Description

Di(1-benzotriazolyl)carbonate (CAS No. 88544-01-8) is a high-purity chemical reagent with the molecular formula C₁₃H₈N₆O₃, widely utilized in organic synthesis and peptide coupling reactions. This compound, also known as bis(benzotriazol-1-yl) carbonate (IUPAC name), serves as an efficient activating agent for carboxylic acids, enabling the formation of amides, esters, and other derivatives under mild conditions. Its benzotriazole-based structure ensures high reactivity while minimizing racemization, making it ideal for sensitive applications in pharmaceuticals and bioconjugation. Packaged under inert conditions to ensure stability, this product is rigorously tested for purity (typically ≥95% by HPLC) and is available in research-grade quantities. Suitable for use in anhydrous environments, it is a preferred choice for chemists seeking reliable and selective coupling reagents.

Properties

• CAS Number: 88544-01-8
• Complexity: 389
• IUPAC Name: bis(benzotriazol-1-yl) carbonate
• InChI: InChI=1S/C13H8N6O3/c20-13(21-18-11-7-3-1-5-9(11)14-16-18)22-19-12-8-4-2-6-10(12)15-17-19/h1-8H
• InChI Key: PPQNDCSTOHZQEH-UHFFFAOYSA-N
• Exact Mass: 296.06578814
• Molecular Formula: C13H8N6O3
• Molecular Weight: 296.24
• SMILES: C1=CC=C2C(=C1)N=NN2OC(=O)ON3C4=CC=CC=C4N=N3
• Topological: 97
• Monoisotopic Mass: 296.06578814
• Synonyms: 88544-01-8, di(1-benzotriazolyl)carbonate, 635-480-6, di(benzotriazol-1-yl)carbonate, Carbonic acid,bis(1H-benzotriazol-1-yl) ester, bis(1H-benzo[d][1,2,3]triazol-1-yl) carbonate, bis(1H-1,2,3-benzotriazol-1-yl) carbonate, BIS(HYDROXYBENZOTRIAZOLYL) CARBONATE, bis(1-benzotriazolyl) carbonate, dibenzotriazolyl carbonate, 1H-Benzotriazole, 1,1′-[carbonylbis(oxy)]bis-, SCHEMBL39113, Bis-benzotriazol-1-yl carbonate, bis(benzotriazol-1-yl) carbonate, Bis(hydroxybenzotriazolyl)carbonate, PPQNDCSTOHZQEH-UHFFFAOYSA-N, Bis(1H-benzotriazol-1-yl)carbonate, MFCD00043132, SY309278, DB-077877, G61216

Application

Di(1-benzotriazolyl)carbonate is extensively used as a coupling reagent in peptide synthesis, facilitating the formation of amide bonds without epimerization. It is also employed in the preparation of activated esters and carbamates, particularly in pharmaceutical intermediate synthesis. Researchers leverage its selectivity for carboxyl group activation in complex molecular architectures, including nucleotide derivatives and polymer chemistry.

Safety and Hazards

GHS Hazard Statements

• H228 (100%): Flammable solid [Danger Flammable solids]
• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
• H350 (100%): May cause cancer [Danger Carcinogenicity]

Precautionary Statements

• P203, P210, P240, P241, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501

Hazard Classes and Categories

• Flam. Sol. 1 (100%)
• Acute Tox. 4 (100%)
• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (100%)
• STOT SE 3 (100%)
• Carc. 1B (100%)

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