be used in the synthesis of PROTACs[1].
Characteristics
74.7
0
1.5±0.1 g/cm3
103-106 °C
185.1±23.2 °C
1.565
Soluble in methanol, dimethyl formamide, alcohol and dimethyl sulfoxide. Slightly soluble in water.
Safety Information
NONH for all modes of transport
3
R36/37/38
S26-S36
Xi: Irritant;
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 495 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
3-Maleimidopropionic acid Use and Manufacturing
First, 3-maleimidopropionic acid was synthesized according todescribed literature methods with modification [26, 27]. A suspensionof maleic anhydride (3.21 g, 32.78 mmol) and β-alanine (3 g, 33.67 mmol) in glacial AcOH (30 mL) was heated to reflux (bath temperature:170–180 °C) for 90min. The solutionwas cooled to roomtemperatureand the solvent was evaporated in vacuo. Residual AcOH wasremoved by coevaporation with toluene under vacuum (2 × 50 mL).The residue was treated with water (100 mL) and EtOAc (200 mL).The organic layer was separated while the aqueous layer was extractedwith EtOAc (2 × 100 mL). The combined organic extracts were dried(Na2SO4) and evaporated in vacuo. The crude product was purified bysilica gel column chromatography, eluting with 50percent ethyl acetate inhexanes, to afford 3-maleimidopropionic acid (3.7 g, 21.88 mmol, 67percentyield), the spectroscopic data of which was consistent with reporteddata.(27) 1H NMR (CDCl3) δ 8.93 (br s, 1H), 6.71 (s, 2H), 3.80 (t, J =7.2 Hz, 2H), 3.62–3.66 (m, 24H), 2.67 (t, J = 7.2 Hz, 2H).
A sulfhydryl reactive heterobifunctional crosslinking reagent.
Computed Properties
Molecular Weight:169.13
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:169.03750770
Monoisotopic Mass:169.03750770
Topological Polar Surface Area:74.7
Heavy Atom Count:12
Complexity:251
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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