| Identification | More | [Name]
Benzyloxyacetic acid | [CAS]
30379-55-6 | [Synonyms]
ACETIC ACID, (PHENYLMETHOXY)-
BENZYLOXYACETIC ACID
PHENYLMETHOXY ACETIC ACID
RARECHEM AL BE 0628
benzyloxy acctic acid | [Molecular Formula]
C9H10O3 | [MDL Number]
MFCD00274211 | [Molecular Weight]
166.17 | [MOL File]
30379-55-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
80-81 °C | [Boiling point ]
137-139 °C/0.6 mmHg (lit.) | [density ]
1.162 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.526(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [form ]
clear liquid | [pka]
3.52±0.10(Predicted) | [color ]
Colorless to Light orange to Yellow | [InChI]
InChI=1S/C9H10O3/c10-9(11)7-12-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11) | [InChIKey]
GRZHHTYDZVRPIC-UHFFFAOYSA-N | [SMILES]
C(O)(=O)COCC1=CC=CC=C1 | [CAS DataBase Reference]
30379-55-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
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
| [HazardClass ]
IRRITANT | [HS Code ]
29189900 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless liquid | [Uses]
It is a compound for proteomics research use. It may be used for following synthesis mixed benzyloxyacetic pivalic anhydride, chiral glycolates, 1,2:4,5-di-O-isopropylidene-β-D-fructopyranos-3-yl benzyloxyacetate, via esterification, tetra aqua(1,10-phenanthroline-[κ]2N,N?)magnesium(II) bis[(2,4-dichlorophenyl)acetate], as ligand in the preparation of diaquabis(benzyloxyacetato)copper(II) complex. | [Definition]
ChEBI: (benzyloxy)acetic acid is a monocarboxylic acid that is benzyl alcohol in which the hydroxy group is replaced by a carboxymethoxy group. It is a monocarboxylic acid, an ether and a member of benzenes. It is functionally related to a benzyl alcohol and a glycolic acid. | [General Description]
In vitro activities of phenoxy and benzyloxyacetic acid derivatives as antisickling agents has been investigated by the application of quantitative structure activity relationship (QSAR) of Hansch-type. | [Synthesis]
1. 960 g of tetrahydrofuran and 41 g of toluene were added to the reaction flask.
2. 534.0 g of potassium hydroxide was added in four batches at 10-20 °C. 3.
3. After the potassium hydroxide was added, 1371.1 g of benzyl alcohol was added in three batches.
4. 300.1 g of chloroacetic acid was dissolved in 480.5 g of tetrahydrofuran to prepare a tetrahydrofuran solution of chloroacetic acid.
5. The tetrahydrofuran solution of chloroacetic acid was added dropwise to the above reaction system, and the reaction temperature was maintained at 70-80 °C. 6.
6. React until the chloroacetic acid is completely consumed.
7. Cool the reaction system and add 3.12 kg of purified water. 8.
8. Remove the tetrahydrofuran by pressurized distillation. 9.
9. The aqueous phase was extracted four times with toluene. 10.
10. Adjust the pH of the aqueous phase to 3 with hydrochloric acid at 10-20°C. 11.
11. the aqueous phase was extracted twice with methyl tert-butyl ether.
12. The organic phase was concentrated to give 421.3 g of benzyloxyacetic acid (compound 3) in 88.3% yield and 99.2% GC purity. 13. The product was analyzed by 1H NMR.
13. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 12.28 (br, 1H), 7.34-7.30 (m, 5H), 4.59 (s, 2H), 4.12 (s, 2H). | [References]
[1] Chemistry - A European Journal, 1999, vol. 5, # 1, p. 121 - 161
[2] Tetrahedron, 2002, vol. 58, # 38, p. 7663 - 7679
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 3, p. 695 - 703
[4] Patent: US2017/190684, 2017, A1. Location in patent: Paragraph 0065; 0066; 0081
[5] Journal of the American Chemical Society, 2003, vol. 125, # 13, p. 3793 - 3798 |
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