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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
BCCM5643
BCCH8627
BCCH7021
BCCG5247

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Discovery of 3, 5-bis (trifluoromethyl) benzyl L-arylglycinamide based potent CCR2 antagonists.
Yang L, et al.
Bioorganic & Medicinal Chemistry, 16(14), 3735-3739 (2006)
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)
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
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