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Basic Information
CAS No.: 99-89-8
Name: 4-Isopropylphenol
Article Data: 135
Molecular Structure:
Molecular Structure of 99-89-8 (4-Isopropylphenol)
Formula: C9H12O
Molecular Weight: 136.194
Synonyms: Phenol,p-isopropyl- (8CI);4-(1-Methylethyl)phenol;4-Isopropylphenol;Australol;NSC1888;p-Cumenol;p-Isopropylphenol;
EINECS: 202-798-8
Density: 0.987 g/cm3
Melting Point: 59-62 ºC
Boiling Point: 208.6 °C at 760 mmHg
Flash Point: 95.3 °C
Solubility: Slightly soluble in water, soluble in ethanol and ethyl ether
Appearance: white to beige crystalline solid
Hazard Symbols: CorrosiveC
Risk Codes: 22-34-43-52/53
Safety: 26-36/37/39-45-61
Transport Information: UN 2430
PSA: 20.23000
LogP: 2.51560
Synthetic route
4132-79-0

4-isopropyl-phenetole

99-89-8

4-Isopropylphenol

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 200 - 220℃; for 0.5h; Microwave irradiation; Inert atmosphere;99%
With hydrogen iodide
4132-48-3

1-methoxy-4-(1-methylethyl)benzene

99-89-8

4-Isopropylphenol

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 220℃; for 0.666667h; Inert atmosphere; Microwave irradiation;98%
With trimethylsilyl iodide at 105 - 114℃; for 0.25h; Microwave irradiation; Inert atmosphere;92%
With tetrachlorosilane; borontrifluoride acetic acid; lithium iodide In toluene; acetonitrile at 70℃; for 10h;89%
With hydrogen iodide
16152-51-5

(4-isopropylphenyl)boronic acid

7722-84-1

dihydrogen peroxide

99-89-8

4-Isopropylphenol

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;97%
25237-77-8

(4-isopropylphenoxy)trimethylsilane

99-89-8

4-Isopropylphenol

Conditions
ConditionsYield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;96%
With poly (ethylene glycol)-sulfonated sodium montmorillonite nanocomposite In methanol at 20℃; for 0.166667h;91%
28530-35-0

4-propoxycumene

99-89-8

4-Isopropylphenol

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 200 - 220℃; for 0.5h; Microwave irradiation; Inert atmosphere;96%
16152-51-5

(4-isopropylphenyl)boronic acid

99-89-8

4-Isopropylphenol

Conditions
ConditionsYield
With dihydrogen peroxide In ethanol at 20℃; for 0.166667h;96%
With iron(III) oxide; oxygen In tetrahydrofuran Irradiation;95%
With iron(III) oxide; oxygen In tetrahydrofuran at 20℃; Irradiation;95%
1338215-41-0

[2-(4-isopropylphenoxy)ethyl]trimethylsilane

99-89-8

4-Isopropylphenol

Conditions
ConditionsYield
Stage #1: [2-(4-isopropylphenoxy)ethyl]trimethylsilane With cesium fluoride In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere;
Stage #2: With water In N,N-dimethyl-formamide Inert atmosphere;
88%
41485-62-5

4-isopropylphenyl lithium

99-89-8

4-Isopropylphenol

Conditions
ConditionsYield
With titanium(IV) isopropylate; tert.-butylhydroperoxide In diethyl ether at -78℃; for 12h;80%

4-hydroxy-4-isopropylcyclohexa-2,5-dien-1-one

99-89-8

4-Isopropylphenol

Conditions
ConditionsYield
With sodium hydride; bis(pinacol)diborane In 1,2-dichloro-ethane at 70℃; for 12h; Inert atmosphere;77%
127-91-3

(1R,5R)-(+)-β-pinene

A

99-89-8

4-Isopropylphenol

B

77982-63-9

nopinone

Conditions
ConditionsYield
Stage #1: (1R,5R)-(+)-β-pinene With ozone In methanol
Stage #2: With iron(III) chloride hexahydrate In methanol at 60℃; for 2h;
A 15%
B 70%
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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

Specification

The IUPAC name of p-Isopropylphenol is 4-propan-2-ylphenol. With the CAS registry number 99-89-8, it is also named as 1-Hydroxy-4-isopropylbenzene. It is white to beige crystalline solid which is slightly soluble in water, soluble in ethanol and ethyl ether. In addition, thischemical is toxic and flammable. When heated to decomposition it emits acrid smoke and fumes. So the storage environment should be ventilate, low-temperature and dry. Keep p-Isopropylphenol separate from oxidant.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.82; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.82; (4)ACD/LogD (pH 7.4): 2.82; (5)ACD/BCF (pH 5.5): 81.99; (6)ACD/BCF (pH 7.4): 81.86; (7)ACD/KOC (pH 5.5): 815.63; (8)ACD/KOC (pH 7.4): 814.34; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.525; (13)Molar Refractivity: 42.31 cm3; (14)Molar Volume: 137.9 cm3; (15)Polarizability: 16.77×10-24 cm3; (16)Surface Tension: 35.7 dyne/cm; (17)Enthalpy of Vaporization: 46.3 kJ/mol; (18)Vapour Pressure: 0.147 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Tautomer Count: 2; (21)Exact Mass: 136.088815; (22)MonoIsotopic Mass: 136.088815; (23)Topological Polar Surface Area: 20.2; (24)Heavy Atom Count: 10; (25)Complexity: 90.9.

Preparation of p-Isopropylphenol: It can be obtained by C9H11Li. This reaction needs reagent tBuOOH and Ti(OiPr)4 and solvent diethyl ether at temperature of -78 °C. The reaction time is 12 hours. The yield is 80%. 

Uses of p-Isopropylphenol: It is used in organic synthesis. For example: it can react with trichloromethane to get 2-hydroxy-5-isopropyl-benzaldehyde. This reaction which is Reimer-Tiemann reaction needs reagent sodium hydroxide and solvent ethanol and H2O at temperature of 70 °C. 

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. It may cause sensitization by skin contact and may cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) And people should avoid release it to the environment.

People can use the following data to convert to the molecule structure.
1. SMILES:Oc1ccc(cc1)C(C)C
2. InChI:InChI=1/C9H12O/c1-7(2)8-3-5-9(10)6-4-8/h3-7,10H,1-2H3

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 40mg/kg (40mg/kg) BEHAVIORAL: SLEEP Journal of Medicinal Chemistry. Vol. 23, Pg. 1350, 1980.
mouse LD50 oral 875mg/kg (875mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(1), Pg. 94, 1981.
mouse LDLo intraperitoneal 250mg/kg (250mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 5, Pg. 339, 1953.