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100-41-4

Basic Information
CAS No.: 100-41-4
Name: Ethylbenzene
Article Data: 1946
Molecular Structure:
Molecular Structure of 100-41-4 (Ethylbenzene)
Formula: C8H10
Molecular Weight: 106.167
Synonyms: EB;Ethylbenzol;NSC 406903;Phenylethane;a-Methyltoluene;
EINECS: 202-849-4
Density: 0.865 g/cm3
Melting Point: -95 °C(lit.)
Boiling Point: 136.248 °C at 760 mmHg
Flash Point: 25.941 °C
Solubility: 0.0206 g/100 mL in water
Appearance: colourless liquid
Hazard Symbols: HighlyF+,HarmfulXn,IrritantXi,FlammableF,ToxicT
Risk Codes: 12-19-22-66-67-20-11-48/20/22-40-38-36/37/38-23/24/25-46-45-39/23/24/25-23/25
Safety: 9-16-29-33-24/25-36/37-36-45-36/37/39-26-23-53-7-24
Transport Information: UN 1175 3/PG 2
PSA: 0.00000
LogP: 2.24900
Synthetic route
100-41-4

ethylbenzene

Conditions
ConditionsYield
With hydrogen; p In methanol for 0.316667h; other substrates;100%
With polymeric thiol; hydrogen; palladium on activated charcoal for 1h; Product distribution; var. catalysts, further thiol; poisoning effect of thiols;100%
With hydrogen; Pd-1percent Ho In neat (no solvent) at 90℃; for 0.00583333h; Product distribution; selective hydrogenation; variation of temperature and contact time;100%
100-40-3

4-ethenylcyclohexene

100-41-4

ethylbenzene

Conditions
ConditionsYield
With n-butyllithium; potassium 2-methylbutan-2-olate Mechanism; 1) r.t., 17 h, 2) reflux, 7 h; further reagent: D2O;100%
at 400℃; Leiten ueber Chrom(III)-oxyd;
at 300 - 320℃; Leiten ueber Nickel-Aluminiumoxyd;
98-85-1, 13323-81-4

1-Phenylethanol

100-41-4

ethylbenzene

Conditions
ConditionsYield
With formic acid; ammonium formate; 5%-palladium/activated carbon In ethanol; water at 80℃; Product distribution / selectivity;100%
With palladium dichloride In methanol at 40℃; for 18h; Inert atmosphere; Green chemistry; chemoselective reaction;99%
With hydrogen; palladium diacetate; sodium dioctyl sulfosuccinate In tetrahydrofuran at 25℃; under 760.051 Torr; for 24h;99%
536-74-3

phenylacetylene

100-41-4

ethylbenzene

Conditions
ConditionsYield
With hydrogen; palladium on C60 In methanol under 760 Torr; for 0.216667h; Ambient temperature; other substrates: cyclohexene, hex-1-ene, other catalysts: palladium on activated charcoal, C60, other reaction time;100%
silver tetrafluoroborate; (Ph2PCH2PPh2CHC(O)Ph)>I In dichloromethane at 65℃; for 18h; Pressure (range begins): 120 ;100%
With hydrogen; N,N′-bis(salicylidene)-ethylenediamino‑palladium In methanol for 0.85h;100%
98-86-2

acetophenone

100-41-4

ethylbenzene

Conditions
ConditionsYield
With hydrogen at 80℃; under 37503.8 Torr; for 0.5h; Autoclave; chemoselective reaction;100%
With hydrogen In ethanol at 39.84℃; under 760.051 Torr; for 5h;100%
With Pd/C; hydrogen In chloroform at 20℃; under 760.051 Torr; for 8h; Catalytic behavior;100%
1333-74-0

hydrogen

100-41-4

ethylbenzene

Conditions
ConditionsYield
With C52H46ClN3P2Ru In dichloromethane-d2 at 50℃; under 3040.2 Torr; for 16h; Reagent/catalyst; Time;100%
With [Ir(6-Neo)(COD)Cl] In ethanol under 3750.38 Torr; for 1h; Solvent;100 %Spectr.
at 80℃; under 30003 Torr; for 24h; Reagent/catalyst;
1333-74-0

hydrogen

100-41-4

ethylbenzene

Conditions
ConditionsYield
With C61H98ClN3P2Ru In dichloromethane-d2 at 50℃; under 3040.2 Torr; for 14h;100%
766-77-8

Dimethylphenylsilane

A

100-41-4

ethylbenzene

B

128756-74-1

dimethyl(phenyl)(2-phenylethenyl)silane

Conditions
ConditionsYield
With C11H14FeO4Si2 In toluene at 50℃; for 24h; Kinetics; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique;A n/a
B 100%
141-78-6

ethyl acetate

71-43-2

benzene

100-41-4

ethylbenzene

Conditions
ConditionsYield
With hydrogen at 240 - 400℃; under 15001.5 Torr; Reagent/catalyst; Temperature;99.5%
74-85-1

ethene

71-43-2

benzene

100-41-4

ethylbenzene

Conditions
ConditionsYield
Product distribution; Heating; synthesis by chemorectification;99%
mesoporous ZSM-5 Si/Al=120 at 310 - 370℃; under 1875.19 - 3750.38 Torr; Product distribution / selectivity;75%
boron trifluoride at 180℃; under 22501.8 Torr; Product distribution; other temperatures, other volumetric rates;59.9%
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  • Ethylbenzene 100-41-4CAS NO.: 100-41-4

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Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program. Community Right-To-Know List.

Standards and Recommendations

OSHA PEL: TWA 100 ppm; STEL 125 ppm
ACGIH TLV: TWA 100 ppm; STEL 125 ppm; Confirmed Animal Carcinogen with Unknown Revelance to Humans; BEI: 1.5 g/g creatinine of manelic acid) in urine at end of shift at end of workweek
DFG MAK: 100 ppm (440 mg/m3)
NIOSH REL: (Ethyl Benzene) TWA 100 ppm; STEL 125 ppm
DOT Classification:  3; Label: Flammable Liquid

Analytical Methods

For occupational chemical analysis use NIOSH: Hydrocarbons, Aromatic, 1501.

Specification

The IUPAC name of this chemical is Ethylbenzene. With the CAS registry number 100-41-4, it is also named as Aethylbenzol. The product's categories are Pharmaceutical Intermediates; Organics; Analytical Chemistry; Standard Solution of Volatile Organic Compounds for Water & Soil Analysis; Standard Solutions (VOC); Amber Glass Bottles; ReagentPlus(R) Solvent Grade Products; Solvent Bottles; E-FAlphabetic. It is colourless liquid with an aromatic odor, which can react vigorously with strong oxidizing materials. It is toxic and flammable by fire, heat and oxidants. So the storage environment should be ventilate, low-temperature and dry. Keep Ethyl benzene separate from oxidant and acid. 

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.23; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.229; (4)ACD/LogD (pH 7.4): 3.229; (5)ACD/BCF (pH 5.5): 167.574; (6)ACD/BCF (pH 7.4): 167.574; (7)ACD/KOC (pH 5.5): 1360.491; (8)ACD/KOC (pH 7.4): 1360.491; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1 ; (12)Index of Refraction: 1.497; (13)Molar Refractivity: 35.802 cm3; (14)Molar Volume: 122.251 cm3; (15)Polarizability: 14.193×10-24 cm3; (16)Surface Tension: 29.072 dyne/cm; (17)Enthalpy of Vaporization: 35.57 kJ/mol; (18)Vapour Pressure: 9.213 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 106.07825; (21)MonoIsotopic Mass: 106.07825; (22)Heavy Atom Count: 8; (23)Complexity: 51.1.

Preparation of Ethyl benzene: It is manufactured from benzene and ethylene by several modifications of the older mixed liquid-gas reaction system using aluminum chloride as a catalyst (Friedel-Crafts reaction). The reaction takes place in the gas phase over a fixed-bed unit at 370 °C under apressure of 1450 to 2850 kPa. Unchanged and polyethylated materials are recirculated, making a yield of 98 percent possible. The catalyst dperates several days before requiring regeneration.
 C6H6 + CH2=CH2 (+AlCl3/HCl or zeolite) → C6H5CH2CH3(+AlCl3/HCl or zeolite)
Excess benzene is used if the formation of di- and trimEthylbenzenes is to be avoided or minimized. The benzene is recycled. In the more modem process the reaction takes place in the liquid phase, using a zeolite catalyst and cycle lengths in excess of 3 years are expected for the catalyst.

Uses of Ethyl benzene: It is important in the petrochemical industry as an intermediate in the production of styrene, which in turn is used for making polystyrene, a commonly used plastic material. It is also used as a solvent for aluminum bromide in the anhydrous electrodeposition of aluminum. In addition, it is used as intermediate syntomycin and chloramphenicol. Besides, it can react with tert-butyl hydroperoxide to get 1-phenylethyl tert-butyl peroxide and 1-phenyl-ethanone. This reaction needs catalyzer vanadium-substituted V-MCM-41 (A) zeolite and solvent acetone at temperature of 60 °C. The reaction time is 8 hours. 

When you are using this chemical, please be cautious about it as the following:
It is extremely flammable, so people should keep it away from sources of ignition. And it may form explosive peroxides. In addition, this chemical is not only harmful if swallowed, but also toxic by inhalation, in contact with skin and if swallowed. So people should avoid contact with skin and eyes. Besides, it may cause cancer and may cause heritable genetic damage. 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.) 

People can use the following data to convert to the molecule structure.
1. SMILES:CCc1ccccc1
2. InChI:InChI=1/C8H10/c1-2-8-6-4-3-5-7-8/h3-7H,2H2,1H3

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LCLo inhalation 10000ppm (10000ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: TREMOR
Public Health Reports. Vol. 45, Pg. 1241, 1930.
human TCLo inhalation 100ppm/8H (100ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: SLEEP

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
American Industrial Hygiene Association Journal. Vol. 31, Pg. 206, 1970.
 
mouse LCLo inhalation 50gm/m3/2H (50000mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 5(5), Pg. 3, 1961.
mouse LD50 intraperitoneal 2624uL/kg (2.624mL/kg)   Archives of Toxicology. Vol. 58, Pg. 106, 1985.
rabbit LD50 skin 17800uL/kg (17.8mL/kg)   Food and Cosmetics Toxicology. Vol. 13, Pg. 803, 1975.
rat LCLo inhalation 4000ppm/4H (4000ppm)   American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.
rat LD50 oral 3500mg/kg (3500mg/kg) LIVER: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
AMA Archives of Industrial Health. Vol. 14, Pg. 387, 1956.