16227-10-4

Basic information

• Product Name: 4-Butyl-4H-1,2,4-triazole
• Synonyms: 4-BUTYL-4H-1,2,4-TRIAZOLE;4-butyl-1,2,4-triazole;Triazbutil;4-N-BUTYL-4H-1,2,4-TRIAZOLE;Butrizol;Dithane R-24;RH-124;4H-1,2,4-Triazole, 4-butyl-
• CAS NO: 16227-10-4
• Molecular Formula: C₆H₁₁N₃
• Molecular Weight: 125.17
• EINECS: 240-351-9
• Mol File: 16227-10-4.mol

Chemical Properties

• Boiling Point: 222.65°C (rough estimate)
• Flash Point: 87.4°C
• Appearance: /
• Density: 0.9805 (rough estimate)
• Refractive Index: 1.4690 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Butyl-4H-1,2,4-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Butyl-4H-1,2,4-triazole(16227-10-4)
• EPA Substance Registry System: 4-Butyl-4H-1,2,4-triazole(16227-10-4)

Safety Data

• RIDADR: 2902
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 16227-10-4(Hazardous Substances Data)

Usage

Uses

Used in the Oil and Gas Industry:
4-Butyl-4H-1,2,4-triazole is used as a corrosion inhibitor for metals, specifically in the oil and gas industry, to protect metal surfaces from corrosion by forming a protective layer that prevents the degradation of the metal.
Used in Pharmaceutical Research:
4-Butyl-4H-1,2,4-triazole is also being studied for its potential use in pharmaceuticals, where its unique chemical properties may contribute to the development of new drugs or therapeutic agents.
Used in Organic Synthesis:
Furthermore, this chemical compound is utilized as a building block in organic synthesis, playing a crucial role in the creation of various organic compounds and contributing to the advancement of chemical research and development.

InChI:InChI=1/C40H32N8O2.2ClH/c1-49-37-27-31(23-25-35(37)47-43-39(29-15-7-3-8-16-29)41-45(47)33-19-11-5-12-20-33)32-24-26-36(38(28-32)50-2)48-44-40(30-17-9-4-10-18-30)42-46(48)34-21-13-6-14-22-34;;/h3-28H,1-2H3;2*1H/q+2;;/p-2

Synthetic route

1,2,4-Triazole (288-88-0) + 1-bromo-butane (109-65-9) → 1-butyl-1H-[1,2,4]triazole (6086-22-2) + 4-n-butyl-1,2,4-triazole (16227-10-4)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0 - 20℃; Alkylation;	A 85% B n/a
With aluminum oxide; potassium fluoride; tetrabutylammomium bromide for 24h; Ambient temperature; Yield given. Yields of byproduct given;
With sodium hydroxide In N,N-dimethyl-formamide at 20℃; Alkylation;

1,2,4-Triazole (288-88-0) + 1-bromo-butane (109-65-9) → 1-butyl-1H-[1,2,4]triazole (6086-22-2) + 4-n-butyl-1,2,4-triazole (16227-10-4) + 1,4-dibutyl-4H-1,2,4-triazol-1-ium bromide

Conditions	Yield
With lithium hydroxide; tetrabutylammomium bromide for 24h; Product distribution; Ambient temperature; also benzotriazole; other alkyl halides; var. base as reagents; also reactions in the absence of base; var. temperatures and reaction time; also with conventional heating or microwave heating instead of phase transfer catalysis;

N-butylamine (109-73-9) + orthoformic acid triethyl ester (122-51-0) + formic acid hydrazide (624-84-0) → 4-n-butyl-1,2,4-triazole (16227-10-4)

Conditions	Yield
Stage #1: orthoformic acid triethyl ester; formic acid hydrazide In methanol Heating; Stage #2: N-butylamine In methanol Heating; Further stages.;

1,2,4-Triazole (288-88-0) + Dibutyl carbonate (542-52-9) → 4-n-butyl-1,2,4-triazole (16227-10-4)

Conditions	Yield
With magnesium carbonate at 200℃; for 20h; Inert atmosphere;	5.25 g

methyl bromide (74-83-9) + 4-n-butyl-1,2,4-triazole (16227-10-4) → 4-butyl-1-methyl-4H-1,2,4-triazol-1-ium bromide (1268852-02-3)

Conditions	Yield
In acetonitrile for 36h; Reflux; Inert atmosphere; Schlenk technique;	96%

t-butyl bromide (507-19-7) + 4-n-butyl-1,2,4-triazole (16227-10-4) → 4-butyl-1-tert-butyl-4H-1,2,4-triazol-1-ium bromide

Conditions	Yield
In acetonitrile for 36h; Reflux; Inert atmosphere; Schlenk technique;	92%

4-n-butyl-1,2,4-triazole (16227-10-4) → BH2(C2H2N3(C4H9))2(1+)*I(1-)=[BH2(C2H2N3(C4H9))2]I (1343472-85-4)

Conditions	Yield
With trimethylamine-borane; iodine In toluene for 24h; Reflux;	85.8%

trimethylamine-borane (75-22-9) + iodine (7553-56-2) + 4-n-butyl-1,2,4-triazole (16227-10-4) → BH2(C2H2N3(C4H9))2(1+)*I(1-)=[BH2(C2H2N3(C4H9))2]I (1343472-85-4)

Conditions	Yield
In toluene I2 added to toluene soln. of Me3NBH3 , stirred at room temp. for 1 h, ligand added (1:2:4 molar ratio), mixt. refluxed for 24 h; filtered off, washed (hexane, Et2O, toluene), dried (80°C, vac.),recrystd. (hot EtOH), elem. anal.;	85.8%

Upstream product

• 288-88-0 1,2,4-Triazole 
• 109-65-9 1-bromo-butane 
• 109-73-9 N-butylamine 
• 122-51-0 orthoformic acid triethyl ester 
• 624-84-0 formic acid hydrazide 
• 542-52-9 Dibutyl carbonate 

Downstream Products

• 79917-90-1 1-butyl-3-methylimidazolium chloride 

Relevant articles and documents

Azacyclo-dicarbene subunit borane ionic liquid and preparation method thereof

The invention relates to an azacyclo-dicarbene subunit borane ionic liquid and a preparation method thereof. The azacyclo-dicarbene subunit borane ionic liquid has a structural formula I as shown in the specification. A method for preparing the compound of formula I comprises the following main steps: performing an alkylation reaction on 1,2,4-triazole and a carbonic ester compound, further performing a quaternary amination reaction with halogenated hydrocarbon, and finally performing a reaction with sodium borohydride, thereby obtaining a target product. The ionic liquid provided by the invention can be used as a self-combustion type green rocket propellant, and has the advantages of being short in ignition delay time, good in water stability, large in density ratio impact value, and thelike. In the formula I, R1 is selected from any one of alkyl, and R2 is selected from any one of hydrocarbyl substituent groups.

Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides

The invention relates to novel pyrazolyl benzyl ethers, to a plurality of processes for their preparation and to their use for controlling harmful organisms.

Spin-transition behaviour in chains of FeII bridged by 4-substituted 1,2,4-triazoles carrying alkyl tails

A family of polymeric 1-dimensional chains of iron(II) species showing the spin-crossover phenomenon has been synthesized using 4-n-alkyl-1,2,4-triazoles as bridging ligands. The influence of the length of the alkyl tails on the triazole ligands on characteristic features of the spin transition was studied, showing degrading of steepness with increasing length. A set of four counter ions has been used to access a wider range of transition temperatures. Large hysteresis loops are detected with small tails, mainly for the methyl and ethyl substituted products. In most cases longer tails weaken co-operativity and hysteresis gradually decreases to zero. However it is shown that with certain anions hysteresis remains, even with very long tails on the triazoles. Weakening of the co-operativity mainly arises from a diminution of the length of the polymeric chains with increasing alkyl tails on the triazole. This effect is anion dependent. A strong interaction along the polymeric chains is confirmed.

An investigation into the alkylation of 1,2,4-triazole

The alkylation of 1,2,4-triazole with 4-nitrobenzyl halides and a variety of bases afforded the 1- and 4-alkylated isomers with a consistent regioselectivity of 90:10. Previously reported regiospecific alkylations of 1,2,4-triazole were re-examined and the quoted isomer ratios were shown to depend on the isolation procedure. The use of DBU as base in the alkylation of 1,2,4-triazole allows for a convenient and high yielding synthesis of 1- substituted-1,2,4-triazoles. (C) 2000 Elsevier Science Ltd.

SELECTIVE ALKYLATIONS OF 1,2,4-TRIAZOLE AND BENZOTRIAZOLE IN THE ABSENCE OF SOLVENT

Alkylation of 1,2,4-triazole and benzotriazole has been performed either in basic media under solvent free phase transfer catalysis conditions or in the absence of base by conventional and microwave heating.Several parameters affecting the selectivity have been studied.In the case of triazole alkylation, microwave irradiation produces specific (non thermal) effects both on reactivity and selectivity.

Cyanide process for the preparation of 4H-1,2,4-triazoles

This invention relates to a novel process for the preparation of 4H-substituted-1,2,4-triazoles. In this process, 4H-substituted-1,2,4-triazoles are prepared by the reaction of an amine with hydrazine and a nitrile.