2-bromoacetonitrile

• ChemBase ID: 8902
• Molecular Formular: C2H2BrN
• Molecular Mass: 119.94798
• Monoisotopic Mass: 118.93706107
• SMILES: BrCC#N
• Canonical SMILES: BrCC#N
• InChI: InChI=1S/C2H2BrN/c3-1-2-4/h1H2
• InChIKey: REXUYBKPWIPONM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromoacetonitrile
• IUPAC Traditional name: 2-bromoacetonitrile
• Synonyms: Bromoacetonitrile; Bromoacetonitrile; 2-Bromoacetonitrile; 溴乙腈

Database IDs

• CAS Number: 590-17-0
• EC Number: 209-672-1
• MDL Number: MFCD00001884
• Beilstein Number: 956569
• PubChem SID: 160972209; 24854561; 24849900
• PubChem CID: 11534

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.55744225
• LogD (pH = 7.4): 0.55744225
• Log P: 0.55744225
• Molar Refractivity: 19.3597 cm^3
• Polarizability: 7.298889 Å^3
• Polar Surface Area: 23.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 150°C; 60-62 °C/24 mmHg(lit.); 60-62°C/24mm
• Flash Point: 110 °C; 230 °F; 81°C(178°F)
• Density: 1.722; 1.722 g/mL at 25 °C(lit.)
• Refractive Index: 1.4800; n20/D 1.479; n20/D 1.479(lit.)

Safety Information

• Storage Warning: LACHRYMATOR, TOXIC, CORROSIVE
• RTECS: AL7970000
• European Hazard Symbols: Toxic (T)
• UN Number: 3276; UN2922
• German water hazard class: 3
• Hazard Class: 6.1; 8
• Packing Group: 3; II
• Risk Statements: 23/24/25-34; 23/24/25-36/37/38
• Safety Statements: 26-27-36/37/39-45; 26-36-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H314-H318-H227; H301-H311-H315-H319-H331-H335
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A; P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3276 6.1/PG 3

Product Information

• Purity: ≥97.0% (GC); 95+%; 96%; 97%; 98%
• Grade: purum
• Linear Formula: BrCH2CN

DETAILS

Sigma Aldrich - 242489

Packaging
5, 25, 100 g in glass bottle

REFERENCES

• Phenols can be protected (K₂CO₃, acetone) as their cyanomethyl ethers which can be cleaved by hydrogenation of the nitrile: Tetrahedron Lett., 34, 7567 (1993).
• The Reformatsky-type reaction with cyclohexanone is more successful in the presence of a Zn/Ag couple than with the conventional Zn-Cu couple: Synth. Commun., 19, 2355 (1989). Good yields of ?-hydroxy nitriles have also been achieved from aldehydes and ketones using Zn and TMS chloride: Tetrahedron Lett., 31, 2205 (1990). The condensation with aldehydes can also be mediated by active Ni: Tetrahedron Lett., 26, 155 (1985). The reaction with aldehydes in the presence of Zn and tri-n-butylphosphine gives ɑ?-unsaturated nitriles directly: Synth. Commun., 20, 3277 (1990).