3-N-Maleimidobenzoic acid
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3-N-Maleimidobenzoic acid

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3-N-Maleimidobenzoic acid (CAS# 17057-07-7 ) is a useful research chemical.

Category
Cyclic Amino Acids
Catalog number
BAT-004856
CAS number
17057-07-7
Molecular Formula
C11H7NO4
Molecular Weight
217.18
3-N-Maleimidobenzoic acid
IUPAC Name
3-(2,5-dioxopyrrol-1-yl)benzoic acid
Synonyms
3-Maleimido-benzoic acid; 3-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid; 3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoic acid; NSC201626
Appearance
Light yellow powder
Purity
≥ 95 % (NMR)
Density
1.5±0.1 g/cm3
Melting Point
228-229 ℃
Boiling Point
455.2±28.0 ℃ at 760 mmHg
Storage
Store at 2-8 ℃
InChI
InChI=1S/C11H7NO4/c13-9-4-5-10(14)12(9)8-3-1-2-7(6-8)11(15)16/h1-6H,(H,15,16)
InChI Key
ZJGBFJBMTKEFNQ-UHFFFAOYSA-N
Canonical SMILES
C1=CC(=CC(=C1)N2C(=O)C=CC2=O)C(=O)O
1. Atroposelective Synthesis of 1,1'-Bipyrroles Bearing a Chiral N-N Axis: Chiral Phosphoric Acid Catalysis with Lewis Acid Induced Enantiodivergence
Yaru Gao, Luo-Yu Wang, Tao Zhang, Bin-Miao Yang, Yu Zhao Angew Chem Int Ed Engl. 2022 Apr 11;61(16):e202200371. doi: 10.1002/anie.202200371. Epub 2022 Feb 24.
We present herein a highly efficient atroposelective synthesis of axially chiral 1,1'-bipyrroles bearing an N-N linkage from simple hydrazine and 1,4-diones. Further product derivatizations led to axially chiral bifunctional compounds with high potential in asymmetric catalysis. For this chrial phosphoric acid (CPA)-catalyzed double Paal-Knorr reaction, an intriguing Fe(OTf)3 -induced enantiodivergence was also observed.
2. The Stephan Curve revisited
William H Bowen Odontology. 2013 Jan;101(1):2-8. doi: 10.1007/s10266-012-0092-z. Epub 2012 Dec 6.
The Stephan Curve has played a dominant role in caries research over the past several decades. What is so remarkable about the Stephan Curve is the plethora of interactions it illustrates and yet acid production remains the dominant focus. Using sophisticated technology, it is possible to measure pH changes in plaque; however, these observations may carry a false sense of accuracy. Recent observations have shown that there may be multiple pH values within the plaque matrix, thus emphasizing the importance of the milieu within which acid is formed. Although acid production is indeed the immediate proximate cause of tooth dissolution, the influence of alkali production within plaque has received relative scant attention. Excessive reliance on Stephan Curve leads to describing foods as "safe" if they do not lower the pH below the so-called "critical pH" at which point it is postulated enamel dissolves. Acid production is just one of many biological processes that occur within plaque when exposed to sugar. Exploration of methods to enhance alkali production could produce rich research dividends.
3. Organocatalytic asymmetric synthesis of β(3)-amino acid derivatives
Sun Min Kim, Jung Woon Yang Org Biomol Chem. 2013 Aug 7;11(29):4737-49. doi: 10.1039/c3ob40917a. Epub 2013 Jun 7.
β(3)-Amino acid derivatives are an essential resource for pharmaceutical production, medicinal chemistry, and biochemistry. In this article, recent developments in versatile organocatalysis, i.e., Brønsted acid catalysis, Brønsted base catalysis, Lewis acid catalysis, Lewis base catalysis, and phase-transfer catalysis, for the asymmetric synthesis of β(3)-amino acid derivatives will be presented.
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