Product Name

  • Name

    1,4-Dinitrosobenzene

  • EINECS 203-272-0
  • CAS No. 105-12-4
  • Article Data16
  • CAS DataBase
  • Density 1.3 g/cm3
  • Solubility
  • Melting Point 146.5oC
  • Formula C6H4 N2 O2
  • Boiling Point 259.7 °C at 760 mmHg
  • Molecular Weight 136.11
  • Flash Point 103.5 °C
  • Transport Information
  • Appearance
  • Safety Poison by inhalation route. Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx.
  • Risk Codes R20/22
  • Molecular Structure Molecular Structure of 105-12-4 (1,4-Dinitrosobenzene)
  • Hazard Symbols Xn
  • Synonyms Benzene,p-dinitroso- (6CI,7CI,8CI); 1,4-Dinitrosobenzene; Actor DB; NSC 4771; RD3435-49; p-Dinitrosobenzene
  • PSA 58.86000
  • LogP 2.48240

Synthetic route

p-benzoquinone dioxime
105-11-3, 6133-83-1, 6421-98-3

p-benzoquinone dioxime

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide at 50℃; for 4h;97%
With oxygen; Nitrogen dioxide In dichloromethane for 10h; Ambient temperature;90%
With alkaline solution; potassium hexacyanoferrate(III)
N,N'-dinitroso-1,4-phenylenedihydroxylamine
24924-26-3

N,N'-dinitroso-1,4-phenylenedihydroxylamine

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

Conditions
ConditionsYield
(heating);
O,O'-bis(1,3,5-tri-tert-butyl-4-oxo-2,5-cyclohexadienyl)-p-benzoquinone dioxime
52211-69-5

O,O'-bis(1,3,5-tri-tert-butyl-4-oxo-2,5-cyclohexadienyl)-p-benzoquinone dioxime

[1,4]Benzoquinone bis-[O-(1-tert-butoxy-3,5-di-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-oxime]
57435-52-6

[1,4]Benzoquinone bis-[O-(1-tert-butoxy-3,5-di-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-oxime]

A

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

B

2,4,6-tri-tert-butylphenoxyl
3315-32-0, 2525-39-5

2,4,6-tri-tert-butylphenoxyl

C

2,6-di-tert-butyl-4-tert-butoxyphenoxyl
2606-99-7

2,6-di-tert-butyl-4-tert-butoxyphenoxyl

Conditions
ConditionsYield
In benzene Heating;
O,O'-bis(1,3,5-tri-tert-butyl-4-oxo-2,5-cyclohexadienyl)-p-benzoquinone dioxime
52211-69-5

O,O'-bis(1,3,5-tri-tert-butyl-4-oxo-2,5-cyclohexadienyl)-p-benzoquinone dioxime

A

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

B

2,4,6-tri-tert-butylphenoxyl
3315-32-0, 2525-39-5

2,4,6-tri-tert-butylphenoxyl

Conditions
ConditionsYield
In benzene Heating;
In benzene Equilibrium constant; Mechanism; Thermodynamic data; Heating;
1.4-bis--benzene

1.4-bis--benzene

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

Conditions
ConditionsYield
With sulfuric acid
p-benzoquinone dioxime
105-11-3, 6133-83-1, 6421-98-3

p-benzoquinone dioxime

alkaline aqueous NaOCl solution

alkaline aqueous NaOCl solution

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

sulfuric acid
7664-93-9

sulfuric acid

1,4-diisonitramino-benzene

1,4-diisonitramino-benzene

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

1,4-Benzochinondioxim
105-11-3, 6133-83-1, 6421-98-3

1,4-Benzochinondioxim

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) NO, NaOMe, MeOH, (ii) HCl
2: (heating)
View Scheme
1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

Conditions
ConditionsYield
With dihydrogen peroxide; CpMo(CO)3(CCPh) In tert-butyl alcohol at 20℃; for 12h;
2-methoxyacetic acid
625-45-6

2-methoxyacetic acid

p-benzoquinone
106-51-4

p-benzoquinone

A

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

B

2-(methoxymethyl)-1,4-dinitrosobenzene

2-(methoxymethyl)-1,4-dinitrosobenzene

Conditions
ConditionsYield
Stage #1: 2-methoxyacetic acid; p-benzoquinone With ammonium persulfate; silver nitrate In water at 65℃; for 0.25h;
Stage #2: With sodium acetate In ethanol for 12h; Reflux;
Stage #3: With hydrogenchloride; dihydrogen peroxide In water at 55℃; for 0.5h;
A n/a
B 0.68g
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

para-dinitrobenzene
100-25-4

para-dinitrobenzene

Conditions
ConditionsYield
With dihydrogen peroxide In trifluoroacetic acid for 10h; Ambient temperature;95%
With dihydrogen peroxide; trifluoroacetic acid
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With Saccharomyces cerevisiae BY In methanol at 20℃; pH=7.0; aq. buffer; Enzymatic reaction;90%
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Benzenesulfinic acid
618-41-7

Benzenesulfinic acid

C18H16N2O6S2*2C2H6OS

C18H16N2O6S2*2C2H6OS

Conditions
ConditionsYield
at 20℃; for 24h; Addition;72.8%
p-toluene sulfinic acid
536-57-2

p-toluene sulfinic acid

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

C20H20N2O6S2

C20H20N2O6S2

Conditions
ConditionsYield
In various solvent(s) for 2h; Addition;56%
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

Benzenesulfinic acid
618-41-7

Benzenesulfinic acid

N,N'-bis(phenylsulfonyl)-N,N'-dihydroxy-p-phenylenediamine

N,N'-bis(phenylsulfonyl)-N,N'-dihydroxy-p-phenylenediamine

Conditions
ConditionsYield
In various solvent(s) for 2h; Addition;31%
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

acetic acid-[4-(4-amino-phenylazo)-anilide]
61893-92-3

acetic acid-[4-(4-amino-phenylazo)-anilide]

1,4-bis-[4-(4-acetylamino-phenylazo)-phenylazo]-benzene

1,4-bis-[4-(4-acetylamino-phenylazo)-phenylazo]-benzene

Conditions
ConditionsYield
With ethanol; acetic acid
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

1,4-diazidobenzene
2294-47-5

1,4-diazidobenzene

Conditions
ConditionsYield
With hydrogen azide; ethanol
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

4-nitro-aniline
100-01-6

4-nitro-aniline

1,4-bis-(4-nitro-phenylazo)-benzene

1,4-bis-(4-nitro-phenylazo)-benzene

Conditions
ConditionsYield
With acetic acid und Erhitzen des Reaktionsprodukts mit Zink in Pyridin unter Stickstoff und Erhitzen der Reaktionsloesung mit Acetanhydrid;
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

aniline yellow
60-09-3

aniline yellow

A

1,4-bis-[4-(phenyl-trans-azo)-phenyl-trans-azo]-benzene
96374-99-1

1,4-bis-[4-(phenyl-trans-azo)-phenyl-trans-azo]-benzene

B

1-(4-phenylazo-phenylazo)-4-(4-phenylazo-phenyl-NNO-azoxy)-benzene

1-(4-phenylazo-phenylazo)-4-(4-phenylazo-phenyl-NNO-azoxy)-benzene

Conditions
ConditionsYield
With acetic acid
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

aniline
62-53-3

aniline

1-phenylazo-4-(phenyl-NNO-azoxy)-benzene
54915-73-0

1-phenylazo-4-(phenyl-NNO-azoxy)-benzene

Conditions
ConditionsYield
With ethanol; acetic acid
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

4-bromo-aniline
106-40-1

4-bromo-aniline

1,4-bis-(4-bromo-phenyl-trans-azo)-benzene

1,4-bis-(4-bromo-phenyl-trans-azo)-benzene

Conditions
ConditionsYield
With acetic acid und Hydrieren des Reaktionsprodukts an Raney-Nickel in Pyridin;
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

N-acetyl-p-phenylenediamine
122-80-5

N-acetyl-p-phenylenediamine

A

1-(4-acetylamino-phenylazo)-4-(4-acetylamino-phenyl-NNO-azoxy)-benzene
864849-81-0

1-(4-acetylamino-phenylazo)-4-(4-acetylamino-phenyl-NNO-azoxy)-benzene

B

1,4-bis-(4-acetylamino-phenylazo)-benzene

1,4-bis-(4-acetylamino-phenylazo)-benzene

Conditions
ConditionsYield
With ethanol; acetic acid
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

2,4,6-tri-tert-butylphenoxyl
3315-32-0, 2525-39-5

2,4,6-tri-tert-butylphenoxyl

O,O'-bis(1,3,5-tri-tert-butyl-4-oxo-2,5-cyclohexadienyl)-p-benzoquinone dioxime
52211-69-5

O,O'-bis(1,3,5-tri-tert-butyl-4-oxo-2,5-cyclohexadienyl)-p-benzoquinone dioxime

Conditions
ConditionsYield
In benzene Equilibrium constant; Mechanism; Thermodynamic data; Heating;
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

2,4,6-tri-tert-butylphenoxol
732-26-3

2,4,6-tri-tert-butylphenoxol

p-Benzochinon-dioxim-bis-(1,3,5-tri-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-ether
52211-69-5

p-Benzochinon-dioxim-bis-(1,3,5-tri-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-ether

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

nitric acid
7697-37-2

nitric acid

para-dinitrobenzene
100-25-4

para-dinitrobenzene

ethanol
64-17-5

ethanol

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

acetic acid
64-19-7

acetic acid

N-acetyl-p-phenylenediamine
122-80-5

N-acetyl-p-phenylenediamine

A

1,4-bis-(4-acetylamino-phenylazo)-benzene

1,4-bis-(4-acetylamino-phenylazo)-benzene

B

4'-acetylamino-4-<4-acetylamino-phenylazo>-azoxybenzene

4'-acetylamino-4-<4-acetylamino-phenylazo>-azoxybenzene

ethanol
64-17-5

ethanol

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

acetic acid
64-19-7

acetic acid

aniline
62-53-3

aniline

A

p-benzoquinone dioxime
105-11-3, 6133-83-1, 6421-98-3

p-benzoquinone dioxime

B

4-phenylazo-azoxybenzene

4-phenylazo-azoxybenzene

ethanol
64-17-5

ethanol

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

hydrazine hydrate
7803-57-8

hydrazine hydrate

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

acetic acid
64-19-7

acetic acid

aniline yellow
60-09-3

aniline yellow

A

benzen--azoxybenzen-<4'azo 1>-benzen-<4 azo>-benzene

benzen--azoxybenzen-<4'azo 1>-benzen-<4 azo>-benzene

B

benzen--benzen-<4 azo 1>-benzen-<4 azo 1>-benzen-<4 azo>-benzene

benzen--benzen-<4 azo 1>-benzen-<4 azo 1>-benzen-<4 azo>-benzene

p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

1-(phenyl-NNO-azoxy)-4-(phenyl-ONN-azoxy)-benzene
876500-17-3

1-(phenyl-NNO-azoxy)-4-(phenyl-ONN-azoxy)-benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; ethanol
2: acetic acid; aqueous hydrogen peroxide
View Scheme

1,4-Dinitrosobenzene Toxicity Data With Reference

1.   

orl-rat LD50:1020 mg/kg

    KCRZAE    Kauchuk i Rezina.(11),(1985),38.
2.   

ihl-rat LCLo:200 mg/m3/2H

    KCRZAE    Kauchuk i Rezina.(11),(1985),38.
3.   

orl-mus LD50:1230 mg/kg

    KCRZAE    Kauchuk i Rezina.(11),(1985),38.
4.   

ihl-mus LCLo:200 mg/m3/2H

    KCRZAE    Kauchuk i Rezina.(11),(1985),38.

1,4-Dinitrosobenzene Consensus Reports

Reported in EPA TSCA Inventory.

1,4-Dinitrosobenzene Safety Profile

Poison by inhalation route. Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx.
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