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N'-(Ethylkohlenstoffimidoyl)-N,N-dimethylpropan-1,3-diaminmonohydrochlorid

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Struktur
25952-53-8
CAS-Nr.
25952-53-8
Bezeichnung:
N'-(Ethylkohlenstoffimidoyl)-N,N-dimethylpropan-1,3-diaminmonohydrochlorid
Englisch Name:
1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
Synonyma:
EDCI;EDC.HCl;EDAC;EDARAVONE;WSC;1-ETHYL-3-(3-DIMETHYLAMINOPROPYL) CARBODIIMIDE;WSCI;WSCD;1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride;EDC.HCI
CBNumber:
CB7403031
Summenformel:
C8H18ClN3
Molgewicht:
191.7
MOL-Datei:
25952-53-8.mol

N'-(Ethylkohlenstoffimidoyl)-N,N-dimethylpropan-1,3-diaminmonohydrochlorid Eigenschaften

Schmelzpunkt:
110-115 °C(lit.)
Dichte
0.877 g/mL at 20 °C(lit.)
Dampfdruck
0.002Pa at 20℃
Brechungsindex
n20/D 1.461
storage temp. 
-20°C
L?slichkeit
H2O: soluble1 gm/10 ml, clear to very slightly hazy, colorless to very faintly yellow
Aggregatzustand
Crystalline Powder
Farbe
White to off-white
Wasserl?slichkeit
Soluble
Sensitive 
Hygroscopic
BRN 
5764110
Stabilit?t:
Stable, but sensitive to moisture. Incompatible with strong acids, strong oxidizing agents, moisture.
InChIKey
FPQQSJJWHUJYPU-UHFFFAOYSA-N
LogP
-2.98 at 25℃
CAS Datenbank
25952-53-8(CAS DataBase Reference)
EPA chemische Informationen
1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride (25952-53-8)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher C,Xi
R-S?tze: 34-36/37/38-41-37/38-20/21/22
S-S?tze: 26-36/37/39-45-37/39-36
RIDADR  UN 2735 8/PG 3
WGK Germany  3
RTECS-Nr. FF2200000
1-3-10
Hazard Note  Irritant
TSCA  Y
HS Code  29252000
Toxizit?t LD50 intravenous in mouse: 56mg/kg
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitssch?dlich bei Verschlucken. Akute Toxizit?t oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
H311 Giftig bei Hautkontakt. Akute Toxizit?t dermal Kategorie 3 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P280, P302+P352, P312, P322, P361,P363, P405, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H317 Kann allergische Hautreaktionen verursachen. Sensibilisierung der Haut Kategorie 1A Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H373 Kann die Organe sch?digen bei l?ngerer oder wiederholter Exposition. Spezifische Zielorgan-Toxizit?t (wiederholte Exposition) Kategorie 2 Warnung P260, P314, P501
H410 Sehr giftig für Wasserorganismen mit langfristiger Wirkung. Langfristig (chronisch) gew?ssergef?hrdend Kategorie 1 Warnung GHS hazard pictogramssrc="/GHS09.jpg" width="20" height="20" /> P273, P391, P501
Sicherheit
P260 Dampf/Aerosol/Nebel nicht einatmen.
P273 Freisetzung in die Umwelt vermeiden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P301+P312 BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P314 Bei Unwohlsein ?rztlichen Rat einholen / ?rztliche Hilfe hinzuziehen.

N'-(Ethylkohlenstoffimidoyl)-N,N-dimethylpropan-1,3-diaminmonohydrochlorid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R34:Verursacht Ver?tzungen.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R41:Gefahr ernster Augensch?den.
R37/38:Reizt die Atmungsorgane und die Haut.
R20/21/22:Gesundheitssch?dlich beim Einatmen,Verschlucken und Berührung mit der Haut.

S-S?tze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Chemische Eigenschaften

EDC-HCl, or 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, is a white crystalline powder that easily deliquescent and can dissolve in both water and ethanol. It is commonly used as an activating reagent in amide synthesis to activate carboxyl groups. It can also activate phosphate groups, cross-link proteins and nucleic acids, and produce immunocouplers. EDC-HCl is commonly applied in the pH range of 4.0-6.0 and is often used in conjunction with N-Hydroxysuccinimide (NHS) or N-Hydroxysulfosuccinimide sodium salt to improve coupling efficiency.

Application

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is water-soluble carbodiimide, widely used for peptide coupling.
N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride has been used for the formation of FND (fluorescent nanodiamonds)-transferrin bioconjugates.
It has been used for crosslinking polyethylenimine to gold particles.
It has been used as a carbodiimide linkage agent for coating of carboxylated polystyrene beads with biotinylated BSA (bovine serum albumin).

Allgemeine Beschreibung

EDC hydrochloride is a water-soluble derivative of carbodiimide useful for conjugating haptens to proteins and polypeptides. Used to modify NMDA receptors and as a condensing agent in peptide synthesis. The major advantage of EDAC coupling is the easy removal of excess reagent and the corresponding urea by washing with dilute acid or water. Carbodiimides catalyze the formation of amide bonds, carboxylic acids, and amines by activating the carboxylate to form an O-acylurea. This intermediate can be attacked by an amine directly to form an amide. EDAC is released as a soluble urea derivative.

Biochem/physiol Actions

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(25952-53-8) is a water soluble condensing reagent. EDAC is generally utilized as a carboxyl activating agent for amide bonding with primary amines. Additionally, it reacts with phosphate groups. It has been utilized in peptide synthesis, crosslinking proteins to nucleic acids as well as preparation of immunoconjugates.

Mechanism of action

Carboxyl group activation with EDC. xHCl proceeds similarly to other carbodiimide couplings. The reaction of a carboxylic acid and the carbodiimide forms an O-acylisourea intermediate. The O-acylisourea is a highly reactive species that readily reacts with amines, peptide coupling additives, or reducing agents. EDC. HCl is transformed into the corresponding urea during coupling reactions. It has the advantage over DCU in that it can be removed from the reaction mixture by extraction or be washed out from solid phase synthesis applications. However, the O-acylisourea can rearrange irreversibly to an N-acyl urea and racemise the α-carbon of the amino acid via the formation of an oxazol-4(5H)-one [azlactone]. N-Acylurea formation and racemisation may be reduced by using intermediate nucleophiles, which convert the O-acylurea to an activated ester containing the nucleophile. The mechanism of amide bond formation applies both to EDC and EDC.HCl. The differences are that the free base can be applied as a bifunctional reagent: a coupling agent (carbodiimide) and a base (dimethylamino). At the same time, the HCl salt can form an O-acylisourea cyclic intermediate.

Synthese

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride can be used for the synthesis of amides.It is used as a coupling agent in the synthesis of esters from carboxylic acids using dimethylaminopyridine as the catalyst.
Preparation method of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(CN104193654A)

l?uterung methode

It is an excellent H2O-soluble peptide coupling reagent. It is purified by dissolving (ca 1g) in CH2Cl2 (10mL) at room temperature and then add dry Et2O (~110mL) dropwise and the crystals that separate are collected, washed with dry Et2O, recrystallised from CH2Cl2/Et2O and dried in a vacuum over P2O5. It is important to work in a dry atmosphere or work rapidly and then dry the solid as soon as possible. The material is moderately hygroscopic, but once it becomes wet it reacts slowly with H2O. Store it away from moisture at -20o to slow down the hydrolysis process. The free base has b 47-48o/0.27mm, 53-54o/0.6mm, n 1.4582. The methiodide is recrystallised from CHCl3/EtOAc, the crystals are filtered off, washed with dry Et2O, recrystallised from CHCl3/Et2O, and dried in vacuo over P2O5, m 93-95o, 94-95o. [Sheehan et al. J Am Chem Soc 87 2492 1965, Sheehan & Cruickshank Org Synth Coll Vol V 555 1973.] § A polymer bound version is commercially available.

N'-(Ethylkohlenstoffimidoyl)-N,N-dimethylpropan-1,3-diaminmonohydrochlorid Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


N'-(Ethylkohlenstoffimidoyl)-N,N-dimethylpropan-1,3-diaminmonohydrochlorid Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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25952-53-8(N'-(Ethylkohlenstoffimidoyl)-N,N-dimethylpropan-1,3-diaminmonohydrochlorid)Verwandte Suche:


  • edc(reagent)
  • WATER-SOLUBLE CARBODIIMIDE
  • 1-ETHYL-3-(3-DIMETHYLAMINOPROPYL)- &
  • N-(DIMETHYLAMINOPROPYL)-N'-ETHYLCARBO- DI IMIDE HCL
  • 1-(3-(DIMETHYLAMINO)PROPYL)-3-ETHYL-CARBODIIMIDE HYDROCHLORIDE, 98+%
  • 1-(3-Dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDC)
  • EDC (WSC-HCl)
  • WS.HCl
  • 1-ethyl-3-(3-Dimethylaminopropyl) carbodiimide HCl(EDC HCl)
  • eDC [1-(3-Dimethylaminopropyl)-3-ethyl-carbodiimide]
  • eDC HCl [1-ethyl-3-(3-Dimethylaminopropyl) carbodiimide HCl]
  • 1-ETHYL-3-(3-DIMETHYLAMINOPROPYL)-*CARBO DIIMIDE HYD
  • 1-ETHYL-3-(3-DIMETHYLAMINOPROPYL)*CARBOD IIMIDE HYDR
  • EDAC hydrochloride, EDC hydrochloride
  • 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, anhydrous
  • 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Hydrochloride [Coupling Agent for Peptides Synthesis]
  • N-(3-Dimethylaminopropyl)-Nμ-ethylcarbodiimide hydrochloride (EDC) 98%
  • Carbodiimide, (3-dimethylaminopropyl)ethyl-, monohydrochloride
  • N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride ,99%
  • Edccl
  • 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide·hydrochloric acid
  • 1-Ethyl-3-[3-(dimethylamino)propyl]carbodiimide·hydrochloric acid
  • N-[3-(Dimethylamino)propyl]-N'-ethylcarbodiimide·hydrochloric acid
  • N-Ethyl-N'-[3-(dimethylamino)propyl]carbodiimide·hydrochloric acid
  • EDAC hydrochloride (N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimi
  • 1-(3-DiMethylaMinopropyl)-3-ethylcarbodiiMide hydrochloride CAS: 25952-53-8
  • (3-DiMethylaMino-propyl)-ethyl-carbodiiMide Hydrochloride, EDC HCl, EDAC, EDCI, Water Soluble CarbodiiMide.
  • 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Hydrochloride EDC EDAC EDCI
  • EDAC · HCl, N-(3-DiMethylaMinopropyl)-N'-ethylcarbodiiMide · HCl, Water-soluble CarbodiiMide, WSC, EDC · HCl
  • EDCHC1/EDACHC1
  • N-(3-DIMETHYLAMINOPROPYL)-N'-ETHYLCARBOD
  • -(3-DiMethylaMinopropyl)-3-ethylcarbodiiMide hydrochloride
  • 1-(3-DiMethylaMinopropyl)-3-ethylcabodiiMide HCl
  • 3-(ethyliMinoMethyleneaMino)-N,N-diMethylpropan-1-aMine
  • EDC hydrochloride, N,N-Dimethyl-3-{[(ethylimino)methylidene]amino}propylamine hydrochloride
  • 1-[3-(DIMETHYLAMINO)PROPYL]-3-ETHYLCARBODIIMIDE(EDC.HCL)
  • 1ETHYL33DIMETHYLAMINOPROPYLCARBODIIMIDEHYDROCHLOR
  • 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide Hydrochloride (EDCI)
  • N-ETHYL-N''-(3-DIMETHYLAMINOPROPYL)CARBODIIMIDE HYDROCHLORIDE, EDAC, WSC
  • N-(3-DIETHYLAMINOPROPYL) -N -ETHYLCARBODIIMIDE HYD
  • N-(3-DIETHYLAMINOPROPYL)-N -ETHYLCARBODIIMIDE HYDR
  • 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
  • N'-(ethylcarbonimidoyl)-N,N-dimethylpropane-1,3-diamine monohydrochloride
  • N-Ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride
  • (E)-3-(ETHYLDIAZENYL)-N,N-DIMETHYLPROPAN-1-AMINE HYDROCHLORIDE
  • EDAC HYDROCHLORIDE (N-(3-DIMETHYLAMINOPROPYL)-N''-ETHYLCARBODIIMIDE HYDROCHLORIDE)
  • EDC.HCL 1-[3-(DIMETHYLAMINO)PROPYL]-3-ETHYLCARBODIIMIDE HYDROCHLORIDE
  • N3-(ETHYLCARBONIMIDOYL)-N1,N1-DIMETHYL-1,3-PROPANEDIAMINE HYDROCHLORIDE
  • N-(3-Dimethylaminopropyl)-N''-ethylcar
  • ETHYL-3-(3-DIMETHYLAMINOPROPYL)CARBODIIMIDE HCL
  • 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride / EDAC / EDCI
  • 1-Ethyl-3-(3-Dimethylaminopropyl)carbodiiamide Hydrochloride
  • 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC-HCl)
  • N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride,N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride, EDAC, EDC hydrochloride, WSC hydrochloride
  • N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride commercial grade, powder
  • EDAC.HC
  • N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide h
  • N-[3-(Dimethylamino)prop-1-yl]-N'-ethylcarbodiimide hydrochloride
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