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3-Ethynyltoluene

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Name

3-Ethynyltoluene

EINECS -0
CAS No. 766-82-5 Density 0.93 g/cm3
PSA 0.00000 LogP 1.97630
Solubility N/A Melting Point N/A
Formula C9H8 Boiling Point 176.3 °C at 760 mmHg
Molecular Weight 116.163 Flash Point 47.4 °C
Transport Information UN 1993 3/PG 3 Appearance Clear light yellow to brown liquid
Safety 16-26-36 Risk Codes 10-36/37/38-65
Molecular Structure Molecular Structure of 766-82-5 (3-Ethynyltoluene) Hazard Symbols IrritantXi
Synonyms

Toluene,m-ethynyl- (6CI,7CI,8CI);(3-Methylphenyl)ethyne;1-Ethynyl-3-methylbenzene;1-Methyl-3-ethynylbenzene;3-Methylphenylacetylene;3-Tolylacetylene;m-Ethynyltoluene;m-Methylphenylacetylene;m-Tolylacetylene;

Article Data 33

3-Ethynyltoluene Synthetic route

40230-90-8

(2-(3-methylphenyl)ethynyl)trimethylsilane

766-82-5

1-ethynyl-3-methyl-benzene

Conditions
ConditionsYield
With potassium carbonate In methanol at 25℃; for 3h;93%
With potassium trimethylsilonate In dimethyl sulfoxide at 60℃; under 760.051 Torr; for 7h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube;93%
With potassium carbonate In methanol; dichloromethane for 1h; Inert atmosphere;72%
1184-85-6

N-methylmethane sulphonamide

33675-43-3

1-(bromo-ethynyl)-3-methyl-benzene

766-82-5

1-ethynyl-3-methyl-benzene

Conditions
ConditionsYield
With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate; toluene at 80℃; Inert atmosphere;90%
63079-66-3

2-methyl-4-(3'-methylphenyl)but-3-yn-2-ol

766-82-5

1-ethynyl-3-methyl-benzene

Conditions
ConditionsYield
With potassium hydroxide In methanol; toluene at 140℃;72%
16035-10-2

1-(1,1-Dichloro-ethyl)-3-methyl-benzene

766-82-5

1-ethynyl-3-methyl-benzene

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;46%
625-95-6

3-Iodotoluene

766-82-5

1-ethynyl-3-methyl-benzene

Conditions
ConditionsYield
37%
Multi-step reaction with 2 steps
1: dimethylformamide / 160 °C
2: (i) EtMgBr, (ii) KOH
View Scheme
Multi-step reaction with 2 steps
1: (i) nBuLi, (ii) CuI, (iii) /BRN= 1903634/
2: (i) aq. CF3CO2H, (ii) NaOMe
View Scheme
75-07-0

acetaldehyde

28987-79-3

m-tolylmagnesium bromide

766-82-5

1-ethynyl-3-methyl-benzene

Conditions
ConditionsYield
Multistep reaction;
67-56-1

methanol

593-53-3

Methyl fluoride

536-74-3

phenylacetylene

A

673-32-5

1-Phenylprop-1-yne

B

766-47-2

1-ethynyl-2-methylbenzene

C

766-82-5

1-ethynyl-3-methyl-benzene

D

577-16-2, 122382-54-1

2-Methylacetophenone

E

766-97-2

4-n-methylphenylacetylene

Conditions
ConditionsYield
at 37℃; under 700 Torr; Product distribution; Mechanism; Irradiation; various concentration of substrates, addition of various amounts of NEt3;
593-53-3

Methyl fluoride

536-74-3

phenylacetylene

A

673-32-5

1-Phenylprop-1-yne

B

766-47-2

1-ethynyl-2-methylbenzene

C

766-82-5

1-ethynyl-3-methyl-benzene

D

766-97-2

4-n-methylphenylacetylene

Conditions
ConditionsYield
at 37℃; under 700 Torr; Product distribution; Mechanism; Irradiation; various concentration of substrates, addition of various amounts of NEt3;
14674-99-8

1-phenyl-3-(3-methylphenyl)prop-2-yn-1-one

766-82-5

1-ethynyl-3-methyl-benzene

Conditions
ConditionsYield
(i) EtMgBr, (ii) KOH; Multistep reaction;
62358-87-6

1-(3-tolyl)-3,3-diethoxyprop-1-yne

766-82-5

1-ethynyl-3-methyl-benzene

Conditions
ConditionsYield
(i) aq. CF3CO2H, (ii) NaOMe; Multistep reaction;

3-Ethynyltoluene Specification

The IUPAC name of 3-Ethynyltoluene is 1-ethynyl-3-methylbenzene. With the CAS registry number 766-82-5, it is also named as 3-Methylphenylacetylene. The product's categories are Acetylenes; Acetylenic Hydrocarbons; Alkynes; Organic Building Blocks; Terminal. It is clear light yellow to brown liquid which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.86; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.86; (4)ACD/LogD (pH 7.4): 2.86; (5)ACD/BCF (pH 5.5): 87.83; (6)ACD/BCF (pH 7.4): 87.83; (7)ACD/KOC (pH 5.5): 856.8; (8)ACD/KOC (pH 7.4): 856.8; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.534; (13)Molar Refractivity: 38.43 cm3; (14)Molar Volume: 123.6 cm3; (15)Polarizability: 15.23×10-24 cm3; (16)Surface Tension: 35.3 dyne/cm; (17)Enthalpy of Vaporization: 39.57 kJ/mol; (18)Vapour Pressure: 1.48 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 116.0626; (21)MonoIsotopic Mass: 116.0626; (22)Heavy Atom Count: 9; (23)Complexity: 126.

Preparation of 3-Ethynyltoluene: It can be obtained by 1-(1,1-dichloro-ethyl)-3-methyl-benzene. This reaction needs reagent KOH and solvent ethanol by heating. The yield is 46%.

Uses of 3-Ethynyltoluene: It can react with 2-trimethylsilanylethynyl-benzaldehyde to get 3-m-tolyl-1-(2-trimethylsilanylethynyl-phenyl)-prop-2-yn-1-ol. This reaction needs reagent n-BuLi and solvent tetrahydrofuran at temperature of 0 °C. The yield is 54%.

When you are using this chemical, please be cautious about it as the following:
It is flammable, so people should keep it away from sources of ignition. It is also irritating to eyes, respiratory system and skin. And it may cause lung damage if swallowed. 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.

People can use the following data to convert to the molecule structure. 
1. SMILES:C#Cc1cccc(c1)C
2. InChI:InChI=1/C9H8/c1-3-9-6-4-5-8(2)7-9/h1,4-7H,2H3 
3. InChIKey:RENYIDZOAFFNHC-UHFFFAOYAT

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