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81831

Sigma-Aldrich

Propargyl bromide solution

purum, ~80% in toluene

Sinônimo(s):

3-Bromo-1-propyne

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About This Item

Fórmula linear:
HC≡CCH2Br
Número CAS:
106-96-7
Peso molecular:
118.96
Beilstein:
605309
Número MDL:
MFCD00000241
Código UNSPSC:
12352100
ID de substância PubChem:
329769220
NACRES:
NA.22

grau

purum

Nível de qualidade

200

forma

liquid

contém

~0.3% magnesium oxide light as stabilizer

concentração

~80% in toluene

densidade

1.39 g/mL at 20 °C

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

BrCC#C

InChI

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

chave InChI

YORCIIVHUBAYBQ-UHFFFAOYSA-N

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Descrição geral

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.

Aplicação

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

Palavra indicadora

Danger

Classificações de perigo

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

Órgãos-alvo

Central nervous system, Respiratory system

Código de classe de armazenamento

3 - Flammable liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

64.4 °F - closed cup

Ponto de fulgor (°C)

18 °C - closed cup

Equipamento de proteção individual

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

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Certificados de análise (COA)

Lot/Batch Number
BCCL6404
BCCM2933
BCCL2113
BCCK0080
BCCG8687

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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
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)
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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