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p-Allylphenol

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Name

p-Allylphenol

EINECS 207-929-2
CAS No. 501-92-8 Density 1.014 g/cm3
PSA 20.23000 LogP 2.12070
Solubility N/A Melting Point 15.8°
Formula C9H10O Boiling Point 238 °C at 760 mmHg
Molecular Weight 134.178 Flash Point 102.6 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 501-92-8 (4-ALLYLPHENOL) Hazard Symbols N/A
Synonyms

Phenol, 4-(2-propenyl)- (9CI);3-(p-Hydroxyphenyl)-1-propene;4-(2-Propenyl)phenol;NSC 290195;p-Hydroxyallylbenzene;

Article Data 77

p-Allylphenol Synthetic route

140-67-0

Estragole

501-92-8

4-(prop-2-enyl)phenol

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;100%
With boron tribromide In dichloromethane at 0℃; for 1h; Inert atmosphere;97.5%
With dimethylsulfide; boron tribromide Heating;95%
106-48-9

4-chloro-phenol

762-72-1

allyl-trimethyl-silane

501-92-8

4-(prop-2-enyl)phenol

Conditions
ConditionsYield
With caesium carbonate In 2,2,2-trifluoroethanol for 14h; Irradiation;87%
With caesium carbonate In 2,2,2-trifluoroethanol for 4h; Irradiation; Flow reactor;70%
95081-49-5

4-[3-(2-Nitro-phenylselanyl)-propyl]-phenol

501-92-8

4-(prop-2-enyl)phenol

Conditions
ConditionsYield
With dihydrogen peroxide In tetrahydrofuran at 40℃; for 3.5h;80%
3698-32-6

p-ethoxyallylbenzene

501-92-8

4-(prop-2-enyl)phenol

Conditions
ConditionsYield
Stage #1: p-ethoxyallylbenzene With aluminum (III) chloride; N,N-dimethyl-aniline In toluene at 100 - 110℃; for 2 - 3h;
Stage #2: With hydrogenchloride; water In toluene at 20℃; pH=1 - 2; Product distribution / selectivity;
80%
540-38-5

4-Iodophenol

106-95-6

allyl bromide

501-92-8

4-(prop-2-enyl)phenol

Conditions
ConditionsYield
Stage #1: p-Iodophenol With dilithium tetra(tert-butyl)zincate In tetrahydrofuran at 40℃; for 2h;
Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 12h;
79%
Stage #1: p-Iodophenol With dilithium tetra(tert-butyl)zincate In tetrahydrofuran at -78 - 40℃; Inert atmosphere;
Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; chemoselective reaction;
79%

allylboronic acid N-methyl-iminodiacetic acid ester

106-48-9

4-chloro-phenol

501-92-8

4-(prop-2-enyl)phenol

Conditions
ConditionsYield
With potassium carbonate In water at 135℃; for 0.3h; Suzuki-Miyaura Coupling; Microwave irradiation; Sealed tube;75%
106-48-9

4-chloro-phenol

762-72-1

allyl-trimethyl-silane

A

501-92-8

4-(prop-2-enyl)phenol

B

108-95-2

phenol

Conditions
ConditionsYield
In water; acetonitrile for 2.5h; Concentration; Irradiation; Flow reactor;A 75%
B 7 %Chromat.
4873-09-0

allyl tosylate

108-95-2

phenol

501-92-8

4-(prop-2-enyl)phenol

Conditions
ConditionsYield
{(norbornadiene)rhodium(I)(NCCH3)2}(PF6) In toluene at 0℃; for 24h;54%
140-67-0

Estragole

A

501-92-8

4-(prop-2-enyl)phenol

B

4-(2-bromopropyl)phenol

Conditions
ConditionsYield
Stage #1: Estragole With boron tribromide In dichloromethane at 0 - 20℃; for 3.75h; Inert atmosphere;
Stage #2: With water In dichloromethane Inert atmosphere;
A 49%
B 31%
1415236-88-2

2-(4-(allyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

501-92-8

4-(prop-2-enyl)phenol

Conditions
ConditionsYield
With C14H16N6; palladium diacetate; calcium hydroxide In N,N-dimethyl acetamide; water at 70℃; for 48h; Inert atmosphere;43%

p-Allylphenol Specification

The Phenol,4-(2-propen-1-yl)-, with the CAS registry number 501-92-8 and EINECS registry number 207-929-2, has the systematic name of 4-allylphenol, and the IUPAC name of 4-prop-2-enylphenol. The molecular formula of the chemical is C9H10O.

The characteristics of Phenol,4-(2-propen-1-yl)- are as followings: (1)ACD/LogP: 2.50; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.5; (4)ACD/LogD (pH 7.4): 2.5 ; (5)#H bond acceptors: 1; (6)#H bond donors: 1; (7)#Freely Rotating Bonds: 3; (8)Polar Surface Area: 20.23 Å2; (9)Index of Refraction: 1.548; (10)Molar Refractivity: 42.04 cm3; (11)Molar Volume: 132.2 cm3; (12)Polarizability: 16.66×10-24cm3; (13)Surface Tension: 37.6 dyne/cm; (14)Density: 1.014 g/cm3; (15)Flash Point: 102.6 °C; (16)Enthalpy of Vaporization: 49.41 kJ/mol; (17)Boiling Point: 238 °C at 760 mmHg; (18)Vapour Pressure: 0.0282 mmHg at 25°C.  

Uses of Phenol,4-(2-propen-1-yl)-: It can react with 2-methyl-propene to produce 1-allyl-4-tert-butoxy-benzene. This reaction will need reagent CF3SO3H, and the menstruum CH2Cl2. The reaction time is 3 hours with temperature of -78°C, and the yield is about 96%.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: Oc1ccc(CC=C)cc1
(2)InChI: InChI=1/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2
(3)InChIKey: RGIBXDHONMXTLI-UHFFFAOYAI

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