dithiobutylamine

{{One source|date=July 2023}}

{{chembox

| Verifiedfields =

| Watchedfields =

| verifiedrevid =

| Reference = {{cite journal | last1=Lukesh | first1=John C. | last2=Palte | first2=Michael J. | last3=Raines | first3=Ronald T. | title=A Potent, Versatile Disulfide-Reducing Agent from Aspartic Acid | journal=Journal of the American Chemical Society | publisher=American Chemical Society (ACS) | volume=134 | issue=9 | date=2012-02-21 | issn=0002-7863 | doi=10.1021/ja211931f | pages=4057–4059| pmid=22353145 | pmc=3353773 }}

| ImageFile = Dithiobutylamine structure.svg

| ImageSize =

| ImageAlt = Skeletal formula of dithiobutylamine

| ImageFile1 =

| ImageAlt1 = Ball-and-stick model of the dithiobutylamine molecule

| PIN = (S)-2-aminobutane-1,4-dithiol

| OtherNames = DTBA

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref =

| ChemSpiderID = 32696684

| ChEMBL_Ref =

| ChEMBL =

| UNII_Ref =

| UNII =

| StdInChI = 1S/C4H11NS2/c5-4(3-7)1-2-6/h4,6-7H,1-3,5H2/t4-/m0/s1

| StdInChIKey = VGLCUHJZKWYDPC-BYPYZUCNSA-N

| CASNo_Ref = (2S)

| CASNo = 1363594-47-1

| CASNo1 = 1363376-98-0

| CASNo1_Comment = (hydrochloride)

| PubChem = 89734616

| DrugBank_Ref =

| DrugBank =

| ChEBI_Ref =

| ChEBI =

| SMILES = SC[C@H](CCS)N

}}

|Section2={{Chembox Properties

| C=4 | H=11 | N=1 | S=2

| MolarMass = 137.26 g/mol

| Appearance = White solid

| Density =

| Odor = Nearly odorless

| MeltingPtC =

| MeltingPt_notes =

| BoilingPtC =

| BoilingPt_notes =

| Solubility = Soluble

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Dithiobutylamine (DTBA) is a reducing agent intended as an alternative for DTT in biochemical uses. It was designed to be easily synthesized in non-racemic form, to have a lower pKa (allowing more effective reduction at neutral pH), and to have a low disulfide E°′ reduction potential. It was rationally designed & reported in 2012. It is commercially available.

See also

References

{{Reflist}}

{{refbegin}}

{{refend}}

Category:Thiols

Category:Reducing agents

{{organic-compound-stub}}