Propargyl bromide

• Catalog No.: L10595
• CAS Number: 106-96-7
• M. F.: C3H3Br
• M. W.: 118.95992
• Purity: 97%, 80% w/w in toluene

SYNONYMS

• Title: 炔丙基溴
• IUPAC name: 3-bromoprop-1-yne
• IUPAC Traditional name: 1-propyne, 3-bromo-
• Synonyms: 3-Bromo-1-propyne

DATABASE IDS

• MDL Number: MFCD00000241
• CAS Number: 106-96-7
• EC Number: 203-447-1
• Beilstein Number: 605309

PROPERTIES

• Purity: 97%, 80% w/w in toluene
• Boiling Point: 88-90°C
• Density: 1.335
• Flash Point: 3°C(37°F)
• Melting Point: -61°C
• Refractive Index: 1.4940
• GHS Hazard statements: H225-H301-H335-H336-H304-H361-H373-H314
• European Hazard Symbols: Toxic (T)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 11-25-34-37-48/20-63-65-67
• RTECS: UK4375000
• Safety Statements: 9-16-20-23-26-33-36/37/39-45-60
• Storage Warning: Light Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2924
• Packing Group: II

REFERENCES

• 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).