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1,3-Dinitrobenzene

Product Name:
1,3-Dinitrobenzene
CAS No.
99-65-0
Chemical Name:
1,3-Dinitrobenzene
CBNumber:
CB9854770
Molecular Formula:
C6H4N2O4
Formula Weight:
168.11
MOL File:
99-65-0.mol
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1,3-Dinitrobenzene Property

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
color 
White to yellowish crystals
Specific Gravity
1.368
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)
NIST Chemistry Reference
Benzene, 1,3-dinitro-(99-65-0)
EPA Substance Registry System
m-Dinitrobenzene (99-65-0)
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Safety

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
Hazardous Substances Data
99-65-0(Hazardous Substances Data)
Toxicity
LD50 in male, female rats (mg/kg): 91, 81 orally (Cody)
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N-Bromosuccinimide Price More Price(9)

Sigma-Aldrich Gold
Product number:
02827
Product name :
1,3-Dinitrobenzene
Purity:
certified reference material, TraceCERT
Packaging:
100mg
Price:
$34.1
Updated:
2020/08/18
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Buy
Sigma-Aldrich Gold
Product number:
41980
Product name :
1,3-Dinitrobenzene
Purity:
for HPLC derivatization, for the detection of steroids
Packaging:
50g
Price:
$186
Updated:
2020/08/18
Buy:
Buy
TCI Chemical Gold
Product number:
D0817
Product name :
1,3-Dinitrobenzene
Purity:
>99.0%(GC)
Packaging:
25g
Price:
$32
Updated:
2018/11/22
Buy:
Buy
TCI Chemical Gold
Product number:
D0817
Product name :
1,3-Dinitrobenzene
Purity:
>99.0%(GC)
Packaging:
250g
Price:
$136
Updated:
2018/11/22
Buy:
Buy
Sigma-Aldrich Gold
Product number:
442244
Product name :
1,3-Dinitrobenzene
Purity:
analytical standard
Packaging:
442244
Price:
$31.4
Updated:
2018/11/23
Buy:
Buy
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1,3-Dinitrobenzene Chemical Properties,Usage,Production

Chemical Properties

orange to yellow crystalline powder

Uses

Organic synthesis; dyes.

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

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.]

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