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17020

Sigma-Aldrich

Ethyl bromoacetate

purum, ≥97.0% (GC)

Synonym(s):

Bromoacetic acid ethyl ester, Ethyl 2-bromoacetate

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About This Item

Linear Formula:
BrCH2COOC2H5
CAS Number:
105-36-2
Molecular Weight:
167.00
Beilstein:
506456
EC Number:
203-290-9
MDL number:
MFCD00000191
UNSPSC Code:
12352100
PubChem Substance ID:
329751440
NACRES:
NA.22

vapor pressure

2.6 mmHg ( 25 °C)

grade

purum

Assay

≥97.0% (GC)

refractive index

n20/D 1.451 (lit.)
n20/D 1.451

bp

159 °C (lit.)

solubility

water: insoluble

density

1.506 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)CBr

InChI

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

InChI key

PQJJJMRNHATNKG-UHFFFAOYSA-N

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Application

Ethyl bromoacetate was used in the synthesis of:
  • artificial diethylstilbestrol antigen
  • 3-phenyl-1-naphthol, a key intermediate in the synthesis of vanol
  • novel pyrazolothiazol-4(5H)-ones
  • steroidal thiazolidinone derivatives

Caution

may discolor to brown on storage

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Statements

H226,H300 + H310 + H330

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

116.6 °F - closed cup

Flash Point(C)

47 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW6415
BCCH9830
BCCF7865
BCCB5329
BCBT0734

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Osama I el-Sabbagh et al.
European journal of medicinal chemistry, 44(9), 3746-3753 (2009-05-08)
New N-acetyl (5-8) and N-thiocarbamoyl (9-12) derivatives of 4,5-dihydropyrazole were synthesized starting from alpha,beta-unsaturated ketones under the effect of hydrazine hydrate and thiosemicarbazide, respectively. N-Thiocarbamoylpyrazole derivatives (9-12) were cyclized using either ethyl bromoacetate or phenacyl bromides to afford the novel
B Falkiewicz
Nucleic acids symposium series, (42)(42), 153-154 (2000-04-26)
Peptide nucleic acids (PNAs) make a promising group of DNA analogues. The backbone of typical PNA oligomers is composed of N-(2-aminoethyl)glycine units, linked by the peptide bonds. The backbone secondary amine groups are acylated with carboxyalkyl derivatives of nucleobases. One
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%
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
Niangoran Koissi et al.
Nucleosides, nucleotides & nucleic acids, 26(8-9), 1203-1206 (2007-12-07)
Three protected derivatives of 1,N(6)-ethenoadenine nucleosides, viz. 3-[5-O-(4,4'-dimethoxytrityl) of 7-formyl-(1) and 7-(1,2-diacetyloxypropyl)-2'-deoxyadenosine (2), and 3-[5-O-(4,4'-dimethoxytrityl)-2-O-(tert-butyldimethylsilyl)-7-(ethoxycarbonyl)adenosine (3), expected to allow introduction of formyletheno and carboxyethenoadenine adducts into oligonucleotides by the conventional phosphoramidite chemistry, have been synthesized.
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