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Merck
CN

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:
106-96-7
Molecular Weight:
118.96
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
329769220
MDL number:
MFCD00000241
Beilstein/REAXYS Number:
605309

Key Documents

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Product Name

Propargyl bromide solution, purum, ~80% in toluene

InChI

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

SMILES string

BrCC#C

InChI key

YORCIIVHUBAYBQ-UHFFFAOYSA-N

grade

purum

form

liquid

contains

~0.3% magnesium oxide light as stabilizer

concentration

~80% in toluene

density

1.39 g/mL at 20 °C

functional group

alkyl halide
bromo

storage temp.

2-8°C

Quality Level

200

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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

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.

signalword

Danger

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

3 - Flammable liquids

wgk

WGK 3

flash_point_f

64.4 °F - closed cup

flash_point_c

18 °C - closed cup

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCN8126
BCCN5268
BCCN3595
BCCM7893
BCCL6404

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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
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)
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
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
Lyudmila A Grischenko et al.
Carbohydrate research, 376, 7-14 (2013-06-04)
New arabinogalactan propargyl ethers with degree of substitution (DS) up to 2.8 have been obtained by propargylation of arabino-3,6-galactan (AG) with propargyl bromide (PB) in the two-phase system 30-60% КОН aqueous solution/toluene in the presence of triethylbenzylammonium chloride (TEBAС) or
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