22713-34-4

Basic information

• Product Name: 1-methoxy-1H-benzotriazole
• Synonyms: 1H-1,2,3-benzotriazole, 1-methoxy-; 1-methoxy-1H-1,2,3-benzotriazole; 1-Methoxy-1H-benzotriazole
• CAS NO: 22713-34-4
• Molecular Formula: C₇H₇N₃O
• Molecular Weight: 149.15
• Mol File: 22713-34-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 249.2°C at 760 mmHg
• Flash Point: 104.5°C
• Density: 1.3g/cm³
• Vapor Pressure: 0.0232mmHg at 25°C
• Refractive Index: 1.638
• CAS DataBase Reference: 1-methoxy-1H-benzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methoxy-1H-benzotriazole(22713-34-4)
• EPA Substance Registry System: 1-methoxy-1H-benzotriazole(22713-34-4)

Safety Data

• Hazardous Substances Data: 22713-34-4(Hazardous Substances Data)

Usage

Common Uses

Corrosion inhibitor, intermediate in pharmaceuticals and agrochemicals synthesis

Chemical Structure

Derivative of benzotriazole with a methoxy group at the 1-position

Primary Function

Metal passivator (prevents corrosion of metals)

Corrosion Protection

Forms a protective layer on metal surfaces (copper, brass, and aluminum)

Inhibition Mechanism

Prevents oxidation and corrosion

Additional Uses

Stabilizer in polymer manufacturing, additive in oil and gas drilling fluids

Safety Profile

Relatively safe, low toxicity, and low environmental impact

Upstream product

• 2592-95-2 benzotriazol-1-ol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 95-14-7 1,2,3-Benzotriazole 
• 56602-33-6 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 
• 21978-63-2 1H-benzo[d][1,2,3]triazol-1-yl 4-methanebenzenesulfonate 
• 76266-27-8 1H-benzotriazole-1-carboxylic acid methyl ester 3-oxide 
• 2273-05-4 1-hydroxy-benzotriazole tautomer 

Downstream Products

• 2592-95-2 benzotriazol-1-ol 

Relevant articles and documents

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Synthesis and evaluation of 1-hydroxybenzotriazole derivatives: Dual inhibitors of carbonic anhydrase ii and sodium hydrogen exchanger i

Ischemia reperfusion injury is responsible for impaired graft functioning in organ transplants, cerebral dysfunction, ischemic heart diseases, systemic inflammatory response syndrome, gastrointestinal dysfunction, and multiple organ dysfunction syndromes. Intracellular pH is critical for cell survival in ischemia reperfusion injury. Sodium hydrogen exchanger I and carbonic anhydrase II are critical in the regulation of intracellular pH. Inhibition of sodium hydrogen exchanger I and carbonic anhydrase II during reperfusion is found to ameliorate ischemia reperfusion injury separately. An attempt is made to synthesize dual inhibitors of sodium hydrogen exchanger and carbonic anhydrase to have better potential drug molecule in ischemia reperfusion injury treatment. The hydroxybenzotriazole is considered as a central pharmacophore for this dual activity and 12 derivatives are synthesized. All derivatives are tested for sodium hydrogen exchanger I and carbonic anhydrase II inhibitory activity. The tosylate derivative (12) is found to be the most potent derivative with IC50 158.7± 8.4 μM for carbonic anhydrase II and 31.07 ± 1.06 μM for sodium hydrogen exchanger I. Although the potency is less than standard drugs but this is the first report of dual inhibitor of carbonic anhydrase II and sodium hydrogen exchanger.

Facile synthesis of 1-Alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications

(1H-Benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), 1H-benzo[d][1,2,3]triazol-1-yl 4- methylbenzenesulfonate (Bt-OTs), and 3H-[1,2,3]triazolo[4,5-b]pyridine-3-yl 4-methylbenzenesulfonate (At-OTs) are classically utilized in peptide synthesis for amide-bond formation. However, a previously undescribed reaction of these compounds with alcohols in the presence of a base, leads to 1-alkoxy-1H-benzo- (Bt-OR) and 7-azabenzotriazoles (At-OR). Although BOP undergoes reactions with alcohols to furnish 1-alkoxy-1H-benzotriazoles, Bt-OTs proved to be superior. Both, primary and secondary alcohols undergo reaction under generally mild reaction conditions. Correspondingly, 1-alkoxy-1H-7-azabenzotriazoles were synthesized from At-OTs. Mechanistically, there are three pathways by which these peptide-coupling agents can react with alcohols. From 31P{1H}, [18O]-labeling, and other chemical experiments, phosphonium and tosylate derivatives of alcohols seem to be intermediates. These then react with BtO- and AtO- produced in situ. In order to demonstrate broader utility, this novel reaction has been used to prepare a series of acyclic nucleoside-like compounds. Because BtO- is a nucleofuge, several Bt-OCH2Ar substrates have been evaluated in nucleophilic substitution reactions. Finally, the possible formation of Pd πallyl complexes by departure of BtO- has been queried. Thus, alpha-allylation of three cyclic ketones was evaluated with 1-(cinnamyloxy)-1H-benzo[d][1,2,3]triazole, via in situ formation of pyrrolidine enamines and Pd catalysis.

Comparison of the effects of 5- and 6-HOAt on model peptide coupling reactions relative to the cases for the 4- and 7-isomers

(equation presented) Synthesis of 5- and 6-HOAt has completed the full set of the four HOAt isomers derived from HOBt by insertion of a single nitrogen atom in the benzenoid nucleus. Comparison of the reactivity of all four isomers in model peptide coupling reactions has confirmed the unique character of the 7-isomer in promoting selectivity and maintaining configuration at the reactive carboxylic acid residue.