ChemicalBook > CAS DataBase List > [3-(4-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL

[3-(4-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL

Product Name
[3-(4-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL
CAS No.
206055-86-9
Chemical Name
[3-(4-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL
Synonyms
(3-(4-methoxyphenyl)isoxazol-5;Methoxyphenylisoxazolylmethanol;5-Isoxazolemethanol, 3-(4-methoxyphenyl)-;[3-(4-METHOXYPHENYL)-5-ISOXAZOLYL]METHANOL;(3-(4-METHOXY PHENYL)ISOXAZOLE-5-YL)METHANOL;[3-(4-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL;[3-(4-methoxyphenyl)-1,2-oxazol-5-yl]methanol;5-(Hydroxymethyl)-3-(4-methoxyphenyl)isoxazole;(3-(4-Methoxyphenyl)isoxazol-5-yl)methanol - [M89222];5-(Hydroxymethyl)-3-(4-methoxyphenyl)isoxazole, 4-[5-(Hydroxymethyl)isoxazol-3-yl]anisole
CBNumber
CB6680444
Molecular Formula
C11H11NO3
Formula Weight
205.21
MOL File
206055-86-9.mol
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[3-(4-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL Property

Melting point:
97-98°C
Boiling point:
396.1±37.0 °C(Predicted)
Density 
1.217±0.06 g/cm3(Predicted)
storage temp. 
Store at room temperature
pka
13.32±0.10(Predicted)
form 
solid
Appearance
White to off-white Solid
CAS DataBase Reference
206055-86-9(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi,Xn
Risk Statements 
22
HazardClass 
IRRITANT
HS Code 
2934999090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC
Product number
M226495
Product name
[3-(4-Methoxyphenyl)isoxazol-5-yl]methanol
Packaging
100mg
Price
$60
Updated
2021/12/16
Apolloscientific
Product number
OR14216
Product name
[3-(4-Methoxyphenyl)isoxazol-5-yl]methanol
Packaging
250mg
Price
$21
Updated
2021/12/16
SynQuest Laboratories
Product number
4H07-1-Y2
Product name
5-(Hydroxymethyl)-3-(4-methoxyphenyl)isoxazole
Packaging
250mg
Price
$23
Updated
2021/12/16
SynQuest Laboratories
Product number
4H07-1-Y2
Product name
5-(Hydroxymethyl)-3-(4-methoxyphenyl)isoxazole
Packaging
1g
Price
$69
Updated
2021/12/16
AK Scientific
Product number
W4332
Product name
[3-(4-Methoxyphenyl)isoxazol-5-yl]methanol
Packaging
1g
Price
$197
Updated
2021/12/16
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[3-(4-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL Chemical Properties,Usage,Production

Synthesis

107-19-7

38435-51-7

206055-86-9

General procedure for the synthesis of [3-(4-methoxyphenyl)-5-isoxazolyl]methanol from 2-propyn-1-ol and α-chloro-4-methoxybenzaldehyde oxime: N-chlorosuccinimide (NCS) (in small amount) was slowly added to a solution of (E)-4-methoxybenzaldehyde oxime (790.0 mg, 5.3 mmol) in DMF (15.8 mL). If the reaction temperature did not increase, 1 N HCl (50.0 μL) was added to promote the reaction. Subsequently, NCS (774.2 mg, 5.8 mmol) was added. The reaction mixture was stirred at room temperature for 1 h and the progress of the reaction was monitored by TLC. Upon completion of the reaction, the reaction was quenched by the addition of ether (20.0 mL) and washed with NaCl solution (2 × 20.0 mL). The organic phase was dried with anhydrous Na2SO4 and the solvent was subsequently removed by rotary evaporation. The resulting carboxyiminocarbonyl chloride was dissolved in t-BuOH:H2O (1:1, 3.8 mL), followed by sequential addition of ethynyl alcohol (340.0 μL, 5.8 mmol), CuSO4 (7.5 mg, dissolved in 50.0 μL of water), sodium ascorbate (104.40 mg, 0.5 mmol) and NaHCO3 (1.3 g, 15.8 mmol). The reaction mixture was stirred for 4 h, after which it was diluted with ethyl acetate (20.0 mL) and washed with H2O (2 × 20.0 mL). The organic phase was dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. Purification by column chromatography [eluent: hexane:ethyl acetate, 8:2 (v/v)] afforded the target compound [3-(4-methoxyphenyl)-5-isoxazolyl]methanol (d1) as a pale yellow solid (890.0 mg, 4.3 mmol, 82% yield). Melting point: 90-92 °C. Rf value: 0.40 [Expanding agent: hexane:ethyl acetate, 60:40 (v/v)]. IR (KBr, cm-1): 3352, 2837, 1610, 1527, 1431, 1259, 1082, 840, 802. 1H NMR (400 MHz, CDCl3) δ: 7.74 (d, J = 8.5 Hz, 2H), 6.98 (d, J = 8.5 Hz, 2H), 6.52 (s, 1H), 4.81 (s, 2H), 3.86 (s, 3H).13C NMR (100 MHz, CDCl3) δ: 171.5, 162.1, 161.0, 128.2, 121.4, 114.3, 99.8, 56.7, 55.4. 55.4.

References

[1] Journal of the Iranian Chemical Society, 2014, vol. 11, # 2, p. 361 - 367
[2] Journal of the Chinese Chemical Society, 2007, vol. 54, # 3, p. 643 - 652
[3] Synthesis, 2002, # 12, p. 1663 - 1668
[4] Patent: EP2308838, 2011, A1. Location in patent: Page/Page column 79-80
[5] Letters in Organic Chemistry, 2011, vol. 8, # 4, p. 278 - 281

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Raw materials

Preparation Products

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206055-86-9, [3-(4-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOLRelated Search:


  • 5-(Hydroxymethyl)-3-(4-methoxyphenyl)isoxazole
  • 5-(Hydroxymethyl)-3-(4-methoxyphenyl)isoxazole, 4-[5-(Hydroxymethyl)isoxazol-3-yl]anisole
  • [3-(4-METHOXYPHENYL)-5-ISOXAZOLYL]METHANOL
  • [3-(4-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL
  • (3-(4-methoxyphenyl)isoxazol-5
  • Methoxyphenylisoxazolylmethanol
  • [3-(4-methoxyphenyl)-1,2-oxazol-5-yl]methanol
  • 5-Isoxazolemethanol, 3-(4-methoxyphenyl)-
  • (3-(4-METHOXY PHENYL)ISOXAZOLE-5-YL)METHANOL
  • (3-(4-Methoxyphenyl)isoxazol-5-yl)methanol - [M89222]
  • 206055-86-9
  • API intermediates
  • pharmacetical