7289-92-1

Basic information

• Product Name: TRIS(DIMETHYLAMINO)ANTIMONY
• Synonyms: TRIS(DIMETHYLAMINO)ANTIMONY;ANTIMONY TRIS(DIMETHYLAMIDE);TRIS(DIMETHYLAMINO)ANTIMONY, 99.99%;TRIS(DIMETHYLAMINO)ANTIMONY (99.99%-SB) SPECTRO;Tris(dimethylamino)antimony(99.-sb)spectro;Tris(dimethylamino)antimony(99.-sb)spectro-;Tris(dimethylamino)stibine;Tris(dimethylamino)antimonium
• CAS NO: 7289-92-1
• Molecular Formula: C₆H₁₈N₃Sb
• Molecular Weight: 253.99
• Product Categories: inorganic antimony compound;ALD Precursors
• Mol File: 7289-92-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 300℃
• Boiling Point: 32-34 °C0.45 mm Hg
• Flash Point: 7 °F
• Appearance: colorless/liquid
• Density: 1.325 g/mL at 25 °C(lit.)
• Storage Temp.: Flammables + water-Freezer (-20°C)e area
• Sensitive: air sensitive, moisture sensitiv
• CAS DataBase Reference: TRIS(DIMETHYLAMINO)ANTIMONY(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS(DIMETHYLAMINO)ANTIMONY(7289-92-1)
• EPA Substance Registry System: TRIS(DIMETHYLAMINO)ANTIMONY(7289-92-1)

Safety Data

• Hazard Codes: C,N
• Statements: 10-14-20/22-34-51/53
• Safety Statements: 16-26-36/37/39-45-61
• RIDADR: UN 3398 4.3/PG 1
• WGK Germany: 2
• Hazardous Substances Data: 7289-92-1(Hazardous Substances Data)

Usage

Chemical Properties

Yellow liquid

InChI:InChI=1/3C2H6N.Sb/c3*1-3-2;/h3*1-2H3;/q3*-1;+3/rC6H18N3Sb/c1-7(2)10(8(3)4)9(5)6/h1-6H3

Synthetic route

antimony(III) chloride (10025-91-9) + lithium dimethylamide (3585-33-9) → tris(dimethylamino)stibine (7289-92-1)

Conditions	Yield
In diethyl ether under Ar; from a 1:3 stoich. react. of SbCl3 and Me2NLi in Et2O; according to A. Kiennemann et al., J. Organomet. Chem., 1972, 35, 143; purifn. by distn.;

Ketene (463-51-4) + tris(dimethylamino)stibine (7289-92-1) → tris(dimethylcarbamoylmethyl)stibine (113359-20-9)

Conditions	Yield
In diethyl ether under N2 or Ar, ketene passed into ethereal soln. of Sb(NMe2)3 at -20°C; after removal of solvent residue dried under reduced pressure (ca. 1E-2 Pa) for 4 h;	98%

tri(n-butyl)aluminium (1116-70-7) + tris(dimethylamino)stibine (7289-92-1) → {(C4H9)2AlN(CH3)2}2 + tributylstibine (2155-73-9)

Conditions	Yield
In neat (no solvent) under N2; Al-compd. added slowly over a period of 2 h to Sb-compd. at 0°C with stirring, warmed slowly to room temp., stirred for 4 h, heated for 12 h at 120°C;; monitored by NMR, fractional distn., Al-compd. isolated by distn.;;	A 95% B 87%
In benzene-d6 addn. of Al-compd. to soln. of Sb-compd. in a NMR tube;; not isolated, monitored by 1H-, 13C-NMR spectroscopy;;

triisobutylaluminum (100-99-2) + tris(dimethylamino)stibine (7289-92-1) → [(C4H9)2Al(N(CH3)2)2Al(C4H9)2] + triisobutylantimony (42966-06-3)

Conditions	Yield
In neat (no solvent) under N2; Al-compd. added slowly over a period of 2 h to Sb-compd. at 0°C with stirring, warmed slowly to room temp., stirred for 4 h, heated for 12 h at 120°C;; monitored by NMR, fractional distn., Al-compd. isolated by sublimation; elem. anal.;;	A 95% B 63%
In benzene-d6 addn. of Al-compd. to soln. of Sb-compd. in a NMR tube;; not isolated, monitored by 1H-, 13C-NMR spctroscopy;;

trimethylaluminum (75-24-1) + tris(dimethylamino)stibine (7289-92-1) → tetramethylbis[μ-(N-mrthylmethanaminato)]dialuminum (22450-81-3) + trimethylantimony (594-10-5)

Conditions	Yield
In neat (no solvent) under N2; Al-compd. added slowly over a period of 2 h to Sb-compd. at 0°C with stirring, warmed slowly to room temp., stirred for 4 h, heated for 12 h at 120°C;; monitored by NMR, fractional distn., Al-compd. isolated by sublimation;;	A 93% B 82%
In benzene-d6 addn. of Al-compd. to soln. of Sb-compd. in a NMR tube;; not isolated, monitored by 1H-, 13C-NMR spectroscopy;;

benzyl sodium (1121-53-5) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + tris(dimethylamino)stibine (7289-92-1) + cyclohexylphosphine (822-68-4) → Sb7Na3((CH3)2NCH2CH2N(CH3)2)3(C4H8O)3

Conditions	Yield
In tetrahydrofuran; hexane; toluene under Ar; Sb(NMe2)3 in toluene added to chilled soln. of C6H11PH2 (1:1)in hexane; warmed to room temp.; stirred for 10 min; added to soln. prepared from PhCH2Na and CyPH2 in hexane-THF at -20°C; excess TMEDAadded; warmed to 25°C; reflux; filtered while warm; stored at -35°C;	93%

tri-n-propylaluminum (102-67-0) + tris(dimethylamino)stibine (7289-92-1) → {(C3H7)2AlN(CH3)2}2 + tripropylstibine (5613-69-4)

Conditions	Yield
In neat (no solvent) under N2; Al-compd. added slowly over a period of 2 h to Sb-compd. at 0°C with stirring, warmed slowly to room temp., stirred for 4 h, heated for 12 h at 120°C;; monitored by NMR, fractional distn., Al-compd. isolated by distn.;;	A 91% B 83%
In benzene-d6 addn. of Al-compd. to soln. of Sb-compd. in a NMR tube;; not isolated, monitored by 1H-, 13C-NMR spectroscopy;;

carbon dioxide (124-38-9) + tris(dimethylamino)stibine (7289-92-1) → tris(N,N-dimethylcarbamato)antimony(III) (473302-00-0)

Conditions	Yield
In hexane through soln. Sb(NMe2)3 in hexane CO2 was bubbled for 30 min; solvent was removed in vacuo, residue was recrystd. from toluene at -20°C; elem. anal.;	91%

triethylaluminum (97-93-8) + tris(dimethylamino)stibine (7289-92-1) → [(C2H5)2Al(N(CH3)2)2Al(C2H5)2] + triethylantimony (617-85-6)

Conditions	Yield
In neat (no solvent) under N2; Al-compd. added slowly over a period of 2 h to Sb-compd. at 0°C with stirring, warmed slowly to room temp., stirred for 4 h, heated for 12 h at 120°C; monitored by NMR, fractional distn., Al-compd. isolated by distn.;;	A 89% B 83%
In benzene-d6 addn. of Al-compd. to soln. of Sb-compd. in a NMR tube; not isolated, monitored by 1H-, 13C-NMR spectroscopy;;

hexane (110-54-3) + tris(dimethylamino)stibine (7289-92-1) + 5,11,17,23,29-penta-tert-butyl-31-n-benzoxy-32,33,34,35-tetrahydroxycalix<5>arene (166302-06-3) → [Sb2O(monobenzyl-para-t-butylcalix[5]arene(4-))]*1.5(hexane)

Conditions	Yield
In benzene (N2) soln. Sb(NMe2)3 in benzene was added dropwise to soln. t-BuC5(Bn)(H)4 in benzene and stirred for 48 h at room temp.; soln. was evapd., residue was crystd. by hexane diffusion into soln. in benzene; elem. anal.;	89%

n-butyllithium (109-72-8, 29786-93-4) + tris(dimethylamino)stibine (7289-92-1) + cyclohexylamine (108-91-8) → Li[(((CH3)2N)Sb(NC6H11)2)2Sb]

Conditions	Yield
With ((CH3)2CH)2NH In hexane; toluene under Ar; adding n-BuLi in hexanes to soln. of i-Pr2NH in hexane, heating briefly to reflux, cooling to room temp., adding this to mixt. of Sb(NMe2)3 (in toluene) and C6H11NH2 (previously briefly refluxed and cooledto room temp.); filtration, reducing filtrate under vac. until ppt. appeared, warming ppt. back into soln., crystn. by storage at 25°C (24 h);	88%

tris(dimethylamino)stibine (7289-92-1) + 2,2'-((4-bromophenyl)methylene)bis(3-methyl-1H-indole) (620177-71-1) → Di-(3-methylindol-2-yl)dimethylamidoantimony-4-bromophenylmethane (1401085-50-4)

Conditions	Yield
In toluene at -78 - 25℃; for 3h;	88%

tris(dimethylamino)stibine (7289-92-1) + HSeSi(Si(CH3)3)3 (148808-60-0) → Sb(3+)*3SeSi(Si(CH3)3)3(1-)=Sb[SeSi(Si(CH3)3)3]3

Conditions	Yield
In hexane N2-atmosphere; stirring Sb-compd. with 3 equiv. of Se-compd. (-78°C, 10 min), warming to room temp., stirring for 2 h; evapn. (reduced pressure), extn. into O(SiMe3)2, filtration, concn., crystn. (-40°C, several d), filtration; elem. anal.;	87%

2.6-dimethylphenol (576-26-1) + tris(dimethylamino)stibine (7289-92-1) → Sb(OC6H3Me2-2,6)3

Conditions	Yield
In hexane 2,6-dimethylphenol in hexane was added slowly to soln. tris(dimethylamino)antimony(III) in hexane and stirred overnight; solvent was removed in vacuo, residue was dissolved in toluene; elem. anal.;	84%

tris(dimethylamino)stibine (7289-92-1) + (2,6-iPr2C6H3)N(SiMe3)Si(OH)3 (163631-37-6) → [Sb(SiO3((2,6-iPr2C6H3)NSiMe3))]4 (934165-80-7)

Conditions	Yield
In tetrahydrofuran; hexane byproducts: HNMe2; under dry oxygen-free N2; metal compd. added dropwise to suspn. of Si compd. (1:1) at room temp., stirred for 24 h at room temp., refluxed for 1h, coooled, concd.; crystd. in 4 d, elem. anal.;	83%

tetrahydrofuran (109-99-9) + tris(dimethylamino)stibine (7289-92-1) + calix[6]arene (96107-95-8) → [Sb2(calix[6]arene(6-))]*1.5THF*1.5pentane

Conditions	Yield
In toluene (N2) soln. Sb(NMe2)3 in toluene was added dropwise to suspn. HC6(H)6 in toluene and stirred for 48 h; ppt. was centrifugated and washed with toluene; elem. anal.;	83%

tetrahydrofuran (109-99-9) + H2(CH2C6H2(C(CH3)3)O)5(CH2C6H5)Si(CH3)2 (1192283-08-1) + tris(dimethylamino)stibine (7289-92-1) → Sb(N(CH3)2)(CH2C6H2(C(CH3)3)O)5(CH2C6H5)Si(CH3)2*OC4H8

Conditions	Yield
In toluene (N2) soln. Sb(NMe2)3 in toluene was added dropwise to soln. ligand in tiluene, stirred for 24 h at room temp.; solvent was removed in vacuo, residue was dissolved in pentane and centrifuged, THF was added and placed in freezer at -35°C for 4 days; elem. anal.;	83%

antimony(III) chloride (10025-91-9) + tris(dimethylamino)stibine (7289-92-1) → dimethylaminochloroethoxostibane

Conditions	Yield
With ethanol In diethyl ether exclusion of air and moisture; dropwise addn. of SbCl3 in ether to a soln. of Sb(NMe2)3 in ether (molar ratio amide:chloride = 2:1) at -78°C with stirring; after 2 h dropwise addn. of EtOH in ether, stirring for 12 h; ppt. is filtd. at -78°C, dried in vac.; elem. anal.;	82%

antimony(III) chloride (10025-91-9) + tris(dimethylamino)stibine (7289-92-1) → dimethylaminodichlorostibane

Conditions	Yield
In diethyl ether; hexane exclusion of air and moisture; dropwise addn. of Sb(NMe2)3 in hexane toa soln. of SbCl3 (molar ratio amide:chloride = 1:2) in ether at -78°C with stirring; mixt. stirred for 12 h at this temp.; solid is filtd. at -78°C, washed (ether); elem. anal.;	81%

n-butyllithium (109-72-8, 29786-93-4) + tris(dimethylamino)stibine (7289-92-1) + cyclohexylamine (108-91-8) → ((C6H11NLi)3Sb)2

Conditions	Yield
In hexane; toluene 20°C; filtering, pptn. on concg. (vac.);	80%

antimony(III) chloride (10025-91-9) + tris(dimethylamino)stibine (7289-92-1) → bis(dimethylamino)chlorostibane

Conditions	Yield
In diethyl ether; hexane exclusion of air and moisture; dropwise addn. of SbCl3 in ether to a soln. of Sb(NMe2)3 in hexane (molar ratio amide:chloride = 2:1) at -78°C with stirring, reaction time 24 h; solid is filtd. at -78°C; elem. anal.;	77%

tris(dimethylamino)stibine (7289-92-1) + tris(trimethylsilyl)silyltellurol (133100-98-8) → Sb(3+)*3TeSi(Si(CH3)3)3(1-)=Sb[TeSi(Si(CH3)3)3]3

Conditions	Yield
In hexane N2-atmosphere; stirring Sb-compd. with 3 equiv. of Te-compd. (-78°C, 15 min), warming to room temp., stirring for 60 min; evapn. (reduced pressure), extn. into O(SiMe3)2, filtration, concn., crystn. (-40°C, 24 h), filtration; elem. anal.;	75%

antimony(III) chloride (10025-91-9) + tris(dimethylamino)stibine (7289-92-1) → dimethylaminochloromethoxostibane

Conditions	Yield
With methanol In diethyl ether exclusion of air and moisture; dropwise addn. of SbCl3 in ether to a soln. of Sb(NMe2)3 in ether (molar ratio amide:chloride = 2:1) at -78°C with stirring; after 2 h dropwise addn. of MeOH in ether, stirring for 12 h; ppt. is filtd. at -78°C, dried in vac.; elem. anal.;	74%

((CH3)3SiNHC6H4)2NH (205517-60-8) + tris(dimethylamino)stibine (7289-92-1) → C18H26N3SbSi2

Conditions	Yield
Stage #1: ((CH3)3SiNHC6H4)2NH; tris(dimethylamino)stibine In hexane at -30 - 20℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; Stage #2: In hexane under 0.00750075 Torr; for 20h; Schlenk technique; Glovebox; Inert atmosphere;	72%

5,11,17,23,29,35-hexakis(tert-butyl)-37,38,39,40,41-hexakis(hydroxy)calix[6]arene (189832-67-5) + tris(dimethylamino)stibine (7289-92-1) → [Sb2(para-tert-butylcalix[6]arene(6-))] (1185419-79-7)

Conditions	Yield
In benzene (N2) soln. Sb(NMe2)3 in benzene was added dropwise to suspn. t-BuC6(H)6 in benzene and stirred for 48 h; ppt. was filtered and washed with benzene; elem. anal.;	71%

n-butyllithium (109-72-8, 29786-93-4) + tert-butylphosphine (2501-94-2) + tris(dimethylamino)stibine (7289-92-1) → Sb7(3-) + (((CH3)3CP)3Sb)2 (511242-27-6)

Conditions	Yield
In tetrahydrofuran; hexane; toluene byproducts: Sb; (Ar); react. of a soln. of phosphine in THF with a soln. of lithium compd. in hexanes at 0°C, addn. of a soln. of antimony compd. in toluene, warming to room temp., refluxing for 10 min; storage at room temp. for 7 d; elem. anal.;	A 0% B 69%

(2,6-diisopropylphenylimino)(2,2,6,6-tetramethylpiperidino)borane (113748-54-2) + tris(dimethylamino)stibine (7289-92-1) → {(2,6-diisopropylphenyl)(dimethylamino(2,2,6,6-tetramethylpiperidino)boryl)amino}bis(dimethylamino)stibane (117499-86-2)

Conditions	Yield
In hexane; pentane (N2 or Ar); to suspn. of borane in pentane was dropped soln. of As(OCH3)3 in hexane with stirring, after stirring for 12 h solvents were removed in vac.; residue was recrystd. from hexane; elem. anal.;	68%

[Ga(2-((2,6-diisoproylphenyl)amino)-4-((2,6-diisopropylphenyl)imino)-2-pentene)] (317322-17-1) + tris(dimethylamino)stibine (7289-92-1) → C62H94Ga2N6Sb2

Conditions	Yield
In toluene at 75℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox;	64%

[((2,6-(isopropyl)2C6H3)NC(CH3)CHC(CH3)N(2,6-(isopropyl)2C6H3))Al(methyl)OH] + tris(dimethylamino)stibine (7289-92-1) → [HC(CMeN(C6H3(i-Pr)2))2Al(Me)(μ-O)]2Sb(NMe2)

Conditions	Yield
In toluene toluene soln. of Al compd. added dropwise to toluene soln. of Sb compd. (2:1 molar ratio) at 0°C, react. mixt. warmed to room temp., stirred overnight; evapd., extd. (n-hexane), elem. anal.;	60%

tris(dimethylamino)stibine (7289-92-1) + cyclohexylamine (108-91-8) + benzyl rubidium → [Sb3(NC6H11)4(NHC6H11)2Rb(C4H8O)2]

Conditions	Yield
In tetrahydrofuran; toluene byproducts: toluene, dimethylamine; (argon); addn. of cyclohexylamine in toluene at -78°C to RbCH2C6H5 in toluene, warming to room temp. and stirring 5 min, cooling to -78°C, addn. of Sb(NMe2)3 in THF, stirring (20 min), warming to room temp.; filtration (Celite), removal of solvents (vac.), addn. of Et2O and THF, crystn. upon storage (-15°C, 12 h); elem. anal.;	59%

tris(dimethylamino)stibine (7289-92-1) + (tert-butylimino)(2,2,6,6-tetramethylpiperidino)borane (89201-97-8) → {t-butyl(dimethylamino(2,2,6,6-tetramethylpiperidino)boryl)amino}bis(dimethylamino)stibane (117499-82-8)

Conditions	Yield
In hexane (N2 or Ar); to soln. of borane was dropped Sb(NMe2)3 soln. with stirring, after stirring for 12 h solvent was removed in vac.; residue was recrystd. from hexane; elem. anal.;	58%

Upstream product

• 10025-91-9 antimony(III) chloride 
• 3585-33-9 lithium dimethylamide 

Downstream Products

• 2543-57-9 1-Dimethylamino-3-butanon 
• 22450-81-3 tetramethylbis[μ-(N-mrthylmethanaminato)]dialuminum 
• 594-10-5 trimethylantimony 
• 617-85-6 triethylantimony 
• 2155-73-9 tributylstibine 
• 117499-86-2 {(2,6-diisopropylphenyl)(dimethylamino(2,2,6,6-tetramethylpiperidino)boryl)amino}bis(dimethylamino)stibane 
• 113359-30-1 tris(dimethylcarbamoyldiphenylmethyl)stibine 

Relevant articles and documents

A mechanistic study of the C-P bond cleavage reaction of 1,2-(PH 2)2-C6H4 with nBuLi/ Sb(NMe2)3

In situ 31P NMR spectroscopic studies of the reaction of the primary diphosphine 1,2-(PH2)2-C6H4 with the mixed-metal base system nBuLi/Sb(NMe2) 3, combined with X-ray structural investigations, strongly support a mechanism involving a series of deprotonation steps followed by antimony-mediated reductive C-P bond cleavage. The central intermediate in this reaction is the tetraphosphide dianion [C6H4P 2]22- ([4]) from which the final products, the 1,2,3-triphospholide anion [C6H4P3]- (3) and [PhPHLi] (8·Li), are evolved. An EPR spectrocopic study suggests that homolytic C-P bond cleavage is likely to be involved in this final step.