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591-80-0

Basic Information
CAS No.: 591-80-0
Name: Allylacetic acid
Article Data: 107
Cas Database
Molecular Structure:
Molecular Structure of 591-80-0 (Allylacetic acid)
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: CorrosiveC
Risk Codes: 22-34
Safety: 26-36/37/39-45
Transport Information: UN 2922
PSA: 37.30000
LogP: 1.03720
Synthetic route
2583-25-7

allylmalonic acid

591-80-0

pent-4-enoic acid

Conditions
ConditionsYield
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%
90711-60-7

prop-2-en-1-yl 2-iodoacetate

591-80-0

pent-4-enoic acid

Conditions
ConditionsYield
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%
polymer, 38% reactive sites, 2,5 mmol/g; monomer(s): styrene, 4-vinylbenzylchloride, bromoacetic acid, allyltributyltin

polymer, 38% reactive sites, 2,5 mmol/g; monomer(s): styrene, 4-vinylbenzylchloride, bromoacetic acid, allyltributyltin

591-80-0

pent-4-enoic acid

Conditions
ConditionsYield
With lithium hydroxide; tetrabutylammomium bromide In tetrahydrofuran; water for 12h; Heating;84%
64096-43-1

β-(trimethylsilyl)cyclopentanone

591-80-0

pent-4-enoic acid

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile at 60℃; for 1.5h; Ring cleavage;82%
69962-08-9

(Z)-5-(Ethylthio)-3-pentenoic Acid

A

591-80-0

pent-4-enoic acid

B

33698-87-2

(Z)-pent-3-enoic acid

Conditions
ConditionsYield
With ammonia; lithium for 1h;A 8%
B 70%
2067-33-6

5-bromopentanoic acid

107-19-7

propargyl alcohol

A

591-80-0

pent-4-enoic acid

B

103675-09-8

5-Hydroxy-pentanoic acid prop-2-ynyl ester

Conditions
ConditionsYield
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%

5-acetoxy-4-iodopentanoic acid

591-80-0

pent-4-enoic acid

Conditions
ConditionsYield
With zinc In tetrahydrofuran63%
821-09-0

n-Pent-4-enyl alcohol

591-80-0

pent-4-enoic acid

Conditions
ConditionsYield
With chromic acid; acetone59%
With chromium(VI) oxide; sulfuric acid In acetone
57-57-8

β-Propiolactone

1826-67-1

vinyl magnesium bromide

591-80-0

pent-4-enoic acid

Conditions
ConditionsYield
copper(l) chloride at 0℃; for 0.25h;59%
142920-94-3

2-Benzoyl-3-oxo-hept-6-enoic acid methyl ester

A

591-80-0

pent-4-enoic acid

B

36568-12-4

methyl 3,5-dioxo-5-phenylpentanoate

Conditions
ConditionsYield
With ammonium hydroxide; water; ammonium chlorideA 43%
B 56%
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    Product Name: Allylacetic acid CAS: 591-80-0 MF: C5H8O2 MW: 100.12 EINECS: 209-732-7 Mol File: 591-80-0.mol Allylacetic acid Structure Allylacetic acid Chemical Properties Melting point -22.5 °C (lit.) Boiling point 83

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

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%.

Allylacetic acid can be prepared by pent-4-enoic acid ethyl ester at the temperature of 90 °C

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%.

Allylacetic acid can be used to produce pent-4-enoic acid ethyl ester by heating

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.