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113034

Sigma-Aldrich

Oxalyl bromide

97%

Synonym(s):

Ethanedioyl dibromide, NSC 96957

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About This Item

Linear Formula:
BrCOCOBr
CAS Number:
15219-34-8
Molecular Weight:
215.83
Beilstein:
1744437
EC Number:
239-271-7
MDL number:
MFCD00000113
UNSPSC Code:
12352101
PubChem Substance ID:
24847129
NACRES:
NA.22

Quality Level

100

Assay

97%

reaction suitability

reagent type: oxidant

refractive index

n20/D 1.522 (lit.)

bp

16-17 °C/10 mmHg (lit.)

mp

−19 °C (lit.)

storage temp.

2-8°C

SMILES string

BrC(=O)C(Br)=O

InChI

1S/C2Br2O2/c3-1(5)2(4)6

InChI key

JAZLVNXWYDFQFE-UHFFFAOYSA-N

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Application

Used in synthetic applications of carbon-substituted iminium salts

Reactant for:
  • Synthesis of mutasynthons added to cultures of A. pretiosum for mutasynthetic generation of ansamitocin derivatives
  • Oxalic acid formation from hydroxyl radical substitutions
  • Cyclization to produce CRF1 receptor antagonists
  • Preparation, optical and electrochemical studies of thiophene end capped olig(2,3-alkylthieno[3,4-b]pyrazine)
  • Asymmetrical synthesis of glycosyl chlorides and bromides
Converts cyclopentane-1,3-dione to 3-bromocyclopenten-2-one.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H332

Hazard Classifications

Acute Tox. 4 Inhalation - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Marco Luparia et al.
Organic letters, 8(10), 2147-2150 (2006-05-05)
[reaction: see text] We describe a new approach to 2,3-disubstituted cyclopentenols and cyclopentenones through two consecutive regioselective additions of equal or different electrophiles to a cyclopentene bisanionic synthon. Indeed, on exposure to BuLi, 3-bromo-2-iodocyclopent-2-enol O-TBS ether undergoes iodine-lithium permutation with

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