No renderable structure data available
C1=CC=C(C=C1)N(C2=CC=CC=C2)C(=O)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1,1-diphenylurea |
|---|---|
| IUPAC Name | — |
| CAS Number | 603-54-3 |
| Database ID | 33603 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1,1-diphenylurea (CAS 603-54-3) 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 33603
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-f84e9b2b4fe54e919a6842f34c5a3cc6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Freshly distilled acetaldehyde (0.22 mole) is added during 0.5 hr to a stirred solution of 0.1 mole each of 1,1-diphenylurea and triphenyl phosphite in 130g of benzene at 60° C. The solution is warmed at reflux (65°-70° with Dry Ice-cooled condenser) for 1.25 hr, giving a dark brown solution having a small 31P nmr peak at -126.2 ppm for unreacted phosphite and a large product peak at -18.4 ppm (~1:5 areas). The reaction mixture is stripped to 130°/3mm. The residue is diluted with 200 ml of acetonitrile and 10 g of H2O, and this solution is warmed at reflux for 3 hr. Solid that separates during warming is recrystallized from acetic acid-water to give a white solid; mp 186°-187° dec; P31 nmr -21.6 ppm; 1H nmr δ10.0 (s, 2, OH), 7.3 (m, 10, C 6 H5), 5.4 (d of d, 1, J = 9 and 5Hz, NH), 4.1 (m, 1, CH), 1.3 (d of d, 3, J = 16 and 7 Hz, CH3); acidity 2.00 equiv/mole, pK1 = 2.20, pK2 = 8.62. The solution is warmed at reflux giving a dark brown solution is stripped to 130° this solution is warmed at reflux for 3 hr Solid that separates during warming is recrystallized from acetic acid-water to give a white solid
Source ID: ord-b771fd40c53d4ad99a4beb553179bb79Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Freshly distilled acetaldehyde (0.22 mole) is added during 0.5 hr to a stirred solution of 0.1 mole each of 1,1-diphenylurea and triphenyl phosphite in 130g of benzene at 60° C. The solution is warmed at reflux (65°-70° with Dry Ice-cooled condenser) for 1.25 hr, giving a dark brown solution having a small 31P nmr peak at -126.2 ppm for unreacted phosphite and a large product peak at -18.4 ppm (~1:5 areas). The reaction mixture is stripped to 130°/3mm. The residue is diluted with 200 ml of acetonitrile and 10 g of H2O, and this solution is warmed at reflux for 3 hr. Solid that separates during warming is recrystallized from acetic acid-water to give a white solid; mp 186°-187° dec; P31 nmr -21.6 ppm; 1H nmr δ10.0 (s, 2, OH), 7.3 (m, 10, C 6 H5), 5.4 (d of d, 1, J = 9 and 5Hz, NH), 4.1 (m, 1, CH), 1.3 (d of d, 3, J = 16 and 7 Hz, CH3); acidity 2.00 equiv/mole, pK1 = 2.20, pK2 = 8.62. The solution is warmed at reflux giving a dark brown solution is stripped to 130° this solution is warmed at reflux for 3 hr Solid that separates during warming is recrystallized from acetic acid-water to give a white solid
Source ID: ord-b771fd40c53d4ad99a4beb553179bb79Conditions: temp:87.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 21.2g (0.1 mole) of 1,1-diphenylurea, 15.1g (0.1 mole) of 4-nitrobenzaldehyde, and 31.0g (0.1 mole) of triphenyl phosphite in 50g of benzene is stirred under nitrogen and warmed at reflux (87° C.) for 2 hours to give a light yellow solution: 31P nmr -13.2 (d, J = 23Hz), -127.8 ppm (area ratio 5:1). Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil remaining, causing 32g of solid to separate after a few minutes. A portion is recrystallized from acetonitrile to give a white solid: mp 157°-162°; 31P nmr -13.2 ppm (d, J = 24Hz); molecular weight (CHCl3) 565 (calcd 579). warmed to give a light yellow solution Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil to separate after a few minutes A portion is recrystallized from acetonitrile to give a white solid
Source ID: ord-9e76a56994ea4e6c8c3c87f8f119245cConditions: temp:87.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 21.2g (0.1 mole) of 1,1-diphenylurea, 15.1g (0.1 mole) of 4-nitrobenzaldehyde, and 31.0g (0.1 mole) of triphenyl phosphite in 50g of benzene is stirred under nitrogen and warmed at reflux (87° C.) for 2 hours to give a light yellow solution: 31P nmr -13.2 (d, J = 23Hz), -127.8 ppm (area ratio 5:1). Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil remaining, causing 32g of solid to separate after a few minutes. A portion is recrystallized from acetonitrile to give a white solid: mp 157°-162°; 31P nmr -13.2 ppm (d, J = 24Hz); molecular weight (CHCl3) 565 (calcd 579). warmed to give a light yellow solution Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil to separate after a few minutes A portion is recrystallized from acetonitrile to give a white solid
Source ID: ord-9e76a56994ea4e6c8c3c87f8f119245cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Freshly distilled acetaldehyde (0.22 mole) is added during 0.5 hr to a stirred solution of 0.1 mole each of 1,1-diphenylurea and triphenyl phosphite in 130g of benzene at 60°C. The solution is warmed at reflux (65°-70° with Dry Ice-cooled condenser) for 1.25 hr, giving a dark brown solution having a small 31P nmr peak at -126.2 ppm for unreacted phosphite and a large product peak at -18.4 ppm (~1:5 areas). The reaction mixture is stripped to 130°/3mm. The residue is diluted with 200 ml of acetonitrile and 10g of H2O, and this solution is warmed at reflux for 3 hr. Solid that separates during warming is recrystallized from acetic acid-water to give a white solid: mp 186°-187° dec; p31 nmr -21.6 ppm; 1H nmr δ10.0 (s, 2, OH), 7.3 (m, 10, C6H5 ), 5.4 (d of d, 1, J = 9 and 5Hz, NH), 4.1 (m, 1, CH), 1.3 (d of d, 3, J = 16 and 7 Hz, CH3); acidity 2.00 equiv/ mole, pK1 = 2.20, pK2 = 8.62. The solution is warmed at reflux giving a dark brown solution is stripped to 130° this solution is warmed at reflux for 3 hr Solid that separates during warming is recrystallized from acetic acid-water to give a white solid
Source ID: ord-05bd4ff8d0544eceae7fc02c3017323cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Freshly distilled acetaldehyde (0.22 mole) is added during 0.5 hr to a stirred solution of 0.1 mole each of 1,1-diphenylurea and triphenyl phosphite in 130g of benzene at 60°C. The solution is warmed at reflux (65°-70° with Dry Ice-cooled condenser) for 1.25 hr, giving a dark brown solution having a small 31P nmr peak at -126.2 ppm for unreacted phosphite and a large product peak at -18.4 ppm (~1:5 areas). The reaction mixture is stripped to 130°/3mm. The residue is diluted with 200 ml of acetonitrile and 10g of H2O, and this solution is warmed at reflux for 3 hr. Solid that separates during warming is recrystallized from acetic acid-water to give a white solid: mp 186°-187° dec; p31 nmr -21.6 ppm; 1H nmr δ10.0 (s, 2, OH), 7.3 (m, 10, C6H5 ), 5.4 (d of d, 1, J = 9 and 5Hz, NH), 4.1 (m, 1, CH), 1.3 (d of d, 3, J = 16 and 7 Hz, CH3); acidity 2.00 equiv/ mole, pK1 = 2.20, pK2 = 8.62. The solution is warmed at reflux giving a dark brown solution is stripped to 130° this solution is warmed at reflux for 3 hr Solid that separates during warming is recrystallized from acetic acid-water to give a white solid
Source ID: ord-05bd4ff8d0544eceae7fc02c3017323cConditions: temp:87.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 21.2g (0.1 mole) of 1,1-diphenylurea. 15.1g (0.1 mole) of 4-nitrobenzaldehyde, and 31.0g (0.1 mole) of triphenyl phosphite in 50g of benzene is stirred under nitrogen and warmed at reflux (87°C) for 2 hours to give a light yellow solution: 31P nmr -13.2 (d, J = 23Hz), -127.8 ppm (area ratio 5:1). Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil remaining, causing 32g of solid to separate after a few minutes. A portion is recrystallized from acetonitrile to give a white solid: mp 157°-162°; 31P nmr -13.2 ppm (d, J = 24Hz); molecular weight (CHCl3) 565 (calcd 579). warmed to give a light yellow solution Most of the benzene is removed at reduced pressure, and ether to separate after a few minutes A portion is recrystallized from acetonitrile to give a white solid
Source ID: ord-f6296ca2f8e9471080675ad4f21eef53Conditions: temp:87.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 21.2g (0.1 mole) of 1,1diphenylurea, 15.1g (0.1 mole) of 4-nitrobenzaldehyde, and 31.0g (0.1 mole) of triphenyl phosphite in 50g of benzene is stirred under nitrogen and warmed at reflux (87° C) for 2 hours to give a light yellow solution: 31P nmr -13.2 (d, J = 23Hz), 127.8 ppm (area ratio 5:1). Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil remaining, causing 32g of solid to separate after a few minutes. A portion is recrystallized from acetonitrile to give a white solid: mp 157°-162°; 31P nmr -13.2 ppm (d, J = 24Hz); molecular weight (CHCl3) 565 (calcd 579). warmed to give a light yellow solution Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil to separate after a few minutes A portion is recrystallized from acetonitrile to give a white solid
Source ID: ord-f61df7b8542b466e981e5a526e84a0f1Conditions: temp:87.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 21.2g (0.1 mole) of 1,1diphenylurea, 15.1g (0.1 mole) of 4-nitrobenzaldehyde, and 31.0g (0.1 mole) of triphenyl phosphite in 50g of benzene is stirred under nitrogen and warmed at reflux (87° C) for 2 hours to give a light yellow solution: 31P nmr -13.2 (d, J = 23Hz), 127.8 ppm (area ratio 5:1). Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil remaining, causing 32g of solid to separate after a few minutes. A portion is recrystallized from acetonitrile to give a white solid: mp 157°-162°; 31P nmr -13.2 ppm (d, J = 24Hz); molecular weight (CHCl3) 565 (calcd 579). warmed to give a light yellow solution Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil to separate after a few minutes A portion is recrystallized from acetonitrile to give a white solid
Source ID: ord-f61df7b8542b466e981e5a526e84a0f1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Freshly distilled acetaldehyde (0.22 mole) is added during 0.5 hr to a stirred solution of 0.1 mole each of 1,1-diphenylurea and triphenyl phosphite in 130g of benzene at 60° C. The solution is warmed at reflux (65°-70° with Dry Ice-cooled condenser) for 1.25 hr, giving a dark brown solution having a small 31P nmr peak at -126.2 ppm for unreacted phosphite and a large product peak at -18.4 ppm (~1:5 areas). The reaction mixture is stripped to 130°/3mm. The residue is diluted with 200 ml of acetonitrile and 10 g of H2O, and this solution is warmed at reflux for 3 hr. Solid that separates during warming is recrystallized from acetic acid-water to give a white solid; mp 186°-187° dec; P31 nmr -21.6 ppm; 1H nmr δ10.0 (s, 2, OH), 7.3 (m, 10, C 6 H5), 5.4 (d of d, 1, J = 9 and 5Hz, NH), 4.1 (m, 1, CH), 1.3 (d of d, 3, J = 16 and 7 Hz, CH3); acidity 2.00 equiv/mole, pK1 = 2.20, pK2 = 8.62. The solution is warmed at reflux giving a dark brown solution is stripped to 130° this solution is warmed at reflux for 3 hr Solid that separates during warming is recrystallized from acetic acid-water to give a white solid
Source ID: ord-b771fd40c53d4ad99a4beb553179bb79Conditions: temp:87.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 21.2g (0.1 mole) of 1,1-diphenylurea, 15.1g (0.1 mole) of 4-nitrobenzaldehyde, and 31.0g (0.1 mole) of triphenyl phosphite in 50g of benzene is stirred under nitrogen and warmed at reflux (87° C.) for 2 hours to give a light yellow solution: 31P nmr -13.2 (d, J = 23Hz), -127.8 ppm (area ratio 5:1). Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil remaining, causing 32g of solid to separate after a few minutes. A portion is recrystallized from acetonitrile to give a white solid: mp 157°-162°; 31P nmr -13.2 ppm (d, J = 24Hz); molecular weight (CHCl3) 565 (calcd 579). warmed to give a light yellow solution Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil to separate after a few minutes A portion is recrystallized from acetonitrile to give a white solid
Source ID: ord-9e76a56994ea4e6c8c3c87f8f119245cPubChem References
These sources are listed in the compound's public database record.
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