3-bromoprop-1-yne

• ChemBase ID: 73508
• Molecular Formular: C3H3Br
• Molecular Mass: 118.95992
• Monoisotopic Mass: 117.9418121
• SMILES: BrCC#C
• Canonical SMILES: BrCC#C
• InChI: InChI=1S/C3H3Br/c1-2-3-4/h1H,3H2
• InChIKey: YORCIIVHUBAYBQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-bromoprop-1-yne
• IUPAC Traditional name: 1-propyne, 3-bromo-
• Synonyms: Bromopropyne; 1-Brom-2-propie; 1-Bromo-2-propyne Gamma-bromoallylene; 1-Bromo-2-propyne; 2-Propynyl bromide; Propargyl bromide; Propynyl bromide; gamma-Bromoallylene; Propargyl bromide; 3-Bromo-1-propyne; Propargyl bromide solution; Propargyl bromide; 3-Bromoprop-1-yne; Propargyl bromide, 80% solution in toluene; 3-溴-1-丙炔; 炔丙基溴 溶液; 溴丙炔; 炔丙基溴

Database IDs

• CAS Number: 106-96-7
• EC Number: 203-447-1
• MDL Number: MFCD00000241
• Beilstein Number: 605309
• PubChem SID: 24898595; 24877746; 162038427
• PubChem CID: 7842
• Chemspider ID: 7554
• Wikipedia Title: Propargyl_bromide

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.2495931
• LogD (pH = 7.4): 1.2495931
• Log P: 1.2495931
• Molar Refractivity: 21.876 cm^3
• Polarizability: 8.031745 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Insoluble in water; Soluble in organic solvents
• Apperance: colourless liquid
• Melting Point: -61°C; -61.1°C; -61°C
• Boiling Point: 88-90 °C; 88-90°C; 88-90°C; 89°C; 97 °C
• Flash Point: 18 °C; 18°C; 18°C (64.4°F); 3°C(37°F); 44.6 °F; 64.4 °F; 7 °C
• Auto Ignition Point: 324°C (615.2°F)
• Density: 1.335; 1.335 g/mL at 25 °C; 1.34 g/mL at 25 °C; 1.38 g/mL at 20 °C; 1.57 g/mL (20 °C)
• Refractive Index: 1.494; 1.4940; n20/D 1.494
• Vapor Pressure: 72 mbar (20 °C)
• Partition Coefficient: 1.179

Safety Information

• Storage Warning: Highly Flammable/Toxic/Corrosive/Teratogenic/Lachrymatory/Light Sensitive/Store under Argon/Keep Cold; Light Sensitive
• RTECS: UK4375000
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 2345; UN2924
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-20/21-25-36/37/38; 11-25-34-37-48/20-63-65-67; 63-11-25-36/37/38-48/20-65-67
• Safety Statements: 16-26-36/37-45; 16-26-36/37-45-62; 9-16-20-23-26-33-36/37/39-45-60; R
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• Main Hazard: Highly Flammable, Toxic, Corrosive
• NFPA704:
  

  3

  3

  4
• GHS Hazard statements: H225-H301-H304-H315-H319-H335-H336-H361d-H373; H225-H301-H315-H319-H335; H225-H301-H335-H336-H304-H361-H373-H314
• GHS Precautionary statements: P210-P261-P281-P301 + P310-P305 + P351 + P338-P331; P210-P261-P301 + P310-P305 + P351 + P338; P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2345 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: 80% in toluene, stab. with MgO; 97%, 80% w/w in toluene
• Concentration: ~80% in toluene; 80 wt. % in toluene; 80 wt. % in xylene
• Grade: purum
• Contains: ~0.3% magnesium oxide light as stabilizer; 0.3% magnesium oxide as stabilizer
• Linear Formula: HC≡CCH2Br

DETAILS

Apollo Scientific Ltd - OR01606

Stabilised with MgO

Sigma Aldrich - 530409

Packaging
50, 125 g in glass bottle

Sigma Aldrich - P51001

Packaging
5, 25 kg in steel drum
50, 125, 625 g in Sure/Seal™
Application
Used to make propargylic amines employed in enyne metathesis.1Employed in the propargylation of spiro ketones,2 allylic alcohols,3 and enone complexes.4

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).