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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/REAXYS Number:
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

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

116.6 °F - closed cup

flash_point_c

47 °C - closed cup

ppe

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

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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
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.
Zhensheng Ding et al.
Chemistry, an Asian journal, 6(8), 2130-2146 (2011-05-21)
Vanol is a member of the vaulted biaryl family of ligands and it has been proven to be very effective in a number of asymmetric catalytic reactions. The previous synthesis of vanol, while effective, is limited by the cost of
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
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
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