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528-29-0

Basic Information
CAS No.: 528-29-0
Name: 1,2-Dinitrobenzene
Article Data: 92
Molecular Structure:
Molecular Structure of 528-29-0 (1,2-Dinitrobenzene)
Formula: C6H4N2O4
Molecular Weight: 168.109
Synonyms: Benzene,o-dinitro- (8CI);NSC 60682;Ortho-dinitrobenzene;o-Dinitrobenzene;
EINECS: 208-431-8
Density: 1.486 g/cm3
Melting Point: 116 °C
Boiling Point: 319.9 °C at 760 mmHg
Flash Point: 169.2 °C
Solubility: water: 150 mg/L (20 °C)
Appearance: light yellow-brown powder
Hazard Symbols: VeryT+,DangerousN
Risk Codes: 26/27/28-33-50/53
Safety: 28-36/37-45-60-61-28A
Transport Information: UN 3443 6.1/PG 2
PSA: 91.64000
LogP: 2.54940
Synthetic route
98-95-3

nitrobenzene

A

99-65-0

meta-dinitrobenzene

B

528-29-0

1,2-Dinitrobenzene

Conditions
ConditionsYield
With nitric acid at 50℃; for 3h;A 90.2%
B 8.8%
With nitric acid; sulfuric acid; sulfur trioxide In dichloromethane at 25℃; for 1.3h; Yield given. Yields of byproduct given;
With sulfuric acid; uronium nitrate at 25℃; for 24h;
88-74-4

2-nitro-aniline

528-29-0

1,2-Dinitrobenzene

Conditions
ConditionsYield
With sulfuric acid; acetic acid; tetra-n-propylammonium bromate for 1.25h; Heating;88%
With sodium perborate In acetic acid at 50 - 55℃;76%
With sodium perborate In acetic acid at 50 - 60℃; for 2h;76%
95-54-5

1,2-diamino-benzene

528-29-0

1,2-Dinitrobenzene

Conditions
ConditionsYield
With water; fluorine In chloroform; acetonitrile at -15℃; for 0.0333333h;85%
With 3,3-dimethyldioxirane Yield given;
24564-52-1

4-(dimethylamino)benzenediazonium tetrafluoroborate

dipotassium salt of o-dinitrobenzene dianion

A

121-69-7

N,N-dimethyl-aniline

B

528-29-0

1,2-Dinitrobenzene

C

3010-38-6

N,N-dimethyl-4-[(2-nitrophenyl)diazenyl]aniline

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 1h;A 60%
B 83%
C 13%
In tetrahydrofuran at -30℃; for 1h; Product distribution; also in MeCN;A 60%
B 83%
C 13%
at -30℃; Mechanism; Product distribution; effect of solvents and 18-crown-6- additive;
24564-52-1

4-(dimethylamino)benzenediazonium tetrafluoroborate

C6H4N2O4(1-)*K(1+)

A

121-69-7

N,N-dimethyl-aniline

B

119525-59-6

3-nitro-4-hydroxy-4'-N,N-dimethylaminoazobenzene

C

528-29-0

1,2-Dinitrobenzene

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 1h;A 13%
B 46%
C 71%
24564-52-1

4-(dimethylamino)benzenediazonium tetrafluoroborate

potassium salt of the o-dinitrobenzene anion radical

A

121-69-7

N,N-dimethyl-aniline

B

119525-59-6

3-nitro-4-hydroxy-4'-N,N-dimethylaminoazobenzene

C

528-29-0

1,2-Dinitrobenzene

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 1h; Product distribution; also in DMSO and in the presence of 18-crown-6;A 13%
B 46%
C 71%
459-64-3

4-methoxybenzenediazonium tetrafluoroborate

potassium salt of the o-dinitrobenzene anion radical

A

100-66-3

methoxybenzene

B

120124-71-2

4-methoxy-3'-(2''-nitrobenzene-α-azoxy)-4'-hydroxyazobenzene

C

528-29-0

1,2-Dinitrobenzene

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 1h; Product distribution; also in DMSO and in the presence of 18-crown-6;A 20%
B 42%
C 65%
456-27-9

4-nitrobenzenediazonium tetrafluoroborate

C6H4N2O4(1-)*K(1+)

A

88210-30-4

3,4'-dinitro-4-hydroxyazobenzene

B

98-95-3

nitrobenzene

C

528-29-0

1,2-Dinitrobenzene

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 1h;A 58%
B n/a
C 63%
456-27-9

4-nitrobenzenediazonium tetrafluoroborate

potassium salt of the o-dinitrobenzene anion radical

A

88210-30-4

3,4'-dinitro-4-hydroxyazobenzene

B

98-95-3

nitrobenzene

C

528-29-0

1,2-Dinitrobenzene

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 1h; Product distribution; also in DMSO and in the presence of 18-crown-6;A 58%
B 27%
C 63%
544-92-3

copper(I) cyanide

88-74-4

2-nitro-aniline

A

98-95-3

nitrobenzene

B

612-24-8

o-nitrobenzonitrile

C

528-29-0

1,2-Dinitrobenzene

D

88-75-5

2-hydroxynitrobenzene

Conditions
ConditionsYield
With tert.-butylnitrite In dimethyl sulfoxide at 60℃; for 1.5h;A 16%
B 38%
C 8%
D 6%
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Chemistry

MF: C6H4N2O4
MW: 168.11
EINECS: 208-431-8
Density: 1.486 g/cm3
Flash Point: 150 °C
Stability: Highly reactive
Melting Point: 116-119 ºC
IUPAC Name: 1,2-dinitrobenzene
Water Solubility: 150 mg/L (20 ºC)
Appearance: Colorless to yellow solid
Enthalpy of Vaporization: 53.92 kJ/mol 
Boiling Point: 319.9 °C at 760 mmHg 
Vapour Pressure: 0.000614 mmHg at 25°C  
Air & Water: Reactions Slowly mixes with water.
Synonyms: 1,2-Dinitro-benzen ; 1,2-Dinitrobenzol ; Benzene, o-dinitro- ; Benzene,1,2-dinitro- ; Benzene,1,2-dinitro-(9CI) ; Benzene,o-dinitro- ; NSC60682 ; O-dinitro-benzen
Following is the molecular structure of O-dinitrobenzen (528-29-0):

 

Uses

 O-dinitrobenzen (528-29-0)is used for the synthesis of dyestuffs, dyestuff intermediates, explosives, and celluloid production.

Production

 Reactivity Profile of O-dinitrobenzen (528-29-0): 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. If heat and reaction conditions of the nitration are not controlled, detonation comparable to TNT may occur. Mixture of 1,3-dinitrobenzene with tetranitromethane was found highly explosive. 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.

Safety Profile

Suspected carcinogen. Poison by inhalation and ingestion. Moderately toxic by skin contact. Can cause liver, kidney, and central nervous system injury. Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. A severe explosion hazard when shocked or exposed to heat or flame. It is used in bursting charges and to fill artillery shells. Mixtures with nitric acid are highly explosive. To fight fire, use water, CO2, dry chemical. Dangerous; when heated to decomposition it emits highly toxic fumes of NOx and explodes.
Safety Information of O-dinitrobenzen (528-29-0):
Hazard Codes: T+,N
T+: Very Toxic  N: Dangerous for the environment
Risk Statements: 26/27/28-33-50/53
26/27/28: Very Toxic by inhalation, in contact with skin and if swallowed
33:  Danger of cumulative effects 
50/53: Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment   
Safety Statements: 28-36/37-45-60-61-28A
28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer
36/37: Wear suitable protective clothing and gloves 
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
60: This material and/or its container must be disposed of as hazardous waste 
61: Avoid release to the environment. Refer to special instructions safety data sheet 
RIDADR: UN 3443 6.1/PG 2
WGK Germany: 3
RTECS: CZ7450000
HazardClass: 6.1(a)
PackingGroup: II
HS Code: 29042000
 

Standards and Recommendations

OSHA PEL: TWA 1 mg/m3 (skin)
ACGIH TLV: TWA 0.15 ppm (skin)
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
DOT Classification:  6.1; Label: Poison