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1,3-Dinitrobenzene

1,3-Dinitrobenzene
1,3-Dinitrobenzene structure
CAS No.
99-65-0
Chemical Name:
1,3-Dinitrobenzene
Synonyms
m-dnb;1,3-DNB;nsc-7189;1.3-Dinitr;Binitrobenzene;Dwunitrobenzen;o-Dinitrobezene;M-DINITROBENZENE;m-dimitrobenzene;3-dinitrobenzene
CBNumber:
CB9854770
Molecular Formula:
C6H4N2O4
Formula Weight:
168.11
MOL File:
99-65-0.mol

1,3-Dinitrobenzene Properties

Melting point:
86 °C
Boiling point:
297 °C(lit.)
Density 
1.575
vapor pressure 
8.15 x 10-4 mmHg at 35 °C (Hine et al., 1963)
refractive index 
1.4660 (estimate)
Flash point:
150 °C
storage temp. 
2-8°C
form 
solid
Specific Gravity
1.368
color 
White to yellowish crystals
Water Solubility 
500 mg/L (20 ºC)
Merck 
14,3273
BRN 
1105654
Exposure limits
NIOSH REL: TWA 1, IDLH 50; OSHA PEL: TWA 1; ACGIH TLV: TWA 0.15 ppm for all isomers (adopted).
Stability:
Stable. Incompatible with reducing agents, oxidizing agents, strong bases. May explode if heated.
CAS DataBase Reference
99-65-0(CAS DataBase Reference)
EWG's Food Scores
1-2
FDA UNII
DK8B627BU0
Proposition 65 List
m-Dinitrobenzene
NIST Chemistry Reference
Benzene, 1,3-dinitro-(99-65-0)
EPA Substance Registry System
m-Dinitrobenzene (99-65-0)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS06,GHS07,GHS08,GHS09
Signal word  Danger
Hazard statements  H300+H310+H330-H373-H410-H320-H335-H341-H370-H372-H301-H310-H330-H400
Precautionary statements  P260-P264-P273-P280-P284-P301+P310-P262-P302+P352+P310-P304+P340+P310-P201-P202-P270-P271-P301+P310+P330-P302+P352+P310+P361+P364-P305+P351+P338+P337+P313-P307+P311-P391-P403+P233-P405-P501-P301+P310a-P304+P340-P320-P330-P501a
Hazard Codes  T+,N,T,F,Xn
Risk Statements  26/27/28-33-50/53-40-36/37/38-23/24/25-11-52/53-36-20/21/22
Safety Statements  28-36/37-45-60-61-28A-27-16-26
RIDADR  UN 3443 6.1/PG 2
WGK Germany  3
RTECS  CZ7350000
TSCA  Yes
HazardClass  6.1
PackingGroup  II
HS Code  29042090
Toxicity LD50 in male, female rats (mg/kg): 91, 81 orally (Cody)

1,3-Dinitrobenzene price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 02827 1,3-Dinitrobenzene certified reference material, TraceCERT 99-65-0 100mg $83.3 2021-03-22 Buy
Sigma-Aldrich 41980 1,3-Dinitrobenzene for HPLC derivatization, for the detection of steroids 99-65-0 50g $186 2020-08-18 Buy
TCI Chemical D0817 1,3-Dinitrobenzene >99.0%(GC) 99-65-0 25g $32 2018-11-22 Buy
TCI Chemical D0817 1,3-Dinitrobenzene >99.0%(GC) 99-65-0 250g $136 2018-11-22 Buy
Sigma-Aldrich 41980 1,3-Dinitrobenzene for HPLC derivatization, for the detection of steroids 99-65-0 250g $614 2020-08-18 Buy

1,3-Dinitrobenzene Chemical Properties,Uses,Production

Description

1,3-Dinitrobenzene (1,3-DNB) is an impurity present in the manufacture of 2,4,6-trinitrotoluene. Workers in munitions plants are at risk of exposure. While it does not bioaccumulate, it persists in the environments (air, water, and soil) with slow rates of degradation. Metabolism in animals (rabbits) results in reduction of the nitro functionalities to amine functionalities to produce 2,4-diaminophenol, m-nitroaniline, m-phenylenediamine, and 2-amino-4-nitrophenol. Human exposure is generally dermal contact or inhalation of vapor.

Chemical Properties

orange to yellow crystalline powder

Uses

Organic synthesis; dyes.

Uses

Dinitrobenzene (as a mixture of 1,2-dinitro- 1,3-dinitro- and 1,4-dinitro-isomers) is used in the manufacture of dyes and explosives, and in organic syntheses.

Definition

ChEBI: A dinitrobenzene that is benzene disubstituted at positions 1 and 3 with nitro groups.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 4243, 1973 DOI: 10.1021/jo00964a007
Synthesis, p. 1085, 1992 DOI: 10.1055/s-1992-26309

General Description

Yellow solid with a slight odor. Sinks in water.

Air & Water Reactions

Slowly mixes with water.

Reactivity Profile

All three isomers have similar properties and may react vigorously with oxidizing materials. Their reaction with nitric acid (nitration) will lead to a mixture of trinitrobenzenes possessing high-explosive properties [Urbanski, 1967, vol. 3, p. 290]. If heat and reaction conditions of the nitration are not controlled, detonation comparable to TNT may occur [Anon., J. R. Inst. Chem., 1960, 84, p. 451]. Mixture of 1,3-dinitrobenzene with tetranitromethane was found highly explosive [Urbanski, 1964, vol. 1, 592]. 1,2-dinitrobenzene is a severe explosion hazard when shocked or exposed to heat or flame. When heated to decomposition all dinitrobenzens emit toxic fumes of nitrogen oxides [Sax, 9th ed., 1996, p. 1374].

Health Hazard

Inhalation or ingestion causes loss of color, nausea, headache, dizziness, drowsiness, and collapse. Eyes are irritated by liquid. Stains skin yellow; if contact is prolonged, can be absorbed into blood and cause same symptoms as for inhalation.

Fire Hazard

Behavior in Fire: May explode

Safety Profile

Suspected carcinogen. Human poison by ingestion. Experimental poison by ingestion, intraperitoneal, and intravenous routes. Human systemic effects by skin contact: cyanosis and motor activity changes. Experimental reproductive effects. An eye irritant. Mutation data reported. Mixture with nitric acid is a high explosive. Mixture with tetranitromethane is a hgh explosive very sensitive to sparks. When heated to decomposition it emits toxic fumes of NOx. See also 0and pDINITROBENZENE.

Environmental Fate

Biological. Under anaerobic and aerobic conditions using a sewage inoculum, 1,3- dinitrobenzene degraded to nitroaniline (Hallas and Alexander, 1983). In activated sludge inoculum, following a 20-d adaptation period, no degradation was observed (Pitter, 1976).
Photolytic. Low et al. (1991) reported that the nitro-containing compounds (e.g., 2,4- dinitrophenol) undergo degradation by UV light in the presence of titanium dioxide yielding ammonium, carbonate, and nitrate ions. By analogy, 1,3-dinitrobenzene should degrade forming identical ions.
Chemical/Physical. Releases toxic nitrogen oxides when heated to decomposition (Sax and Lewis, 1987). 1,3-Dinitrobenzene will not hydrolyze in water (Kollig, 1993).

Solubility in organics

Soluble in acetone, ether, pyrimidine (Weast, 1986), alcohol (27 g/L), pyridine (3,940 g/kg at 20–25 °C) (Dehn, 1917); freely soluble in benzene, chloroform, ethyl acetate (Windholz et al., 1983), and toluene.

Purification Methods

Crystallise 1,3-dinitrobenzene from alkaline EtOH solution (20g in 750mL 95% EtOH at 40o, plus 100mL of 2M NaOH) by cooling and adding 2.5L of H2O. The precipitate, after filtering off, is washed with H2O, sucked dry, and crystallised from 120mL, then 80mL of absolute EtOH [Callow et al. Biochem J 32 1312 1938]. Alternatively crystallise it from MeOH, CCl4 or EtOAc. It can be sublimed in a vacuum. [Tanner J Org Chem 52 2142 1987, Beilstein 5 IV 739.]

Toxicity evaluation

Cultured astrocytes and brain capillary endothelial cells were exposed to 1 mM concentrations for 1 day in an in vitro blood–brain barrier (BBB) model, resulting in cell death.

1,3-Dinitrobenzene Preparation Products And Raw materials

Raw materials

Preparation Products


1,3-Dinitrobenzene Spectrum


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