| Identification | More | [Name]
4-METHOXYPHENYLACETYL CHLORIDE | [CAS]
4693-91-8 | [Synonyms]
4-METHOXYBENZENEACETYL CHLORIDE
4-METHOXYPHENYLACETYL CHLORIDE
4-METHOXYPHENYLACETYL CHLORIDE 98%
p-Methoxyphenylacetyl chloride | [EINECS(EC#)]
-0 | [Molecular Formula]
C9H9ClO2 | [MDL Number]
MFCD00075474 | [Molecular Weight]
184.62 | [MOL File]
4693-91-8.mol |
| Chemical Properties | Back Directory | [Appearance]
clear light yellow liquid | [Boiling point ]
143 °C10 mm Hg(lit.) | [density ]
1.208 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.54(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [form ]
Liquid | [color ]
Clear light yellow | [Sensitive ]
Moisture Sensitive | [Detection Methods]
NMR,MS | [BRN ]
908061 | [InChI]
1S/C9H9ClO2/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3 | [InChIKey]
CXJOONIFSVSFAD-UHFFFAOYSA-N | [SMILES]
COc1ccc(CC(Cl)=O)cc1 | [CAS DataBase Reference]
4693-91-8(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R14:Reacts violently with water.
R34:Causes burns.
R37:Irritating to the respiratory system. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3265 8/PG 2
| [WGK Germany ]
3
| [F ]
8-10 | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29189900 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Skin Corr. 1B |
| Hazard Information | Back Directory | [Chemical Properties]
clear light yellow liquid | [Uses]
4-Methoxyphenylacetyl chloride may be used in the synthesis of:
- substituted spiro[4.5]decane
- 1-(4′-hydroxybenzyl)-6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline (higenamine), a cardiotonic principle of aconite root
- 2,5-naphthyridine
- (R)-(+)-nor-roefractine
| [Synthesis]
The general procedure for the synthesis of 4-methoxyphenylacetyl chloride from 4-methoxyphenylacetic acid was as follows: 16.62 g (0.1 mol) of 4-methoxyphenylacetic acid was dissolved in 10 mL of benzene, followed by the slow addition of 29 mL (0.2 mol) of thionyl chloride to the solution. The reaction mixture was heated to reflux temperature and stirred continuously for 1 hour under this condition. Upon completion of the reaction, the residual thionyl chloride in the reaction solution and the concentrated solvent were removed by distillation under reduced pressure to afford 4-methoxybenzeneacetyl chloride (Compound I) as a liquid phase product in quantitative yield. The obtained product can be used for subsequent reaction without further purification. | [References]
[1] European Journal of Medicinal Chemistry, 2005, vol. 40, # 8, p. 764 - 771
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6160 - 6163
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2899 - 2903
[4] Patent: WO2005/92896, 2005, A1. Location in patent: Page/Page column 27
[5] Chinese Chemical Letters, 2013, vol. 24, # 8, p. 673 - 676 |
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