2-Chloro-1,3-benzoxazole-5-carbonitrile

Base Information

• Chemical Name: 2-Chloro-1,3-benzoxazole-5-carbonitrile
• CAS No.: 114997-92-1
• Molecular Formula: C₈H₃ClN₂O
• Molecular Weight: 178.578
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID001296052
• Nikkaji Number: J1.899.918H
• Mol file: 114997-92-1.mol

Synonyms:2-Chloro-1,3-benzoxazole-5-carbonitrile;114997-92-1;2-Chlorobenzo[d]oxazole-5-carbonitrile;2-Chlorobenzoxazole-5-carbonitrile;2-chlorobenzooxazole-5-carbonitrile;2-chloro-benzooxazole-5-carbonitrile;SCHEMBL1121673;2-Chloro-5-cyanobenzo[d]oxazole;YXXCZHJSELQADZ-UHFFFAOYSA-N;2-Chloro-5-benzoxazolecarbonitrile;DTXSID001296052;2-chlorobenzo-oxazole-5-carbonitrile;MFCD20482750;AS-9379;EN300-1697980

Chemical Property of 2-Chloro-1,3-benzoxazole-5-carbonitrile

Chemical Property:

• PSA: 49.82000
• LogP: 2.35288
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 177.9933904
• Heavy Atom Count: 12
• Complexity: 224

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloro-1,3-benzoxazole-5-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1C#N)N=C(O2)Cl

Technology Process of 2-Chloro-1,3-benzoxazole-5-carbonitrile

There total 6 articles about 2-Chloro-1,3-benzoxazole-5-carbonitrile 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: 98.0%

5-cyanobenzo[d]oxazole-2-(3H)-thiazone (93794-41-3) → 2-chloro-5-cyanobenzo[d]oxazole (114997-92-1)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; at 65 - 70 ℃; for 0.5h;

DOI:10.1021/jo952101z

Reference yield:

4-hydroxy-3-nitrobenzonitrile (3272-08-0) → 2-chloro-5-cyanobenzo[d]oxazole (114997-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / hydrogen / palladium on charcoal / ethanol; ethyl acetate / Ambient temperature

2: 86 percent / pyridine / 2 h / Heating

3: 98 percent / thionyl chloride, DMF / 0.5 h / 65 - 70 °C

With pyridine; thionyl chloride; hydrogen; N,N-dimethyl-formamide; palladium on activated charcoal; In ethanol; ethyl acetate;

DOI:10.1021/jo952101z

Reference yield:

3-amino-4-hydroxybenzonitrile (14543-43-2) → 2-chloro-5-cyanobenzo[d]oxazole (114997-92-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / pyridine / 2 h / Heating

2: 98 percent / thionyl chloride, DMF / 0.5 h / 65 - 70 °C

With pyridine; thionyl chloride; N,N-dimethyl-formamide;

DOI:10.1021/jo952101z

upstream raw materials:

2-mercaptobenzo[d]oxazole-5-carbonitrile

5-cyanobenzo[d]oxazole-2-(3H)-thiazone

4-hydroxy-3-nitrobenzonitrile

3-amino-4-hydroxybenzonitrile

Downstream raw materials:

2-(5-acetoxyamidinobenzoxazol-2-yl)-5-(4-acetoxyamidinophenyl)furan

2-(5-hydroxyamidinobenzoxazol-2-yl)-5-(4-hydroxyamidinophenyl)furan

2-(5-cyanobenzoxazol-2-yl)-5-(4-cyanophenyl)thiophene

2-(5-cyanobenzoxazol-2-yl)-5-(4-cyanophenyl)furan

Refernces

• 1、 -. "BENZOTHIAZOLES HAVING HISTAMINE H3 RECEPTOR ACTIVITY". Page/Page column 62. . Retrieved 2008/06/13.
• 2、 Lok, Roger,Leone, Ronald E.,Williams, Antony J.. "Facile rearrangements of alkynylamino heterocycles with noble metal cations". . p. 3289 - 3297. Retrieved 2007/10/03.