29872-21-7

Usage

Appearance

Pale yellow solid

Usage

Organic synthesis, production of pharmaceuticals and fine chemicals

Chemical classification

Nitroaromatic derivative

Functional groups

Nitro group (NO2) and iodomethyl group (CH2I)

Nitro group attachment

Benzene ring

Iodomethyl group function

Introduces other chemical substituents onto the benzene ring

Hazardous material

Yes, requires appropriate handling and storage safety measures

Upstream product

• 612-23-7 2-nitrobenzyl chloride 
• 88-72-2 1-methyl-2-nitrobenzene 
• 100-44-7 benzyl chloride 
• 612-25-9 2-Nitrobenzyl alcohol 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 85071-27-8 2-nitrobenzyl thiocyanate 
• 91997-40-9 2-nitrobenzyl selenocyanate 

Downstream Products

• 85071-27-8 2-nitrobenzyl thiocyanate 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 612-23-7 2-nitrobenzyl chloride 
• 136794-73-5 4'-O-demethyl-4β-[(2''-nitrobenzyl)amino]-4-desoxypodophyllotoxin 
• 143879-96-3 ethyl 1-(2-nitrobenzyl)-2-pyrrolecarboxylate 
• 97420-74-1 1-(2-aminobenzyl)-2-ethoxycarbonyl-1H-imidazole 
• 97420-72-9 1-(2-nitrobenzyl)-2-ethoxycarbonyl-1H-imidazole 
• 153776-33-1 1-(2-nitrobenzyl)-2-trichloroacetyl-1H-imidazole 
• 220368-29-6 2-[(N-4-chlorophenyl)-1H-pyrazol-3-yloxymethyl]-1-nitrobenzene 
• 693788-57-7 bis(2-nitrobenzyl)(2-aminobenzyl)amine 
• 876752-35-1 1-{2-{[bis(2-nitrobenzyl)amino]methyl}phenyl}-3-{6-{3-{2-{[bis(2-nitrobenzyl)amino]methyl}phenyl}ureido}hexyl}urea 
• 876752-36-2 1-{2-{[bis(2-aminobenzyl)amino]methyl}phenyl}-3-{6-{3-{2-{[bis(2-aminobenzyl)amino]methyl}phenyl}ureido}hexyl}urea 
• 693788-56-6 bis(2-nitrobenzyl)(2-azidobenzyl)amine 
• 42467-41-4 2,2'-(oxybis(methylene))bis(nitrobenzene) 

Relevant academic research and scientific papers

Design, synthesis and anticancer activities of novel otobain derivatives

A series of novel racemic otobain derivatives was designed and synthesised using 2-piperonyl-1,3-dithianes in the conjugate addition-alkylation to 5H-furan-2-one, followed by cationic cyclisation. All the synthesised compounds were consequently evaluated for their anticancer activity against several human cancers in vitro. The efficacy of the most active compound 27g was comparable with etoposide, with IC50 values ranging from 1.06 μM to 4.16 μM in different cancer cell lines. Notably, compound 27g strongly induced cell cycle arrest and increased the expression of mitosis-specific markers MPM-2 and phosphorylated histone H3, but it did not trigger cell apoptosis. Further a colony formation assay showed that compound 27g effectively inhibited the anchor growth of lung cancer cells in a dose-dependent manner. More importantly, compound 27g at 40 mg kg-1 significantly suppressed tumour volume (P 0.01) and tumour weight (P 0.05) in a human lung cancer cell xenograft mouse model without causing systematic toxicity in mice. Our findings indicated that compound 27g has significant potential for further drug development.

Synthesis of 2 [(N-4-chlorphenyl)-1H-pyrazol-3-yloxymethyl] nitrobenzene

The invention discloses synthesis of 2 [(N-4-chlorphenyl)-1H-pyrazole-3-yloxymethyl] nitrobenzene, which comprises the following steps of: synthesizing o-nitrobenzyl iodide from o-nitrotoluene, potassium iodide and hydrogen peroxide in a diluted hydrochloric acid system, and then reacting the o-nitrobenzyl iodide with 1-(4-chlorphenyl)-3-pyrazole alcohol to obtain 2 [(N-4-chlorphenyl)-1H-pyrazole-3-yloxymethyl] nitrobenzene. According to the synthetic method of the 2 [(N-4-chlorphenyl)-1H-pyrazol-3-yloxymethyl] nitrobenzene, almost no by-product is generated, diiodo compounds are not easy to generate, and the conversion rate of o-nitrotoluene is high and can reach 99% or above.

Scalable, easy synthesis, and efficient isolation of arylnitromethanes: a revival of the Victor Meyer reaction

A modified approach to synthesize and isolate arylnitromethanes is described. The method takes advantage of the significant difference in acidity between the arylnitromethane and the major impurity of the reaction, the nitrite ester. The arylnitromethanes resulting from this process are obtained in high yields and are analytically pure, i.e., they do not require distillation or further purification, which is a comfortable improvement of the ancestral Victor Meyer reaction.

Novel aminotetrazole derivatives as selective STAT3 non-peptide inhibitors

The development of inhibitors blocking STAT3 transcriptional activity is a promising therapeutic approach against cancer and inflammatory diseases. In this context, the selectivity of inhibitors against the STAT1 transcription factor is crucial as STAT3 and STAT1 play opposite roles in the apoptosis of tumor cells and polarization of the immune response. A structure-based virtual screening followed by a luciferase-containing promoter assay on STAT3 and STAT1 signaling were used to identify a selective STAT3 inhibitor. An important role of the aminotetrazole group in modulating STAT3 and STAT1 inhibitory activities has been established. Optimization of the hit compound leads to 23. This compound inhibits growth and survival of cells with STAT3 signaling pathway while displaying a minimal effect on STAT1 signaling. Moreover, it prevents lymphocyte T polarization into Th17 and Treg without affecting their differentiation into Th1 lymphocyte.

4-Aminophenyldiphenylphosphinite (APDPP), a new heterogeneous and acid scavenger phosphinite - Conversion of alcohols, trimethylsilyl, and tetrahydropyranyl ethers to alkyl halides with halogens or N-halosuccinimides

A new heterogeneous phosphinite, 4-aminophenyldiphenylphosphinite (APDPP), is prepared and used for the efficient conversion of alcohols, trimethylsilyl ethers, and tetrahydropyranyl ethers to their corresponding bromides, iodides, and chlorides in the presence of molecular halogens or N-halosuccinimides. The amino group in this phosphinite acts as an acid scavenger and removes the produced acid. A simple filtration easily removes the phosphinate by-product.

Convenient and efficient method for the iodination of benzylic and aliphatic alcohols by using Al(HSO4)3/KI in nonaqueous solution

A simple and efficient method for the iodination of benzylic and aliphatic alcohols by using Al(HSO4)3/KI in n-hexane as solvent is reported. Mild reaction conditions and good to excellent yields of the products are the noteworthy advantages of the method. Copyright Taylor & Francis LLC.

Facile preparation of benzylic iodides under solvent-free conditions using microwave irradiation

Benzylic alcohols are rapidly converted to the corresponding benzylic iodides using combination of p-toluenesulfonic acid (PTSA) and potassium iodide under solvent-free microwave irradiation conditions.

Self-Assembly of Tris,(2-ureidobenzyl)amines: A New Type of Capped, Capsule-Like Dimeric Aggregates Derived from a Highly Flexible Skeleton

A set of tris(2-ureidobenzyl)-amines 3 was prepared and their dimerization processes thoroughly investigated. In spite of their inherent flexibility, tris(ureas) 3 form dimeric aggregates both in the solid state and in solution. Evidence for the existence

Antitumor agents. 120. New 4-substituted benzylamine and benzyl ether derivatives of 4'-O-demethylepipodophyollotoxin as potent inhibitors of human DNA topoisomerase II

A number of new 4'-O-demethylepipodophyllotoxin derivatives possessing various 4β-N- or 4β-O-benzyl groups have been synthesized and evaluated for their inhibitory activity against the human DNA topoisomerase II as well as for their activity in causing cellular protein-linked DNA breakage. The 4β-N-benzyl derivatives 9-22 are, in general, as active or more active than etoposide (1). The most active compounds are 14, 16, and 17, which are more than 2-fold more potent than 1. The results indicated that a basic unsubstituted 4β-benzylamino moiety is structurally required for the enhanced activity. Replacement of the benzyl nitrogen with oxygen gave compounds (23 and 24) which are inactive. The ability of these compounds to inhibit human DNA topoisomerase II and to cause protein-linked DNA breakage appears to have no direct correlation with cytotoxicity in KB cells.

Substitution Reactions toward 2-Nitrobenzyl Pseudohalides. The Crystal Structure of 2-Nitrobenzyl Tellurocyanate

The reactions between 2-nitrobenzyl pseudohalides, 2-NO2-PhCH2XCN, and pseudohalide ions, NCX- (X = S, Se or Te) have been studied kinetically in acetonitrile at 25.0 deg C.The reactions proceed through nucleophilic attack at the methylene carbon atom, forming exclusively the exchange products.The average nucleophilicity order, NCTe- >> NCSe- > NCS-, and the average leaving group order, NCTe- >/= NCSe- >/= NCS-, lead to a carbon basicity order NCTe- > NCSe- >/= NCS-, which is confirmed with equilibrium studies.A crystal structure determination of 2-nitrobenzyl tellurocyanate at ca. 135 deg C has revealed that the TeCN group is syn-clinal (gauche) to the C(CH2)-C(Ar) bond with a torsion angle of -48.5(5) deg.The TeCC plane forms an angle of 103.4(5) deg with the phenyl ring plane.In this conformation the steric influence of the 2-NO2 group in substitution reactions at the methylene carbon atom will be negligible except for bulky nucleophiles.The tellurium atom forms two fairly strong intermolecular bonds to nitrogen atoms from neighbouring tellurocyanate groups, viz. 2.889(6) Angstroem trans to the cyano group and 3.382(6) Angstroem trans to the methylene group.In the crystalline state the compound may be considered both as a tellurium(II) complex and as an organic pseudohalide.No intermolecular tellurium-oxygen contacts could be observed.