612-23-7

Basic information

• Product Name: 2-NITROBENZYL CHLORIDE
• Synonyms: 1-Nitro-2-(chloromethyl)benzene;2-(Chloromethyl)nitrobenzene, alpha-Chloro-2-nitrotoluene;2-Nitrobenzyl chloride 99%;2-NITROBENZYL CHLORIDE;A-CHLORO-O-NITROTOLUENE;AKOS BBS-00004020;ALPHA-CHLORO-O-NITROTOLUENE;ALPHA-CHLORO-2-NITROTOLUENE
• CAS NO: 612-23-7
• Molecular Formula: C₇H₆ClNO₂
• Molecular Weight: 171.58
• EINECS: 210-300-5
• Mol File: 612-23-7.mol

Chemical Properties

• Melting Point: 46-48 °C(lit.)
• Boiling Point: 127-133 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Yellow to tan/Crystals, Crystalline Powder or Chunks
• Density: 1,556 g/cm3
• Vapor Pressure: 0.0123mmHg at 25°C
• Refractive Index: 1.5557 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: ethanol: soluble98%
• Water Solubility: Soluble in acetone, alcohol benzene, diethyl ether, and ethanol (98%). Insoluble in water.
• Stability: Stable. Incompatible with bases, moisture, acohols, oxidizing agents, amines. Corrodes steel.
• BRN: 388396
• CAS DataBase Reference: 2-NITROBENZYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROBENZYL CHLORIDE(612-23-7)
• EPA Substance Registry System: 2-NITROBENZYL CHLORIDE(612-23-7)

Safety Data

• Hazard Codes: C
• Statements: 34-36
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: XS9092000
• F: 19-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 612-23-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Nitrobenzyl chloride is used as a pharmaceutical intermediate for the synthesis of various drugs and drug candidates. It is particularly useful in the introduction of the photo-labile 2-nitrobenzyl protecting group for the phenolic OH group of tyrosine, which can be selectively removed by light irradiation. This property is useful in the development of drugs that require controlled release or activation upon exposure to light.
Used in Biochemistry Research:
2-Nitrobenzyl chloride has been used in the synthesis of S-(2-nitrobenzyl)cysteine, a modified amino acid that can be incorporated into proteins, such as human erythropoietin. This allows researchers to study the effects of specific modifications on protein function and stability.
Used in Organic Synthesis:
2-Nitrobenzyl chloride is also used in the preparation of various organic compounds, such as 4,4′-dinitrostillbene, which is a fluorescent compound used in the study of molecular interactions and as a probe in chemical biology research.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A halogenated aromatic nitro compound. Aromatic nitro compounds range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups.

Health Hazard

ACUTE/CHRONIC HAZARDS: Toxic. Lachrymator. Causes irritation on contact. Hazardous decomposition products. Mutagen.

Fire Hazard

2-NITROBENZYL CHLORIDE is combustible.

Biochem/physiol Actions

2-Nitrobenzyl chloride reacts with N-methyldiethanolamine and further reaction of the resulting quaternary diol with thionyl chloride at room temperature yields nitrobenzyl mustard quaternary salts.

InChI:InChI=1/C7H6ClNO2/c8-5-6-3-1-2-4-7(6)9(10)11/h1-4H,5H2

Upstream product

• 88-72-2 1-methyl-2-nitrobenzene 
• 612-25-9 2-Nitrobenzyl alcohol 
• 591-09-3 nitro acetate 
• 100-44-7 benzyl chloride 
• 29872-21-7 o-nitrobenzyl iodide 
• 21050-13-5 bis(triphenylphosphine)iminium chloride 
• 91997-40-9 2-nitrobenzyl selenocyanate 
• 85071-27-8 2-nitrobenzyl thiocyanate 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 24974-75-2 2-nitrobenzylsulfonyl chloride 
• 7647-01-0 hydrogenchloride 
• 331463-81-1 3-methoxy-4-(o-nitrobenzyloxy)benzaldehyde 
• 108-88-3 toluene 

Downstream Products

• 55581-63-0 1-(2-nitro-benzyl)-pyrrolidine 
• 50591-66-7 1-[(2-nitrophenyl)methyl]piperidine 
• 117877-52-8 o-nitrobenzyl pyridinium chloride 
• 121159-52-2 4-methyl-3-(2-nitro-benzyl)-thiazolium; chloride 
• 39101-27-4 N-(o-nitrobenzyl)-succinimide 
• 42784-64-5 5-(2-hydroxy-ethyl)-4-methyl-3-(2-nitro-benzyl)-thiazolium; chloride 
• 55581-64-1 N,N-dimethyl-1-(2-nitrophenyl)methylamine 
• 850638-61-8 1,3,5-tris-(2-nitro-benzyl)-hexahydro-[1,3,5]triazine 
• 861296-30-2 2,2-bis-(2-nitro-benzyl)-acetoacetic acid ethyl ester 
• 1904-78-5 2-nitrobenzylamine 
• 285992-78-1 [1]naphthyl-(2-nitro-benzyl)-amine 

Relevant articles and documents

Bambusurils Bearing Nitro Groups and Their Further Modifications

Bambusurils are recently developed neutral anion receptors that show a high affinity towards many inorganic anions, not only in organic solvents but also in water. However, the number of water-soluble bambusurils and also those bearing functional groups is very limited. In this paper we report the synthesis of four- and six-membered bambusurils containing eight and twelve nitro groups. All the nitro groups on the bambusuril portals could be transformed into amino functions, which provided the macrocycles with water solubility and allowed their further modification. For example, we have demonstrated the conversion of amino groups on the bambusurils into the corresponding urea-functionalized bambusuril derivatives. We also report the first example of a bambusuril bearing only two functional groups, which was prepared by the condensation of two different glycolurils.

Synthetic method for o-nitrobenzyl chloride

The invention discloses a synthetic method for o-nitrobenzyl chloride. The synthetic method comprises the following steps: adding a catalyst into o-nitrotoluene, carrying out heating and stirring, slowly introducing chlorine and recovering o-nitrotoluene after completion of reaction so as to obtain o-nitrobenzyl chloride. The synthetic method provided by the invention overcomes defects like low yield and a great number of by-products of conventional thermal chlorination methods and luminescence methods for synthesis of o-nitrobenzyl chloride; the catalyst is added into o-nitrotoluene, chlorine is introduced after heating and stirring, and o-nitrotoluene is recovered after completion of the reaction, so o-nitrobenzyl chloride is obtained; and with the synthetic method provided by the invention, o-nitrobenzyl chloride (in terms of actual consumption of o-nitrotoluene) with a purity of no less than 99% and a yield of no less than 80% can be obtained, higher than the purity and yield of o-nitrobenzyl chloride produced by using the thermal chlorination methods and luminescence methods.

Ortho-nitro benzyl chloride by a synthetic method of preparing pyraclostrobin intermediate (by machine translation)

This invention relates to a kind of the ortho-nitro benzyl chloride preparation pyraclostrobin method for synthesizing intermediate, comprising the following steps: in the ortho-nitro toluene, a catalyst is added, heating and stirring, and slowly inject chlorine, after the end of reaction, recovering O-nitro-toluene, ortho-nitro benzyl chloride obtained; the ortho-nitro benzyl chloride and 1 the [...] (the 4 [...] chlorolphenyl) - 3 the the pyrazole is mellow[...] for etherification reaction, to obtain the 2 [...] [(N -4 the [...] chlorolphenyl) - 3 the pyrazole oxygen radical[...] methyl] nitrobenzene. In this invention to replace nitryl chlorine animal pennitryl bromination animal pen and adjacent to the 1 [...] (the 4 [...] chlorolphenyl) - 3 the reaction the pyrazole is mellow[...], pyraclostrobin intermediates prepared by the 2 [...] [(N -4 the [...] chlorolphenyl) - 3 the pyrazole oxygen radical[...] methyl] nitrobenzene, avoid the use of a defect method for synthesis of O- nitryl bromination animal pen, content can be used for preparing ≥ 98%, yield ≥ 90% ether product. (by machine translation)

Treatment of alcohols with tosyl chloride does not always lead to the formation of tosylates

Treatment of substituted benzyl alcohols with tosyl chloride resulted in the formation of the corresponding chlorides, not the usual tosylates. A series of experiments demonstrated that it was possible to predict whether chlorination or tosylation would occur for substituted benzyl alcohols and pyridine methanols. Treatment of electron withdrawing group-substituted benzyl alcohols with tosyl chloride gave the corresponding chlorides in moderate yields under mild conditions, which provided a simple way to directly prepare chlorides from alcohols.

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.

Oxidation of benzylic alcohols and ethers to carbonyl derivatives by nitric acid in dichloromethane

Nitric acid in dichloromethane may be successfully employed for the oxidation of benzylic alcohols and ethers to the corresponding carbonyl compounds. The proposed method proved to be of general applicability, affording very good yields of aldehydes and ketones and showing interesting chemoselectivity in many instances, allowing competitive aromatic nitration to be avoided, as well as - in the case of aldehydes - any further oxidation to carboxylic acids. The reaction probably proceeds by a radical mechanism, the active species in the oxidation process being NO2. Competitive formation of nitro esters was observed in some cases, whereas poor results were obtained with allylic and non-benzylic substrates. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Nickel-catalyzed benzylic oxidation with NaOCl

Ni(bpy)2Cl2 has been found to be an efficient catalyst for the oxidation of various alkylbenzenes with hypochlorite. Substituted toluenes having electron withdrawing group at 4-position were oxidized to the corresponding substituted benzoic acids in excellent yields.

trans-2,2′-dinitrostilbene as a precursor of 0-nitrobenzaldehyde, a key intermediate for pharmaceuticals: Reactivity and molecular structure studies

A novel synthesis of o-nitrobenzaldehyde by means of the ozonolysis-reductive hydrolysis of symmetrical trans-2,2′-dinitrostilbene is reported, yielding only the ortho isomer of nitrobenzaldehyde. This new route reduces environmental hazards in the synthesis of o-mtrobenzaldehyde. The central ethylene bond of trans-2,2′-dinitrostilbene showed a high reactivity for the ozonolysis reaction. The molecular structures of 2-nitrobenzaldehyde and trans-2,2′-dinitrostilbene were studied theoretically by means of ab initio quantum mechanical calculations at the 6-31G*//6-31G* level. A non-coplanar conformer was found for o-nitrobenzaldehyde, where the carbonyl and nitro groups are slightly twisted with respect to the phenyl ring. Also, a non-coplanar minimal s-trans-gauchels-transgauche conformer (NO2-aryl-C=C-aryl-NO2) was found for trans-2,2′-dinitrostilbene, where the aromatic groups are twisted with respect to the central double bond, and the nitro groups are also twisted out the planes of the aromatic rings. This structure is consistent with certain experimental physical-chemical properties of this molecule.

New applications of tungsten hexachloride (WCl6) in organic synthesis. Halo-de-hydroxylation and dihalo-de-oxo-bisubstitution reactions

Tungsten hexachloride (WCl6) has been used for the halo-de-hydroxylation and dihalo-de-oxo-bisubstitution reactions of benzylic alcohols, benzaldehydes, acyloins, and epoxides to their chlorides, gem-dichlorides, vic-trichlorides, and vic-dichlorides respectively.