2-(3,4-dimethoxyphenyl)acetonitrile

• ChemBase ID: 53515
• Molecular Formular: C10H11NO2
• Molecular Mass: 177.19984
• Monoisotopic Mass: 177.0789786
• SMILES: N#CCc1cc(c(cc1)OC)OC
• Canonical SMILES: N#CCc1ccc(c(c1)OC)OC
• InChI: InChI=1S/C10H11NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5H2,1-2H3
• InChIKey: ASLSUMISAQDOOB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dimethoxyphenyl)acetonitrile
• IUPAC Traditional name: benzylcyanide,3,4-dimethoxy
• Synonyms: (3,4-Dimethoxyphenyl)acetonitrile; VERATRYLCYANIDE; Homoveratronitrile; 3,4-Dimethoxyphenylacetonitrile; 2-(3,4-Dimethoxyphenyl)acetonitrile; 3,4-Dimethoxybenzeneacetonitrile; 3,4-Dimethoxybenzyl cyanide; NSC 6324; Veratryl Cyanide; Homoveratronitrile; 3,4-Dimethoxyphenylacetonitrile; (3,4-Dimethoxyphenyl)acetonitrile; 3,4-Dimethoxybenzylcyanide; Homoveratronitrile; (3,4-Dimethoxyphenyl)acetonitrile; 高藜芦腈; 3,4-二甲氧基苯乙腈; (3,4-二甲氧苯基)乙腈; 3,4-二甲氧基苯乙腈; 高藜芦腈; (3,4-二甲氧苯基)乙腈

Database IDs

• CAS Number: 93-17-4
• EC Number: 202-225-1
• MDL Number: MFCD00001911
• Beilstein Number: 1956100
• PubChem SID: 162058278; 24847718
• PubChem CID: 66727

CALCULATED PROPERTIES

• Acid pKa: 13.910174
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.3536004
• LogD (pH = 7.4): 1.3536003
• Log P: 1.3536004
• Molar Refractivity: 49.2713 cm^3
• Polarizability: 18.8871 Å^3
• Polar Surface Area: 42.25 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Ethyl Acetate; methanol: soluble0.1 g/mL, clear
• Apperance: White Solid; yellow
• Melting Point: 62-63.5 °C(lit.); 62-64 °C; 62-65°C; 64-66°C
• Boiling Point: 171-178 °C/10 mmHg(lit.); 177-178°C/10mm
• Flash Point: 250 °C; 482 °F
• Fluorescence: λex 430 nm; λem 511 nm (pH 7.1)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• RTECS: AL9325000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 21/22; 22
• Safety Statements: 36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H302-H312
• GHS Precautionary statements: P280H
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (GC); 98%
• Grade: purum
• Linear Formula: (CH3O)2C6H3CH2CN

DETAILS

MP Biomedicals - 05202826

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 126349

Packaging
100, 500 g in glass bottle

Toronto Research Chemicals - H669530

An impurity of Verapamil (V125000). An intermediate in the preparation of the muscle relaxant Papverine (P190500).

REFERENCES

• Marek, E.M. et al.: Khim.-Farmat. Zhur., 17, 1377 (1983)
• Lacroix, P. et al.: J. Pharmac. Biomed. Anal., 9, 817 (1983)
• Reaction with dimethylamine in the presence of CuCl gives the N,N-dimethylamidine, which, on borohydride reduction, provides an efficient route to the N,N-dimethylphenethylamine: Tetrahedron Lett., 34, 6395 (1993); Org. Synth., 76, 133 (1998). The method is applicable to other alkyl nitriles and to both primary and secondary amines, providing a general route to secondary and tertiary amines from the corresponding nitriles: