6-Chloro-1-hydroxibenzotriazol

Base Information

• Chemical Name: 6-Chloro-1-hydroxibenzotriazol
• CAS No.: 26198-19-6
• Molecular Formula: C6H4 Cl N3 O
• Molecular Weight: 169.57
• Hs Code.: 29339980
• Mol file: 26198-19-6.mol

Synonyms:1-Hydroxy-6-chloro-1,2,3-benzotriazole;1-Hydroxy-6-chlorobenzotriazole;6-Chloro-1-hydroxy-1H-benzotriazole;NSC 30573;Cl-HOBt;

Chemical Property of 6-Chloro-1-hydroxibenzotriazol

Chemical Property:

• Vapor Pressure: 2.66E-06mmHg at 25°C
• Melting Point: 197 °C
• Refractive Index: 1.758
• Boiling Point: 379.5 °C at 760 mmHg
• PKA: 6.69±0.58(Predicted)
• Flash Point: 183.3 °C
• PSA: 50.94000
• Density: 1.71 g/cm³
• LogP: 1.32200
• Storage Temp.: Store at R.T.

Purity/Quality:

99% ^*data from raw suppliers

1-Hydroxy-6-chlorobenzotriazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,E
• Statements: 22-44-36/37/38-20/21/22-2
• Safety Statements: 15-36-26-35

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-Chloro-1-hydroxibenzotriazol

There total 4 articles about 6-Chloro-1-hydroxibenzotriazol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

2,5-dichloronitrobenzene (89-61-2) → 6-chloro-1-hydroxybenzotriazole (26198-19-6)

Guidance literature:

With hydrazine hydrate; In ethanol; for 36h; Reflux;

DOI:10.1002/adsc.201700071

Reference yield:

piperidine (110-89-4) + 6-chloro-1H-benzo[d][1,2,3]triazol-1-yl diethylcarbamate (1250853-37-2) → N,N-diethylpiperidine-4-carboxamide (59486-99-6) + 6-chloro-1-hydroxybenzotriazole (26198-19-6)

Guidance literature:

In acetonitrile; at 30 ℃; Temperature; Kinetics;

DOI:10.5012/bkcs.2010.31.01.075

Reference yield:

morpholine (110-91-8,99108-56-2) + 6-chloro-1H-benzo[d][1,2,3]triazol-1-yl diethylcarbamate (1250853-37-2) → N,N-diethylmorpholine-4-carboxamide (89609-67-6) + 6-chloro-1-hydroxybenzotriazole (26198-19-6)

Guidance literature:

In acetonitrile; at 30 ℃; Temperature; Kinetics;

DOI:10.5012/bkcs.2010.31.01.075

upstream raw materials:

piperidine

6-chloro-1H-benzo[d][1,2,3]triazol-1-yl diethylcarbamate

morpholine

2,5-dichloronitrobenzene

Downstream raw materials:

1,1'-di(6-chlorobenzotriazolo) oxallate(Cl-DBTO)

(S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid 6-chloro-benzotriazol-1-yl ester

6-chloro-1H-benzo[d][1,2,3]triazol-1-yl ethyl carbonate

1-tert-butoxycarbonyloxy-6-chloro-1H-benzotriazole

Refernces

A comparison of catalysts to promote imidazolide couplings including the identification of 2-hydroxy-5-nitropyridine as a new, safe, and effective catalyst

10.1021/op0580062

The research aimed to evaluate and compare the safety and catalytic effectiveness of five catalysts in promoting imidazolide couplings, a reaction type crucial for amide bond formation in pharmaceutical synthesis. The catalysts tested were 1-hydroxybenzotriazole (HOBt), 6-chloro-1-hydroxybenzotriazole (Cl-HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), 2-hydroxypyridine (HOPy), and the newly identified 2-hydroxy-5-nitropyridine (NO2-HOPy). The study assessed reaction rate enhancement, shock sensitivity, and differential scanning calorimetry (DSC) data. The findings indicated that NO2-HOPy emerged as a safe, effective, and readily available alternative to the commonly used HOBt, offering a favorable balance between catalytic performance and safety. The research concluded that NO2-HOPy is a promising catalyst for imidazolide couplings, particularly given its lack of shock sensitivity and relatively high decomposition onset temperature, making it a safer option compared to the more hazardous HOAt.

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