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B62404

Sigma-Aldrich

1-Bromo-3-chloropropane

99%

Synonym(s):

I-BCP, Trimethylene bromochloride, Trimethylene chlorobromide

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About This Item

Linear Formula:
Cl(CH2)3Br
CAS Number:
109-70-6
Molecular Weight:
157.44
Beilstein:
605278
EC Number:
203-697-1
MDL number:
MFCD00000998
UNSPSC Code:
12352100
PubChem Substance ID:
24891900
NACRES:
NA.22

Assay

99%

form

liquid

refractive index

n20/D 1.486 (lit.)

bp

144-145 °C (lit.)

density

1.592 g/mL at 25 °C (lit.)

SMILES string

ClCCCBr

InChI

1S/C3H6BrCl/c4-2-1-3-5/h1-3H2

InChI key

MFESCIUQSIBMSM-UHFFFAOYSA-N

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Application

1-Bromo-3-chloropropane is generally used as C3 linker/spacer in a wide range of molecules including medicinally important compounds. Some of the examples are:
  • Synthesis of polymer nanoparticles (NPs) to deliver doxorubicin, camptothecin, and cisplatin.
  • Synthesis of antiprion active acridine derivatives for prion infection.
  • Total synthesis of aspidospermine, aspidospermidine, and quebrachamine and (±)-crispine A.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H302,H331,H335,H341,H412

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Muta. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Cascade condensation, cyclization, intermolecular dipolar cycloaddition by multi-component coupling and application to a synthesis of (?)-crispine A.
Coldham, Iain et al.
Organic & Biomolecular Chemistry, 7(8), 1674-1679 (2009)
Discovery of novel and potent thiazoloquinazolines as selective Aurora A and B kinase inhibitors.
Jung, Frederic H et al.
Journal of Medicinal Chemistry, 49(3), 955-970 (2006)
Highly efficient synthesis of tricyclic amines by a cyclization/cycloaddition cascade: total syntheses of aspidospermine, aspidospermidine, and quebrachamine.
Coldham, Iain et al.
Angewandte Chemie (International Edition in English), 46(32), 6159-6162 (2007)
A chimeric ligand approach leading to potent antiprion active acridine derivatives: design, synthesis, and biological investigations.
Dollinger, Silke et al.
Journal of Medicinal Chemistry, 49(22), 6591-6595 (2006)
Design, synthesis, and evaluation of novel fluoroquinolone- aminoglycoside hybrid antibiotics.
Pokrovskaya, Varvara et al.
Journal of Medicinal Chemistry, 52(8), 2243-2254 (2009)
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