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81831

Sigma-Aldrich

Propargyl bromide solution

purum, ~80% in toluene

Synonyme(s) :

3-Bromo-1-propyne

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About This Item

Formule linéaire :
HC≡CCH2Br
Numéro CAS:
106-96-7
Poids moléculaire :
118.96
Numéro Beilstein :
605309
Numéro MDL:
MFCD00000241
Code UNSPSC :
12352100
ID de substance PubChem :
329769220
Nomenclature NACRES :
NA.22

Qualité

purum

Niveau de qualité

200

Forme

liquid

Contient

~0.3% magnesium oxide light as stabilizer

Concentration

~80% in toluene

Densité

1.39 g/mL at 20 °C

Température de stockage

2-8°C

Chaîne SMILES 

BrCC#C

InChI

1S/C3H3Br/c1-2-3-4/h1H,3H2

Clé InChI

YORCIIVHUBAYBQ-UHFFFAOYSA-N

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Catégories apparentées

Description générale

The product is 80% solution of propargyl bromide in toluene. Propargyl bromide (3-bromopropyne, C3H3Br, or 3BP) possess propargyl group, which is an important three-carbon building block. It participates in the stereoselective propargylation reaction of α-alkoxy aldehydes. It is used to compose a soil fumigant trizone.

Application

Propargyl bromide solution may be used in the synthesis of the following:
  • new arabinogalactan propargyl ethers with degree of substitution (DS) up to 2.8, by propargylation of arabino-3,6-galactan
  • conjugated polyelectrolyte with polyacetylene as the backbone and pyridinium as side groups, poly(propargyl pyridinium bromide)
  • benzodiazepine derivative, 4-phenyl-1-(prop-2-yn-1-yl)-1H-1,5-benzodiazepin-2(3H)-one
  • N(3)-propargylated 2′-deoxyuridine, which can be encorporated in the DNA
  • chiral oxygenated acyclic natural products, via distereoselective propargylation of α-hydroxy aldehydes

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 3 Oral - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3

Organes cibles

Central nervous system, Respiratory system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

64.4 °F - closed cup

Point d'éclair (°C)

18 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificats d'analyse (COA)

Lot/Batch Number
BCCL6404
BCCM2933
BCCL2113
BCCK0080
BCCG8687

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Consulter la Bibliothèque de documents

Diastereoselective propargylation of α-alkoxy aldehydes with propargyl bromide and zinc. A versatile and efficient method for the synthesis of chiral oxygenated acyclic natural products.
Wu W-L, et al.
The Journal of Organic Chemistry, 60(10), 3257-3259 (1995)
Yates et al.
Journal of agricultural and food chemistry, 46(2), 755-761 (2001-02-07)
During the 1960s, propargyl bromide (3-bromopropyne, C(3)H(3)Br, or 3BP) was used in a soil fumigant Trizone, a combination of chloropicrin, methyl bromide, and propargyl bromide. Since a great deal of attention is being placed on finding replacements for methyl bromide
Venkata Ramana Sirivolu et al.
Chembiochem : a European journal of chemical biology, 9(14), 2305-2316 (2008-09-10)
5-Tripropargylamine-2'-deoxyuridine (1 a) containing two terminal triple bonds was synthesized by a Pd-assisted Sonogashira cross-coupling reaction and was subsequently converted into the corresponding phosphoramidite building block (9) and employed in solid-phase oligonucleotide synthesis. T(m) experiments demonstrate that the presence of
Mohamed Loughzail et al.
Acta crystallographica. Section E, Structure reports online, 67(Pt 8), o2075-o2076 (2011-11-18)
4-Phenyl-1H-1,5-benzodiazepin-2(3H)-one reacts in the pres-ence of a concentrated aqueous solution of sodium hydroxide and a quaternary ammonium salt (as catalyst) in benzene (phase transfer catalysis) with propargyl bromide, affording the title benzodiazepine derivative, C(18)H(14)N(2)O. In the mol-ecule, the mean plane
Changming Zhou et al.
The journal of physical chemistry. B, 116(37), 11552-11559 (2012-08-30)
Poly(propargyl pyridinium bromide), a kind of conjugated polyelectrolyte with polyacetylene as the backbone and pyridinium as side groups, was synthesized simply via reaction between pyridine and propargyl bromide under mild conditions. The resultant polymer was characterized by (1)H NMR, elemental
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