3-(Benzyloxy)-3-chloro-3H-diazirene

Base Information

• Chemical Name: 3-(Benzyloxy)-3-chloro-3H-diazirene
• CAS No.: 113711-60-7
• Molecular Formula: C8H7ClN2O
• Molecular Weight: 182.609
• DSSTox Substance ID: DTXSID40549605
• Nikkaji Number: J792.923D
• Mol file: 113711-60-7.mol

Synonyms:113711-60-7;3-(Benzyloxy)-3-chloro-3H-diazirene;3-chloro-3-phenylmethoxydiazirine;3-(benzyloxy)-3-chloro-3H-diazirine;3H-Diazirine, 3-chloro-3-(phenylmethoxy)-;DTXSID40549605

Chemical Property of 3-(Benzyloxy)-3-chloro-3H-diazirene

Chemical Property:

• Boiling Point: 229.3±50.0℃ (760 Torr)
• Flash Point: 92.5±30.1℃
• PSA: 33.95000
• Density: 1.35±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 1.39030
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 182.0246905
• Heavy Atom Count: 12
• Complexity: 184

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2(N=N2)Cl

Technology Process of 3-(Benzyloxy)-3-chloro-3H-diazirene

There total 4 articles about 3-(Benzyloxy)-3-chloro-3H-diazirene 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: 57.0%

O-benzylisourea tosylate (113711-61-8) → 3-chloro-3-benzyloxydiazirine (113711-60-7)

Guidance literature:

With hypochlorite;

DOI:10.1016/S0040-4039(00)96022-2

Reference yield:

2-benzyl-isourea; compound with methanesulfonic acid → 3-chloro-3-benzyloxydiazirine (113711-60-7)

Guidance literature:

With sodium hypochlorite; lithium bromide; In dimethyl sulfoxide; pentane; at 20 ℃;

DOI:10.1021/ol0400443

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → 3-chloro-3-benzyloxydiazirine (113711-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 25 °C

2: aq. NaOCl; LiBr / pentane; dimethylsulfoxide / 20 °C

With sodium hypochlorite; lithium bromide; In tetrahydrofuran; dimethyl sulfoxide; pentane;

DOI:10.1021/ol0400443

upstream raw materials:

O-benzylisourea tosylate

benzyl alcohol

Downstream raw materials:

benzyl methyl ether

benzyl chloride

benzyl alcohol

1-Benzyloxy-2,3-dimethyl-cyclopropanecarbonitrile

Refernces

THE FRAGMENTATION OF BENZYLOXYCHLOROCARBENE: FORMATION OF BENZYL CATION

10.1016/S0040-4039(00)96022-2

The study investigates the thermal decomposition of 3-benzyloxy-3-chlorodiazirine in acetonitrile at 25°C to produce benzyloxychlorocarbene, which further fragments to form the benzyl cation. The researchers conducted a detailed analysis of the reaction, examining the effects of different solvents and solvent conditions on the fragmentation process. They found that the reaction proceeded cleanly in acetonitrile, with only minor solvent effects on the rate constant. The study also included an Arrhenius study to determine the energy of activation and a Hammett study to understand the reaction's sensitivity to substituent effects. The researchers proposed that the thermal fragmentation of benzyloxychlorocarbene yields intermediates such as ion pairs and suggested that the geometry of the diazirine prior to decomposition may influence the distribution of these ion pairs. Additionally, they explored the photolytic decomposition of the compound and observed the formation of benzyl radical, although they concluded that this was not the principal pathway for the fragmentation of the carbene. The study was supported by the National Science Foundation and contributed to the understanding of carbene chemistry and the formation of carbocations.

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