trans-2-Phenylcyclopropyl isocyanate

Base Information

• Chemical Name: trans-2-Phenylcyclopropyl isocyanate
• CAS No.: 35019-96-6
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.188
• European Community (EC) Number: 252-320-7,627-559-9
• NSC Number: 80668
• DSSTox Substance ID: DTXSID30188542
• Nikkaji Number: J283.231C
• Mol file: 35019-96-6.mol

Synonyms:trans-2-Phenylcyclopropyl isocyanate;63009-74-5;[(1s,2r)-2-isocyanatocyclopropyl]benzene;35019-96-6;(1)-trans-2-Phenylcyclopropyl isocyanate;EINECS 252-320-7;Benzene, (2-isocyanatocyclopropyl)-, trans-;((1s,2r)-2-isocyanatocyclopropyl)benzene;trans-2-Phenylcyclopropyl isocyanate, 90%, remainder predominantly cis;Trans-2-phenylcyclopropylisocyanate;NSC80668;SCHEMBL660964;DTXSID30188542;CCG-40371;MFCD00001273;NSC-80668;trans-2-phenyl-cyclopropyl-isocyanate;AKOS015950679;1beta-Phenyl-2alpha-isocyanatocyclopropane;(+-)-trans-2-phenylcyclopropyl isocyanate;(+/-) ((1S,2R)-2-isocyanatocyclopropyl)benzene;(+/-)((1S,2R)-2-isocyanatocyclopropyl)benzene;A834141;Benzene, [(1R,2S)-2-isocyanatocyclopropyl]-, rel-

Chemical Property of trans-2-Phenylcyclopropyl isocyanate

Chemical Property:

• Boiling Point: 263.1±0.0 °C(Predicted)
• PSA: 29.43000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 1.87830
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 159.068413911
• Heavy Atom Count: 12
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C1N=C=O)C2=CC=CC=C2
• Isomeric SMILES: C1[C@H]([C@@H]1N=C=O)C2=CC=CC=C2

Technology Process of trans-2-Phenylcyclopropyl isocyanate

There total 21 articles about trans-2-Phenylcyclopropyl isocyanate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

trans-2-phenylcyclopropane-1-carboxylic acid (939-90-2) → trans-(2-isocyanatocyclopropyl)benzene (35019-96-6,63006-15-5,63009-74-5,79082-68-1)

Guidance literature:

Multistep reaction; (i) ClCO₂Et, Et₃N, aq. acetone, (ii) NaN₃, (iii) toluene, (heating);

Reference yield:

1-Bromo-2-iodobenzene (583-55-1) → trans-(2-isocyanatocyclopropyl)benzene (35019-96-6,63006-15-5,63009-74-5,79082-68-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / K₂CO₃; n-Bu₄NCl / Pd(OAc)2 / dimethylformamide / 19 h / 50 °C

2: 98 percent / Pd(OAc)2 / diethyl ether / 2 h / -10 °C

3: 53 percent / aq. NaOH / methanol / 2 h / 20 °C

4: Et₃N / acetone / 2.5 h / -10 °C

5: aq. NaN₃ / acetone / 0.5 h / -10 °C

6: toluene / Heating

7: tributyltin hydride / 0.5 h / Photolysis; Heating

With sodium hydroxide; sodium azide; tetrabutyl-ammonium chloride; tri-n-butyl-tin hydride; potassium carbonate; triethylamine; palladium diacetate; In methanol; diethyl ether; N,N-dimethyl-formamide; acetone; toluene; 6: Curtius rearrangement;

DOI:10.1039/b405735j

Reference yield:

methyl (2E)-3-(2-bromophenyl)-2-propenoate (102540-15-8,123100-53-8,92991-89-4) → trans-(2-isocyanatocyclopropyl)benzene (35019-96-6,63006-15-5,63009-74-5,79082-68-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / Pd(OAc)2 / diethyl ether / 2 h / -10 °C

2: 53 percent / aq. NaOH / methanol / 2 h / 20 °C

3: Et₃N / acetone / 2.5 h / -10 °C

4: aq. NaN₃ / acetone / 0.5 h / -10 °C

5: toluene / Heating

6: tributyltin hydride / 0.5 h / Photolysis; Heating

With sodium hydroxide; sodium azide; tri-n-butyl-tin hydride; triethylamine; palladium diacetate; In methanol; diethyl ether; acetone; toluene; 5: Curtius rearrangement;

DOI:10.1039/b405735j

upstream raw materials:

trans-2-phenylcyclopropane-1-carboxylic acid

1-Bromo-2-iodobenzene

methyl (2E)-3-(2-bromophenyl)-2-propenoate

ortho-bromobenzaldehyde

Downstream raw materials:

(+/-)-N-<2-Chlor-aethyl>-N'-<2-trans-phenyl-cyclopropyl>-harnstoff

4,5-dihydro-4-oxo-2-<(2-trans-phenylcyclopropyl)amino>-3-furancarboxylic acid ethyl ester

((1SR,2RS)-tert-butyl-2-phenylcyclopropyl)carbamate