5-Amino-3-phenylisoxazole

Base Information

• Chemical Name: 5-Amino-3-phenylisoxazole
• CAS No.: 4369-55-5
• Molecular Formula: C9H8 N2 O
• Molecular Weight: 160.175
• Hs Code.: 29349990
• European Community (EC) Number: 624-755-6
• NSC Number: 93157
• DSSTox Substance ID: DTXSID20293957
• Nikkaji Number: J80.808C
• Wikidata: Q72502072
• Mol file: 4369-55-5.mol

Synonyms:5-Amino-3-phenylisoxazole;4369-55-5;3-phenylisoxazol-5-amine;3-phenyl-1,2-oxazol-5-amine;5-Isoxazolamine, 3-phenyl-;3-phenyl-5-isoxazolamine;3-phenyl-isoxazol-5-ylamine;MFCD00464114;Isoxazole, 5-amino-3-phenyl-;3-Phenylisoxazole-5-amine;5- Amino-3-phenylisoxazol;5-Amino-3-phenyl isoxazole;U 10776;SCHEMBL224856;DTXSID20293957;HLOHVVZZMMMDMM-UHFFFAOYSA-N;5-Amino-3-phenylisoxazole, 97%;HMS1737N08;NSC93157;AR2465;BBL028663;GEO-00211;NSC-93157;STK350764;AKOS000261628;AA-0865;CS-W017937;SB37185;AM803906;SY014437;BB 0218355;EN300-23673;A826402;AI-031/31962041;ISOXAZOLE, 5-AMINO-3-PHENYL UPJOHN U-10776;F3284-8011;Z164676856

Chemical Property of 5-Amino-3-phenylisoxazole

Chemical Property:

• Vapor Pressure: 5.91E-06mmHg at 25°C
• Melting Point: 110-114 °C(lit.)
• Boiling Point: 379.3°Cat760mmHg
• PKA: -1.69±0.10(Predicted)
• Flash Point: 183.2°C
• PSA: 52.05000
• Density: 1.204g/cm³
• LogP: 2.50500
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 160.063662883
• Heavy Atom Count: 12
• Complexity: 146

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Phenylisoxazol-5-amine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NOC(=C2)N

Technology Process of 5-Amino-3-phenylisoxazole

There total 17 articles about 5-Amino-3-phenylisoxazole 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: 90.0%

sodium cyanide (773837-37-9) + N-(1-phenylvinyl)-O-(trimethylsilyl)-N-((trimethylsilyl)oxy)hydroxylamine (344899-62-3) → 3-phenyl-isoxazol-5-ylamine (4369-55-5)

Guidance literature:

sodium cyanide; With magnesium(II) perchlorate; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;

N-(1-phenylvinyl)-O-(trimethylsilyl)-N-((trimethylsilyl)oxy)hydroxylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.201801761

Reference yield: 82.0%

Benzoylacetonitrile (614-16-4) → 3-phenyl-isoxazol-5-ylamine (4369-55-5)

Guidance literature:

With hydroxylamine hydrochloride; sodium hydroxide; In water; at 100 ℃;

DOI:10.1016/j.bmc.2020.115742

Reference yield: 78.0%

potassium cyanide (151-50-8) + α-bromoacetophenone oxime (17082-13-2) → 3-phenyl-isoxazol-5-ylamine (4369-55-5)

Guidance literature:

In ethanol; Ambient temperature;

DOI:10.1002/ardp.19873200903

upstream raw materials:

2-benzoyl-3-phenylacrylonitrile

5-amino-3-phenyl-isoxazole-4-carboxylic acid ethyl ester

3-amino-3-phenylacrylonitrile

3-Phenyl-2-propynonitrile

Downstream raw materials:

5-formylamino-3-phenylisoxazole

N-(3-phenyl-1,2-oxazol-5-yl)acetamide

benzylidene-(3-phenyl-isoxazol-5-yl)-amine

N-acetyl-sulfanilic acid-(3-phenyl-isoxazol-5-ylamide)

Refernces

• 1、 Liu, Hui,Yan, Yingkun,Li, Min,Zhang, Xiaomei. "An enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived: N -Boc ketimines". supporting information. p. 3820 - 3824. Retrieved 2021/05/14.
• 2、 Ge, Yun,Sun, Wangbin,Chen, Yang,Huang, Yulin,Liu, Zhuang,Jiang, Yaojia,Loh, Teck-Peng. "Reactions of 5-Aminoisoxazoles with α-Diazocarbonyl Compounds: Wolff Rearrangement vs N-H Insertion". . p. 2676 - 2688. Retrieved 2019/02/26.