3913-23-3

Basic information

• Product Name: 2-METHOXY-5-NITROBENZYL BROMIDE
• Synonyms: 2-(bromomethyl)-1-methoxy-4-nitro-benzen;2-(bromomethyl)-4-nitro-anisol;alpha-bromo-2-methoxy-6-nitro-toluen;koshlandreagentno.2;2-BROMOMETHYL-4-NITROANISOLE;2-METHOXY-5-NITROBENZYL BROMIDE;KOSHLAND II;KOSHLAND'S REAGENT II
• CAS NO: 3913-23-3
• Molecular Formula: C₈H₈BrNO₃
• Molecular Weight: 246.06
• EINECS: 223-471-6
• Product Categories: Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 3913-23-3.mol

Chemical Properties

• Melting Point: 76-78 °C(lit.)
• Boiling Point: 348.7 °C at 760 mmHg
• Flash Point: 164.7 °C
• Appearance: UN 3261
• Density: 1.589±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 9.94E-05mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-METHOXY-5-NITROBENZYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHOXY-5-NITROBENZYL BROMIDE(3913-23-3)
• EPA Substance Registry System: 2-METHOXY-5-NITROBENZYL BROMIDE(3913-23-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: XS7966500
• F: 19-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3913-23-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxy-5-nitrobenzyl bromide is used as a modifying agent for enhancing the activity of tryptophan residues in mouse interferon. This modification improves the effectiveness of the interferon, which plays a crucial role in the immune response against various diseases and conditions.
Used in Chemical Synthesis:
2-Methoxy-5-nitrobenzyl bromide is used as a reagent for sulfhydryl modification, which is an essential process in the synthesis of certain chemicals and compounds. Its ability to modify sulfhydryl groups makes it a valuable tool in the development of new chemical entities and pharmaceuticals.

Biochem/physiol Actions

2-Methoxy-5-nitrobenzyl bromide inactivates cytochrome P-450 in male rat liver microsomes.

InChI:InChI=1/C8H8BrNO3/c1-13-8-3-2-7(10(11)12)4-6(8)5-9/h2-4H,5H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 100-17-4 para-methoxynitrobenzene 
• 5804-49-9 2-methoxy-5-nitrophenylmethanol 
• 10035-10-6 hydrogen bromide 
• 7383-11-1 2-aminomethyl-4-nitro-phenol 
• 25016-02-8 2-methoxy-5-nitrobenzaldehyde 
• 39224-61-8 2-hydroxy-5-nitrobenzyl alcohol 

Downstream Products

• 853655-27-3 6-(3-tert-butyl-ureido)-2-(2-methoxy-5-nitro-benzylsulfanyl)-3-propyl-3H-benzoimidazole-4-carboxylic acid methyl ester 
• 954123-81-0 tert-butyl 4-((2-methoxy-5-nitrobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate 

Relevant articles and documents

THERAPEUTIC COMPOUNDS

The invention provides compounds of formula (I): wherein, A, C, D, X, and Y have any of the values defined in the specification, and salts thereof. The compounds are SIRT2 inhibitors and are useful for treating SIRT2 associated conditions.

New hits as antagonists of GPR103 identified by HTS

Preclinical data indicate that GPR103 receptor and its endogenous neuropeptides QRFP26 and QRFP43 are involved in appetite regulation. A high throughput screening (HTS) for small molecule GPR103 antagonists was performed with the clinical goal to target weight management by modulation of appetite. A high hit rate from the HTS and initial low confirmation with respect to functional versus affinity data challenged us to revise the established screening cascade. To secure high quality data while increasing throughput, the binding assay was optimized on quality to run at single concentration. This strategy enabled evaluation of a larger fraction of chemical clusters and singletons delivering 17 new compound classes for GPR103 antagonism. Representative compounds from three clusters are presented. One of the identified clusters was further investigated, and an initial structure-activity relationship study is reported. The most potent compound identified had a pIC50 of 7.9 with an improved ligand lipophilic efficiency.

COMPOUNDS THAT MODULATE EGFR ACTIVITY AND METHODS FOR TREATING OR PREVENTING CONDITIONS THEREWITH

Provided are compounds and methods for treating or preventing kinase-mediated disorders therewith.

Discovery of a clinical stage multi-kinase inhibitor sodium (E)-2-{2-methoxy-5-[(2′,4′,6′-trimethoxystyrylsulfonyl)methyl] phenylamino}acetate (ON 01910.Na): Synthesis, structure-activity relationship, and biological activity

Cyclin D proteins are elevated in many cancer cells, and targeted deletion of cyclin D1 gene in the mammary tissues protects mice from breast cancer. Accordingly, there is an increasing awareness of this novel nonenzymatic target for cancer therapeutics. We have developed novel, nonalkylating styrylbenzylsulfones that induce cell death in wide variety of cancer cells without affecting the proliferation and survival of normal cells. The development of derivatized styrylbenzylsulfones followed logically from a tumor cell cytotoxicity screen performed in our laboratory that did not have an a priori target profile. Modifications of some of the precursor molecules led to lead optimization with regard to tumor cell cytotoxicity. In this report we describe the synthesis and structure-activity relationships of novel, nonalkylating (E)-styrylbenzylsulfones and the development of the novel anticancer agent sodium (E)-2-{2-methoxy-5-[(2′,4′,6′- trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na), which is in phase III trials for myelodysplastic syndromes (MDS) associated with aberrant expression of cyclin D proteins.

N-phenyl-N-acetamidoglycinamides, their preparation and medicaments containing them

Compounds of formula: STR1 in which R1 represents a hydrogen atom or an alkyl, alkoxycarbonyl or an unsubstituted or substituted phenyl radical, R2 represents a hydrogen atom or an unsubstituted or substituted alkyl radical, R3 represents an alkyl, phenylalkyl, indanyl, cycloalkylalkyl or an unsubstituted or substituted phenyl radical, or R2 and R3 form a heterocycle together with the nitrogen atom to which they are attached, and R4 represents an unsubstituted or substituted phenyl radical, a naphthyl, indolyl or quinolyl radical or a phenylamino radical in which the phenyl ring is unsubstituted or substituted, their preparation and medicaments containing them.