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616-44-4

Basic Information
CAS No.: 616-44-4
Name: 3-Methylthiophene
Article Data: 52
Cas Database
Molecular Structure:
Molecular Structure of 616-44-4 (3-Methylthiophene)
Formula: C5H6S
Molecular Weight: 98.1686
Synonyms: 5-17-01-00331 (Beilstein Handbook Reference);3-Thiotolene;Thiophene,3-methyl-;beta-Methylthiophene;
EINECS: 210-482-6
Density: 1.013 g/cm3
Melting Point: -69 °C(lit.)
Boiling Point: 114.2 °C at 760 mmHg
Flash Point: 11.1 °C
Solubility: Insoluble in water
Appearance: clear colorless to light yellow liquid
Hazard Symbols: FlammableF, HarmfulXn, IrritantXi
Risk Codes: 11-20/22-36/37/38-37
Safety: 7-16-29-33-36-37/39-26-7/9
Transport Information: UN 1993 3/PG 2
PSA: 28.24000
LogP: 2.05650
Synthetic route
17249-90-0

2,5-Dichloro-3-methylthiophene

616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; potassium hydroxide In methanol at 80℃; under 60006 Torr; for 24h;95.33%
872-31-1

3-Bromothiophene

bis(μ-[2-(dimethylamino)ethanolato-N,O:O]tetramethyldiindium

bis(μ-[2-(dimethylamino)ethanolato-N,O:O]tetramethyldiindium

616-44-4

3-Methylthiophene

Conditions
ConditionsYield
bis-triphenylphosphine-palladium(II) chloride In benzene at 80℃; for 24h;93%
10486-61-0

3-thienyl iodide

31729-70-1

bis(iodozinc)methane

616-44-4

3-Methylthiophene

Conditions
ConditionsYield
Stage #1: 3-thienyl iodide; bis(iodozinc)methane With tris-(dibenzylideneacetone)dipalladium(0); tris<3,5-bis(trifluoromethyl)phenyl>phosphane In tetrahydrofuran at 40℃; for 0.5h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water chemoselective reaction;
73%
71637-34-8

3-hydroxymethyl-thiophene

201230-82-2

carbon monoxide

A

6964-21-2

thiophen-3-yl-acetic acid

B

616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction;A 34%
B 11%
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 42h;A 34 % Spectr.
B 11 % Spectr.
188290-36-0

thiophene

cis-Cp(*)W(CO)2(MeCN)(4-methyl-2-thienyl)

A

616-44-4

3-Methylthiophene

cis-Cp(*)W(CO)2(MeCN)(-2-thienyl)

cis-Cp(*)W(CO)2(d3-MeCN)(-2-thienyl)

Conditions
ConditionsYield
A 32%
B 33%
C 6%
33922-80-4

bis-(1-propenyl) sulfide

A

188290-36-0

thiophene

B

554-14-3

2-Methylthiophene

C

872-55-9

2-ethylthiophene

D

616-44-4

3-Methylthiophene

Conditions
ConditionsYield
at 500 - 520℃; pyrolysis at atmospheric pressure in a nitrogen stream; Further byproducts given;A 32%
B n/a
C 25%
D n/a
77-77-0

Divinyl sulfone

A

188290-36-0

thiophene

B

554-14-3

2-Methylthiophene

C

616-44-4

3-Methylthiophene

D

108-88-3

toluene

E

95-15-8

Benzo[b]thiophene

F

71-43-2

benzene

Conditions
ConditionsYield
With hydrogen sulfide at 580℃; thermal transformations of divinyl sulfone; further gaseous medium;A 12%
B 1.1%
C 3%
D 3.6%
E 0.4%
F 11%
513-35-9

2-methyl-but-2-ene

616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With aluminium oxide-chromium oxide; sulfur dioxide
123-51-3

i-Amyl alcohol

616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With aluminium oxide-chromium oxide; sulfur dioxide
78-78-4

methylbutane

616-44-4

3-Methylthiophene

Conditions
ConditionsYield
With aluminium oxide-chromium oxide; sulfur dioxide
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Reported in EPA TSCA Inventory.

Specification

The IUPAC name of this chemical is 3-methylthiophene. With the CAS registry number 616-44-4, it is also named as Thiophene, 3-methyl-. The product's categories are thiophenes; heterocycles; thiophene & benzothiophene; heterocyclic compounds; 3-alkylthiophenes (for conduting polymer research); functional materials; reagents for conducting polymer research; heterocyclic building blocks. It is clear colorless to light yellow liquid which is miscible with ethanol, ether, acetone, benzene and carbon tetrachloride, soluble in chloroform, and insoluble in water. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of 3-Methylthiophene can be summarized as: (1)ACD/LogP: 2.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.36; (4)ACD/LogD (pH 7.4): 2.36; (5)#Freely Rotating Bonds: 0; (6)Index of Refraction: 1.531; (7)Molar Refractivity: 29.46 cm3; (8)Molar Volume: 95.1 cm3; (9)Polarizability: 11.67×10-24 cm3; (10)Surface Tension: 32.9 dyne/cm; (11)Flash Point: 11.1 °C; (12)Enthalpy of Vaporization: 34.24 kJ/mol; (13)Boiling Point: 114.2 °C at 760 mmHg; (14)Vapour Pressure: 23.8 mmHg at 25°C; (15)Exact Mass: 98.019021; (16)MonoIsotopic Mass: 98.019021; (17)Topological Polar Surface Area: 28.2; (18)Heavy Atom Count: 6; (19)Complexity: 43.2.

Uses of 3-Methylthiophene: It can be used as pharmaceutical intermediate. And it reacts with N,N-dimethyl-formamide to get 3-methyl-thiophene-2-carbaldehyde. This reaction needs reagent phosphoryl chloride by anschliessend Hydrolysieren.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable, so people should keep away from sources of ignition. And it is harmful by inhalation and if swallowed. In addition, this chemical is irritating to eyes, respiratory system and skin. 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 gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:Cc1ccsc1
2. InChI:InChI=1/C5H6S/c1-5-2-3-6-4-5/h2-4H,1H3 
3. InChIKey:QENGPZGAWFQWCZ-UHFFFAOYAK

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LC50 inhalation 18gm/m3 (18000mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.
mammal (species unspecified) LD50 unreported 1600mg/kg (1600mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.
mouse LC50 inhalation 18gm/m3/2H (18000mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 87, 1982.
mouse LD50 oral 1800mg/kg (1800mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 87, 1982.