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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.)

functional group

bromo
ester

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
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.
Salman Ahmad Khan et al.
European journal of medicinal chemistry, 44(6), 2597-2600 (2009-02-13)
Steroidal thiazolidinone derivatives were prepared by the multi-step reactions of steroid. It is prepared from steroidal thiosemicarbazones with ethyl bromoacetate in dioxane. Steroidal thiosemicarbazones were prepared by the reaction of thiosemicarbazide with steroidal ketones. The structures of these compounds were
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
Occupational allergic contact dermatitis in a chemist from ethyl bromoacetate and bromoacetonitrile.
B Hernández-Machín et al.
Contact dermatitis, 52(2), 115-116 (2005-02-24)
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