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106-96-7 - Propargyl bromide, 97%, 80% w/w in toluene, stab. with magnesium oxide - 3-Bromo-1-propyne - L10595 - Alfa Aesar

L10595 Propargyl bromide, 97%, 80% w/w in toluene, stab. with magnesium oxide

Codice CAS
106-96-7
Sinonimi
3-Bromo-1-propyne

Dimensioni Prezzo ($) Quantità Disponibilità
25g 35,40
100g 101,00
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Propargyl bromide, 97%, 80% w/w in toluene, stab. with magnesium oxide

MDL
MFCD00000241
EINECS
203-447-1

Proprietà chimiche

Formula
C3H3Br
Peso formula
118.97
Punto di fusione
-61°
Punto di ebollizione
88-90°
Punto di infiammabilità
3°(37°F)
Densità
1.335
Indice di rifrazione
1.4940
Sensibilità
Light Sensitive
Solubilità
Miscible with ethanol, ether, benzene, carbon tetrachloride and chloroform. Immiscible with water.

Applicazioni

Propargyl bromide is used as an alkylating agent as well as an intermediate for the synthesis of organic compounds, agrochemicals and pharmaceuticals. It reacts with magnesium in presence of ether to get a Grignard reagent namely allenylmagnesium bromide, which on further reaction with propargyl bromide prepares bis-allene 1,2,4,5-hexatetraene. Also, used as metal brightening agents, corrosion inhibitor and soil fumigant.

Note

Light sensitive. Store in a cool place. Incompatible withbases, strong oxidizing agents, copper, peroxides, silver, silver oxides, mercury and mercury oxides.

Letteratura

With Mg in ether, generates allenylmagnesium bromide which can be coupled with a further molecule of propargyl bromide to give the bis-allene 1,2,4,5-hexatetraene: Org. Synth. Coll., 7, 485 (1990). Diels-Alder reaction of the product with Dimethyl­ acetyl­enedicarboxyl­ate, A11437 leads to a para-cyclophane.

Barbier-type reaction with aldehydes in aqueous THF gives the secondary alcohols in moderate to good yields: Synth. Commun., 25, 2923 (1995); partial rearrangement to the allene could occur; cf Allyl­ bromide, A11766, for similar reactions. For reaction with aldehydes in the presence of Zn in THF, and transformation of the resulting secondary alcohols into pyruvate esters, see: J. Chem. Chem. Commun ., 1289 (1991).

For conversion to dimethyl-2-propynylsulfonium bromide and condensation with 2,4-pentanedione and other active methylene compounds in a versatile, high-yield synthesis of substituted furans, see: J. Chem. Soc., Perkin 1, 65 (1973); Org. Synth. Coll ., 6, 31 (1988).

For diastereoselective propargylation of ɑ -alkoxy aldehydes and application in the synthesis of oxygenated acyclic natural products, see: J. Org. Chem., 60, 3257 (1995).

Zhou, C.; Gao, Y.; Chen, D. Investigation of pyridine/propargyl bromide reaction and strong fluorescence enhancements of the resultant poly (propargyl pyridinium bromide). J. Phys. Chem. B 2012, 116 (37), 11552-11559.

Musalova, M. V.; Musalov, M. V.; Potapov, V. A.; Amosova, S. V. Selective synthesis of allenyl aryl tellurides from diaryl ditellurides and propargyl bromide. Russ. J. Org. Chem. 2012, 48 (12), 1569-1570.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H225-H301-H333-H314-H318-H361-H335-H336-H373-H304

Highly flammable liquid and vapour. Toxic if swallowed. May be harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Suspected of damaging fertility or the unborn child. May cause respiratory irritation. May cause drowsiness or dizziness. May cause damage to organs through prolonged or repeated exposure. May be fatal if swallowed and enters airways.

Dichiarazioni precauzionali: P210-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
605309
Classe di rischio
3
Gruppo di imballaggio
II
Codice tariffe armonizzato
2903.39
TSCA
Yes
RTECS
UK4375000

Raccomandato

  • A10788

    2,2,2-Trifluoroethanol, 99+%
  • A11477

    3-Butyn-1-ol, 98%
  • A11766

    Allyl bromide, 99%, stab. with 300-1000ppm Propylene oxide
  • A13535

    Benzyl bromide, 99%
  • 13431

    Sodium hydride, 57-63% oil dispersion

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