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133973

Sigma-Aldrich

Ethyl bromoacetate

reagent grade, 98%

Sinónimos:

Bromoacetic acid ethyl ester, Ethyl 2-bromoacetate

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About This Item

Fórmula lineal:
BrCH2COOC2H5
Número de CAS:
105-36-2
Peso molecular:
167.00
Beilstein:
506456
Número CE:
203-290-9
Número MDL:
MFCD00000191
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24848125
NACRES:
NA.22
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grado

reagent grade

Nivel de calidad

200

presión de vapor

2.6 mmHg ( 25 °C)

Ensayo

98%

Formulario

liquid

índice de refracción

n20/D 1.451 (lit.)

bp

159 °C (lit.)

solubilidad

water: insoluble

densidad

1.506 g/mL at 25 °C (lit.)

grupo funcional

bromo
ester

cadena SMILES

CCOC(=O)CBr

InChI

1S/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3

Clave InChI

PQJJJMRNHATNKG-UHFFFAOYSA-N

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Descripción general

Ethyl bromoacetate is commonly used in organic synthesis as an alkylating agent and acylation reagent.[1][2] Ethyl bromoacetate on derivatisation reaction with p-t-butyl calix[4]arene yields 1,3-diester substituted calix[4]arene[3]. It also undergoes Suzuki type cross-coupling reactions with arylboronic acids cocatalyzed by copper(I) oxide[4].

Aplicación

Ethyl bromoacetate was used to prepare reversibly photoresponsive coumarin-stabilized polymeric nanoparticles in an aqueous medium, which act as a detectable drug carrier[5].

Pictogramas

FlameSkull and crossbones
GHS02,GHS06

Palabra de señalización

Danger

Frases de peligro

H226,H300 + H310 + H330

Clasificaciones de peligro

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Flam. Liq. 3

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

116.6 °F - closed cup

Punto de inflamabilidad (°C)

47 °C - closed cup

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análisis (COA)

Lot/Batch Number
STBK8715
MKCS7144
STBK2621
MKCN2346
STBJ5511

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Jae Woo Chung et al.
Small (Weinheim an der Bergstrasse, Germany), 8(11), 1693-1700 (2012-03-29)
The ability to create aqueous suspended stable nanoparticles of the hydrophobic homopolymer poly(ϵ-caprolactone) end-functionalized with coumarin moieties (CPCL) is demonstrated. Nanoparticles of CPCL are prepared in a continuous manner using nanoprecipitation. The resulting nanoparticles are spherical in morphology, about 40
Unusual pathway of alkylation of 2-(4-bromobenzylidene)-p-menthan-3-one with ethyl bromoacetate
AI Krivoshei, et al.
Russian Chemical Bulletin, 56, 2506-2509 (2007)
Gillian McMahon et al.
Talanta, 57(6), 1119-1132 (2008-10-31)
A series of derivatisation reactions between p-t-butyl calix[4]arene and ethyl bromoacetate were carried out in order to prepare 1,3 diester substituted calix[4]arene. Mass spectral data, obtained from direct injection of samples, indicated that the reactions were rich in the desired
A M Seldes et al.
Steroids, 39(2), 181-190 (1982-02-01)
Reformatsky reaction of 3beta, 21-diacyloxy-and 3beta-methoxy-21-acyloxy-5-pregnen-20-one with ethyl bromoacetate yields, through an intramolecular 1,2-acyl migration, 38, 20 XI-acyloxy-14alpha-card-5-enolides were converted into the respective 20 XI-hydroxy-14alpha-card-5-enolides and the 14 alpha-carda-5,20(22)-dienolides. Experimental support to the proposed intramolecular 1,2-acyl migration is provided by
Monika Wujec et al.
The journal of physical chemistry. B, 112(39), 12414-12419 (2008-09-11)
The influence of the implicit solvent model on transition state structures of two S N2 reactions of biochemical importance is presented. In the considered methyl transfer reaction, we show experimentally that the rate constant in blood serum is about 60%
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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