80866-80-4

Basic information

• Product Name: 2-CHLORO-5-NITROBENZYL ALCOHOL
• Synonyms: 2-CHLORO-5-NITROBENZYL ALCOHOL;(2-CHLORO-5-NITROPHENYL)METHANOL;RARECHEM AL BD 0191;2-Chloro-5-nitrobenzenemethanol;2-Chloro-5-nitrobenzyl alcohol,97%;2-Chloro-5-nitrobenzyl alcohol 97%
• CAS NO: 80866-80-4
• Molecular Formula: C₇H₆ClNO₃
• Molecular Weight: 187.58
• EINECS: 279-584-6
• Product Categories: Benzhydrols, Benzyl & Special Alcohols;Alcohols;C7 to C8;Oxygen Compounds
• Mol File: 80866-80-4.mol

Chemical Properties

• Melting Point: 75-79 °C(lit.)
• Boiling Point: 344.1 °C at 760 mmHg
• Flash Point: 161.9 °C
• Appearance: Beige/Powder
• Density: 1.4219 (rough estimate)
• Vapor Pressure: 2.56E-05mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• PKA: 13.40±0.10(Predicted)
• BRN: 3248759
• CAS DataBase Reference: 2-CHLORO-5-NITROBENZYL ALCOHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-5-NITROBENZYL ALCOHOL(80866-80-4)
• EPA Substance Registry System: 2-CHLORO-5-NITROBENZYL ALCOHOL(80866-80-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 80866-80-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Chloro-5-nitrobenzyl alcohol is used as a key intermediate in the preparation of macrobicyclic triphosphazides and tri-λ5-phosphazenes. These compounds have potential applications in various fields, such as materials science, pharmaceuticals, and catalysis, due to their unique properties and structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-chloro-5-nitrobenzyl alcohol can be used as a building block for the synthesis of various drug candidates. Its unique functional groups allow for the development of new chemical entities with potential therapeutic applications.
Used in Materials Science:
2-Chloro-5-nitrobenzyl alcohol can be utilized in the development of novel materials with specific properties, such as high thermal stability, chemical resistance, or unique optical characteristics. These materials can find applications in various industries, including aerospace, automotive, and electronics.
Used in Catalysts:
The presence of the chloro and nitro groups in 2-chloro-5-nitrobenzyl alcohol makes it a potential candidate for use in the development of catalysts for various chemical reactions. These catalysts can improve the efficiency and selectivity of chemical processes, leading to more sustainable and environmentally friendly production methods.

InChI:InChI=1/C7H6ClNO3/c8-7-2-1-6(9(11)12)3-5(7)4-10/h1-3,10H,4H2

Upstream product

• 6361-21-3 2-chloro-5-nitrobenzaldehyde 
• 2516-96-3 2-chloro-5-nitrobenzoic acid 

Downstream Products

• 100527-80-8 2-(2-chloro-5-nitro-benzyloxy)-5-nitro-benzaldehyde 
• 52427-01-7 2-(bromomethyl)-1-chloro-4-nitrobenzene 
• 902140-48-1 5-azido-2-chlorobenzyl chloride 
• 902140-50-5 5-azido-2-chlorobenzylamine 
• 902140-45-8 5-azido-2-chlorobenzyl alcohol 
• 902140-49-2 N-(5-azido-2-chlorobenzyl)phthalimide 
• 902140-51-6 N,N-bis(5-azido-2-bromobenzyl)-N-(5-azido-2-chlorobenzyl)amine 
• 902140-67-4 C₆₂H₅₄Br₂ClN₁₀P₃ 
• 1341693-01-3 4-chloro-3-[(cyclopentylsulfanyl)methyl]aniline 
• 1569737-05-8 N-{4-chloro-3-[(cyclopentylsulfanyl)methyl]phenyl}thiophene-2-carboximidamide 
• 1251929-41-5 tert-butyl N-[3-(bromomethyl)-4-chlorophenyl]carbamate 
• 1569737-95-6 tert-butyl N-[4-chloro-3-[(cyclopentylsulfanyl)methyl]phenyl]carbamate 
• 105191-50-2 <(5-Cyan-1,1-dioxobenzothien-2-yl)methyl>triphenylphosphoniumbromid 
• 105191-33-1 <(5-Cyanbenzothien-2-yl)methyl>triphenylphosphoniumbromid 

Relevant articles and documents

Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water

Developing and/or modifying fundamental chemical reactions using chemical industry-favorite heterogeneous recoverable catalytic systems in the water solvent is very important. In this paper, we developed convenient, green, and efficient approaches for the chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes in the presence of the recoverable heterogeneous carbon-supported palladium (Pd/C) catalytic system in water. The utilize of the simple, effective, and recoverable catalyst and also using of water as an entirely green solvent along with relatively short reaction times and good-to-excellent yields of the desired products are some of the noticeable features of the presented synthetic protocols. Graphic abstract: [Figure not available: see fulltext.].

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

Storing redox equivalent in the phenalenyl backbone towards catalytic multi-electron reduction

Storing and transferring electrons for multi-electron reduction processes are considered to be the key steps in various important chemical and biological transformations. In this work, we accomplished multi-electron reduction of a carboxylic acid via a hydrosilylation pathway where a redox-active phenalenyl backbone in Co(PLY-O,O)2(THF)2, stores electrons and plays a preponderant role in the entire process. This reduction proceeds by single electron transfer (SET) from the mono-reduced ligand backbone leading to the cleavage of the Si-H bond. Several important intermediates along the catalytic reduction reaction have been isolated and well characterized to prove that the redox equivalent is stored in the form of a C-H bond in the PLY backbone via a ligand dearomatization process. The ligand's extensive participation in storing a hydride equivalent has been conclusively elucidated via a deuterium labelling experiment. This is a rare example where the ligand orchestrates the multielectron reduction process leaving only the metal to maintain the conformational requirements and fine tunes the electronics of the catalyst.

CK2 INHIBITORS, COMPOSITIONS AND METHODS THEREOF

The present invention provides synthesis, pharmaceutically acceptable formulations and uses of compounds in accordance with Formula (I), or a stereoisomer, a tautomer or a pharmaceutically acceptable salt thereof. For Formula (I) compounds R1, R2, R3, Ar and Z are as defined in the specification. The inventive Formula (I) compounds are inhibitors of CK2 and find utility in any number of therapeutic applications, including but not limited to treatment of proliferative disorders such as cancer, inflammation and immunological disorders.

Transfer hydrogenation of aromatic and linear aldehydes catalyzed using Cp*Ir(pyridinesulfonamide)Cl complexes under base-free conditions

Cp*Ir(pyridinesulfonamide)Cl (Cp*?=?pentamethylcyclopentadienyl) precatalysts 1–7 are active for the transfer hydrogenation of aryl, alkyl, and heterocyclic aldehydes. Catalysis is conducted under base-free conditions in air without dried or degassed substrates and solvents. These reductions occur rapidly in moderate to high conversion (39–100%). Benzaldehyde derivatives are reduced to alcohols within 30?min?at 85?°C using 1?mol% iridium precatalyst; reduction also occurs at lower temperatures and loadings (60?°C, 0.50?mol% precatalyst). Benzaldehyde derivatives that possess electron-rich and electron-poor substituents in the para position, including base-sensitive 4-hydroxybenzaldehyde, are readily reduced. Aryl aldehydes containing electron-poor groups are reduced faster than substrates possessing electron-rich moieties. Reduction of the positional isomers of methoxybenzaldehyde and isopropylbenzaldehyde shows highest reduction for the ortho isomer, followed by the meta isomer. Heterocyclic substrates, including biomass derived 5-hydroxymethylfurfural and 2-furfural, were reduced selectively to the alcohol. Decyl aldehyde was reduced to the linear alcohol; importantly self-condensation was not observed. Competition studies demonstrated selective reduction of aldehydes over ketones and a mercury poisoning experiment supports a homogeneous catalyzed pathway.

N-Benzyl-4-((heteroaryl)methyl)benzamides: A New Class of Direct NADH-Dependent 2-trans Enoyl-Acyl Carrier Protein Reductase (InhA) Inhibitors with Antitubercular Activity

Isoniazid (INH) remains one of the cornerstones of antitubercular chemotherapy for drug-sensitive strains of M.tuberculosis bacteria. However, the increasing prevalence of multidrug-resistant (MDR) and extensively drug-resistant (XDR) strains containing mutations in the KatG enzyme, which is responsible for the activation of INH into its antitubercular form, have rendered this drug of little or no use in many cases of drug-resistant tuberculosis. Presented herein is a novel family of antitubercular direct NADH-dependent 2-trans enoyl-acyl carrier protein reductase (InhA) inhibitors based on an N-benzyl-4-((heteroaryl)methyl)benzamide template; unlike INH, these do not require prior activation by KatG. Given their direct InhA target engagement, these compounds should be able to circumvent KatG-related resistance in the clinic. The lead molecules were shown to be potent inhibitors of InhA and showed activity against M.tuberculosis bacteria. This new family of inhibitors was found to be chemically tractable, as exemplified by the facile synthesis of analogues and the establishment of structure-activity relationships. Furthermore, a co-crystal structure of the initial hit with the enzyme is disclosed, providing valuable information toward the design of new InhA inhibitors for the treatment of MDR/XDR tuberculosis.

SUBSTITUTED PYRROLO[1,2-A]PYRIMIDINES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted pyrrolo[l,2-a]pyrimi dines and related organic compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted pyrrolo[1,2-a]pyrimidines compounds described herein include substituted 2,4-dimethyl-N-phenylpyrrolo[l,2-a]pyrimidine-8-carboxamide compounds and variants thereof.

SUBSTITUTED IMIDAZO[1,5-A]PYRIMIDINES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted imidazo[1,5-a]pyrimidines and related organic compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted imidazo[1,5-a]pyrimidine compounds described herein include substituted 2,4-dimethyl-N-phenylimidazo[1,5-a]pyrimidine-8-carboxamide compounds and variants thereof.

SUBSTITUTED PYRAZOLO(1,5-A)PYRIMIDINES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted pyrazolo[l,5-a]pyrimidine and related organic compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted pyrazolo[l,5-a]pyrimidine compounds described herein include 5,7- dimethyl-N-phenylpyrazolo[l,5-a]pyrimidine-3-carboxamide compounds and variants thereof.

Synthesis of N-carboxyalkyl-1,4-benzothiazepine-3(2H)-one derivatives using esters of N-(2-chloro-5-nitrobenzyl)amino acids

Two alternative approaches for synthesis of esters of N-(2-chloro-5- nitrobenzyl) amino acids have been developed and compared. We have found synthesis of N-(2-chloro-5-nitrobenzyl) amino acids via alkylation of esters of amino acids in DMF in the presence of Et3N and NaI to be more convenient and have higher yields in comparison with reduction of Schiff bases obtained from 2-chloro-5-nitrobenzaldehyde and corresponding esters of amino acids by NaBH4. Treatment of the solutions of esters of N-(2-chloro-5-nitrobenzyl) amino acids in DMSO with methyl thioglycolate and following intramolecular acylation in xylene led to N-carboxyalkyl-1,4- benzothiazepine-3(2H)-one derivatives in 24-76 % yields. Graphical abstract: [Figure not available: see fulltext.]