ChemicalBook--->CAS DataBase List--->22042-71-3

22042-71-3

22042-71-3 Structure

22042-71-3 Structure
IdentificationMore
[Name]

4-Formylphenoxyacetic acid
[CAS]

22042-71-3
[Synonyms]

4-FORMYL-PAA LINKER
4-FORMYLPHENOXYACETIC ACID
AKOS AU36-M42
AKOS B004256
ASISCHEM R21550
P-FORMYLPHENOXYACETIC ACID
(4-formylphenoxy)-aceticaci
[EINECS(EC#)]

244-749-3
[Molecular Formula]

C9H8O4
[MDL Number]

MFCD00016613
[Molecular Weight]

180.16
[MOL File]

22042-71-3.mol
Chemical PropertiesBack Directory
[Appearance]

BEIGE CRYSTALLINE POWDER
[Melting point ]

193-196 °C
[Boiling point ]

272.96°C (rough estimate)
[density ]

1.2933 (rough estimate)
[refractive index ]

1.4500 (estimate)
[storage temp. ]

2-8°C
[solubility ]

Soluble in hot methanol within almost transparency.
[form ]

Crystalline Powder
[pka]

3.04±0.10(Predicted)
[color ]

Beige
[Sensitive ]

Air Sensitive
[BRN ]

779885
[InChI]

InChI=1S/C9H8O4/c10-5-7-1-3-8(4-2-7)13-6-9(11)12/h1-5H,6H2,(H,11,12)
[InChIKey]

OYNIIKHNXNPSAG-UHFFFAOYSA-N
[SMILES]

C(O)(=O)COC1=CC=C(C=O)C=C1
[CAS DataBase Reference]

22042-71-3(CAS DataBase Reference)
[EPA Substance Registry System]

22042-71-3(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P280a-P304+P340-P405-P501a-P261-P305+P351+P338
[Hazard Codes ]

Xn,Xi
[Risk Statements ]

R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[TSCA ]

Yes
[HazardClass ]

IRRITANT
[HS Code ]

29189900
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Hazard InformationBack Directory
[Chemical Properties]

BEIGE CRYSTALLINE POWDER
[Uses]

4-Formylphenoxyacetic acid is used as an organic chemical synthesis intermediate.
[General Description]

4-Formylphenoxyacetic acid is a formylphenoxyaliphatic acid that reacts with dimedone to form 1,8-dioxo-octahydroxanthenes. It participates in the synthesis of 4-substituted benzaldehyde derivatives and 4-carboxypheoxyacetic acid.
[Synthesis]

4-Hydroxybenzaldehyde

123-08-0

Bromoacetic acid

79-08-3

4-Formylphenoxyacetic acid

22042-71-3

The general procedure for the synthesis of 2-(4-formylphenoxy)acetic acid from p-hydroxybenzaldehyde and bromoacetic acid was as follows: potassium carbonate (24.9 g, 180.0 mmol) was added to a solution of 4-hydroxybenzaldehyde (10.0 g, 82.0 mmol) in acetone (150 mL) and the reaction mixture was stirred for 15 min at 40 °C. Subsequently, bromoacetic acid (12.0 g, 86.0 mmol) was added slowly in batches and the reaction mixture was heated to reflux for 18 hours. After completion of the reaction, the reaction mixture was cooled and diluted by adding water (200 mL). The reaction mixture was extracted with ethyl acetate (2 x 200 mL) and after combining the organic phases, the aqueous layer was adjusted to pH 2 with 6N hydrochloric acid. the aqueous layer was again extracted with ethyl acetate (2 x 400 mL), the organic phases were combined and washed with water (200 mL), dried with anhydrous sodium sulfate and finally concentrated under vacuum. The residue was ground with isohexane to afford the target compound 2-(4-formylphenoxy)acetic acid (13.5 g, 91% yield) as a creamy white solid.1H NMR (d6-DMSO) δ: 13.12 (br s, 1H), 9.87 (s, 1H), 7.88-7.85 (m, 2H), 7.12-7.10 (m, 2H). 4.83 (s, 2H).

[References]

[1] Patent: WO2015/86509, 2015, A1. Location in patent: Page/Page column 92; 93
[2] Main Group Metal Chemistry, 2015, vol. 38, # 5-6, p. 157 - 164
[3] Patent: WO2004/89945, 2004, A1. Location in patent: Page 8
[4] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 230 - 239
Spectrum DetailBack Directory
[Spectrum Detail]

4-Formylphenoxyacetic acid(22042-71-3)MS
4-Formylphenoxyacetic acid(22042-71-3)1HNMR
4-Formylphenoxyacetic acid(22042-71-3)13CNMR
4-Formylphenoxyacetic acid(22042-71-3)IR1
4-Formylphenoxyacetic acid(22042-71-3)IR2
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

4-Formylphenoxyacetic acid, 99%(22042-71-3)
[Alfa Aesar]

4-Formylphenoxyacetic acid, 98%(22042-71-3)
[Sigma Aldrich]

22042-71-3(sigmaaldrich)
[TCI AMERICA]

4-Formylphenoxyacetic Acid,>95.0%(T)(22042-71-3)
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