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17000

Sigma-Aldrich

Bromoacetic acid

ReagentPlus®, ≥99.0%

Synonym(s):

α-Bromoacetic acid, Monobromoacetic acid

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$131.00
500 G
$586.00

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25 G
$60.50
100 G
$131.00
500 G
$586.00

About This Item

Linear Formula:
BrCH2COOH
CAS Number:
79-08-3
Molecular Weight:
138.95
Beilstein/REAXYS Number:
506167
EC Number:
201-175-8
MDL number:
MFCD00002678
UNSPSC Code:
12352106
PubChem Substance ID:
329751436
NACRES:
NA.22

$60.50

Available to ship onApril 29, 2025Details

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Quality Level

200

product line

ReagentPlus®

assay

≥99.0% (GC)
≥99.0%

form

solid

impurities

≤1% dibromoacetic acid (1H-NMR)

bp

208 °C (lit.)

mp

46-49 °C
47-49 °C (lit.)

solubility

chloroform: 10%, clear, colorless

functional group

bromo
carboxylic acid

SMILES string

NC(=O)C=C
OC(=O)CBr

InChI

1S/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5)

InChI key

KDPAWGWELVVRCH-UHFFFAOYSA-N

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Application

Bromoacetic acid is mainly used for the N-terminal bromoacylation of resin bound peptides.[1][2]
It can also be used:
  • To synthesize (Z)-2-(cyclooct-4-en-1-yloxy)acetic acid.[3]
  • To synthesize α-bromo-phenylacetamide.[4]
  • To convert aromatic thiosemicarbazones to thiazolylhydrazones.[5]

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Aquatic Acute 1 - Eye Dam. 1 - Skin Corr. 1A - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN1047
BCCM0401
BCCM5643
BCCH8627
BCCH7021

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Peptide ligation through click chemistry for the generation of assembled and scaffolded peptides.
Franke R, et al.
Tetrahedron Letters, 46(26), 4479-4482 (2005)
Efficient method for the preparation of peptoids [oligo (N-substituted glycines)] by submonomer solid-phase synthesis.
Zuckermann R N, et al.
Journal of the American Chemical Society, 114(26), 10646-10647 (1992)
Amandine M N Caruana et al.
Marine environmental research, 160, 105014-105014 (2020-09-11)
Alexandrium minutum and Alexandrium pacificum are representatives of the dinoflagellate genus that regularly proliferate on the French coasts and other global coastlines. These harmful species may threaten shellfish harvest and human health due to their ability to synthesize neurotoxic alkaloids
Ryo Kato et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 228, 117656-117656 (2019-11-22)
To sense hydrophilic anions in protic solvents, we fabricated polymethylmethacrylate (PMMA) nanofibers incorporating 4-nitrophenyl azo thiourea polymer as a chromoionophore. When methanol solutions containing anions contacted the PMMA nanofiber, a bathochromic shift from 386 nm was observed in the absorption maximum
Shanshan Lv et al.
Langmuir : the ACS journal of surfaces and colloids, 35(22), 7255-7260 (2019-05-16)
Clay nanosheets (CNSs) have been widely used in the design of nanocomposite biomaterials. CNSs display a disk-like morphology with strong negatively charged surfaces. It has been shown that guanidinium-containing molecules can bind CNSs through noncovalent salt-bridge interactions and thus serve
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