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Cas Database

6066-82-6

6066-82-6

Identification

  • Product Name:N-Hydroxysuccinimide

  • CAS Number: 6066-82-6

  • EINECS:228-001-3

  • Molecular Weight:115.089

  • Molecular Formula: C4H5NO3

  • HS Code:29251995

  • Mol File:6066-82-6.mol

Synonyms:Succinimide, N-hydroxy-;2,5-Pyrrolidinedione, 1-hydroxy-;Hydroxysuccinimide;Succinimide, N-hydroxy- (8CI);1-Hydroxy-2,5-pyrrolidinedione;1-Hydroxysuccinimide;1-Hydroxy-pyrrolidine-2,5-dione;N-Hydroxy Succinimide;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • 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

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  • Manufacture/Brand:TRC
  • Product Description:N-Hydroxysuccinimide
  • Packaging:25g
  • Price:$ 85
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  • Manufacture/Brand:TRC
  • Product Description:N-Hydroxysuccinimide
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N-Hydroxysuccinimide >98.0%(T)
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  • Price:$ 33
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N-Hydroxysuccinimide >98.0%(T)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N-Hydroxysuccinimide [Coupling Reagent for Peptide] >98.0%(GC)(T)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N-Hydroxysuccinimide >98.0%(T)
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N-Hydroxysuccinimide 97%
  • Packaging:500 g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N-Hydroxysuccinimide 97%
  • Packaging:25 g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N-Hydroxysuccinimide 97%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:N-Hydroxysuccinimide 98%
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Relevant articles and documentsAll total 63 Articles be found

TRPA1 is activated by direct addition of cysteine residues to the N-hydroxysuccinyl esters of acrylic and cinnamic acids

Sadofsky, Laura R.,Boa, Andrew N.,Maher, Sarah A.,Birrell, Mark A.,Belvisi, Maria G.,Morice, Alyn H.

, p. 30 - 36 (2011)

The nociceptor TRPA1 is thought to be activated through covalent modification of specific cysteine residues on the N terminal of the channel. The precise mechanism of covalent modification with unsaturated carbonyl-containing compounds is unclear, therefore by examining a range of compounds which can undergo both conjugate and/or direct addition reactions we sought to further elucidate the mechanism(s) whereby TRPA1 can be activated by covalent modification. Calcium signalling was used to determine the mechanism of activation of TRPA1 expressed in HEK293 cells with a series of related compounds which were capable of either direct and/or conjugate addition processes. These results were confirmed using physiological recordings with isolated vagus nerve preparations. We found negligible channel activation with chemicals which could only react with cysteine residues via conjugate addition such as acrylamide, acrylic acid, and cinnamic acid. Compounds able to react via either conjugate or direct addition, such as acrolein, methyl vinyl ketone, mesityl oxide, acrylic acid NHS ester, cinnamaldehyde and cinnamic acid NHS ester, activated TRPA1 in a concentration dependent manner as did compounds only capable of direct addition, namely propionic acid NHS ester and hydrocinnamic acid NHS ester. These compounds failed to activate TRPV1 expressed in HEK293 cells or mock transfected HEK293 cells. For molecules capable of direct or conjugate additions, the results suggest for the first time that TRPA1 may be activated preferentially by direct addition of the thiol group of TRPA1 cysteines to the agonist carbonyl carbon of α,β-unsaturated carbonyl-containing compounds.

A Catalyst-Free Synthesis of Fused Perfluoroalkylated 2,3-Dihydroisoxazoles via Oxa-Michael-Aldol Annulation

Zhou, Wei,Yao, Lan,Liu, Yongxiurong,Shen, Lichun,Chen, Jie,Deng, Hongmei,Shao, Min,Zhang, Hui,Tang, Xiaojun,Cao, Weiguo

supporting information, p. 429 - 438 (2021/10/01)

A novel synthesis of fused perfluoroalkylated 2,3-dihydroisoxazoles is achieved via oxa-Michael-aldol annulation between perfluoroalk- 2-ynoates and N-hydroxyimides. This method provides a convenient route for the synthesis of pyrrolidin-2-one-fused perfluoroalkylated 2,3-dihydroisoxazoles in yields of up to 97%. Diverse and pharmaceutically attractive polycyclic scaffolds can be obtained rapidly and efficiently under these mild, catalyst-free conditions.

DLL3-TARGETING MULTISPECIFIC ANTIGEN-BINDING MOLECULES AND USES THEREOF

-

, (2021/10/02)

The disclosure provides multispecific antigen-binding molecules that comprise a first antigen-binding moiety and a second antigen-binding moiety, each of which is capable of binding to CD3 and CD137, but does not bind to CD3 and CD137 at the same time; and a third antigen-binding moiety that is capable of binding to DLL3, preferably human DLL3, which induce T-cell dependent cytotoxity more efficiently whilst circumventing adverse toxicity concerns or side effects that other multispecific antigen-binding molecules may have. The present invention provides multispecific antigen-binding molecules and pharmaceutical compositions that can treat various cancers, especially those associated with DLL3, by comprising the antigen-binding molecule as an active ingredient.

A METHOD FOR PREPARING N-SUBSTITUTED SUCCINIMIDE

-

Paragraph 0089; 0091-0093; 0095-0108; 0113, (2021/10/27)

N -substituted succinimides are disclosed. , The 1-substituted succinimide prepared by reacting a succinic acid with 1-order amine is reacted with an acid catalyst, a metal catalyst, and a reducing agent to produce N - N -substituted succinimide, which is industrially useful and can be widely applied to various industrial fields.

Synthesis method of N-(benzyloxycarbonyloxy)succinimide

-

Paragraph 0005; 0008; 0012; 0015, (2020/05/05)

The invention relates to a synthesis method of N-(benzyloxycarbonyloxy)succinimide; the invention mainly solves the technical problems of high raw material cost, overhigh reaction rate, severe heat release, high possibility of generating impurities, high product loss during refining and the like in an existing synthesis method. The synthesis method comprises the following steps: dissociating hydroxylamine hydrochloride in an aqueous solution by using NaOH, and carrying out a reaction with succinic anhydride to generate HOSu; carrying out a reaction of HOSu with Cbz-Cl in a mixed solution of water and ethyl acetate to generate a target compound Cbz-OSu. Cbz-OSu is commonly used as a polypeptide commonly used reagent, and a Z-amino protection reagent is selectively introduced in synthesis ofamino acids and aminoglycoside antibiotics.

Method for synthesizing 9-fluorenylmethylsuccinimido carbonate by one-pot two-phase method

-

Paragraph 0011; 0024-0029, (2020/03/03)

The invention relates to the technical field of organic synthesis, specifically to a method for synthesizing 9-fluorenylmethylsuccinimido carbonate by a one-pot two-phase method. The method comprisesthe following steps: adding purified water and hydroxylamine sulfate into a reaction container, dropwise adding liquid caustic soda under stirring, after the liquid caustic soda is dropwise added, adding butanedioic anhydride in batches, and carrying out high-temperature vacuum dehydration under acid catalysis until no water is extracted out so as to prepare an N-hydroxysuccinimide solution; adding a chloroformic acid-9-fluorenyl methyl ester solution into the N-hydroxysuccinimide solution, and controlling a temperature at 0 to 60 DEG C; after the chloroformic acid-9-fluorenyl methyl ester solution is added, starting to dropwise add an aqueous alkali solution; after the aqueous alkali solution is dropwise added, separating out an organic layer, carrying out concentrating to dryness, and carrying out recrystallizing so as to obtain a 9-fluorenylmethylsuccinimido carbonate finished product. The above-mentioned method provided by the invention innovatively adopts the one-pot two-phase method; a reaction liquid containing N-hydroxysuccinimide is directly used for synthesizing the 9-fluorenylmethylsuccinimido carbonate in a two-phase reaction manner; process steps are effectively reduced; and the method is applicable to large-scale industrial production.

Process route upstream and downstream products

Process route

hydroxylamine succinic acid salt
869669-06-7

hydroxylamine succinic acid salt

acetic acid
64-19-7,77671-22-8

acetic acid

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

1-hydroxy-pyrrolidine-2,5-dione

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
Conditions Yield
for 10 - 15h; Product distribution / selectivity; Heating / reflux;
54.4%
3.7%
α-bromopropionyl N-hydroxysuccinimide ester
129779-14-2

α-bromopropionyl N-hydroxysuccinimide ester

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

1-hydroxy-pyrrolidine-2,5-dione

2-Bromopropionic acid
598-72-1,10327-08-9

2-Bromopropionic acid

Conditions
Conditions Yield
With water;
succinic acid anhydride
108-30-5

succinic acid anhydride

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

1-hydroxy-pyrrolidine-2,5-dione

Conditions
Conditions Yield
With hydroxylamine hydrochloride; sodium hydroxide; In water; at 0 - 25 ℃; for 0.5h; Large scale;
90%
With hydroxylamine hydrochloride; sodium methylate; a) methanol, 60 deg C, 1.5 h, b) xylene, reflux, 4 h;
41%
With pyridine; hydroxylamine hydrochloride; for 4h; Heating; Inert atmosphere;
With hydroxylamine; at 160 ℃;
With sulfuric acid; hydroxylamine hydrochloride; In water; at 100 - 160 ℃; Reagent/catalyst;
With pyridine; hydroxylamine hydrochloride; at 80 ℃; for 4h;
4-azidobenzoic acid N-hydroxysuccinimide ester
53053-08-0

4-azidobenzoic acid N-hydroxysuccinimide ester

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

1-hydroxy-pyrrolidine-2,5-dione

Conditions
Conditions Yield
With chitosan; In aq. phosphate buffer; dichloromethane; at 50 ℃; for 5h; Solvent; Temperature; Microwave irradiation;
98.2%
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

α-methyl-ω-(1-(4-hydroxymethyl-2,6-dimethylphenoxy)-acet-2-oxy)poly(ethylene glycol)

α-methyl-ω-(1-(4-hydroxymethyl-2,6-dimethylphenoxy)-acet-2-oxy)poly(ethylene glycol)

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

1-hydroxy-pyrrolidine-2,5-dione

α-methyl-ω-(1-(4-(N-succinimidyloxycarbonyloxymethyl)-2,6-dimethylphenoxy)-acet-2-oxy)poly(ethylene glycol)

α-methyl-ω-(1-(4-(N-succinimidyloxycarbonyloxymethyl)-2,6-dimethylphenoxy)-acet-2-oxy)poly(ethylene glycol)

Conditions
Conditions Yield
With pyridine; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 20h;
79%
succinic acid
110-15-6

succinic acid

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

1-hydroxy-pyrrolidine-2,5-dione

Conditions
Conditions Yield
With hydroxylamine hydrochloride; potassium carbonate; acetic acid; In cyclohexane; at 65 ℃; for 9h; Product distribution / selectivity;
94.7%
With hydroxyammonium sulfate; boric acid; hypophosphorous acid; sodium hydroxide; In toluene; at 95 ℃; Temperature; Reflux;
85.5%
With hydroxylamine; acetic acid; In cyclohexane; water; for 6 - 9h; Product distribution / selectivity; Heating / reflux;
64.9%
With hydroxylamine; acetic acid; In water; for 5h; Product distribution / selectivity; Heating / reflux;
20.8%
With hydroxylamine hydrochloride; potassium carbonate; acetic acid; at 65 ℃; for 5h; Product distribution / selectivity;
10.4%
With hydroxylamine; In water; xylene; for 8h; Product distribution / selectivity; Heating / reflux;
7.1%
hydroxylamine succinic acid salt
869669-06-7

hydroxylamine succinic acid salt

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

1-hydroxy-pyrrolidine-2,5-dione

Conditions
Conditions Yield
With sodium hypophosphite monohydrate; phosphoric acid; zinc(II) acetate dihydrate; at 120 ℃; for 6h; Reagent/catalyst;
85%
estradiol
50-28-2

estradiol

N-Hydroxysulfosuccinimide sodium salt

N-Hydroxysulfosuccinimide sodium salt

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

1-hydroxy-pyrrolidine-2,5-dione

estradiol-3-sulfate
481-96-9

estradiol-3-sulfate

Conditions
Conditions Yield
With AST; In acetone; Enzymatic reaction;
68%
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

poly(ethylene glycol)monomethyl ether

poly(ethylene glycol)monomethyl ether

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

1-hydroxy-pyrrolidine-2,5-dione

α-methyl-ω-(N-succinimidyloxycarbonyloxy)poly(ethylene glycol)

α-methyl-ω-(N-succinimidyloxycarbonyloxy)poly(ethylene glycol)

Conditions
Conditions Yield
With pyridine; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 20h;
3-maleimidopropionic acid N-hydroxysuccinimide ester
55750-62-4

3-maleimidopropionic acid N-hydroxysuccinimide ester

norbiotinamine trifluoroacetate
1206708-71-5

norbiotinamine trifluoroacetate

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

1-hydroxy-pyrrolidine-2,5-dione

N-norbiotinyl-3-maleimidopropionylamide

N-norbiotinyl-3-maleimidopropionylamide

Conditions
Conditions Yield
With triethylamine; In chloroform; at 20 ℃; for 18h; Temperature;

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