676-75-5

Basic information

• Product Name: DIMETHYLARSENIC IODIDE
• Synonyms: ME2ASI;DIMETHYLARSENIC IODIDE;iododimethylarsine;dimethyl iodoarsine;Dimethylarsinous acidiodide;iodo(dimethyl)arsane;DiMethylarsinous iodide
• CAS NO: 676-75-5
• Molecular Formula: C₂H₆AsI
• Molecular Weight: 231.9
• EINECS: 211-630-2
• Product Categories: Apoptosis;Inhibitors;Metabolites & Impurities
• Mol File: 676-75-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 133.4 °C at 760 mmHg
• Flash Point: 45.1 °C
• Appearance: /
• Vapor Pressure: 10.4mmHg at 25°C
• CAS DataBase Reference: DIMETHYLARSENIC IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYLARSENIC IODIDE(676-75-5)
• EPA Substance Registry System: DIMETHYLARSENIC IODIDE(676-75-5)

Safety Data

• Hazardous Substances Data: 676-75-5(Hazardous Substances Data)

Usage

Chemical Properties

Clear Yellow Oil

Uses

Dimethyliodoarsine is a dimethylated metabolite of Arsenic Trioxide that acts as a more potent growth inhibitor and apoptotic inducer in NB4 cells, an APL cell line. Dimethyliodoarsine is an arsenite metabolite in wild type CHO cells and in cells deficient in excision repair cross-complementing 1 and 2. Dimethyliodoarsine is also an inhibitor of Thioredoxin reductase, an enzyme involved in the response of the cell to oxidative stress.

InChI:InChI=1/C2H6AsI/c1-3(2)4/h1-2H3

Synthetic route

Dimethylarsinic acid (75-60-5) → dimethyliodoarsine (676-75-5)

Conditions	Yield
With sulfuric acid; sulfur dioxide; potassium iodide In water for 3h;	76%
With sulfuric acid; sulfur dioxide; potassium iodide
With hydrogenchloride; sulfur dioxide; potassium iodide
Multistep reaction;
With sulfuric acid; sulfur dioxide; potassium iodide In water

sodium cacodylate (124-65-2) → dimethyliodoarsine (676-75-5)

Conditions	Yield
With hydrogenchloride; sulfur dioxide; potassium iodide In water for 2h;	54%

triphenyl phosphite (101-02-0) + dimethylarsinosulfenyl iodide → dimethyliodoarsine (676-75-5) + O,O,O-triphenyl phosphorothioate (597-82-0)

Conditions	Yield
In chloroform-d1 for 6h;	A 22% B n/a

dimethylarsine (593-57-7) + acetyl iodide (507-02-8) → dimethyliodoarsine (676-75-5) + acetaldehyde (75-07-0)

Dimethylchloroarsine (557-89-1) → dimethyliodoarsine (676-75-5)

Conditions	Yield
With ethanol; potassium iodide unter Luftausschluss;
With acetone; sodium iodide unter Luftausschluss;

bis-{dimethylarsenic}-oxide (503-80-0) → dimethyliodoarsine (676-75-5)

Conditions	Yield
With hydrogen iodide bei der Destillation;

tetramethyl-arsonium; triiodide (5814-21-1) → dimethyliodoarsine (676-75-5) + methyl iodide (74-88-4)

Conditions	Yield
Zersetzt sich beim Erhitzen;

tetramethyldiarsine (471-35-2) + methyl iodide (74-88-4) → dimethyliodoarsine (676-75-5)

tetramethyldiarsine (471-35-2) + methyl iodide (74-88-4) → dimethyliodoarsine (676-75-5) + tetramethylarsonium iodide (5814-20-0)

Conditions	Yield
analog reagiert Aethyljodid;

methyl iodide (74-88-4) + methyldiiodoarsine (7207-97-8) → dimethyliodoarsine (676-75-5)

Conditions	Yield
With sodium hydroxide; ethanol und reduziert das Reaktionsprodukt in salzsaurer Loesung mit Schwefeldioxyd;
With sodium hydroxide anschliessend mit wss.HCl und SO2;

methyl iodide (74-88-4) → dimethyliodoarsine (676-75-5)

Conditions	Yield
With arsenic

dimethylphenylarsine (696-26-4) → dimethyliodoarsine (676-75-5)

Conditions	Yield
With hydrogen iodide In dichloromethane

Tri-methylsilyl-(dimethyl)-arsan (6618-05-9) → dimethyliodoarsine (676-75-5)

Conditions	Yield
With Iodine monochloride

methyl iodide (74-88-4) + methyldiiodoarsine (7207-97-8) + aqueous-alcoholic NaOH-solution → dimethyliodoarsine (676-75-5)

(CH3)4AsI+I2 → dimethyliodoarsine (676-75-5)

Conditions	Yield
bei der Destillation;

hydrogenchloride (7647-01-0) + Dimethylarsinic acid (75-60-5) + sulfur dioxide + potassium iodide → dimethyliodoarsine (676-75-5)

Dimethylarsinic acid (75-60-5) + sulfuric acid (7664-93-9) + sulfur dioxide + potassium iodide → dimethyliodoarsine (676-75-5)

Dimethylarsinic acid (75-60-5) + hydrogen iodide (10034-85-2) → dimethyliodoarsine (676-75-5) + water (7732-18-5) + iodine (7553-56-2)

water (7732-18-5) + iodo-dimethyl-arsine; hydriodide → dimethyliodoarsine (676-75-5) + hydrogen iodide (10034-85-2)

arsenic + methyl iodide (74-88-4) → dimethyliodoarsine (676-75-5) + arsenic triiodide (7784-45-4) + tetramethylarsonium iodide (5814-20-0) + methyldiiodoarsine (7207-97-8)

Conditions	Yield
In not given reaction of CH3I with amorphous As at room temperature;;

cacodyl sulfide (591-10-6) + dimethyl iodoborane (17933-09-4) → dimethyliodoarsine (676-75-5) + (CH3)2AsSB(CH3)2 (31732-46-4)

dimethylarsinosulfenyl iodide + triphenylphosphine (603-35-0) → dimethyliodoarsine (676-75-5) + dimethylarsino dimethyldithioarsinate (59840-68-5) + triphenylphosphine sulfide (3878-45-3)

Conditions	Yield
In chloroform-d1 for 1h;

(ClMn(CO)4)2 (18535-43-8, 15444-72-1) + dimethyliodoarsine (676-75-5) → Mn(CO)4Cl(As(CH3)2I) (480431-38-7)

Conditions	Yield
In melt Mn2(CO)8Cl2 in ampoule cooled to -196 °C, (CH3)2AsI added, held at 60 °C 4 h, cooled to room temp.; sublimated in vac., elem. anal.;	100%

pentacarbonylchloromanganese(I) (14100-30-2) + dimethyliodoarsine (676-75-5) → Mn(CO)4Cl(As(CH3)2I) (480431-38-7)

Conditions	Yield
In melt byproducts: CO; Mn(CO)5Cl in ampoule cooled to -196 °C, (CH3)2AsI added, held at 60 °C 4 h, cooled to room temp.; sublimated in vac., elem. anal.;	100%

iodo(pentacarbonyl)manganese(I) (14879-42-6) + dimethyliodoarsine (676-75-5) → Mn(CO)4I(As(CH3)2I) (70675-98-8)

Conditions	Yield
In melt byproducts: CO; Mn(CO)5I in ampoule cooled to -196 °C, (CH3)2AsI added, held at 80 °C 4 h, cooled to room temp.; sublimated in vac., elem. anal.;	100%

bromopentacarbonylmanganese(I) (14516-54-2) + dimethyliodoarsine (676-75-5) → Mn(CO)4Br(As(CH3)2I) (480431-39-8)

Conditions	Yield
In melt byproducts: CO; Mn(CO)5Br in ampoule cooled to -196 °C, (CH3)2AsI added, held at 70 °C 4 h, cooled to room temp.; sublimated in vac., elem. anal.;	100%

Mn2(CO)8I2 (15680-90-7) + dimethyliodoarsine (676-75-5) → Mn(CO)4I(As(CH3)2I) (70675-98-8)

Conditions	Yield
In melt Mn2(CO)8I2 in ampoule cooled to -196 °C, (CH3)2AsI added, held at80 °C 4 h, cooled to room temp.; sublimated in vac., elem. anal.;	100%

[Mn2Br2(CO)8] (18535-44-9) + dimethyliodoarsine (676-75-5) → Mn(CO)4Br(As(CH3)2I) (480431-39-8)

Conditions	Yield
In melt Mn2(CO)8Br2 in ampoule cooled to -196 °C, (CH3)2AsI added, held at 70 °C 4 h, cooled to room temp.; sublimated in vac., elem. anal.;	100%

dimethyliodoarsine (676-75-5) + AsF5 → Diiodo(dimethyl)arsen(V)-hexafluoroarsenat (126949-78-8)

Conditions	Yield
With iodine monofluoride In trichlorofluoromethane 1.) -78 deg C, 15 min, 2.) RT, 30 min;	95%

dimethyliodoarsine (676-75-5) + 3,4,6-tri-O-benzoyl-2-deoxy-1-thio-β-D-arabino-hexopyranose (75744-91-1) → 3,4,6-tri-O-benzoyl-2-deoxy-1-S-dimethylarsino-1-thio-β-D-arabino-hexopyranose (75744-95-5)

Conditions	Yield
With pyridine In dichloromethane Heating;	90%

dimethyliodoarsine (676-75-5) + C22H16(2-)*2C6H16N2*2Li(1+) → 2,2'-bis(dimethylarsinomethyl)-1,1'-binaphthyl (121334-94-9)

Conditions	Yield
In tetrahydrofuran Ambient temperature;	90%

(η(5)-cyclopentadienyl)W(CO)2(C(CH3)) + dimethyliodoarsine (676-75-5) → carbonyliodo(η5cyclopentadienyl)(η3-dimethylarsino-methylketen)tungsten

Conditions	Yield
In dichloromethane (Ar); addn. of org. compd. to W-complex in CH2Cl2, stirring (-78°C); pptn. on addn. of ether/pentane, recryst. (CH2Cl2/ether/pentane), drying (high vac., room temp.); elem. anal.;	86%

carbonyl(η5-cyclopentadienyl)(η2-4-methylphenylketenyl)trimethylphosphinetungsten + dimethyliodoarsine (676-75-5) → Carbonyl(η5-cyclopentadienyl)[(dimethylarsino)(4-methylphenyl)keten]iodo(trimethylphosphan)wolfram (86508-28-3)

Conditions	Yield
In dichloromethane under Ar, dropping of AsI(CH3)2 to the solution of η2-ketenyl complex in dichloromethane at room temp., stirred for 1 h; evapn. in vac., extn. with ether/pentane, recrystn. evapn. in vac., elem. anal.;	85%

(C5H5)W(CO)(P(CH3)3)(CH3CCO) + dimethyliodoarsine (676-75-5) → Carbonyl(η5-cyclopentadienyl)[(dimethylarsino)methylketen]iodo(trimethylphosphan)wolfram (89672-92-4)

Conditions	Yield
In dichloromethane under Ar, dropping of AsI(CH3)2 to the solution of η2-ketenyl complex in dichloromethane at room temp., stirred for 1 h; evapn. in vac., extn. with ether/pentane, recrystn. evapn. in vac., elem. anal.;	82%

(tris(2-diphenylphosphinoethyl)amin)Pd (107087-45-6, 86013-21-0) + dimethyliodoarsine (676-75-5) + sodium tetraphenyl borate (143-66-8) → {(N(CH2CH2P(C6H5)2)3)PdAs(CH3)2}(1+)*B(C6H5)4(1-)={(N(CH2CH2P(C6H5)2)3)PdAs(CH3)2}B(C6H5)4 (132108-07-7)

Conditions	Yield
In ethanol; benzene byproducts: NaI; Room temp. reaction of (np3)Pd with equimolar quantities of Me2AsI in benzene-ethanol soln. under a nitrogen atmosphere.;	80%

(tris(2-diphenylphosphinoethyl)amin)Pt(PPh3) (123224-08-8) + dimethyliodoarsine (676-75-5) + sodium tetraphenyl borate (143-66-8) → {(N(CH2CH2P(C6H5)2)3)PtAs(CH3)2}(1+)*B(C6H5)4(1-)={(N(CH2CH2P(C6H5)2)3)PtAs(CH3)2}B(C6H5)4 (132108-28-2)

Conditions	Yield
In ethanol; benzene byproducts: NaI; Room temp. reaction of (np3)Pt(PPh3) with equimolar quantities of Me2AsI in benzene-ethanol soln. under a nitrogen atmosphere.;	80%

(benzene)tricarbonylchromium (697302-50-4, 697302-51-5, 12082-08-5, 697302-53-7) + dimethyliodoarsine (676-75-5) → (η6-phenyl)tricarbonylchromium dimethylarsine (186464-78-8)

Conditions	Yield
With n-C4H9Li In tetrahydrofuran (Ar); addn. of n-BuLi in hexane to cold soln. of Cr-complex in THF at .-78°C; stirred for 60 min; addn. of Me2AsI in THF; stirred for 60 min at -78°C; slowly warmed to room temp.;; filtration (through SiO2); solvent removed (reduced pressure); crystn. (hexane/CH2Cl2); elem. anal.;	70%
With BuLi In tetrahydrofuran; hexane Ar-atmosphere; addn. of 1 equiv. BuLi (in hexane) to Cr-complex (in THF)at -78°C, stirring (-78°C), addn. of arsine, stirring (-7 8°C, then room temp.); evapn., dissoln. in CH2Cl2, filtration, evapn.; elem. anal.;	70%

N,N'-dimethylbenzylamine (103-83-3) + dimethyliodoarsine (676-75-5) → (2-dimethylarsanyl-benzyl)-dimethyl-amine

Conditions	Yield
Stage #1: N,N'-dimethylbenzylamine With n-butyllithium In diethyl ether; hexane for 24h; Stage #2: dimethyliodoarsine In diethyl ether for 5h;	67%
Stage #1: N,N'-dimethylbenzylamine With n-butyllithium Stage #2: dimethyliodoarsine

hexaaquanickel(II) perchlorate + dimethyliodoarsine (676-75-5) + sodium (7440-23-5) + (+/-)-1-Chloro-2-(methylphenylphosphino)benzene (167384-01-2) → [Ni((+/-)-1-(dimethylarsino)-2-(methylphenylphosphino)benzene)2][ClO4]2

Conditions

Yield

In acetone byproducts: tetramethyldiarsane, methyldiphenylphosphine, methylphenylphosphine; Ar-atmosphere; addn. of Na-foil to Me2AsI (in THF), filtration, addn. to chlorophosphine (-78°C), stirring for 48 h (-20°C), evapn., treatment with CH2Cl2/H2O, evapn. of org. layer, fractional distn., treatment with Ni(ClO4)2 (pptn.); collection, washing (Et2O), drying (vac.); second crop on evapn. of filtrate, extn. into Et2O and addn. of Ni(ClO4)2 (in acetone soln.); elem. anal.;

67%

1-diphenylphosphinomethyl-1,2-dicarba-closo-dodecaborane (36989-07-8) + dimethyliodoarsine (676-75-5) → 1-dimethylarsino-2-diphenylphosphinomethyl-o-carborane (93370-16-2)

Conditions	Yield
With hydrogenchloride; n-butyllithium In benzene inert atmosphere; dropwise addn. of BuLi soln. to B-compd., mixt. stirring (1h), Me2AsCl addn., mixt. heating until reaction complete, cooling,treatment with dild. HCl; extn. (ether), extract drying (Na2SO4), evapn., residue chromy. (silicagel); elem. anal.;	66%

dimethyliodoarsine (676-75-5) + bis-(2-chloroethyl)amine hydrochloride (821-48-7) → bis<-2(dimethylarsinoethyl)>amine (117013-44-2)

Conditions	Yield
In tetrahydrofuran for 3h;	65%

dimethyliodoarsine (676-75-5) + 1,3,4-tri-O-acetyl-2-deoxy-6-thio-β-D-arabino-hexopyranose (75745-01-6) → 1,3,4-tri-O-acetyl-2-deoxy-6-S-dimethylarsino-6-thio-β-D-arabino-hexopyranose (75745-02-7)

Conditions	Yield
With pyridine In toluene for 1h; Heating;	65%

Fe3(CO)9(SC(CH3)3)(1-)*(CH3)3CNH3(1+)=(Fe3(CO)9(SC(CH3)3))((CH3)3CNH3) + dimethyliodoarsine (676-75-5) → Fe2(CO)6(SC(CH3)3)(As(CH3)2) + Fe3(CO)9(μ3-S-t-C4H9)(μ2-As(CH3)2) (87511-05-5)

Conditions	Yield
In diethyl ether; toluene byproducts: [H3N(t-C4H9)]I; under N2, Fe complex dissolved at 20°C in Et2O, treated with toluene, Me2AsI added, stirred for 1 h at room temp.; SiO2 added, dried in high vac., chromd. (SiO2, -20°C, n-pentane/toluene), evapd., recrystd. from toluene at -30°C; elem. anal.;	A n/a B 64%

1-{(dimethylarsino)methyl}-o-carbaborane (77308-89-5) + dimethyliodoarsine (676-75-5) → 1-(dimethylarsino)-2-[(dimethylarsino)methyl]-o-carbaborane (93640-20-1)

Conditions	Yield
With hydrogenchloride; n-butyllithium In benzene inert atmosphere; dropwise addn. of BuLi soln. to B-compd., mixt. stirring (1h), Ph2PCl addn., mixt. heating until reaction complete, cooling, treatment with dild. HCl; extn. (ether), extract drying (Na2SO4), evapn., residue chromy. (silicagel); elem. anal.;	62%

dimethyliodoarsine (676-75-5) + C8H20Li4N4P4 (79807-06-0) → 2,4,6,8-Tetrakis-dimethylarsanylmethyl-2,4,6,8-tetramethyl-2λ5,4λ5,6λ5,8λ5-[1,3,5,7,2,4,6,8]tetrazatetraphosphocine (79807-01-5)

Conditions	Yield
With potassium fluoride In diethyl ether at -78℃; for 0.166667h;	55%

ethyleneimine (151-56-4) + dimethyliodoarsine (676-75-5) → (2-aminoethyl)-dimethylarsine

Conditions	Yield
With sodium In tetrahydrofuran at 35℃; for 60h;	51%

dimethyliodoarsine (676-75-5) + (R)-2,3-dibenzyloxypropyl 5-bromo-5-deoxy-2,3-O-isopropylidene-β-D-riboside (175877-63-1) → (R)-2,3-dibenzyloxypropyl 5-deoxy-5-dimethylarsino-2,3-O-isopropylidene-β-D-riboside (370860-10-9)

Conditions	Yield
Stage #1: dimethyliodoarsine With sodium In tetrahydrofuran at 20℃; for 1.5h; Stage #2: (R)-2,3-dibenzyloxypropyl 5-bromo-5-deoxy-2,3-O-isopropylidene-β-D-riboside In tetrahydrofuran for 1h;	41%

dimethyliodoarsine (676-75-5) + (R)-2,3-dibenzyloxypropyl 5-chloro-5-deoxy-2,3-O-isopropylidene-β-D-riboside (370860-11-0) → (R)-2,3-dibenzyloxypropyl 5-deoxy-5-dimethylarsino-2,3-O-isopropylidene-β-D-riboside (370860-10-9)

Conditions	Yield
Stage #1: dimethyliodoarsine With sodium In tetrahydrofuran at 20℃; for 1.5h; Stage #2: (R)-2,3-dibenzyloxypropyl 5-chloro-5-deoxy-2,3-O-isopropylidene-β-D-riboside In tetrahydrofuran for 3h;	41%

(R)-N,N-dimethyl-1-ferrocenylethylamine (31886-58-5) + dimethyliodoarsine (676-75-5) → Fe(C5H5)(C5H3)CHCH3N(CH3)2As(CH3)2

Conditions	Yield
With n-butyllithium In diethyl ether the amine was stirred with n-BuLi in diethyl ether for 1.5 h, then the halide was added and stirred for 3 h; aq. slurry of NaHCO3 was added and stirred for 1 h before filtration. the ppt. was washed with ether, the filtrate and washings were washed with water, the organic layer was dried over K2CO3 and evapd., then chromd.; elem. anal.;	40%

(3,3,3-trifluoro propinyl) magnesiumiodide + dimethyliodoarsine (676-75-5) → Dimethyl-trifluoroprop-1-ynyl-arsane (6618-08-2)

Conditions	Yield
In diethyl ether reaction at 20°C, 2 hours;;	35%
In diethyl ether reaction at 20°C, 2 hours;;	35%

Upstream product

• 5814-21-1 tetramethyl-arsonium; triiodide 
• 74-88-4 methyl iodide 
• 75-60-5 Dimethylarsinic acid 
• 10034-85-2 hydrogen iodide 
• 591-10-6 cacodyl sulfide 
• 17933-09-4 dimethyl iodoborane 
• 124-65-2 sodium cacodylate 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 
• 7647-01-0 hydrogenchloride 
• 7207-97-8 methyldiiodoarsine 
• 6618-05-9 Tri-methylsilyl-(dimethyl)-arsan 
• 696-26-4 dimethylphenylarsine 
• 471-35-2 tetramethyldiarsine 

Downstream Products

• 696-26-4 dimethylphenylarsine 
• 52120-01-1 o-(CH₃)2AsC₆H₄N(CH₃)2 
• 33733-72-1 (CH₃)2As{p-C₆H₄N(CH₃)2} 
• 112325-19-6 diphenyl-(2-dimethylarsino-phenyl)-arsine 
• 108724-58-9 As,As-diethyl-As',As'-dimethyl-As,As'-o-phenylene-di-arsine 
• 860240-87-5 dimethyl-[2]naphthyl-arsine 
• 20690-67-9 (4-bromo-phenyl)-dimethyl-arsine 
• 113924-89-3 1,3-dimethyl-2-<2-(dimethylarsino)phenyl>imidazolidine 
• 7553-56-2 iodine 
• 93370-16-2 1-dimethylarsino-2-diphenylphosphinomethyl-o-carborane 
• 132108-28-2 {(N(CH₂CH₂P(C₆H₅)2)3)PtAs(CH₃)2}⁽¹⁺⁾*B(C₆H₅)4^(1-)={(N(CH₂CH₂P(C₆H₅)2)3)PtAs(CH₃)2}B(C₆H₅)4 
• 132108-07-7 {(N(CH₂CH₂P(C₆H₅)2)3)PdAs(CH₃)2}⁽¹⁺⁾*B(C₆H₅)4^(1-)={(N(CH₂CH₂P(C₆H₅)2)3)PdAs(CH₃)2}B(C₆H₅)4 
• 55094-22-9 dimethylarsinous acid 

Relevant articles and documents

Characterization and Mechanistic Study of the Radical SAM Enzyme ArsS Involved in Arsenosugar Biosynthesis

Arsenosugars are a group of arsenic-containing ribosides that are found predominantly in marine algae but also in terrestrial organisms. It has been proposed that arsenosugar biosynthesis involves a key intermediate 5′-deoxy-5′-dimethylarsinoyl-adenosine (DDMAA), but how DDMAA is produced remains elusive. Now, we report characterization of ArsS as a DDMAA synthase, which catalyzes a radical S-adenosylmethionine (SAM)-mediated alkylation (adenosylation) of dimethylarsenite (DMAsIII) to produce DDMAA. This radical-mediated reaction is redox neutral, and multiple turnover can be achieved without external reductant. Phylogenomic and biochemical analyses revealed that DDMAA synthases are widespread in distinct bacterial phyla with similar catalytic efficiencies; these enzymes likely originated from cyanobacteria. This study reveals a key step in arsenosugar biosynthesis and also a new paradigm in radical SAM chemistry, highlighting the catalytic diversity of this superfamily of enzymes.

The Reaction of Bunsen's Cacodyl Disulfide, Me2As(S)-S-AsMe2, with Iodine: Preparation and Properties of Dimethylarsinosulfenyl Iodide, Me2As-S-I

Bunsen's cacodyl disulfide, Me2As(S)-S-AsMe2 (1), reacted with iodine giving the novel dimethylarsinosulfenyl iodide, Me2As-S-I (3) although theoretical calculations indicated that the AsV compound Me2As(S)-I (4) was more stable in the gas phase. The oily product was stable neat and as a solution in CDCl3 at +4 °C and -20 °C for at least 15 d. Light, H2O, H2O2, and Zn dust, but not NaI or Ag, decomposed it. Compound 3 did not interact with Ph3N, with Ph2NH and PhNH2 it interacted but not reacted. 3 was decomposed by piperidine, with pyridine and 4-dimethylaminopyridine it interacted and produced Me2As-SS-AsMe2 (2) and I2 that formed charge transfer complexes Base·I2, whereas Et3N decomposed 3, and 3Et3N·2I2 was isolated. 3 was desulfurized by Ph3P and (Me2N)3P completely, and by (PhO)3P and (PhS)3P partially. The reactions of 3 with (Me2N)3P, (PhS)3P, and (EtO)3P were complicated. From the AsIII nucleophiles, only Ph3As was bound, while (PhS)3As reacted slowly in a complicated manner with 3. No interaction of 3 with MeOH or PhOH was observed but NaOH, Ag2O, and PhONa decomposed it. Thiophenol produced traces of Me2As-SPh (10) and sodium thiophenolate attacked mainly at AsIII of 3. Thus, externally stabilized sulfenium ions of the type Me2As-S-Nu+I- were not obtained.