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51-28-5

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51-28-5 Usage

Chemical Properties

light yellow crystal powder

Uses

Different sources of media describe the Uses of 51-28-5 differently. You can refer to the following data:
1. Dinitrophenol is used in the manufacture of dyes, as a wood preservative, and as an indicator and analytical reagent.
2. In manufacture of dyes, other organic chemicals, wood preservatives, photographic developer, and explosives
3. 2,4-Dinitrophenol (DNP) can be used: As a reactant for catalytic reduction reactions.To activate carboxylic acids by converting them into dinitrophenyl (DNP) esters.To prepare the corresponding ester via acylation reaction using isobutyric anhydride catalyzed by hafnium triflate.As an effective cocatalyst to accelerate the activity and enantioselectivity of primary amine organocatalyst derived from natural primary amino acids for direct asymmetric aldol reaction. As an alternative activator to tetrazoles in the reaction of phosphoroamidites with nucleosides.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 3445, 1995 DOI: 10.1021/jo00116a034

General Description

Solid yellow crystals. Explosive when dry or with less than 15% water. The primary hazard is from blast of an instantaneous explosion and not flying projectiles and fragments. slightly soluble in water and soluble in ether and solutions of sodium or potassium hydroxide.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

2,4-Dinitrophenol may explode if subjected to heat or flame. may explode if allowed to dry out. Forms explosive salts with alkalis and ammonia. Incompatible with heavy metals and their compounds. Also incompatible with strong oxidizing agents, strong bases and reducing agents. Reacts with combustibles.

Health Hazard

Different sources of media describe the Health Hazard of 51-28-5 differently. You can refer to the following data:
1. DUST: POISONOUS IF INHALED OR IF SKIN IS EXPOSED. SOLID: POISONOUS IF SWALLOWED.
2. 2,4-Dinitrophenol is a severely acute toxicant, exhibiting high toxicity in animals by all routes of administration. It can be absorbed through the intact skin. The toxic effects are heavy sweating, nausea, vomiting, collapse, and death. Ingestion of 1 g of solid can be fatal to humans. A 30-minute exposure to its vapors at a concentration of 300 mg/m3 was lethal to dogs (NIOSH 1986). Chronic effects include polyneuropathy, weight loss, cataracts, and dermatitis.LD50 value, oral (rats): 30 mg/kg.

Fire Hazard

Combustible. May explode if subjected to heat or flame. POISONOUS GAS IS PRODUCED WHEN HEATED. Vapors are toxic. Can detonate or explode when heated under confinement.

Safety Profile

A deadly human poison by ingestion. An experimental poison by ingestion, inhalation, intravenous, intraperitoneal, subcutaneous, and intramuscular routes. Moderately toxic by skin contact. Experimental teratogenic and reproductive effects. Human systemic effects: body temperature increase, change in heart rate, coma. A skin irritant. Mutation data reported. Phytotoxic. A pesticide. An explosive. Forms explosive salts with alkalies and ammonia. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS.

Carcinogenicity

No teratogenic effects have been reported in limited developmental toxicity studies in rodents. Decreased fetal body weight and crown-rump length were noted in rats and mice after parenteral administration. 2,4-DNP was not genotoxic in most in vivo and in vitro studies. An ACGIH threshold limit value (TLV) has not been established for 2,4-DNP.

Metabolic pathway

The bacterial strain RB1, which is isolated by enrichment cultivation with 2,4-dinitrophenol, degrades this phenol into two aliphatic acids. One metabolite results from the release of the 2-nitro group as nitrile, with the production of aliphatic nitro compound, 3-nitroadipate. Then, the 3-nitro group is released from this metabolite as nitrile. The other metabolite is 4,6-dinitrohexanoic acid possessing two nitro groups from 2,4-dinitrophenol.

Purification Methods

Crystallise it from *benzene, EtOH, EtOH/H2O or H2O acidified with dilute HCl, dry it, then recrystallise it from CCl4. Dry it in an oven and store it in a vacuum desiccator over CaSO4. The benzoate has m 132o (from EtOH). [Beilstein 6 IV 1369.]

Check Digit Verification of cas no

The CAS Registry Mumber 51-28-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 51-28:
(4*5)+(3*1)+(2*2)+(1*8)=35
35 % 10 = 5
So 51-28-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H/p-1

51-28-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,4-dinitrophenol

1.2 Other means of identification

Product number -
Other names Phenol, 2,4-dinitro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Phenols/phenoxy acids
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:51-28-5 SDS

51-28-5Synthetic route

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With water; sodium hydroxide at 100℃; for 1.5h;100%
With potassium carbonate In ethanol97.5%
Stage #1: 1-chloro-2,4-dinitro-benzene With sodium hydroxide In water; acetonitrile for 1h; Reflux;
Stage #2: With hydrogenchloride In water; acetonitrile Kinetics; Thermodynamic data; Solvent; Temperature;
97%
N-(2,4-dinitrophenyl)aminoethanol
1945-92-2

N-(2,4-dinitrophenyl)aminoethanol

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With ammonium hydroxide; sodium sulfite In methanol at 70℃; for 48h;100%
triethylamine N-oxide
2687-45-8

triethylamine N-oxide

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

triethylamine hydrochloride
554-68-7

triethylamine hydrochloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 24h;A 98%
B 98.5%
In N,N-dimethyl-formamide for 24h; Ambient temperature;A 98%
B 98.5%
phenol
108-95-2

phenol

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With trichloroisocyanuric acid; silica gel; sodium nitrite at 20℃; for 0.25h;98%
With dinitrogen tetraoxide; ferric nitrate In ethyl acetate for 0.166667h; Heating;96%
With chromium(III) nitrate; dinitrogen tetraoxide In ethyl acetate for 0.25h; Nitration; reflux;95%
2,4-Dinitroanilin
97-02-9

2,4-Dinitroanilin

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With water; sodium hydroxide at 100℃; for 1.5h;98%
With potassium hydroxide
trimethylamine-N-oxide
1184-78-7

trimethylamine-N-oxide

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
for 24h; Ambient temperature;A 97%
B 98%
trimethylamine-N-oxide
1184-78-7

trimethylamine-N-oxide

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 24h; Ambient temperature;A 97%
B 98%
4-nitro-phenol
100-02-7

4-nitro-phenol

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With dimethylbromosulphonium bromide; tetrabutylammonium nitrite In acetonitrile at 20℃; for 24h; regioselective reaction;97%
With perchloric acid; montmorillonite K10 supported ammonium nitrate at 50℃; for 1.5h;95%
With Zn(NO3)2*2N2O4 In dichloromethane at 20℃; for 5h;95%
meta-dinitrobenzene
99-65-0

meta-dinitrobenzene

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With tert.-butylhydroperoxide; potassium tert-butylate; ammonia In tetrahydrofuran for 0.25h;96%
With Cumene hydroperoxide; potassium tert-butylate In N,N,N,N,N,N-hexamethylphosphoric triamide at 15 - 20℃; for 1.5h;92%
With potassium hydroxide; Cumene hydroperoxide In ammonia at -33℃;90%
(E)-O-2,4-dinitrophenyl-2,4-dinitrobenzaldoxime

(E)-O-2,4-dinitrophenyl-2,4-dinitrobenzaldoxime

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

2,4-dinitrobenzonitrile
4110-33-2

2,4-dinitrobenzonitrile

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 25℃; for 7h; Kinetics; Reagent/catalyst;A n/a
B 96%
With triethylamine hydrochloride; triethylamine In water; acetonitrile at 25℃; Rate constant; different Et3N concentrations;
With sodium ethanolate In ethanol at 25℃; Kinetics; Further Variations:; Reagents; Elimination;
salicylic acid
69-72-7

salicylic acid

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

2,6-dinitrophenol
573-56-8

2,6-dinitrophenol

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 12h;A 95%
B 3%
3-(2,4-dinitrophenylamino)propionic acid
3185-97-5

3-(2,4-dinitrophenylamino)propionic acid

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water for 5h; Kinetics; Product distribution; Further Variations:; pH-values; Heating;94%
1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

5-chloro-2,4-dinitrophenol
54715-57-0

5-chloro-2,4-dinitrophenol

Conditions
ConditionsYield
With tert.-butylhydroperoxide; potassium tert-butylate; ammonia In tetrahydrofuran for 0.25h;A n/a
B 93%
With potassium tert-butylperoxide In ammonia at -33℃; Mechanism; competition between hydrogen and halogen substitution; other reagent t-butyl hydroperoxide, cumene hydroperoxide, NaOH, t-BuOK;A 20%
B 50%
With tert.-butylhydroperoxide; potassium tert-butylate; ammonia In tetrahydrofuran for 0.25h;A 50%
B n/a
1-(benzyloxy)-2,4-dinitrobenzene
2734-78-3

1-(benzyloxy)-2,4-dinitrobenzene

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With thiophene; sodium hydrogen sulfate; silica gel for 9h; Heating;93%
N-(2,4-dinitro-phenyl)-L-alanine
1655-52-3

N-(2,4-dinitro-phenyl)-L-alanine

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

2-methyl-5-nitro-1H-benzimidazole 3-oxide
4615-69-4

2-methyl-5-nitro-1H-benzimidazole 3-oxide

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water for 2h; Heating;A n/a
B 88%
2,4-dinitrobenzeneboronic acid

2,4-dinitrobenzeneboronic acid

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With hydrazine hydrate; caesium carbonate at 20℃; for 15h;86%
2,4-Dinitrofluorobenzene
70-34-8

2,4-Dinitrofluorobenzene

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With sodium hydroxide for 1h; Heating;85%
With potassium carbonate In dimethyl sulfoxide for 3h; Heating;79%
With Cumene hydroperoxide; potassium tert-butylate In ammonia at -33℃;63%
phenol
108-95-2

phenol

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With Zn(NO3)2*2N2O4 In ethyl acetate at 20℃; for 4h;A 85%
B 8%
2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With ferric nitrate; 1,3-di-n-butyl-imidazolium tetrafluoroborate at 60℃; for 2h;82%
With Zn(NO3)2*2N2O4 In dichloromethane for 4h; Heating;82%
With N-Bromosuccinimide; silver nitrate In acetonitrile for 7.5h; Reflux;75%
phenol
108-95-2

phenol

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

C

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With NO+*18-crown-6*H(NO3)2- In ethyl acetate for 0.166667h; Nitration; Heating;A 82%
B 8%
C 3%
With silica-acetate; dinitrogen tetraoxide In ethyl acetate for 0.166667h; Heating;A 74%
B 8%
C 10%
2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine
863033-41-4

2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine

benzylamine
100-46-9

benzylamine

A

1-N-benzyl-2',3',5'-tri-O-acetyladenosine
866325-38-4

1-N-benzyl-2',3',5'-tri-O-acetyladenosine

B

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
Stage #1: 2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine; benzylamine In acetonitrile at -30℃;
Stage #2: With water In acetonitrile Heating;
A 81%
B n/a
(p-hydroxyphenyl)boronic acid
71597-85-8

(p-hydroxyphenyl)boronic acid

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
With bismuth (III) nitrate pentahydrate In toluene at 70 - 80℃; for 2h; Inert atmosphere;77%
2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine
863033-41-4

2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine

isopropylamine
75-31-0

isopropylamine

A

2',3',5'-tri-O-acetyl-1-isopropyladenosine

2',3',5'-tri-O-acetyl-1-isopropyladenosine

B

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
Stage #1: 2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine; isopropylamine In acetonitrile at -30℃;
Stage #2: With water In acetonitrile Heating;
A 76%
B n/a
meta-dinitrobenzene
99-65-0

meta-dinitrobenzene

aniline
62-53-3

aniline

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

N-phenyl-2,4-dinitroaniline
961-68-2

N-phenyl-2,4-dinitroaniline

Conditions
ConditionsYield
With potassium permanganate; tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h;A 22%
B 75%
1-phenyl-2-(piperidin-1-yl)ethanone O-(2,4-dinitrophenyl)oxime

1-phenyl-2-(piperidin-1-yl)ethanone O-(2,4-dinitrophenyl)oxime

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

2-hydroxy-5-nitroaniline
99-57-0

2-hydroxy-5-nitroaniline

C

2-Phenyl-5,6,7,8-tetrahydro-imidazo<1,2-a>pyridin
3649-46-5

2-Phenyl-5,6,7,8-tetrahydro-imidazo<1,2-a>pyridin

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; for 5h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation;A 33%
B 22%
C 75%
methanol
67-56-1

methanol

2,4-Dinitrofluorobenzene
70-34-8

2,4-Dinitrofluorobenzene

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

2,4-dinitroanisole
119-27-7

2,4-dinitroanisole

Conditions
ConditionsYield
With sodium hydroxide; cetyltrimethylammonim bromide In water at 26℃; Product distribution; other alcohols, var. concentrations alcohols;A 26%
B 74%
2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

2,6-dinitrophenol
573-56-8

2,6-dinitrophenol

Conditions
ConditionsYield
With perchloric acid; montmorillonite K10 supported ammonium nitrate at 50℃; for 1.5h;A 73%
B 23%
durch Nitrieren; Trennung durch fraktionierte Faellung des Gemisches der Kaliumsalze mit BaCl2;
With tetrachloromethane; nitrosylsulfuric acid at 30℃;
With nitric acid
2,4-dinitrophenyl acrylate
62599-74-0

2,4-dinitrophenyl acrylate

benzaldehyde
100-52-7

benzaldehyde

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

3-(hydroxy(phenyl)methyl)-5-phenyldihydrofuran-2(3H)-one

3-(hydroxy(phenyl)methyl)-5-phenyldihydrofuran-2(3H)-one

Conditions
ConditionsYield
With samarium; copper(l) iodide; potassium iodide In tetrahydrofuran at 20℃; Molecular sieve; diastereoselective reaction;A n/a
B 73%
phenol
108-95-2

phenol

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

2,6-dinitrophenol
573-56-8

2,6-dinitrophenol

Conditions
ConditionsYield
With thionyl chloride; bismuth subnitrate In dichloromethane at 20℃; for 2h;A 72%
B 14%
2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine
863033-41-4

2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine

ethylamine
75-04-7

ethylamine

A

2',3',5'-tri-O-acetyl-1-ethyladenosine

2',3',5'-tri-O-acetyl-1-ethyladenosine

B

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

Conditions
ConditionsYield
Stage #1: 2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine; ethylamine In acetonitrile at -30℃;
Stage #2: With water In acetonitrile Heating;
A 72%
B n/a
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

2-bromo-4,6-dinitrophenol
2316-50-9

2-bromo-4,6-dinitrophenol

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 9.5h; Heating;100%
With N-benzyl-N,N-dimethyl anilinium peroxodisulfate; potassium bromide In acetonitrile for 9.5h; Reflux; regioselective reaction;91%
With poly(4-vinylpyridinium bromochromate) In acetonitrile at 20℃; for 2h; regioselective reaction;82%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

dabsyl chloride
56512-49-3

dabsyl chloride

4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid 2,4-dinitro-phenyl ester
146303-72-2

4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid 2,4-dinitro-phenyl ester

Conditions
ConditionsYield
With carbonate-bicarbonate buffer In acetone; acetonitrile 1.) 15 min, 2.) reflux;100%
With carbonate-bicarbonate buffer In acetone for 0.5h; Heating;
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

1-ethoxy-2-(trimethylsilyl)vinyl acetate
104293-02-9

1-ethoxy-2-(trimethylsilyl)vinyl acetate

2,4-dinitrophenyl acetate
4232-27-3

2,4-dinitrophenyl acetate

Conditions
ConditionsYield
In dichloromethane at 40℃; for 22h;100%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

4BF4(1-)*C86H162N6O2(4+)

4BF4(1-)*C86H162N6O2(4+)

sodium 2,4-dinitrophenoxide
1011-73-0

sodium 2,4-dinitrophenoxide

BF4(1-)*C110H172CoN14O22(1+)

BF4(1-)*C110H172CoN14O22(1+)

Conditions
ConditionsYield
Stage #1: 4BF4(1-)*C86H162N6O2(4+) With cobalt(II) acetate In ethanol at 20℃; for 3h;
Stage #2: 2,4-Dinitrophenol With oxygen In dichloromethane for 3h;
Stage #3: sodium 2,4-dinitrophenoxide With oxygen In dichloromethane Product distribution / selectivity;
100%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

(R,E)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid

(R,E)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid

2,4-dinitrophenyl (R,E)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoate

2,4-dinitrophenyl (R,E)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.5h;100%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

(S,Z)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid

(S,Z)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid

2,4-dinitrophenyl (S,Z)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoate

2,4-dinitrophenyl (S,Z)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.5h;100%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

tert-butyl (3-methoxypyridin-4-yl)carbamate

tert-butyl (3-methoxypyridin-4-yl)carbamate

tert-butyl N-(1-amino-3-methoxy-pyridin-1-ium-4-yl)carbamate 2,4-dinitrophenolate salt

tert-butyl N-(1-amino-3-methoxy-pyridin-1-ium-4-yl)carbamate 2,4-dinitrophenolate salt

Conditions
ConditionsYield
In acetonitrile at 40℃; Inert atmosphere;100%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

C36H58N4O2(2+)*2BF4(1-)

C36H58N4O2(2+)*2BF4(1-)

sodium 2,4-dinitrophenoxide
1011-73-0

sodium 2,4-dinitrophenoxide

C42H59CoN6O7(2+)*2BF4(1-)

C42H59CoN6O7(2+)*2BF4(1-)

Conditions
ConditionsYield
Stage #1: C36H58N4O2(2+)*2BF4(1-); cobalt(II) acetate In ethanol at 20℃; for 2h; Glovebox; Inert atmosphere; Schlenk technique;
Stage #2: 2,4-Dinitrophenol With oxygen In dichloromethane for 2h;
Stage #3: sodium 2,4-dinitrophenoxide In dichloromethane at 20℃;
100%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

C36H52N4O2(2+)*2BF4(1-)

C36H52N4O2(2+)*2BF4(1-)

sodium 2,4-dinitrophenoxide
1011-73-0

sodium 2,4-dinitrophenoxide

C42H53CoN6O7(2+)*2BF4(1-)

C42H53CoN6O7(2+)*2BF4(1-)

Conditions
ConditionsYield
Stage #1: C36H52N4O2(2+)*2BF4(1-); cobalt(II) acetate In ethanol at 20℃; for 2h; Glovebox; Inert atmosphere; Schlenk technique;
Stage #2: 2,4-Dinitrophenol With oxygen In dichloromethane for 2h;
Stage #3: sodium 2,4-dinitrophenoxide In dichloromethane at 20℃;
100%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

benzoic acid
65-85-0

benzoic acid

2,4-dinitrophenyl benzoate
1523-15-5

2,4-dinitrophenyl benzoate

Conditions
ConditionsYield
With iodine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.333333h;99%
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 12h;90%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

2,4-dinitroanisole
119-27-7

2,4-dinitroanisole

Conditions
ConditionsYield
With N-butyl-4-methylpyridinium bromide at 170℃; for 0.5h; Inert atmosphere; Ionic liquid; Green chemistry; chemoselective reaction;99%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

2-hydroxy-5-nitroaniline
99-57-0

2-hydroxy-5-nitroaniline

Conditions
ConditionsYield
With hydrazine hydrate at 90℃; for 18h;98%
With hydrazine hydrate In water at 110℃; Sealed tube; Green chemistry;95%
With hydrazine hydrate In isopropyl alcohol at 110℃; for 0.25h; Catalytic behavior; Sealed tube; chemoselective reaction;94%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

tri(p-tolyl)antimony
5395-43-7

tri(p-tolyl)antimony

toluene
108-88-3

toluene

μ2-oxobis[(2,4-dinitrophenoxo)tris(para-tolyl)antimony] toluene monosolvate

μ2-oxobis[(2,4-dinitrophenoxo)tris(para-tolyl)antimony] toluene monosolvate

Conditions
ConditionsYield
Stage #1: tert.-butylhydroperoxide; 2,4-Dinitrophenol; tri(p-tolyl)antimony In diethyl ether at 20℃; for 24h;
Stage #2: toluene In octane
98%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

2,4-diaminophenol
95-86-3

2,4-diaminophenol

Conditions
ConditionsYield
With sodium tetrahydroborate; pyrographite In tetrahydrofuran; water at 50 - 60℃; for 5h;97%
With sodium tetrahydroborate In ethanol; water at 45℃; for 0.0833333h;96%
Stage #1: 2,4-Dinitrophenol With palladium on activated charcoal In methanol at 20℃; for 0.0833333h; Autoclave; Inert atmosphere;
Stage #2: With hydrogen In methanol at 65℃; under 3600.36 - 6375.64 Torr; for 1.5h; Pressure; Temperature; Autoclave;
96.16%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

N-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

2,4-dinitrophenyl N-phenylbenzimidate
107569-59-5

2,4-dinitrophenyl N-phenylbenzimidate

Conditions
ConditionsYield
diethylamine In diethyl ether96%
triethylamine In 1,4-dioxane
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

acetophenone
98-86-2

acetophenone

3-(2-phenyl-2-oxoethyl)-2,4-bis(aci-nitro)cyclohex-5-en-1-one disodium salt

3-(2-phenyl-2-oxoethyl)-2,4-bis(aci-nitro)cyclohex-5-en-1-one disodium salt

Conditions
ConditionsYield
With sodium ethanolate at 18 - 20℃; for 0.5h;96%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

tert-butylsulfinyl chloride
31562-43-3

tert-butylsulfinyl chloride

2-Methyl-propane-2-sulfinic acid 2,4-dinitro-phenyl ester
112881-95-5

2-Methyl-propane-2-sulfinic acid 2,4-dinitro-phenyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane for 16h; Ambient temperature;95%
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

iodobenzene
591-50-4

iodobenzene

2,4-dinitrophenyl phenyl ether
2486-07-9

2,4-dinitrophenyl phenyl ether

Conditions
ConditionsYield
With sodium hydroxide In neat (no solvent) at 90℃; for 6h; Green chemistry;95%
diethyl sulfate
64-67-5

diethyl sulfate

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

2,4-dinitro-1-ethoxybenzene
610-54-8

2,4-dinitro-1-ethoxybenzene

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran at 70℃; for 0.5h;94%

51-28-5Relevant articles and documents

Synthesis of 2,4-dinitrophenol

Khabarov, Yu.G.,Lakhmanov,Kosyakov,Ul'yanovskii

, p. 1577 - 1580 (2012)

New highly selective method is suggested for synthesis of 2,4-dinitrophenol by nitration of phenol with nitric acid in an aqueous-alcoholic medium at the boiling point of the reaction mixture. The yield of 2,4-dinitrophenol is as high as 80%. Pleiades Publishing, Ltd., 2012.

-

Carmack et al.

, p. 785,789 (1947)

-

Functionalized graphene oxide as a nanocatalyst in dephosphorylation reactions: Pursuing artificial enzymes

Orth, Elisa S.,Fonsaca, Jéssica E.S.,Almeida, Thomas Golin,Domingues, Sergio H.,Ferreira, José G.L.,Zarbin, Aldo J.G.

, p. 9891 - 9894 (2014)

The present study reports for the first time the use of a thiol-functionalized graphene oxide nanocatalyst with impressive activity (>105-fold) in dephosphorylation reactions. The innovative and recyclable nanocatalyst has potential in designing artificial enzymes with targeted multifunctionalities and in detoxification of organophosphorus agents.

Phosphodiester hydrolysis promoted by dinuclear iron(III) complexes

Piovezan, Clovis,Da Silva Lisboa, Fabio,Nunes, Fabio Souza,Drechsel, Sueli Maria

, p. 79 - 85 (2011)

We report the reactivity of three binuclear non-heme Fe(III) compounds, namely [Fe2(bbppnol)(μ-AcO)(H2O)2](ClO 4)2 (1), [Fe2(bbppnol)(μ-AcO) 2](PF6) (2), and [Fe2(bbppnol)(μ-OH)(Cl) 2]?6H2O (3), where H3bbppnol = N,N′-bis(2-hydroxybenzyl)-N,N′-bis(2-methylpyridyl)-1, 3-propanediamine-2-ol, toward the hydrolysis of bis-(2,4-dinitrophenyl)phosphate as models for phosphoesterase activity. The synthesis and characterization of the new complexes 1 and 3 was also described. The reactivity differences observed for these complexes show that the accessibility of the substrate to the reaction site is one of the key steps that determinate the hydrolysis efficiency.

Hasegawa,Abe

, p. 985,986 (1972)

Bowden,Cook

, p. 249 (1970)

An Approach to More Accurate Model Systems for Purple Acid Phosphatases (PAPs)

Bernhardt, Paul V.,Bosch, Simone,Comba, Peter,Gahan, Lawrence R.,Hanson, Graeme R.,Mereacre, Valeriu,Noble, Christopher J.,Powell, Annie K.,Schenk, Gerhard,Wadepohl, Hubert

, p. 7249 - 7263 (2015)

The active site of mammalian purple acid phosphatases (PAPs) have a dinuclear iron site in two accessible oxidation states (FeIII2 and FeIIIFeII), and the heterovalent is the active form, involved in the regulation of phosphate and phosphorylated metabolite levels in a wide range of organisms. Therefore, two sites with different coordination geometries to stabilize the heterovalent active form and, in addition, with hydrogen bond donors to enable the fixation of the substrate and release of the product, are believed to be required for catalytically competent model systems. Two ligands and their dinuclear iron complexes have been studied in detail. The solid-state structures and properties, studied by X-ray crystallography, magnetism, and M?ssbauer spectroscopy, and the solution structural and electronic properties, investigated by mass spectrometry, electronic, nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), and M?ssbauer spectroscopies and electrochemistry, are discussed in detail in order to understand the structures and relative stabilities in solution. In particular, with one of the ligands, a heterovalent FeIIIFeII species has been produced by chemical oxidation of the FeII2 precursor. The phosphatase reactivities of the complexes, in particular, also of the heterovalent complex, are reported. These studies include pH-dependent as well as substrate concentration dependent studies, leading to pH profiles, catalytic efficiencies and turnover numbers, and indicate that the heterovalent diiron complex discussed here is an accurate PAP model system.

Kinetic Study of the Aminolysis and Pyridinolysis of O-Phenyl and O-Ethyl O-(2,4-Dinitrophenyl) Thiocarbonates. A Remarkable Leaving Group Effect

Castro, Enrique A.,Cubillos, Maria,Aliaga, Margarita,Evangelisti, Sandra,Santos, Jose G.

, p. 2411 - 2416 (2004)

The reactions of a series of secondary alicyclic (SA) amines with O-phenyl and O-ethyl O-(2,4-dinitrophenyl) thiocarbonates (1 and 2, respectively) and of a series of pyridines with the former substrate are subjected to a kinetic investigation in water, at 25.0 °C, ionic strength 0.2 M (KCl). Under amine excess over the substrate, all the reactions obey pseudo-first-order kinetics and are first-order in amine. The Broensted-type plots are biphasic, with slopes (at high pKa) of β1 = 0.20 for the reactions of SA amines with 1 and 2 and β1 = 0.10 for the pyridinolysis of 1 and with slopes (at low pKa) of β2 = 0.80 for the reactions of SA amines with 1 and 2 and β2 = 1.0 for the pyridinolysis of 1. The pKa values at the curvature center (pK a0) are 7.7, 7.0, and 7.0, respectively. These results are consistent with the existence of a zwitterionic tetrahedral intermediate (T?) and a change in the rate-determining step with the variation of amine basicity. The larger pKa0 value for the pyridinolysis of 1 compared to that for 2 (pKa0 = 6.8) and the larger pKa0 value for the reactions of SA amines with 1 relative to 2 are explained by the greater inductive electron withdrawal of PhO compared to EtO. The larger pKa0 values for the reactions of SA amines with 1 and 2, relative to their corresponding pyridinolysis, are attributed to the greater nucleofugalities of SA amines compared to isobasic pyridines. The smaller pKa0 value for the reactions of SA amines with 2 than with O-ethyl S-(2,4-dinitrophenyl) dithiocarbonate (pKa0 = 9.2) is explained by the greater nucleofugality from T? of 2,4-dinitrophenoxide (DNPO-) relative to the thio derivative. The stepwise reactions of SA amines with 1 and 2, in contrast to the concerted mechanisms for the reactions of the same amines with the corresponding carbonates, is attributed to stabilization of T? by the change of O- to S-. The simple mechanism for the SA aminolysis of 2 (only one tetrahedral intermediate, T?) is in contrast to the more complex mechanism (two tetrahedral intermediates, T? and T-, the latter formed by deprotonation of T? by the amine) for the same aminolysis of the analogous thionocarbonate with 4-nitrophenoxide (NPO-) as nucleofuge. To our knowledge, this is the first example of a remarkable change in the decomposition path of a tetrahedral intermediate T? by replacement of NPO- with DNPO- as the leaving group of the substrate. This is explained by (i) the greater leaving ability from T? of DNPO- than NPO- and (ii) the similar rates of deprotonation of both T? (formed with DNPO and NPO).

Three new dinuclear nickel(II) complexes with amine pendant-armed ligands: Characterization, DFT study, antibacterial and hydrolase-like activity

Chaves, Cláudia C.V.,Farias, Giliandro,Formagio, Maíra D.,Neves, Ademir,Peralta, Rosane M.,Mikcha, Jane M.G.,de Souza, Bernardo,Peralta, Rosely A.

, (2020)

Herein, we report the synthesis and characterization of three new Ni(II) complexes, namely: [Ni2(H2LEt)(μ-OAc)2(H2O)]BPh4?ClO4 (1), (H2LEt = 2-[(N-benzyl-N-2-pyridyl methylamine)]-4-methyl-6-[N-2(pyridylmethyl)aminomethyl)]-6((2-aminoethyl)amino)methyl phenol); [Ni2(H2LProp)(μ-OAc)2(H2O)](ClO4)2 (2), (H2LProp = 2-[(N-benzyl-N-2-pyridylmethylamine)]-4-methyl-6-[N-(2-pyridylmethyl)aminomethyl]-6-((2-aminopropyl) amino)methylphenol); and [Ni2(LBut)(μ-OAc)2(H2O)](HCl)2 (3), (LBut = 2-[(N-benzyl-N-2-pyridylmethylamine)]-4-methyl-6-[N-(2-pyridylmethyl)aminomethyl]-6-((2-aminobuthyl) amino)methylphenol). All of them were characterized through spectroscopic techniques (elemental analysis, IR, UV–Vis spectroscopy), ESI-MS, electrochemistry and potentiometric titration. Density functional theory (DFT) was used to better understand the electronic and molecular structure of these complexes. The hydrolytic activity of complexes 1–3 towards the 2,4-BDNPP substrate was analyzed and complex 2 presented the highest catalytic efficiency (kcat/KM) of the three, possibly due to a greater interaction with the substrate. The complexes were also screened for their antibacterial activities using both Gram-positive and Gram-negative bacterial strains by minimum inhibitory concentration and minimum bactericidal concentration methods.

Catalysis by Cyclodextrins in Nucleophilic Aromatic Substitution Reactions

Rossi, Rita H. de,Barra, Monica,Vargas, Elba B. de

, p. 2157 - 2162 (1986)

The kinetics of the hydrolysis of 1-X-2,4-dinitrobenzene (X=Cl,F) were studied in the presence of β-cyclodextrin.The overall rate of hydrolysis is catalyzed by the added compound, and the observed catalysis is pH dependent.For the reaction of the fluoro derivative the catalytic factor at 0.01 M β-cyclodextrin changes from 7 at 10 -3 M NaOH to 2.5 at 10 -1 M NaOH.Part of the catalysis is due to nucleophilic reaction of β-cyclodextrin with the substrate and part of it is attributed to the reaction of an inclusion complex formed between the substrate and the β-cyclodextrin.The catalytic factor corresponding to the reaction in the cavity is 1.4 and 2 for the fluoro and chloro derivative, respectively

New La(III) complex immobilized on 3-aminopropyl-functionalized silica as an efficient and reusable catalyst for hydrolysis of phosphate ester bonds

Muxel, Alfredo A.,Neves, Ademir,Camargo, Maryene A.,Bortoluzzi, Adailton J.,Szpoganicz, Bruno,Castellano, Eduardo E.,Castilho, Nathalia,Bortolotto, Tiago,Terenzi, Hernan

, p. 2943 - 2952 (2014)

Described herein is the synthesis, structure, and monoesterase and diesterase activities of a new mononuclear [LaIII(L 1)(NO3)2] (1) complex (H2L 1 = 2-bis[{(2-pyridylmethyl)-aminomethyl}-6-[N-(2-pyridylmethyl) aminomethyl)])-4-methyl-6-formylphenol) in the hydrolysis of 2,4-bis(dinitrophenyl)phosphate (2,4-BDNPP). When covalently linked to 3-aminopropyl-functionalized silica, 1 undergoes disproportionation to form a dinuclear species (APS-1), whose catalytic efficiency is increased when compared to the homogeneous reaction due to second coordination sphere effects which increase the substrate to complex association constant. The anchored catalyst APS-1 can be recovered and reused for subsequent hydrolysis reactions (five times) with only a slight loss in activity. In the presence of DNA, we suggest that 1 is also converted into the dinuclear active species as observed with APS-1, and both were shown to be efficient in DNA cleavage.

MICELLAR CATALYSIS OF ORGANIC REACTIONS. PART 35. KINETIC DETERMINATION OF THE CRITICAL MICELLE CONCENTRATION OF CATIONIC MICELLES IN THE PRESENCE OF ADDITIVES

Broxton, Trevor J.,Christie, John R.,Dole, Anthony J.

, p. 437 - 441 (1994)

The critical micelle concentration of solutions of cetyltrimethylammonium bromide and of tetradecyltrimethylammonium bromides were determined by a kinetic method.This involved the determination of the rates of the hydroxydehalogenation of some activated aromatic substrates over a wide range of detergent concentrations.Measurements were made in solutions containing significant quantities of added hydroxyl ion and substrates which were themselves amphiphilic.Conventional methods cannot be applied with confidence to such systems.The effects of changing hydroxyl ion concentrations, added sodium bromide, changing the nature of the aromatic substrate (whether neutral or charged), the identity of the micellar counterion and the temperature were investigated.It was found that added bromide or hydroxyl ions resulted in a lower CMC whereas increased temperature led to an increase in the CMC.The nature of the micellar counterion (Br, F, OH, SO4) had little effect on the CMC.The presence of a charged aromatic substrate led to a considerable lowering of the CMC, whereas the neutral aromatic substrate used showed very little effect.

Bis(2,4-dinitrophenyl) phosphate hydrolysis mediated by lanthanide ions

Longhinotti, Elisane,Domingos, Josiel B.,Da Silva, Pedro L.F.,Szpoganicz, Bruno,Nome, Faruk

, p. 167 - 172 (2005)

The kinetics of the hydrolysis of bis(2,4-dinitrophenyl) phosphate (BDNPP) were studied in basic solutions in the presence of La3, Sm 3, Tb3+ and Er3. Bis-Tris propane (BTP) buffer was used to stabilize the Ln3 hydroxide complexes in solution. Two equivalents of the 2,4-dinitrophenolate ion (DNP) were liberated for each equivalent of BDNPP and the reaction showed first-order kinetics. Potentiometric titrations showed the formation of dinuclear complexes such as [Ln2(BTP)2(OH)n](6-n), with values of n varying as a function of pH, for all studied metals. Hence the catalytic effect depends on the formation of dinuclear lanthanide ion complexes with several hydroxo ligands. Copyright

DNA phosphodiester bond hydrolysis mediated by Cu(II) and Zn(II) complexes of 1,3,5,-triamino-cyclohexane derivatives

Sissi, Claudia,Mancin, Fabrizio,Palumbo, Manlio,Scrimin, Paolo,Tecilla, Paolo,Tonellato, Umberto

, p. 1265 - 1271 (2000)

The hydrolytic activity of the 1,3,5-triaminocycloxexane derivatives TACH, TACI and TMCA complexed to Zn(II) and Cu(II) towards a model phosphoric ester and plasmid DNA has been evaluated by means of spectroscopic and gel-electrophoresis techniques. At conditions close to physiological, a prominent cleavage effect mediated by the nature of the ligand and metal ion was generally observed. TACI complexes are the most active in relaxing supercoiled DNA, the effect being explained by the affinity of the hydroxylated ligand for the nucleic acid. As indicated by the dependence of cleavage efficiency upon pH, Zn(II)-complexes act by a purely hydrolytic mechanism. In the case of Cu(II)-complexes, although hydrolysis should be prominent, involvement of an oxidative pathway cannot be completely ruled out.

Effect of acetonitrile-water mixtures on the reaction of dinitrochlorobenzene and dinitrochlorobenzo-trifluoride with hydroxide ion

El-Mallah,Senior,Nabil,Ramadan,Hamed

, p. 453 - 463 (2010)

The kinetics of alkaline hydrolysis of 2-chloro-3,5-dinitrobenzotrifluoride 1 and 1-chloro-2,4-dinitrobenzene 2 were studied in various acetonitrile-water (AN-H2O) mixtures (10-90% w/w) at different temperatures. Thermodynamic parameters ΔH# and ΔS# show great variation, whereas ΔG# appears to vary little with the solvent composition presumably due to compensating variations. The results are discussed in terms of the solvent parameters such as preferential solvation, dielectric constant, polarity/polarizability, and hydrogen bond donor and acceptor parameters. It has been found that the factors controlling the reaction rates are the desolvation of OH-, the solvophobicity of the medium, and free water molecules in rich AN mixed solvent. The data showed that the solvatochromic parameters of (AN-H2O) mixed solvent are destroyed in the presence of excess OH-.

Enhancing the activation of persulfate using nitrogen-doped carbon materials in the electric field for the effective removal of: P -nitrophenol

Tang, Mengdi,Zhang, Yonggang

, p. 38003 - 38015 (2021/12/09)

Degradation of nonbiodegradable organic compounds into harmless substances is one of the main challenges in environmental protection. Electrically-activated persulfate process has served as an efficient advanced oxidation process (AOP) to degrade organic compounds. In this study, we synthesized three nitrogen-doped carbon materials, namely, nitrogen-doped activated carbon plus graphene (NC), and nitrogen-doped activated carbon (NAC), nitrogen-doped graphene (NGE), and three nitrogen-doped carbon material-graphite felt (GF) cathodes. The three nitrogen-doped carbon materials (NC, NGE, NAC) were characterized using X-ray diffraction, Raman spectroscopy, X-ray electron spectroscopy, and nitrogen desorption-adsorption. The electron spin resonance technique was used to identify the presence of hydroxyl radicals (OH), sulfate radicals (SO4-) and singlet oxygen (1O2) species. The results showed that NC was more conducive for the production of free radicals. In addition, we applied NC-GF to an electro-activated persulfate system with the degradation of p-nitrophenol and investigated its performance for contaminant degradation under different conditions. In general, the nitrogen-doped carbon electrode electro-activated persulfate process is a promising way to treat organic pollutants in wastewater.

Degradation of Organophosphates Promoted by 1,2,4-Triazole Anion: Exploring Scaffolds for Efficient Catalytic Systems

Fernandes, Juliano M.,Soek, Rafael N.,Do Nascimento, Thalita C.,Menezes, Leociley R. A.,Sassaki, Guilherme L.,Campos, Renan B.

supporting information, p. 4027 - 4034 (2021/03/01)

Organophosphate (OP) pesticides are responsible for numerous human deaths every year. Nucleophilic substitution is an important method to mitigate the toxicity of obsolete stocks of OPs. Herein, the degradation of O,O-diethyl-2,4-dinitrophenyl phosphate (DEDNPP) and pesticide diethyl-4-nitrophenyl phosphate (Paraoxon) promoted by 1,2,4-triazole (TAZ) was investigated by means of kinetic studies, nuclear magnetic resonance (NMR) analyses, and theoretical calculations. Results showed fast degradation of OPs is promoted by the anionic form of the nucleophile (TAZ(-)) in pH > 8.5 (optimal at pH = 11). Rate enhancements of 106 and 105-fold in relation to neutral hydrolysis of DEDNPP and Paraoxon were observed, respectively, consistent with alpha-nucleophiles reactivity. TAZ(-) regioselectively promotes the degradation of DEDNPP via P-O bond break, forming a quickly hydrolyzable phosphorylated intermediate, regenerating the nucleophile. Calculations using M06-2X/6-311++G(d,p) level of theory revealed that the equivalent nitrogen atoms of TAZ(-) are the main nucleophilic center of the molecule. This study expands the knowledge on the reactivity of iminic compounds as detoxificant agents of OPs, indicating the efficiency and selectivity of TAZ(-) in aqueous medium, encouraging the design of novel TAZ-based catalysts.