(isocyanomethyl)benzene

• ChemBase ID: 138980
• Molecular Formular: C8H7N
• Molecular Mass: 117.14788
• Monoisotopic Mass: 117.05784923
• SMILES: [C-]#[N+]Cc1ccccc1
• Canonical SMILES: [C-]#[N+]Cc1ccccc1
• InChI: InChI=1S/C8H7N/c1-9-7-8-5-3-2-4-6-8/h2-6H,7H2
• InChIKey: RIWNFZUWWRVGEU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (isocyanomethyl)benzene
• IUPAC Traditional name: (isocyanomethyl)benzene
• Synonyms: Benzyl isocyanide; (Isocyanomethyl)benzene; Benzyl Isonitrile; Benzyl Isocyanide; 苄异腈

Database IDs

• CAS Number: 10340-91-7
• EC Number: 233-738-9
• MDL Number: MFCD00000004
• PubChem SID: 162233231; 24848098
• PubChem CID: 82558

CALCULATED PROPERTIES

• Acid pKa: 16.15188
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -0.2339359
• LogD (pH = 7.4): -0.23393588
• Log P: -0.2339359
• Molar Refractivity: 46.1242 cm^3
• Polarizability: 14.37477 Å^3
• Polar Surface Area: 4.36 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 105-106 °C/75 mmHg(lit.)
• Flash Point: 174.2 °F; 79 °C
• Density: 0.962 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.521(lit.)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 98%
• Linear Formula: C6H5CH2NC

DETAILS

Sigma Aldrich - 133299

Application
Used in a three-component coupling process leading to O- and N-arylamides.1
Other Notes
May darken in storage
Packaging
1, 5 g in glass bottle
250 mg in glass bottle

Toronto Research Chemicals - B279995

Benzyl Isocyanide is used in the preparation of arylamide compounds. also used as a catalyst in the cycloaddition of norbornenes with internal and terminal acetylenes.

REFERENCES

• Kaim, L.E. et al.: J. Org. Chem., 72, 4169 (2007)