3,4-Dinitrochlorobenzene Chemical Properties

Melting point:

40-41 °C

Boiling point:

16 °C (4 mmHg)

Density 

1.687 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.587(lit.)

Flash point:

>230 °F

storage temp. 

0-10°C

form 

Oily Liquid

color 

Yellow-brown

Water Solubility 

insoluble

BRN 

521564

CAS DataBase Reference

610-40-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 4-chloro-1,2-dinitro-(610-40-2)

EPA Substance Registry System

Benzene, 4-chloro-1,2-dinitro- (610-40-2)

Safety Information

Hazard Codes 

T,N

Risk Statements 

23/24/25-33-50/53

Safety Statements 

28-36/37-45-60-61-28A

RIDADR 

UN 3441 6.1/PG 2

WGK Germany 

3

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

2904990090

MSDS

• Language:English Provider:1-Chloro-3,4-dinitrobenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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3,4-Dinitrochlorobenzene Usage And Synthesis

Description

Securinine is derived from the leaf of Securinega suffruticosa Rehd., which was first separated by V.I.?Murav’eva in 1956 . Securinega suffruticosa Rehd., a kind of subshrub plant, is widely distributed in temperate and subtropical regions . It has strong adaptability and can be planted in most parts of China. Moreover, it is rich in natural resources. Securinega suffruticosa Rehd. is a folk medicine whose root is the main component, with the effects of activating circulation, spleen, and stomach to treat rheumatism waist pain, limb numbness, infant malnutrition, and other diseases. The roots, stems, leaves, flowers, and skin of Securinega suffruticosa Rehd. contain alkaloids, in which securinine is the main ingredient.

Chemical Properties

YELLOW-BROWN OILY LIQUID AFTER MELTING

Physical properties

Appearance: yellow crystalline powder, slightly bitter. Solubility: soluble in anhydrous ethanol or chloroform, insoluble in water. Melting point: 139–140?°C Specific optical rotation: (D) ?1042°(C?=?1, EtOH).

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.

Uses

This compound is a sensitizer.

Uses

3,4-Dinitrochlorobenzene is a useful reactant in organic synthesis.

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.

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