Thiophene

An aromatic compound, C4H4S, 84.143 g/mol. Boiling point 84.0 °C @ 760 MM HG, melting point -39.4 °C, as published.

verified recordOrganic — aromatic compound9 measured properties

Identifiers

Molecular formula: C₄H₄S
Molecular weight: 84.143 g/mol
Exact mass: 84.003371 g/mol
IUPAC name: thiophene
SMILES: c1ccsc1
InChI: InChI=1S/C4H4S/c1-2-4-5-3-1/h1-4H
InChIKey: YTPLMLYBLZKORZ-UHFFFAOYSA-N

Open in ReactionLens Use in reaction prediction

Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Boiling Point: 183.9 °F at 760 mmHg (NTP, 1992)measured · CAMEO Chemicals; 84.0 °C @ 760 MM HGmeasured · Hazardous Substances Data Bank (HSDB)
Melting Point: -36.8 °F (NTP, 1992)measured · CAMEO Chemicals; -39.4 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Density: 1.0649 at 68 °F (NTP, 1992) - Denser than water; will sinkmeasured · CAMEO Chemicals; 1.06494 @ 20 °C/4 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Solubility: less than 1 mg/mL at 75 °F (NTP, 1992)measured · CAMEO Chemicals; MISCIBLE IN ETHANOL, ETHER, ACETONE, AND BENZENE.measured · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 20 mmHg at 32 °F ; 60 mmHg at 68.2 °F; 760 mmHg at 183.9 °F (NTP, 1992)measured · CAMEO Chemicals; 79.7 [mmHg]measured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
LogP: log Kow = 1.81measured · Hazardous Substances Data Bank (HSDB); 1.81measured · Human Metabolome Database (HMDB)
Flash Point: 30 °F (NTP, 1992)measured · CAMEO Chemicals; 30 °F (-1 °C) (CLOSED CUP)measured · Hazardous Substances Data Bank (HSDB)
Viscosity: 0.621 mPa.smeasured · Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA26 793
Refractive Index: INDEX OF REFRACTION: 1.52684 @ 25 °C/Dmeasured · Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1596

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight: 84.14 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 84.0033713 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 1.8calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 28.2 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 22calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 0calculated · reference compound database
H-bond acceptors: 1calculated · reference compound database
logP: 1.7481calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 0 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 0calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 1calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 0calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 24.319 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.4489calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon4 atoms · 57.1% by mass
S Sulfur1 atom · 38.1% by mass
H Hydrogen4 atoms · 4.8% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 5
Total atoms, hydrogen included: 9
Rings: 1
Aromatic rings: 1
Stereocentres: 0
Formal charge: 0

Functional groups

Aromatic ring (five-membered)
A flat five-membered ring with delocalised electrons, such as furan, thiophene or pyrrole.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves Thiophene yet.

Other names for it

The systematic name on this record is thiophene.

The sources also call it Thiofuran, Thiole, Thiophen, Thiotetrole, Thiacyclopentadiene, Thiofurfuran, Divinylene sulfide, Thiaphene, Thiofuram, Furan, thio-, Huile HSO.

Structurally related

Nothing structurally close to Thiophene has a page here yet.

Seen alongside it in reaction records

Molecules that appear in the same recorded reactions as Thiophene. This says nothing about structure: most of them are the bases, solvents, ligands and catalysts the chemistry needed, and they are here because somebody put them in the same flask.

(2-Bromophenyl)(thiophen-2-yl)methanone

used as a reactant

C₁₁H₇BrOS, 267.147 g/mol.

(+/-)-4-(4-aminophenyl)-alpha-phenyl-N-(2,2,2-trifluoroethyl)-1-piperazineacetamide

formed as a product

C₂₀H₂₃F₃N₄O, 392.425 g/mol.

(+/-)-Ethyl 2-(phenylmethyl)-4-[(phenylmethyl)amino]-1-piperidine-carboxylate

formed as a product

C₂₂H₂₈N₂O₂, 352.478 g/mol.

Where these values came from

reference compound database8030
compound record
chemistry engine
structure perception

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.