81831
Propargyl bromide solution
purum, ~80% in toluene
Synonym(s):
3-Bromo-1-propyne
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About This Item
Linear Formula:
HC≡CCH2Br
CAS Number:
Molecular Weight:
118.96
Beilstein:
605309
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
grade
purum
Quality Level
form
liquid
contains
~0.3% magnesium oxide light as stabilizer
concentration
~80% in toluene
density
1.39 g/mL at 20 °C
storage temp.
2-8°C
SMILES string
BrCC#C
InChI
1S/C3H3Br/c1-2-3-4/h1H,3H2
InChI key
YORCIIVHUBAYBQ-UHFFFAOYSA-N
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General description
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Oral - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3
Target Organs
Central nervous system, Respiratory system
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
64.4 °F - closed cup
Flash Point(C)
18 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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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