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81831

Sigma-Aldrich

Propargyl bromide solution

purum, ~80% in toluene

Sinonimo/i:

3-Bromo-1-propyne

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CHF 111.00
250 ML
CHF 370.00

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50 ML
CHF 111.00
250 ML
CHF 370.00

About This Item

Formula condensata:
HC≡CCH2Br
Numero CAS:
106-96-7
Peso molecolare:
118.96
Beilstein:
605309
Numero MDL:
MFCD00000241
Codice UNSPSC:
12352100
ID PubChem:
329769220
NACRES:
NA.22

CHF 111.00

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Grado

purum

Livello qualitativo

200

Stato

liquid

contiene

~0.3% magnesium oxide light as stabilizer

Concentrazione

~80% in toluene

Densità

1.39 g/mL at 20 °C

Gruppo funzionale

alkyl halide
bromo

Temperatura di conservazione

2-8°C

Stringa SMILE

BrCC#C

InChI

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

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Descrizione generale

The product is 80% solution of propargyl bromide in toluene. Propargyl bromide (3-bromopropyne, C3H3Br, or 3BP)[1] possess propargyl group, which is an important three-carbon building block. It participates in the stereoselective propargylation reaction of α-alkoxy aldehydes.[1] It is used to compose a soil fumigant trizone.[2]

Applicazioni

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[3]
  • conjugated polyelectrolyte with polyacetylene as the backbone and pyridinium as side groups, poly(propargyl pyridinium bromide)[4]
  • benzodiazepine derivative, 4-phenyl-1-(prop-2-yn-1-yl)-1H-1,5-benzodiazepin-2(3H)-one[5]
  • N(3)-propargylated 2′-deoxyuridine, which can be encorporated in the DNA[6]
  • chiral oxygenated acyclic natural products, via distereoselective propargylation of α-hydroxy aldehydes[1]

Avvertenze

Danger

Classi di pericolo

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

Organi bersaglio

Central nervous system, Respiratory system

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

64.4 °F - closed cup

Punto d’infiammabilità (°C)

18 °C - closed cup

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
BCCM7893
BCCL6404
BCCM2933
BCCL2113
BCCK0080

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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
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
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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Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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