Standard Article

1-Hydroxybenzotriazole, Polystyrene-supported

  1. Carmen Nájera1,
  2. Marie-Noelle Roy2

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn00265.pub2

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Nájera, C. and Roy, M.-N. 2013. 1-Hydroxybenzotriazole, Polystyrene-supported. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. 1

    Universidad de Alicante, Alicante, Spain

  2. 2

    Université de Montréal, Montreal, QC, Canada

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

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[2592-95-2] (C15H13N3O)n (MW 251.28)

(polystyrene-divinylbenzene (ca. 1 mol %) copolymer resin; reagent used for peptide coupling)

Alternate Name: PS-HOBt, PS-HOBT.

Solubility: insoluble in all solvents; polymer swells in DMF, CH2Cl2, and CH3CN.

Form Supplied in: brown powder; available as 1-hydroxybenzotriazole-6-carboxamidomethyl and 6-sulfonamidomethyl hydrochloric acid.

Analysis of Reagent Activity: the number of active sites on the resin is determined by formation of the polymer-bound acetate ester by treatment of 2 g of polymer with acetic anhydride or acetyl chloride (4 mmol) in CH2Cl2 (10 mL) in the presence of pyridine (0.5 mL). After 30 min stirring at room temperature, the polymer was filtered off and washed with DMF (2 × 20 mL), CH2Cl2 (3 × 20 mL), and dry ether (3 × 20 mL). Subsequent treatment with isopropylamine (large excess) yielded N-isopropylacetamide and recovered polymer.3 Optimal capacity between 0.2 and 1.5 mmol g−1.4

Preparative Methods: prepared from copolystyrene/1 mol % divinylbenzene (100–200 or 200–400 mesh) and 4-chloro-3-nitrobenzyl alcohol using aluminium trichloride at 90 °C, followed by treatment with hydrazine at 100 °C, and final cyclization with hydrochloric acid and neutralization.1

Handling, Storage, and Precautions: very stable, not hygroscopic and can be stored for more than 2 years under ambient conditions.2

Featured Compounds

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  1. 1 - 48
Compound Information
Molecular Weight:355.4323
Molecular Formula:C23H21N3O
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:206.3272
Molecular Formula:C13H22N2
InChIKey:QOSSAOTZNIDXMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:602.6425
Molecular Formula:C33H30N8O4
InChIKey:Not Available
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Compound Information
Molecular Weight:328.384
Molecular Formula:C14H20N2O5S
InChIKey:TXKSEEXWAGLOIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.223
Molecular Formula:C8H14N4O
InChIKey:PZMXDLWWQHYXGY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:492.592
Molecular Formula:C22H32N6O5S
InChIKey:IFFGTBBYPRZJLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:466.181
Molecular Formula:C12H24BrF6N3P2
InChIKey:CYKRMWNZYOIJCH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:113.1576
Molecular Formula:C6H11NO
InChIKey:JBKVHLHDHHXQEQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.0233
Molecular Formula:C2HF3O2
InChIKey:DTQVDTLACAAQTR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:141.2108
Molecular Formula:C8H15NO
InChIKey:YDLSUFFXJYEVHW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:169.264
Molecular Formula:C10H19NO
InChIKey:WULPUQZASCZTPO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:197.3171
Molecular Formula:C12H23NO
InChIKey:Not Available
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Compound Information
Molecular Weight:115.0874
Molecular Formula:C4H5NO3
InChIKey:NQTADLQHYWFPDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:434.511
Molecular Formula:C23H22N4O3S
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:126.1995
Molecular Formula:C7H14N2
InChIKey:BDNKZNFMNDZQMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:VHYFNPMBLIVWCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:33.0299
Molecular Formula:H3NO
InChIKey:AVXURJPOCDRRFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:193.2423
Molecular Formula:C11H15NO2
InChIKey:CJGXMNONHNZEQQ-JTQLQIEISA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:741.668
Molecular Formula:C29H39F6N7O3P2S
InChIKey:Not Available
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:103.1198
Molecular Formula:C4H9NO2
InChIKey:NTNZTEQNFHNYBC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:131.1729
Molecular Formula:C6H13NO2
InChIKey:CEMZBWPSKYISTN-YFKPBYRVSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:129.2432
Molecular Formula:C8H19N
InChIKey:JGFZNNIVVJXRND-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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