HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Iodothiophene
2-IODTHIOPHENE · 2-Iodothiophene · 2-Iodothyophene · 2-iodo-thiophen · 2-THIENYL IODIDE · thiophene,2-iodo- · 2-Iodothiophene>2-Iodine Thiophene · alpha-Iodothiophene
Identifiers & Physical Properties
| CAS No. | 3437-95-4 |
|---|---|
| Molecular formula | C4H3IS |
| Average molar mass | 210.04 g/mol |
| Monoisotopic mass | 209.9000191 g/mol |
| SMILES | Ic1cccs1 |
| InChIKey | ROIMNSWDOJCBFR-UHFFFAOYSA-N |
| PubChem CID | 18921 |
| EC No. | 222-342-1 |
| DTXSID | DTXSID0063026 |
Chemical & Physical Properties
| XLogP | 2.6 |
|---|---|
| Topological polar surface area | 28.2 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 6 |
| Formal charge | 0 |
| Complexity | 46.8 |
| SpringerMaterials Properties | Coriolis coupling |
| Melting point | -40 °C (lit.) |
| Boiling point | 73 °C/15 mmHg (lit.) |
| Density | 1.902 g/mL at 25 °C (lit.) |
| Refractive index | n20/D 1.651(lit.) |
| Flash point | 160 °F |
| Storage conditions | 2-8°C |
| Physical state | Liquid |
| Specific gravity | 1.902 |
| Color | Clear yellow-green to red-brown |
| Sensitivity | Light Sensitive |
| BRN | 104666 |
| InChI | 1S/C4H3IS/c5-4-2-1-3-6-4/h1-3H |
| InChIKey | ROIMNSWDOJCBFR-UHFFFAOYSA-N |
| SMILES | Ic1cccs1 |
| CAS DataBase Reference | 3437-95-4(CAS DataBase Reference) |
| FDA UNII | Z4KJ38KVA6 |
| NIST Chemistry Reference | Thiophene, 2-iodo-(3437-95-4) |
| EPA Substance Registry System | Thiophene, 2-iodo- (3437-95-4) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS05,GHS07 |
| Signal word | Danger |
| GHS hazard statements | H302-H315-H317-H318-H335 |
| GHS precautionary statements | P261-P280-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xn,Xi |
| Risk statements (R) | 22-37/38-41-43-20/21/22-36/37/38 |
| Safety statements (S) | 26-36/37/39-36/37-27 |
| Water hazard class (WGK) | 3 |
| F | 3 |
| TSCA inventory status | TSCA listed |
| Hazard class | IRRITANTAcute Tox. 4 OralEye Dam. 1Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Customs code | 29349990 |
| Storage class | 10 - Combustible liquids |
Safety & Regulations
| GHS classification | DangerH302 (97.8%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (97.8%) |
| F | 3 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29349990 |
| Risk statements (R) | 22-37/38-41-43-20/21/22-36/37/38 |
| Signal word | Danger |
| GHS pictogram | GHS05,GHS07 |
| Hazard symbols | Xn,Xi |
| Safety statements (S) | 26-36/37/39-36/37-27 |
| Hazard class | IRRITANTAcute Tox. 4 OralEye Dam. 1Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Storage class | 10 - Combustible liquids |
| Target organs | Respiratory system |
| GHS hazard statements | H302-H315-H317-H318-H335 |
| GHS precautionary statements | P261-P280-P305+P351+P338 |
Applications & Uses
Uses
2-Iodothiophene was used in the synthesis of (E)-and (Z)-2,3-difluoro-3-aryl substituted acrylic esters. It was also used as monomer in the preparation of thin conductive films via plasma polymerization of 2-iodothiophene.
General Description
Mechanism of the fluoride-free, palladium-catalyzed cross-coupling reaction of 2-iodothiophene with potassium (E)-heptenyldimethylsilanolate has been investigated. 2-Iodothiophene participates in microwave-enhanced, rapid homogeneous-phase version of the Sonogashira reaction.