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C1=CC=C(C=C1)CCC#NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-phenylpropanenitrile |
|---|---|
| IUPAC Name | — |
| CAS Number | 645-59-0 |
| Database ID | 12581 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-phenylpropanenitrile (CAS 645-59-0) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 12581
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b8941d16e1a44b7da11a28b0edb6c1a9Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-ab821c12978c44609302a03f1a92c2ccConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-73922c63fb364c7182783c8699b0bea5Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 3-phenylpropionitrile (2.0 g, 15.25 mmol) and tetrahydrofuran (15 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of lithium bis(trimethylsilyl)amide (16.0 mL, 1 M in THF, 16.0 mmol). After 1 hour, add 2-(t-butyldimethylsilyloxy)ethyl iodide (4.58 g, 16.0 mmol). After the addition of 2-(t-butyldimethylsilyloxy)ethyl iodide is complete, warm slowly to ambient temperature over about 7 hours. Add water and extract twice with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 5% ethyl acetate/hexane to give the title compound: Rf=0.50 (silica gel, 10% ethyl acetate/hexane). warm slowly to ambient temperature over about 7 hours Add water and extract twice with ethyl acetate Dry the combined organic layers over Na2SO4 filter concentrate in vacuo to obtain a residue
Source ID: ord-c984d5919abb4204beeca79607e9afa6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b8941d16e1a44b7da11a28b0edb6c1a9Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b8941d16e1a44b7da11a28b0edb6c1a9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This compound was synthesized in an analogous manner to Example 32 but using 3-phenylpropionitrile (commercially available from Acros Organics Order Number 17399) instead of acetonitrile in the preparation of allyl 4-benzyl-3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate according to Scheme 6 instead of allyl 3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate. MS m/z: 474 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.24 (s, 1H), 8.44 (d, J=5.87 Hz, 1H), 8.11 (d, J=8.61 Hz, 1H), 7.93 (s, 1H), 7.75 (dd, J=8.61, 1.37 Hz, 1H), 7.70 (d, J=5.87 Hz, 1H), 7.55 (d, J=7.82 Hz, 1H), 7.39 (d, J=8.02 Hz, 1H), 7.04-7.24 (m, 8H), 3.82 (m, 3H), 3.60-3.73 (m, 2H), 3.21-3.25 (m, 1H), 3.13 (m, 1H). This compound was synthesized in an analogous manner to Example 32
Source ID: ord-2e22dd050fc94727842265095e967aa5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This compound was synthesized in an analogous manner to N-((S)-2-amino-3-(4-chlorophenyl)propyl)-3-(isoquinolin-6-yl)isoxazol-5-amine starting with commercial available 3-phenylpropionitrile (commercially available from Acros Organics Order Number 17399) instead of acetonitrile. MS m/z: 435 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.43 (br s, 1H), 8.50 (br s, 1H), 8.23 (d, J=8.6, 1H), 8.06 (s, 1H), 7.89 (d, J=9.0, 1H), 7.87 (d, J=9.8, 1H), 7.15-7.42 (m, 10H), 3.89 (s, 2H), 3.70 (m, 1H), 3.57-3.62 (m, 2H), 3.02 (d, J=7.04 Hz, 2H).
Source ID: ord-0d27a5a8e2ef4e31b78299263a022773Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 920 mg sodium (40 mmole) is dissolved in 45 ml ethanol and to the ice-bath cooled solution is added 4.66 g diethyl oxalate (31.9 mmole) and 4.17 g hydrocinnamonitrile (31.9 mmole). The mixture is stirred at room temperature for 1 hour, under reflux for 3 hours, and then allowed to stand at room temperature overnight. Evaporation, acidification of the residue, and extraction with methylene chloride affords ethyl 3-cyano-2-oxo-4-phenylbutanoate in 38% yield. The compound crystallizes from petroleum ether in colorless needles; m.p. 80°-83° C. cooled solution under reflux for 3 hours to stand at room temperature overnight Evaporation, acidification of the residue, and extraction with methylene chloride
Source ID: ord-9f9e9bca059942f389eddd98ba332b47Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 920 mg sodium (40 mmole) is dissolved in 45 ml ethanol and to the ice-bath cooled solution is added 4.66 g diethyl oxalate (31.9 mmole) and 4.17 g hydrocinnamonitrile (31.9 mmole). The mixture is stirred at room temperature for 1 hour, under reflux for 3 hours, and then allowed to stand at room temperature overnight. Evaporation, acidification of the residue, and extraction with methylene chloride affords ethyl 3-cyano-2-oxo-4-phenylbutanoate in 38% yield. The compound crystallizes from petroleum ether in colorless needles; m.p. 80°-83° C. cooled solution under reflux for 3 hours to stand at room temperature overnight Evaporation, acidification of the residue, and extraction with methylene chloride
Source ID: ord-9f9e9bca059942f389eddd98ba332b47Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 3-phenylpropionitrile (2.0 g, 15.25 mmol) and tetrahydrofuran (15 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of lithium bis(trimethylsilyl)amide (16.0 mL, 1 M in THF, 16.0 mmol). After 1 hour, add 2-(t-butyldimethylsilyloxy)ethyl iodide (4.58 g, 16.0 mmol). After the addition of 2-(t-butyldimethylsilyloxy)ethyl iodide is complete, warm slowly to ambient temperature over about 7 hours. Add water and extract twice with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 5% ethyl acetate/hexane to give the title compound: Rf=0.50 (silica gel, 10% ethyl acetate/hexane). warm slowly to ambient temperature over about 7 hours Add water and extract twice with ethyl acetate Dry the combined organic layers over Na2SO4 filter concentrate in vacuo to obtain a residue
Source ID: ord-c984d5919abb4204beeca79607e9afa6Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 3-phenylpropionitrile (2.0 g, 15.25 mmol) and tetrahydrofuran (15 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of lithium bis(trimethylsilyl)amide (16.0 mL, 1 M in THF, 16.0 mmol). After 1 hour, add 2-(t-butyldimethylsilyloxy)ethyl iodide (4.58 g, 16.0 mmol). After the addition of 2-(t-butyldimethylsilyloxy)ethyl iodide is complete, warm slowly to ambient temperature over about 7 hours. Add water and extract twice with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 5% ethyl acetate/hexane to give the title compound: Rf=0.50 (silica gel, 10% ethyl acetate/hexane). warm slowly to ambient temperature over about 7 hours Add water and extract twice with ethyl acetate Dry the combined organic layers over Na2SO4 filter concentrate in vacuo to obtain a residue
Source ID: ord-c984d5919abb4204beeca79607e9afa6PubChem References
These sources are listed in the compound's public database record.
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