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105-12-4

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105-12-4 Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 1901, 1960 DOI: 10.1021/jo01081a019

Check Digit Verification of cas no

The CAS Registry Mumber 105-12-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 5 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 105-12:
(5*1)+(4*0)+(3*5)+(2*1)+(1*2)=24
24 % 10 = 4
So 105-12-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H4N2O2/c9-7-5-1-2-6(8-10)4-3-5/h1-4H

105-12-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4-Dinitrosobenzene

1.2 Other means of identification

Product number -
Other names P-DINITROSOBENZENE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:105-12-4 SDS

105-12-4Synthetic 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

105-12-4Relevant articles and documents

Preparation method for synthesizing p-dinitrosobenzene by wet material

-

, (2022/03/27)

The present application discloses a method for synthesizing p-nitrosobenzene by wet material, comprising: adding phenol to an aqueous solution of sodium nitrite and sodium hydroxide, formulated into a mixed solution of sodium phenol and sodium nitrite, at a predetermined temperature, the mixed solution is added dropwise to the sulfuric acid solution, stirring reaction, filtering, washing to obtain an intermediate p-nitrosophenol wet material; The p-benzoquinone dioxime wet material was dissolved in an aqueous solution of sodium hydroxide to obtain an alkaline p-benzoquinone dioxime solution, and the NaClO dilute solution was added dropwise to the alkaline p-benzoquinone dioxime solution, stirred the reaction, filtered and washed to obtain a p-nitrosobenzene product. The raw material cost of this method is low, the whole process involves only water as a reaction solvent, the operation process is simple, the process wet intermediates do not need to be dried, and the final p-dinitrosobenzene has excellent adhesive adhesion performance.

Selective N-oxidation of aromatic amines to nitroso derivatives using a molybdenum acetylide oxo-peroxo complex as catalyst

Biradar, Ankush V.,Kotbagi, Trupti V.,Dongare, Mohan K.,Umbarkar, Shubhangi B.

, p. 3616 - 3619 (2008/09/19)

The molybdenum acetylide oxo-peroxo complex obtained in situ by the treatment of the corresponding molybdenum acetylide carbonyl complex, CpMo(CO)3(C{triple bond, long}CPh); Cp = η5-C5H5 with H2O2, has been used as an efficient catalyst for selective N-oxidation of primary amines to nitroso derivatives. Excellent amine conversion (up to 100%) and very high selectivity for nitroso compounds (99%) have been obtained using 30% hydrogen peroxide as an oxidant. The oxo peroxo Mo(VI) complex has also been found to be very active for the oxidation of various substituted primary aromatic amines with electron donating as well as electron withdrawing substituents on the aromatic ring.

KINETICS AND MECHANISM OF THE THERMAL DISSOCIATION OF O,O'-BIS(1,3,5-TRI-tert-BUTYL-4-OXO-2,5-CYCLOHEXADIENYL)-p-BENZOQUINONE DIOXIME IN SOLUTION

Khizhnyi, V. A.,Danilova, T. A.,Goloverda, G. Z.,Dobronravova, Z. A.

, p. 776 - 781 (2007/10/02)

The kinetics and mechanism of the thermal dissociation of O,O'-bis(1,3,5-tri-tert-butyl-4-oxo-2,5-cyclohexadienyl)-p-benzoquinone dioxime (quinol ether) in solutions in nonpolar solvents were investigated.The dissociation of the quinol ether is a reversible two-stage process and involves the formation of an intermediate radical.In relation to the reaction conditions (initial concentration, temperature) the dissociation rate of the quinol ether obeys the kinetic equations ω = keff.c1/2 or ω = k1c.The change in the reaction order is due to the ratio of the rates of dissociation of the intermediate radical and of its reaction with the phenoxyl radical.

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