tetrabutylammonium triiodide

{{Chembox

| ImageFile = Tetrabutylammonium triiodide.svg

| ImageSize = 200px

| IUPACName = Tetrabutylazanium triiodide

| OtherNames = TBAI₃

| Section1 = {{Chembox Identifiers

| CASNo = 13311-45-0

| ChemSpiderID = 14389611

| EINECS =

| KEGG = D83000

| PubChem = 16218639

| InChI = 1S/C16H36N.I3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1

| InChIKey = SBSSZSCMFDYICE-UHFFFAOYSA-N

| SMILES = CCCC[N+](CCCC)(CCCC)CCCC.I[I-]I

}}

| Section2 = {{Chembox Properties

| C=16 | H=36 | I=3 | N=1

| Appearance = Black powder

| Density =

| MeltingPtC = 69-71

| BoilingPt =

| Solubility =

}}

| Section3 = {{Chembox Hazards

| GHS_ref={{cite web |title=Tetrabutylammonium triiodide |url=https://pubchem.ncbi.nlm.nih.gov/compound/16218639#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=31 March 2022 |language=en}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319}}

| PPhrases = {{P-phrases|264|264+265|280|302+352|305+351+338|321|332+317|337+317|362+364}}

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Tetra-n-butylammonium triiodide (TBAI₃) is a quaternary ammonium salt with a triiodide counterion. It is a common carrier of the triiodide used in chemical synthesis of photovoltaic materials,{{Cite journal |last1=Starkholm |first1=Allan |last2=Kloo |first2=Lars |last3=Svensson |first3=Per H. |date=2019-01-28 |title=Polyiodide Hybrid Perovskites: A Strategy To Convert Intrinsic 2D Systems into 3D Photovoltaic Materials |url=https://doi.org/10.1021/acsaem.8b01507 |journal=ACS Applied Energy Materials |volume=2 |issue=1 |pages=477–485 |doi=10.1021/acsaem.8b01507 |s2cid=139565235 }} organic conductors and superconductors.{{Cite journal |last1=Shibaeva |first1=Rimma P. |last2=Yagubskii |first2=Eduard B. |date=2004-11-01 |title=Molecular Conductors and Superconductors Based on Trihalides of BEDT-TTF and Some of Its Analogues |url=https://doi.org/10.1021/cr0306642 |journal=Chemical Reviews |volume=104 |issue=11 |pages=5347–5378 |doi=10.1021/cr0306642 |pmid=15535653 |issn=0009-2665}} In crystals, the triiodide moieties are linear and shows high crystallinity.{{Cite journal |date=1981-01-01 |editor-last=Herbstein |editor-first=F. H. |editor2-last=Kaftory |editor2-first=M. |editor3-last=Kapon |editor3-first=M. |editor4-last=Saenger |editor4-first=W. |title=Structures of three crystals containing approximately — linear chains of triiodide ions |url=https://www.degruyter.com/document/doi/10.1524/zkri.1981.154.1-2.11/html |journal=Zeitschrift für Kristallographie - Crystalline Materials |language=en |volume=154 |issue=1–2 |pages=11–30 |doi=10.1524/zkri.1981.154.1-2.11 |bibcode=1981ZK....154...11H |issn=2194-4946|last1=Herbstein |first1=F. H. |last2=Kaftory |first2=M. |last3=Kapon |first3=M. |last4=Saenger |first4=W. }}{{Cite journal |last1=Brotherton |first1=Wendy S. |last2=Clark |first2=Ronald J. |last3=Zhu |first3=Lei |date=2012-08-03 |title=Synthesis of 5-Iodo-1,4-disubstituted-1,2,3-triazoles Mediated by in Situ Generated Copper(I) Catalyst and Electrophilic Triiodide Ion |url=https://doi.org/10.1021/jo300841c |journal=The Journal of Organic Chemistry |volume=77 |issue=15 |pages=6443–6455 |doi=10.1021/jo300841c |pmid=22780866 |issn=0022-3263}} The crystals have a black appearance with a needle or plate-like habit.