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13139-17-8

13139-17-8

Identification

Synonyms:Succinimide, N-(carboxyoxy)-, benzyl ester(8CI);1-[[(Benzyloxy)carbonyl]oxy]-2,5-pyrrolidinedione;Benzyl2,5-dioxopyrrolid-1-yl carbonate;Benzyl N-succinimidyl carbonate;Benzyl succinimidyl carbonate;N-(N-Benzyloxycarbonyloxy)succinimide;N-Benzyloxycarbonyloxysuccinamide;Benzyloxycarbonyloxysuccinimide;Z-OSu;Cbz-OSu;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi,HarmfulXn

  • Hazard Codes:Xi,Xn

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:Usbiological
  • Product Description:Z-Onsu
  • Packaging:25g
  • Price:$ 333
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:N-(N-Benzyloxycarbonyloxy)succinimide
  • Packaging:500g
  • Price:$ 360
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N-Carbobenzoxyoxysuccinimide >98.0%(N)
  • Packaging:250g
  • Price:$ 214
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N-Carbobenzoxyoxysuccinimide >98.0%(N)
  • Packaging:25g
  • Price:$ 43
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N-(Benzyloxycarbonyloxy)succinimide
  • Packaging:25 g
  • Price:$ 24
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N-(Benzyloxycarbonyloxy)succinimide
  • Packaging:100 g
  • Price:$ 40
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:N-(Benzyloxycarbonyloxy)succinimide 98%
  • Packaging:250g
  • Price:$ 234
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:N-(Benzyloxycarbonyloxy)succinimide 98%
  • Packaging:100g
  • Price:$ 165
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:N-(Benzyloxycarbonyloxy)succinimide 98%
  • Packaging:25g
  • Price:$ 81.7
  • Delivery:In stock
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:N-(N-Benzyloxycarbonyloxy)succinimide
  • Packaging:25 g
  • Price:$ 610
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Relevant articles and documentsAll total 12 Articles be found

A large scale synthesis of mono- and di-urethane derivatives of lysine

Wiejak, Stanislaw,Masiukiewicz, Elzbieta,Rzeszotarska, Barbara

, p. 1489 - 1490 (1999)

In the search for a practical route to lysine diurethane derivatives useful for peptide synthesis, we elaborated the synthesis of N(ε)-tert- butoxycarbonyl-L-lysine copper(II) complex (1). This served as substrate for obtaining N(ε)-tert-butoxycarbonyl-L-lysine (2), N(α)-benzyloxycarbonyl- N(ε)-tert-butoxycarbonyl-L-lysine dicyclohexylamine salt (3) and N(α)-(9- fluorenyl)methoxycarbonyl-N(ε)-tert-butoxycarbonyl-L-lysine (4).

A Universal Labeling Strategy for Nucleic Acids in Expansion Microscopy

Hofkens, Johan,Leen, Volker,Rohand, Taoufik,Vandereyken, Katy,Vanheusden, Marisa,Voet, Thierry,Wen, Gang

supporting information, p. 13782 - 13789 (2021/09/11)

Expansion microscopy (ExM) enables the nanoscale imaging of ribonucleic acids (RNAs) on a conventional fluorescence microscope, providing information on the intricate patterns of gene expression at (sub)cellular resolution and within spatial context. To extend the use of such strategies, we examined a series of multivalent reagents that allow the labeling and grafting of deoxyribonucleic acid (DNA) oligonucleotide probes in a unified approach. We show that the reagents are directly compatible with third-generation in situ hybridization chain reaction RNA FISH (fluorescence in situ hybridization) techniques while displaying complete retention of the targeted transcripts. Furthermore, we validate and demonstrate that our labeling method is compatible with multicolor staining. Through oligonucleotide-conjugated antibodies, we demonstrate excellent performance in ×4 ExM and ×10 ExM, achieving a resolution of ~50 nm in ×10 ExM for both pre- and postexpansion labeling strategies. Our results indicate that our multivalent molecules enable the rapid functionalization of DNA oligonucleotides for ExM.

Method for synthesizing N-(carbobenzoxy) succinimide by one-pot two-phase method

-

Paragraph 0024-0029, (2020/02/14)

The invention relates to the technical field of organic chemistry, in particularly to a method for synthesizing N-(carbobenzoxy) succinimide by one-pot two-phase method. The method comprises the following steps: adding purified water and hydroxylamine sulfate into a reaction container, dropwise adding liquid caustic soda while stirring, adding butanedioic anhydride in batches after dropwise addingis finished, and carrying out high-temperature vacuum dehydration under acid catalysis until no water is extracted so as to prepare an N-hydroxysuccinimide solution; adding an alkali into the N-hydroxysuccinimide solution to adjust the pH value of the reaction solution, controlling the temperature at 0-60 DEG C, and dropwise adding benzyl chloroformate; after dropwise adding, separating out an organic layer, concentrating to be dry, and recrystallizing to obtain an N-(carbobenzoxy) succinimide finished product. According to the method provided by the invention, separation and purifying stepsafter synthesis of the N-hydroxysuccinimide are avoided, and the N-(carbobenzoxy) succinimide is synthesized by directly adopting a two-phase method in a one-pot manner, so that the process cost is effectively reduced, the operation steps are reduced, and large-scale industrial production is facilitated.

Scalable synthesis of Nα-benzyloxycarbonyl-L-ornithine and of Nα-(9-fluorenylmethoxy)carbonyl-L-ornithine

Masiukiewicz, Elzbieta,Wiejak, Stanislaw,Rzeszotarska, Barbara

, p. 531 - 537 (2007/10/03)

-

Process route upstream and downstream products

Process route

succinic acid anhydride
108-30-5

succinic acid anhydride

benzyl chloroformate
501-53-1,94274-21-2

benzyl chloroformate

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Conditions
Conditions Yield
succinic acid anhydride; With hydroxylamine sulfate; In water; Alkaline conditions;
With phosphoric acid; In water; toluene; Reflux; Alkaline conditions;
benzyl chloroformate; In toluene; for 2h; Reagent/catalyst;
52.7%
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Conditions
Conditions Yield
With triethylamine; In acetonitrile; at 20 ℃;
With triethylamine; In acetonitrile; at 20 ℃; for 0.75 - 1h; Product distribution / selectivity;
dicyclohexylamine salt of N-hydroxysuccinimide
82911-72-6

dicyclohexylamine salt of N-hydroxysuccinimide

benzyl chloroformate
501-53-1,94274-21-2

benzyl chloroformate

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Conditions
Conditions Yield
In chloroform;
90%
N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 95 percent / acetone
2: 90 percent / CHCl3
In chloroform; acetone;
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Conditions
Conditions Yield
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

benzyl chloroformate
501-53-1,94274-21-2

benzyl chloroformate

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Conditions
Conditions Yield
With sodium hydrogencarbonate; In water; ethyl acetate; at 15 ℃; for 19h; Large scale;
90.5%
With triethylamine; In dichloromethane; at 20 ℃;
75%
With TEA; In 1,2-dimethoxyethane;
25%
With triethylamine; In acetonitrile; at 5 ℃; for 1h;
With sodium carbonate; In water; acetone; for 0.5h;
With sodium carbonate; In water; acetone; at -10 ℃; for 0.5h;
With sodium hydroxide; In water;
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Cbz-D-Phe
2448-45-5

Cbz-D-Phe

Conditions
Conditions Yield
With sodium hydroxide; sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 ℃;
With sodium hydrogencarbonate; sodium carbonate; In water; acetone; at 0 - 20 ℃; for 3.5h;
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

4-amino-n-butyric acid
56-12-2

4-amino-n-butyric acid

4-(benzyloxycarbonylamino)butyric acid
5105-78-2

4-(benzyloxycarbonylamino)butyric acid

Conditions
Conditions Yield
In methanol; dichloromethane; water; N,N-dimethyl-formamide;
With sodium hydrogencarbonate; In tetrahydrofuran; water;
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Nα-benzyloxycarbonyl-L-ornithine
2640-58-6

Nα-benzyloxycarbonyl-L-ornithine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: Cu(CH3COO)2; NaOH / H2O; acetone / 44 h
1.2: 8-quinolinol; Na2CO3 / acetone; H2O / 1.5 h
1.3: H2O; acetone / 1.5 h / 20 °C
2.1: 19.55 g / p-toluenesulfonic acid hydrate; triethylamine / acetone / 1 h / Heating
With sodium hydroxide; copper diacetate; toluene-4-sulfonic acid; triethylamine; In water; acetone;
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

piperidine-4,4-diol hydrochloride
40064-34-4

piperidine-4,4-diol hydrochloride

benzyl 4-oxo-1-piperidinecarboxylate
19099-93-5

benzyl 4-oxo-1-piperidinecarboxylate

Conditions
Conditions Yield
With potassium carbonate; In water; acetonitrile; at 20 ℃;
95%
With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 2h;
90%

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