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M9775

Sigma-Aldrich

4-(N-Maleimido)benzophenone

Synonym(s):

Benzophenone-4-maleimide

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About This Item

Empirical Formula (Hill Notation):
C17H11NO3
CAS Number:
92944-71-3
Molecular Weight:
277.27
MDL number:
MFCD00079465
UNSPSC Code:
12352100
PubChem Substance ID:
57654429
NACRES:
NA.22

reaction suitability

reagent type: cross-linking reagent

solubility

chloroform: 50 mg/mL
DMF: soluble

storage temp.

2-8°C

SMILES string

O=C1C=CC(=O)N1c2ccc(cc2)C(=O)c3ccccc3

InChI

1S/C17H11NO3/c19-15-10-11-16(20)18(15)14-8-6-13(7-9-14)17(21)12-4-2-1-3-5-12/h1-11H

InChI key

OZIZEXQRIOURIJ-UHFFFAOYSA-N

Application

A heterobifunctional cross-linking reagent containing a sulfhydryl-specific group and a photo-active group. Typically, coupled initially by thioether to molecule containing free sulfhydryl buffered at pH 6.8 (6.5-7.0). Second bonding occurs during UV irradiation (250 nm) via diradical excited state. Benzophenones demonstrate greater specificity for C-H insertion and are more stable in water than analogous reagents. In general they are more efficient in attachment because they may be repeatedly irradiated; however, a more intense irradiation may be required. The benzophenone is not sensitive to reduction compared to analogous reagents.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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L Sahlman et al.
The Journal of biological chemistry, 272(47), 29518-29526 (1997-12-31)
Bacterial detoxification of mercuric ion depends on the presence of one or more integral membrane proteins (MerT and/or MerC) whose postulated function is in transport of Hg2+ from a periplasmic Hg2+-binding protein (MerP) to cytoplasmic mercuric reductase. In this study
Mayumi Tamura et al.
Biological & pharmaceutical bulletin, 34(6), 929-932 (2011-06-02)
LEC-1 is the first tandem repeat-type galectin isolated from an animal system; this galectin has two carbohydrate recognition domains in a single polypeptide chain. Because its two lectin domains have different sugar-binding profiles, these domains are thought to interact with
Y Luo et al.
Journal of molecular biology, 296(3), 899-910 (2000-03-15)
The interaction sites of rabbit skeletal troponin I (TnI) with troponin C (TnC), troponin T (TnT), tropomyosin (Tm) and actin were mapped systematically using nine single cysteine residue TnI mutants with mutation sites at positions 6, 48, 64, 89, 104
S Basu et al.
The Biochemical journal, 296 ( Pt 3), 577-583 (1993-12-15)
Treatment of murine leukaemia virus reverse transcriptase with benzophenone 4-maleimide inactivates DNA polymerase activity, but has no effect on the RNAase H function. Kinetic measurements indicated that benzophenone 4-maleimide is a competitive inhibitor with respect to template-primer binding, but is
Yoichiro Arata et al.
Biochemistry, 41(37), 11301-11307 (2002-09-11)
Using a combination of cysteine mutagenesis and covalent cross-linking, we have identified subunits in close proximity to specific sites within subunit B of the vacuolar (H(+))-ATPase (V-ATPase) of yeast. Unique cysteine residues were introduced into subunit B by site-directed mutagenesis
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