610-40-2

Usage

Uses

Used in Organic Synthesis:
3,4-Dinitrochlorobenzene is used as a reactant in organic synthesis for the production of various chemical compounds. Its reactivity allows it to undergo a range of chemical reactions, making it a versatile building block for the synthesis of different organic molecules.
Used in Chemical Research:
3,4-Dinitrochlorobenzene is also used in chemical research as a model compound to study various reaction mechanisms and pathways. Its unique structure and reactivity make it an interesting subject for researchers to explore and understand the underlying principles of chemical reactions.
Used in Pharmaceutical Industry:
3,4-Dinitrochlorobenzene is used as an intermediate in the synthesis of certain pharmaceutical compounds. Its ability to participate in various chemical reactions allows for the creation of new drug candidates with potential therapeutic applications.
Used in Dye Industry:
3,4-Dinitrochlorobenzene is used as a starting material in the production of certain dyes and pigments. Its chemical properties enable the formation of colored compounds that can be used in various applications, such as textiles, plastics, and printing inks.
Used in Pesticide Industry:
3,4-Dinitrochlorobenzene is used as a chemical intermediate in the synthesis of some pesticides. Its reactivity and ability to form various chemical compounds make it a valuable component in the development of effective pest control agents.

History

Securinine was first isolated by a Soviet scholar from the Wusuli region, but its chemical structure was separated and finally determined by Chinese scholars from local sources . The main structural feature is a tetracyclic compound containing an indolizine, pyrrole elidine, or quinolizine ring and an α, β-unsaturated pentahydrin ring whose basic structural skeleton type is as shown in what follows .Owing to the complexity of the chemical reaction of securinine, reports on its chemical reactivity and structural modification have been relatively scarce since securinine was reported on in 1956. However, the research on chemical total synthesis and biological activities of securinine has made a certain amount of progress.Securinine has a rigid molecular structure containing four rings and three chiral centers, which makes synthesis difficult. From 1974 to 1978, three research groups from Japan, the USA, and Canada studied the biosynthesis of securinine by feeding animals with isotope-labeled S. suffruticosa.

Indications

Poliomyelitis sequela and facial paralysis, neurasthenia, hypotension, autonomic dysfunction, and others

Pharmacology

The pharmacological effect of securinine is mainly manifested as a central nervous system excitatory effect. As a GABA receptor inhibitor, it has an excitatory effect similar to that of strychnine on the spinal cord. A low dose of securinine can improve the excitability of brain reflection, while a high dose of securinine will cause febrile seizures, and at the same time securinine can strengthen the conditioned reflex of the cerebral cortex, shorten the latency period, and promote learning and memory capability , and so it is expected to be a promising drug for the treatment of Alzheimer’s disease.，Securinine can improve the hematopoietic environment of patients with aplastic anemia, promote cell proliferation, have a synergistic anti-tumor effect in combination with cyclophosphamide (CTX), and can antagonize bone marrow suppression caused by CTX.?It has an inhibitory effect on cell proliferation of human leukocyte cell K562 and four other kinds of tumor cells.

Clinical Use

In recent years, securinine has been widely used in clinical practice, mainly for the treatment of polio sequelae and facial nerve palsy. It also has a certain effect on neurasthenia, hypotension and dizziness, tinnitus, and deafness caused by autonomic dysfunction. The nitrate and hydrochloride of left-handed securinine are mainly used clinically. In addition, securinine eye drops are found to have a remarkable effect on the treatment of herpes simplex keratitis through initial clinical observation.

InChI:InChI=1/C6H3ClN2O4/c7-4-1-2-5(8(10)11)6(3-4)9(12)13/h1-3H

Synthetic route

3-Chloronitrobenzene (121-73-3) → 3,4-dinitro-chlorobenzene (610-40-2)

Conditions	Yield
With sulfuric acid; nitric acid at 30℃; for 1h;	97%
With sulfuric acid; uronium nitrate at 0 - 20℃; Nitration;	77%
With sulfuric acid; potassium nitrate
With sulfuric acid; potassium nitrate

4-Chloro-2-nitroaniline (89-63-4) → 3,4-dinitro-chlorobenzene (610-40-2)

Conditions	Yield
With sulfuric acid; acetic acid; tetra-n-propylammonium bromate for 1.5h; Heating;	86%

3,4-dinitroaniline (610-41-3) → 3,4-dinitro-chlorobenzene (610-40-2)

Conditions	Yield
With phosphonic Acid; nitrosylsulfuric acid; sulfuric acid Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuCl in konz. wss. HCl;

2-Chloronitrobenzene (88-73-3) → 3,4-dinitro-chlorobenzene (610-40-2)

Conditions	Yield
durch Nitrieren;

3,4-dinitophenol (577-71-9) → 3,4-dinitro-chlorobenzene (610-40-2)

Conditions	Yield
With trichlorophosphate In N,N-dimethyl-formamide for 2h; Ambient temperature;

α-form → 3,4-dinitro-chlorobenzene (610-40-2)

Conditions	Yield
at 39 - 40℃; (Herstellung der β-Form);

β-form → 3,4-dinitro-chlorobenzene (610-40-2)

Conditions	Yield
at 42℃; (Herstellung der fluessigen Form);

3-Chloronitrobenzene (121-73-3) + sulfuric acid (7664-93-9) + nitric acid (7697-37-2) → 3,4-dinitro-chlorobenzene (610-40-2)

3,4-dinitro-chlorobenzene (610-40-2) → 4-Chloro-1,2-phenylenediamine (95-83-0)

Conditions	Yield
With sodium tetrahydroborate; C16H18Cl2N4O2Pd In water at 27℃; for 0.25h;	99%
With hydrogenchloride; tin
With sodium tetrahydroborate In water at 20℃; for 40h;

3,4-dinitro-chlorobenzene (610-40-2) + 1,2-bis(4-methoxyphenyl)-1,2-ethanedione (1226-42-2) → 6-chloro-2,3-bis(4-methoxyphenyl)quinoxaline

Conditions	Yield
With tin(ll) chloride In ethanol; water for 4h; Reflux;	98%

formic acid (64-18-6) + 3,4-dinitro-chlorobenzene (610-40-2) → 5-chloro-1H-benzimidazole (4887-82-5)

Conditions	Yield
With gold nano particles supported on rutile TiO2 In toluene at 70℃; under 750.075 Torr; for 6h; Inert atmosphere; chemoselective reaction;	95%

4,4'-dibromobenzil (35578-47-3) + 3,4-dinitro-chlorobenzene (610-40-2) → 2,3-bis(4-bromophenyl)-6-chloroquinoxaline (1094618-65-1)

Conditions	Yield
With tin(ll) chloride In ethanol; water for 4h; Reflux;	94%

furil (492-94-4) + 3,4-dinitro-chlorobenzene (610-40-2) → 6-chloro-2,3-di(furan-2-yl)-quinoxaline (70976-04-4)

Conditions	Yield
With tin(ll) chloride In ethanol; water for 4h; Reflux;	94%

3,4-dinitro-chlorobenzene (610-40-2) + benzil (134-81-6) → 2,3-diphenyl-6-chloroquinoxaline (36305-60-9)

Conditions	Yield
With tin(ll) chloride In ethanol; water for 4h; Reflux;	94%

3,4-dinitro-chlorobenzene (610-40-2) + phenylacetylene (536-74-3) → 1,2-Dinitro-4-phenylethynyl-benzene

Conditions	Yield
With potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 140℃; for 20h; Sonogashira cross-coupling;	93%

3,4-dinitro-chlorobenzene (610-40-2) + aniline (62-53-3) → 5-chloro-2-nitro-N-phenylaniline (25781-92-4)

Conditions	Yield
In ethanol at 20℃; for 10h; Solvent; Temperature; Time;	90%

3,4-dinitro-chlorobenzene (610-40-2) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With sodium tetrahydroborate In ethanol; water at 20℃; for 4h; Green chemistry;	90%

ethanol (64-17-5) + 3,4-dinitro-chlorobenzene (610-40-2) → 6-chloro-2-methyl-1H-benzo[d]imidazole (2818-69-1)

Conditions	Yield
With titanium(IV) oxide for 4h; Irradiation;	89%

3,4-dinitro-chlorobenzene (610-40-2) → 1,2-diamino-benzene (95-54-5)

Conditions	Yield
With palladium 10% on activated carbon; hydrazine hydrate In methanol at 120℃; for 0.25h; Microwave irradiation;	89%

3,4-dinitro-chlorobenzene (610-40-2) → 1,2,4-Trichlorobenzene (120-82-1)

Conditions	Yield
With Dichlorophenylphosphine In various solvent(s) at 170℃; for 5h;	86%

cyclohexylamine (108-91-8) + 3,4-dinitro-chlorobenzene (610-40-2) → N-cyclohexyl-2-nitro-5-chloro-aniline (28096-58-4)

Conditions	Yield
In ethanol for 8h; Ambient temperature;	85%

propan-1-ol (71-23-8) + 3,4-dinitro-chlorobenzene (610-40-2) → 6-chloro-2-ethylbenzimidazole

Conditions	Yield
With titanium(IV) oxide for 4h; Irradiation;	84%

3,4-dinitro-chlorobenzene (610-40-2) + triethyl phosphite (122-52-1) → C10H13N2O7P

Conditions	Yield
In toluene Michaelis-Arbuzov Synthesis; Reflux;	84%

3,4-dinitro-chlorobenzene (610-40-2) + toluene-4-sulfonic acid hydrazide (1576-35-8) → 3,4-dinitro-1-(4-methylphenylsulfonyl)-benzene (127291-62-7)

Conditions	Yield
With sodium acetate In ethanol for 1h; Heating;	80%

3,4-dinitro-chlorobenzene (610-40-2) → 5-chloro-2-nitrophenylhydrazine (1966-16-1)

Conditions	Yield
With hydrazine hydrate; urea In ethanol	76%
With hydrazine In ethanol at 20℃; for 1h;	62%
With hydrazine hydrate
With ethanol; hydrazine hydrate

4-phenyl-butan-1-ol (3360-41-6) + 3,4-dinitro-chlorobenzene (610-40-2) → 4-(4-phenylbutoxy)-1,2-dinitrobenzene

Conditions	Yield
In tetrahydrofuran; mineral oil	72%

(2R)-methylpiperazine (75336-86-6) + 3,4-dinitro-chlorobenzene (610-40-2) → (R)-1-(3,4-Dinitro-phenyl)-3-methyl-piperazine + (R)-1-(5-chloro-2-nitrophenyl)-3-methylpiperazine (907991-13-3)

Conditions	Yield
With potassium carbonate In ethanol; water for 1h; Heating;	A n/a B 71%

pyrrolidine (123-75-1) + 3,4-dinitro-chlorobenzene (610-40-2) → 4-chloro-2-(1-pyrrolidinyl)nitrobenzene (133387-30-1) + 1-(3,4-dinitro-phenyl)-pyrrolidine

Conditions	Yield
In methanol at 20℃; for 5h;	A 70% B n/a

3,4-dinitro-chlorobenzene (610-40-2) + benzylamine (100-46-9) → N-benzyl-N-(2-nitro-5-chlorophenyl)-amine (10066-19-0) + N-Benzyl-2,4-dinitroanilin

Conditions	Yield
In methanol at 20℃; for 3h;	A 70% B n/a

3,4-dinitro-chlorobenzene (610-40-2) + rac-methylbenzylamine (618-36-0) → N-(1-phenylethyl)-5-chloro-2-nitroaniline (330830-31-4) + (3,4-dinitro-phenyl)-(1-phenyl-ethyl)-amine

Conditions	Yield
In methanol at 20℃; for 3h;	A 68% B n/a

piperidine (110-89-4) + 3,4-dinitro-chlorobenzene (610-40-2) → 1-(5-chloro-2-nitrophenyl)piperidine (53013-43-7) + 1-(3,4-Dinitro-phenyl)-piperidine

Conditions	Yield
In methanol at 20℃; for 5h;	A 65% B n/a

ethanolamine (141-43-5) + 3,4-dinitro-chlorobenzene (610-40-2) → 2-<(5-chloro-2-nitro)phenylamino>ethanol (50610-29-2) + 2-(3,4-dinitro-phenylamino)-ethanol

Conditions	Yield
In methanol at 20℃; for 3h;	A 65% B n/a

2,2-dimethylpropylamine (5813-64-9) + 3,4-dinitro-chlorobenzene (610-40-2) → N-(2,2-dimethylpropyl)-5-chloro-2-nitroaniline (725705-48-6) + (2,2-dimethyl-propyl)-(3,4-dinitro-phenyl)-amine

Conditions	Yield
In methanol at 20℃; for 3h;	A 65% B n/a

3,4-dinitro-chlorobenzene (610-40-2) + (4-aminophenyl)-α-D-glucopyranoside (31302-52-0) → 4-(3,4-dinitrophenylamino)phenyl α-D-glucopyranoside

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 1h;	63%

1-(para-methoxyphenyl)piperazine hydrochloride (84145-43-7) + 3,4-dinitro-chlorobenzene (610-40-2) → 1-(5-chloro-2-nitrophenyl)-4-(4-methoxyphenyl)piperazine (150916-81-7)

Conditions	Yield
With potassium carbonate In ethanol; water for 5h; Heating;	62%

3,4-dinitro-chlorobenzene (610-40-2) + triethyl phosphite (122-52-1) → O,O-diethyl-5-chloro-2-nitrophenylphosphonate

Conditions	Yield
In toluene for 6h; Heating;	60.3%

Upstream product

• 121-73-3 3-Nitrochlorobenzene 
• 610-41-3 3,4-dinitroaniline 
• 88-73-3 2-Chloronitrobenzene 
• 577-71-9 3,4-dinitophenol 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 89-63-4 4-Chloro-2-nitroaniline 

Downstream Products

• 53013-43-7 1-(5-chloro-2-nitrophenyl)piperidine 
• 53013-41-5 4-(2-nitro-5-piperidinophenyl)piperidine 
• 736977-06-3 4-chloro-1-nitro-2-tosylbenzene 
• 89660-11-7 N-(5-chloro-2-nitrophenyl)pyridin-2-amine 
• 350235-57-3 biphenyl-4-yl-(5-chloro-2-nitro-phenyl)-amine 
• 32724-92-8 N-(5-chloro-2-nitrophenyl)-N-(4-methylphenyl)amine 
• 50610-29-2 2-<(5-chloro-2-nitro)phenylamino>ethanol 
• 54920-86-4 2-(5-chloro-2-nitro-phenylsulfanyl)-benzoic acid 
• 6627-53-8 1-chloro-3-methoxy-4-nitrobenzene 
• 672295-04-4 (5-chloro-2-nitro-phenyl)-phenyl sulfone 
• 70019-41-9 4-chloro-2-(methylthio)-1-nitrobenzene 
• 4548-56-5 4-chloro-2-nitrophenyl phenyl sulfide 
• 33358-41-7 (5-chloro-2-nitro-phenyl)-phenyl sulfide 
• 882-33-7 diphenyldisulfane 

Relevant academic research and scientific papers

A convenient method for the oxidation of aromatic amines to nitro compounds using tetra-n-alkylammonium bromates

Tetra-n-propyl and tetra-n-butylammonium bromates were used for the oxidation of a variety of aromatic amines to nitro compounds. Reaction condition and recovery simple and yield of products high.

Regioselective synthesis of 4-halo ortho-dinitrobenzene derivatives

A novel method for the regioselective synthesis of 4-halo ortho- dinitrobenzene derivatives was developed by reacting various meta-halo nitrobenzenes with urea nitrate in concentrated sulfuric acid. (C) 2000 Elsevier Science Ltd.

Reactions of Nitrophenols with Phosphorus Oxychloride in Dimethylformamide

A rapid and simple method for the replacement of hydroxyl group of nitrophenols and related compounds by chlorine using phosphorus oxychloride in dimethylformamide at ambient temperature is described.

Competitive Cyclisations of Singlet and Triplet Nitrenes. Part 8. The 1-(2-Nitrenophenyl)pyrazoles and Related Systems

The title nitrenes, derived by nitro-group deoxygenation with triethyl phosphite or by thermolysis or photolysis of the corresponding azide, have been studied.The effect of substituents (Cl, Br, OMe, NMe2, Me, CF3, and NO2) both meta and para to the nitrene has been examined as a determinant of the preferred mode of cyclisation to either a pyrazolobenzotriazole or a pyrazoloquinoxaline.Similarly, the role of solvents, sensitisers, and quenchers has been studied.Routes to the isomeric 1- and 2-(2-nitrophenyl)-4,5,6,7-tetrahydroindazoles have been defined and the literature corrected by studing the nitrene-mediated cyclisation of these products.The chemistry of the analogous 1-(2-carbenophenyl)- and the 1-(2-nitrenosulphonylphenyl)-3,5-dimethylpyrazoles has also been examined, the former giving 2-(3,5-dimethylpyrazol-1-yl)-benzaldazine and -benzyl alcohol while the latter gave products of intramolecular nitrene attack (a pyrazolobenzothiatriazine) and intermolecular reaction.Rationalisations for all the reaction pathways have been advanced.