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CAS No.: | 591-80-0 |
---|---|
Name: | Allylacetic acid |
Article Data: | 107 |
Molecular Structure: | |
Formula: | C5H8O2 |
Molecular Weight: | 100.117 |
Synonyms: | Pent-4-enoic acid;NSC 9000;delta 4-Pentenoic acid; |
EINECS: | 228-028-0 |
Density: | 0.993 g/cm3 |
Melting Point: | 54-57 °C(lit.) |
Boiling Point: | 188.499 °C at 760 mmHg |
Flash Point: | 78.683 °C |
Solubility: | Soluble in ethanol and diethyl ether, slightly soluble in water |
Appearance: | clear colorless to light yellow liquid |
Hazard Symbols: | C |
Risk Codes: | 22-34 |
Safety: | 26-36/37/39-45 |
Transport Information: | UN 2922 |
PSA: | 37.30000 |
LogP: | 1.03720 |
Conditions | Yield |
---|---|
With poly-4-vinylpyridine In N,N-dimethyl-formamide for 0.0666667h; microwave irradiation; | 96% |
Stage #1: allylmalonic acid In N,N-dimethyl-formamide at 140℃; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide pH=4; | 85% |
In N,N-dimethyl-formamide at 140℃; Inductive heating; | 76% |
prop-2-en-1-yl 2-iodoacetate
pent-4-enoic acid
Conditions | Yield |
---|---|
Stage #1: prop-2-en-1-yl 2-iodoacetate With triethyl borane; oxygen In hexane; dichloromethane at 20℃; for 2h; Stage #2: With zinc In tetrahydrofuran for 4h; Heating; | 85% |
pent-4-enoic acid
Conditions | Yield |
---|---|
With lithium hydroxide; tetrabutylammomium bromide In tetrahydrofuran; water for 12h; Heating; | 84% |
β-(trimethylsilyl)cyclopentanone
pent-4-enoic acid
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In water; acetonitrile at 60℃; for 1.5h; Ring cleavage; | 82% |
(Z)-5-(Ethylthio)-3-pentenoic Acid
A
pent-4-enoic acid
B
(Z)-pent-3-enoic acid
Conditions | Yield |
---|---|
With ammonia; lithium for 1h; | A 8% B 70% |
5-bromopentanoic acid
propargyl alcohol
A
pent-4-enoic acid
B
5-Hydroxy-pentanoic acid prop-2-ynyl ester
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane 1) -80 deg C, 2) room temp., 18 h; | A 5% B 70% |
pent-4-enoic acid
Conditions | Yield |
---|---|
With zinc In tetrahydrofuran | 63% |
Conditions | Yield |
---|---|
With chromic acid; acetone | 59% |
With chromium(VI) oxide; sulfuric acid In acetone |
Conditions | Yield |
---|---|
copper(l) chloride at 0℃; for 0.25h; | 59% |
2-Benzoyl-3-oxo-hept-6-enoic acid methyl ester
A
pent-4-enoic acid
B
methyl 3,5-dioxo-5-phenylpentanoate
Conditions | Yield |
---|---|
With ammonium hydroxide; water; ammonium chloride | A 43% B 56% |
Reported in EPA TSCA Inventory.
The Allylacetic acid, with the CAS registry number 591-80-0, is also known as Pent-4-enoic acid. It belongs to the product categories of Pharmaceutical Intermediates; omega-Functional Alkanols, Carboxylic Acids, Amines & Halides; omega-Unsaturated Carboxylic Acids. Its EINECS number is 228-028-0. This chemical's molecular formula is C5H8O2 and molecular weight is 100.12. What's more, its systematic name is 4-Pentenoic acid. This chemical should be sealed and stored at the temperature of 2 - 8 °C. It is an inhibitor of fatty acid oxidation. It can be used in the manufacturing of flavor concentrates of all types, and it is also used in organic synthesis.
Physical properties of Allylacetic acid are: (1)ACD/LogP: 0.984; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.04; (4)ACD/LogD (pH 7.4): -1.76; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 9.28; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 37.3 Å2; (13)Index of Refraction: 1.439; (14)Molar Refractivity: 26.503 cm3; (15)Molar Volume: 100.789 cm3; (16)Polarizability: 10.507×10-24cm3; (17)Surface Tension: 33.17 dyne/cm; (18)Density: 0.993 g/cm3; (19)Flash Point: 78.683 °C; (20)Enthalpy of Vaporization: 46.82 kJ/mol; (21)Boiling Point: 188.499 °C at 760 mmHg; (22)Vapour Pressure: 0.27 mmHg at 25°C.
Preparation: this chemical can be prepared by pent-4-enoic acid ethyl ester at the temperature of 90 °C. This reaction will need reagent (Bu3Sn)2O and solvent toluene with the reaction time of 48 hours. The yield is about 42%.
Uses of Allylacetic acid: it can be used to produce pent-4-enoic acid ethyl ester by heating. It will need reagent H2SO4 and solvent benzene with the reaction time of 15 hours. The yield is about 78%.
When you are using this chemical, please be cautious about it as the following:
This chemical can cause burns. It is harmful if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CC\C=C
(2)Std. InChI: InChI=1S/C5H8O2/c1-2-3-4-5(6)7/h2H,1,3-4H2,(H,6,7)
(3)Std. InChIKey: HVAMZGADVCBITI-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 315mg/kg (315mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) ENDOCRINE: HYPOGLYCEMIA SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE | Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969. |
mouse | LD50 | oral | 610mg/kg (610mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
mouse | LD50 | subcutaneous | 315mg/kg (315mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE ENDOCRINE: HYPOGLYCEMIA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969. |
rat | LD50 | oral | 470mg/kg (470mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |