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17000

Sigma-Aldrich

Bromoacetic acid

ReagentPlus®, ≥99.0%

Synonym(s):

α-Bromoacetic acid, Monobromoacetic acid

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About This Item

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

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

SMILES string

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.
It can also be used:
  • To synthesize (Z)-2-(cyclooct-4-en-1-yloxy)acetic acid.
  • To synthesize α-bromo-phenylacetamide.
  • To convert aromatic thiosemicarbazones to thiazolylhydrazones.

Legal Information

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

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Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0401
BCCH8627
BCCH7021
BCCG5247
BCCF3487

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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)
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
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
Tetrazine?trans-cyclooctene ligation for the rapid construction of 18F labeled probes.
Li Z, et al.
Chemical Communications (Cambridge, England), 46(42), 8043-8045 (2010)
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