Tert-Butanesulfinamide

{{DISPLAYTITLE:tert-Butanesulfinamide}}

{{Chembox

| Watchedfields = changed

| verifiedrevid = 462801614

| Name =tert-Butanesulfinamide

| ImageFile =

| ImageFileL1 = (R)-Ellmans sulfinamide.png

| ImageAlt = Skeletal formula of (R)-tert-butylsulfinamide

| ImageFileR1 = (S)-Ellmans sulfinamide.png

| ImageAlt1 = Skeletal formula of (S)-tert-butylsulfinamide

| ImageCaptionL1 = (R)-tert-butylsulfinamide

| ImageCaptionR1 = (S)-tert-butylsulfinamide

| ImageFile2 = Tert-Butanesulfinamide-3D-balls.png

| ImageAlt2 = Ball-and-stick model of tert-butanesulfinamide

| PIN = 2-Methylpropane-2-sulfinamide

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 146374-27-8

| CASNo_Comment = (R/S)

| CASNo1_Ref = {{cascite|correct|CAS}}

| CASNo1 = 196929-78-9

| CASNo1_Comment = (R)-(+)

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2 = 343338-28-3

| CASNo2_Comment = (S)-(-)

| ChemSpiderID = 2627606

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 42F4K704G0

| UNII_Comment = (R/S)

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII1 = 7FEC1T720F

| UNII1_Comment = (R)-(+)

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = I85YC2ZA8O

| UNII2_Comment = (S)-(-)

| PubChem = 3382465

| PubChem_Comment = (R/S)

| PubChem1 = 10964479

| PubChem1_Comment = (R)-(+)

| PubChem2 = 11355477

| PubChem2_Comment = (S)-(-)

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| SMILES = O=S(N)C(C)(C)C

| SMILES_Comment = (R/S)

| SMILES1 = O=[S@@](N)C(C)(C)C

| SMILES1_Comment = (R)-(+)

| SMILES2 = O=[S@](N)C(C)(C)C

| SMILES2_Comment = (S)-(-)

| InChI = 1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3

| InChIKey = CESUXLKAADQNTB-UHFFFAOYSA-N

| InChI_Comment = (R/S)

| InChI1 = 1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m1/s1

| InChIKey1 = CESUXLKAADQNTB-SSDOTTSWSA-N

| InChI1_Comment = (R)-(+)

| InChI2 = InChI=1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m0/s1

| InChIKey2 = CESUXLKAADQNTB-ZETCQYMHSA-N

| InChI2_Comment = (S)-(-)

}}

|Section2={{Chembox Properties

| Formula = (CH₃)₃CS(O)NH₂

| MolarMass = 121.20 g/mol

| Appearance = white to off-white crystalline solid

| MeltingPtC = 102 to 105

| MeltingPt_notes =

}}

}}

tert-Butanesulfinamide (also known as 2-methyl-2-propanesulfinamide or Ellman's sulfinamide) is an organosulfur compound and a member of the class of sulfinamides. Both enantiomeric forms are commercially available and are used in asymmetric synthesis as chiral auxiliaries, often as chiral ammonia equivalents for the synthesis of amines.{{cite journal|doi=10.1351/pac200375010039|title=Applications of tert-butanesulfinamide in the asymmetric synthesis of amines|year=2003|last1=Ellman|first1=J. A.|journal=Pure and Applied Chemistry|volume=75|pages=39–46|s2cid=97201636|doi-access=free}}{{cite journal|doi=10.1021/cr900382t|title=Synthesis and Applications oftert-Butanesulfinamide|year=2010|last1=Robak|first1=Maryann T.|last2=Herbage|first2=Melissa A.|last3=Ellman|first3=Jonathan A.|journal=Chemical Reviews|volume=110|issue=6|pages=3600–740|pmid=20420386}}Organic Syntheses, Vol. 82, p.157 (2005). [http://orgsynth.org/orgsyn/pdfs/v82p0157.pdf Link] tert-Butanesulfinamide and the associated synthetic methodology was introduced in 1997 by Jonathan A. Ellman et al.{{cite journal|doi=10.1021/ja972012z|title=Catalytic Asymmetric Synthesis of tert-Butanesulfinamide. Application to the Asymmetric Synthesis of Amines|year=1997|last1=Liu|first1=Guangcheng|last2=Cogan|first2=Derek A.|last3=Ellman|first3=Jonathan A.|journal=Journal of the American Chemical Society|volume=119|issue=41|pages=9913|bibcode=1997JAChS.119.9913L }}