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Allylbenzene

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Name

Allylbenzene

EINECS 206-095-7
CAS No. 300-57-2 Density 0.882 g/cm3
PSA 0.00000 LogP 2.41510
Solubility insoluble in water Melting Point 557 °C
Formula C9H10 Boiling Point 157.3 °C at 760 mmHg
Molecular Weight 118.178 Flash Point 33.3 °C
Transport Information UN 3295 3/PG 3 Appearance colourless liquid
Safety 23-24/25-62 Risk Codes 10-65
Molecular Structure Molecular Structure of 300-57-2 (Allylbenzene) Hazard Symbols HarmfulXn
Synonyms

Benzene,2-propenyl- (9CI);Benzene, allyl- (8CI);1-Benzylethene;1-Phenyl-2-propene;1-Propene, 3-phenyl-;2-Propenylbenzene;3-Phenyl-1-propene;3-Phenylpropene;NSC 18609;

Article Data 471

Allylbenzene Synthetic route

591-87-7

Allyl acetate

934-56-5

trimethyl(phenyl)stannane

300-57-2

allylbenzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In N,N,N,N,N,N-hexamethylphosphoric triamide for 6h;100%
With [Pd(triphenylphosphine)(allyl)(chloride)] In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 5h;96 % Chromat.
106-95-6

allyl bromide

95576-66-2

phenyltriethoxytitanium

300-57-2

allylbenzene

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran; diethyl ether at 25℃; for 3h;100%
107-05-1

3-chloroprop-1-ene

95576-66-2

phenyltriethoxytitanium

300-57-2

allylbenzene

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran; diethyl ether at 25℃; for 1.5h;100%
28557-00-8

phenylzinc chloride

106-95-6

allyl bromide

A

300-57-2

allylbenzene

B

92-52-4

biphenyl

C

zinc dibromide

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Ar atmosphere; stirring (20°C, 5 mole-% catalyst, 3.5 h);A 100%
B 0%
C n/a
bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran Ar atmosphere; stirring (20°C, 5 mole-% catalyst, 3 h);A 55%
B 40%
C n/a
591-87-7

Allyl acetate

28557-00-8

phenylzinc chloride

A

300-57-2

allylbenzene

B

92-52-4

biphenyl

C

557-34-6

zinc diacetate

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Ar atmosphere; stirring (20°C, 5 mole-% catalyst, 5 h);A 100%
B 0%
C n/a
1224431-84-8

C14H15NSe

110-83-8

cyclohexene

A

300-57-2

allylbenzene

B

286-20-4

cyclohexane-1,2-epoxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform-d1 at 20℃;A 100%
B 100%
4119-41-9

1-iodo-3-phenylpropan

A

300-57-2

allylbenzene

B

1087-49-6

1,6-diphenylhexane

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Electrochemical reaction; Inert atmosphere;A 1%
B 99%
108-86-1

bromobenzene

106-95-6

allyl bromide

300-57-2

allylbenzene

Conditions
ConditionsYield
Stage #1: bromobenzene With iodine; magnesium In diethyl ether Inert atmosphere; Reflux;
Stage #2: allyl bromide In diethyl ether at 0 - 20℃; for 2.08333h; Inert atmosphere;
99%
Stage #1: bromobenzene With magnesium In tetrahydrofuran
Stage #2: allyl bromide In tetrahydrofuran
Stage #3: With ammonium chloride In water
With magnesium In tetrahydrofuran at 20℃;
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran at 20℃;
Stage #2: allyl bromide In tetrahydrofuran for 1h;
10147-11-2

propargyl benzene

300-57-2

allylbenzene

Conditions
ConditionsYield
With hydrogen In toluene at 20℃; under 38002.6 Torr; for 12h; Autoclave; chemoselective reaction;99%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 3h;96%
With hydrogen In acetonitrile at 120℃; under 22502.3 Torr; for 15h; Autoclave; Sealed tube;72%
591-87-7

Allyl acetate

555-54-4

diphenylmagnesium

300-57-2

allylbenzene

Conditions
ConditionsYield
Cu(acac)2-PPh3 In tetrahydrofuran at 40℃; for 4h;98%
Cu(acac)2-PPh3 In tetrahydrofuran at 40℃; for 4h; Product distribution; effects of solvent, catalyst and catalyst activator; further solvents, further catalysts;

Allylbenzene Consensus Reports

ALLYLBENZENE is reported in EPA TSCA Inventory.

Allylbenzene Specification

The IUPAC name of Allylbenzene is prop-2-enylbenzene. With the CAS registry number 300-57-2, it is also named as 1-Benzylethene. The product's categories are Aromatic Compounds; Miscellaneous. It is colourless liquid which is soluble in alcohol, ether, benzene and insoluble in water. This chemical is stable and incompatible with strong oxidizing agents. When heated to decomposition it emits acrid smoke and irritating fumes. So the storage environment should be well- ventilated, low-temperature and dry. Keep this chemical separate from raw materials of food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.24; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.24; (4)ACD/LogD (pH 7.4): 3.24; (5)ACD/BCF (pH 5.5): 169.57; (6)ACD/BCF (pH 7.4): 169.57; (7)ACD/KOC (pH 5.5): 1372.1; (8)ACD/KOC (pH 7.4): 1372.1; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.511; (13)Molar Refractivity: 40.16 cm3; (14)Molar Volume: 133.8 cm3; (15)Polarizability: 15.92×10-24 cm3; (16)Surface Tension: 29.7 dyne/cm; (17)Enthalpy of Vaporization: 37.77 kJ/mol; (18)Vapour Pressure: 3.59 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Exact Mass: 118.07825; (21)MonoIsotopic Mass: 118.07825; (22)Heavy Atom Count: 9; (23)Complexity: 78.

Preparation of Allylbenzene: First, using bromobenzene to produce the ether solution of diphenylmagnesium bromide bromide. Then reacting with allyl bromopropylene to get the product.

Uses of Allylbenzene: It is used in organic synthesis. For example: it can react with tetrachloromethane to get (2,4,4,4-tetrachloro-butyl)-benzene. This reaction needs reagent diacetyl peroxide.

When you are using this chemical, please be cautious about it as the following:
It is flammable and may cause lung damage if swallowed. So people should not breathe vapour and avoid contact with skin and eyes. If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label.

People can use the following data to convert to the molecule structure. 
1. SMILES:C=C\Cc1ccccc1
2. InChI:InChI=1/C9H10/c1-2-6-9-7-4-3-5-8-9/h2-5,7-8H,1,6H2
3. InChIKey:HJWLCRVIBGQPNF-UHFFFAOYAO

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 2900mg/kg (2900mg/kg)   Toxicology and Applied Pharmacology. Vol. 7, Pg. 18, 1965.
rat LD50 oral 5540mg/kg (5540mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

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