5810-42-4

Basic information

• Product Name: Tetrapropyl ammonium chloride
• Synonyms: TETRAPROPYLAMMONIUMCHLORIDE,94%;Tetra-n-propylammoniumchloride,98%;1-PROPANAMINIUM,N,N,N-TRIPROPYL-,CHLORIDE;Tetra-n-propylammonium chloride, 99+%;Tetrapropylazanium chloride;Tetrapropylaminium·chloride;TetrapropylaMMoniuM chloride 98%;N3,3,3,3Cl
• CAS NO: 5810-42-4
• Molecular Formula: C₁₂H₂₈N*Cl
• Molecular Weight: 221.81
• EINECS: 227-375-5
• Product Categories: quarternary ammonium salts;Ammonium Chlorides (Quaternary);Quaternary Ammonium Compounds;Ammonium Salts;Greener Alternatives: Catalysis;Phase Transfer Catalysts;Quaternary ammonium salt
• Mol File: 5810-42-4.mol
• Article Data: 0

Chemical Properties

• Melting Point: 240-242 °C(lit.)
• Boiling Point: 358.03°C (rough estimate)
• Appearance: White/Crystals
• Density: 0.9461 (rough estimate)
• Refractive Index: 1.5868 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Soluble in water, acetone
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents. Protect from moisture.
• BRN: 3567732
• CAS DataBase Reference: Tetrapropyl ammonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrapropyl ammonium chloride(5810-42-4)
• EPA Substance Registry System: Tetrapropyl ammonium chloride(5810-42-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 5810-42-4(Hazardous Substances Data)

Usage

Chemical Properties

solid

Uses

Tetra-n-propylammonium chloride is used as phase-transfer type applications.

InChI:InChI=1/C22H16N2O3S/c1-27-19-12-11-14-7-5-6-10-16(14)17(19)13-18-20(25)23-22(28)24(21(18)26)15-8-3-2-4-9-15/h2-13H,1H3,(H,23,25,28)/b18-13-

Synthetic route

3,5-bis(bis[(N'-tert-butylureayl)-N-ethyl]aminomethyl)-1H-pyraze (887280-10-6) + Tetrapropylammonium chloride (5810-42-4) + water (7732-18-5) + cobalt(II) chloride (7646-79-9) → tetrapropylammonium μ-hydroxo-μ-(3,5-bis(bis[(N'-tert-butylureaylato)-N-ethyl]aminatomethyl)-1H-pyrazolato)dicobaltate(II)

Conditions	Yield
With KH In N,N-dimethyl acetamide byproducts: KCl; (Ar); a soln. of ligand treated with KH, CoCl2 added, stirred for 30 min, H2O added, stirred for 30 min, N(C3H7)4Cl added, stirred for 1 h; evapd. (vac., at room temp.), washed (Et2O), dried (vac.), dissolved in CH2Cl2, filtered, evapd. (vac.); elem. anal.;	99%

acetamide (60-35-5) + 3,5-bis(bis[(N'-isopropylureayl)-N-ethyl]aminomethyl)-1H-pyraze (887280-12-8) + Tetrapropylammonium chloride (5810-42-4) + cobalt(II) chloride (7646-79-9) → tetrapropylammonium μ-1,3-acetamido-μ-(3,5-bis(bis[(N'-isopropylureaylato)-N-ethyl]aminatomethyl)-1H-pyrazolato)dicobaltate(II)

Conditions	Yield
With KH In N,N-dimethyl acetamide byproducts: KCl; (Ar); a soln. of C3H2N2(CH2N(C2H4NHC(O)NHCH(CH3)2)2)2 treated with KH, CoCl2 added, stirred, acetamide added, stirred, N(C3H7)4Cl added, stirred; evapd. (vac., at room temp.), washed (Et2O), dried (vac.), dissolved in CH2Cl2, filtered, evapd. (vac.); elem. anal.;	99%

acetamide (60-35-5) + 3,5-bis(bis[(N'-tert-butylureayl)-N-ethyl]aminomethyl)-1H-pyraze (887280-10-6) + Tetrapropylammonium chloride (5810-42-4) + cobalt(II) chloride (7646-79-9) → tetrapropylammonium μ-1,3-acetamido-μ-(3,5-bis(bis[(N'-tert-butylureaylato)-N-ethyl]aminatomethyl)-1H-pyrazolato)dicobaltate(II)

Conditions	Yield
With KH In N,N-dimethyl acetamide byproducts: KCl; (Ar); a soln. of C3H2N2(CH2N(C2H4NHC(O)NHC(CH3)3)2)2 treated with KH, CoCl2 added, stirred for 30 min, acetamide added, stirred for 30 min, N(C3H7)4Cl added, stirred for 1 h; evapd. (vac., at room temp.), washed (Et2O), dried (vac.), dissolved in CH2Cl2, filtered, evapd. (vac.);	99%

N,N-dimethyl acetamide (127-19-5) + 3,5-bis(bis[(N'-isopropylureayl)-N-ethyl]aminomethyl)-1H-pyraze (887280-12-8) + Tetrapropylammonium chloride (5810-42-4) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) → tetrapropylammonium μ-1,3-acetato-μ-(3,5-bis(bis[(N'-isopropylureaylato)-N-ethyl]aminatomethyl)-1H-pyrazolato)dicobaltate(II) N,N-dimethylacetamide adduct (1/1)

Conditions	Yield
With KH In N,N-dimethyl acetamide byproducts: KCl, KCH3COO; (Ar); a soln. of C3H2N2(CH2N(C2H4NHC(O)NHC(CH3)3)2)2 treated with KH, Cosalt added, stirred, N(C3H7)4Cl added, stirred; evapd. (vac., at room temp.), washed (Et2O), dried (vac.), dissolved in CH2Cl2, filtered, evapd. (vac.); elem. anal.;	99%

N,N-dimethyl acetamide (127-19-5) + 3,5-bis(bis[(N'-tert-butylureayl)-N-ethyl]aminomethyl)-1H-pyraze (887280-10-6) + Tetrapropylammonium chloride (5810-42-4) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) → tetrapropylammonium μ-1,3-acetato-μ-(3,5-bis(bis[(N'-tert-butylureaylato)-N-ethyl]aminatomethyl)-1H-pyrazolato)dicobaltate(II) N,N-dimethylacetamide adduct (1/1)

Conditions	Yield
With KH In N,N-dimethyl acetamide byproducts: KCl, KCH3COO; (Ar); a soln. of C3H2N2(CH2N(C2H4NHC(O)NHC(CH3)3)2)2 treated with KH, Cosalt added, stirred for 30 min, N(C3H7)4Cl added, stirred for 1 h; evapd. (vac., at room temp.), washed (Et2O), dried (vac.), dissolved in CH2Cl2, filtered, evapd. (vac.); elem. anal.;	99%

dichloromethane (75-09-2) + 3-(bis[(N'-tert-butylureaylato)-N-ethyl]aminatomethyl)-5-tert-butyl-1H-pyrazole (1000006-56-3) + Tetrapropylammonium chloride (5810-42-4) + water (7732-18-5) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) → tetrapropylammonium 3-(bis[(N'-tert-butylureaylato)-N-ethyl]aminatomethyl)-5-tert-butyl-1H-pyrazolato(hydroxo)cobaltate(II) dichloromethane adduct (1/0.8)

Conditions	Yield
With KH In N,N-dimethyl acetamide byproducts: KCl; (Ar); a soln. of ligand treated with KH, Co salt added, stirred, filtered, H2O added, stirred for 30 min, N(C3H7)4Cl added, stirred for 1 h; dissolved in CH2Cl2, filtered, evapd. (vac.), washed (Et2O/pentane), dried (vac.); elem. anal.;	95%

1,10-bis(phenyliodonium)-closo-decaborate + Tetrapropylammonium chloride (5810-42-4) → B10H8I2(2-)*2C12H28N(1+)

Conditions	Yield
Stage #1: 1,10-bis(phenyliodonium)-closo-decaborate With n-butyllithium In tetrahydrofuran; hexane at -10 - -5℃; for 1h; Inert atmosphere; Stage #2: Tetrapropylammonium chloride Inert atmosphere;	95%

dichloromethane (75-09-2) + 3,5-bis(bis[(N'-isopropylureayl)-N-ethyl]aminomethyl)-1H-pyraze (887280-12-8) + Tetrapropylammonium chloride (5810-42-4) + water (7732-18-5) + cobalt(II) chloride (7646-79-9) → tetrapropylammonium μ-hydroxo-μ-(3,5-bis(bis[(N'-isopropylureaylato)-N-ethyl]aminatomethyl)-1H-pyrazolato)dicobaltate(II) dichloromethane adduct (10/1)

Conditions	Yield
With KH In N,N-dimethyl acetamide byproducts: KCl; (Ar); a soln. of ligand treated with KH, CoCl2 added, stirred, H2O added, stirred, N(C3H7)4Cl added, stirred; evapd. (vac., at room temp.), washed (Et2O), dried (vac.), dissolved in CH2Cl2, filtered, evapd. (vac.); elem. anal.;	94%

potassium hexacyanocobaltate(III) + trimethyltin(IV)chloride (1066-45-1) + Tetrapropylammonium chloride (5810-42-4) → (C3H7)4N(1+)*2Sn(CH3)3(1+)*Co(CN)6(3-)*2H2O=N(C3H7)4(Sn(CH3)3)2Co(CN)6*2H2O

Conditions	Yield
In water K3Co(CN)6 in H2O was added under stirring to soln. of ligand and Sn-complex in H2O, 15 min; filtered, washed with H2O, dried at room temp. for ca. 10 h; elem. anal.;	90%

[(Me3Sn)3Fe(CN)6]n + Tetrapropylammonium chloride (5810-42-4) → (C3H7)4N(1+)*2Sn(CH3)3(1+)*Fe(CN)6(3-)*2H2O=N(C3H7)4(Sn(CH3)3)2Fe(CN)6*2H2O

Conditions	Yield
In water SnFe-complex was reacted with ligand in H2O, stirred for 12 h; filtered, washed with H2O, dried; elem. anal.;	90%

sodium hexachlororhodate(III) + Tetrapropylammonium chloride (5810-42-4) → tetra(n-propyl)ammonium dicarbonyldichlororhodate(I) (66197-27-1)

Conditions	Yield
With CO; HCl In hydrogenchloride stirring Rh-complex (in concd. HCl) under CO for 2 d, addn. of Pr4NCl (in CH2Cl2), shaking; sepn. of org. layer, drying (MgSO4), crystn. on Et2O addn.; elem. anal.;	90%

thionyl chloride (7719-09-7) + Nb6(14+)*14Cl(1-)*8H2O + Tetrapropylammonium chloride (5810-42-4) → [tetrapropylammonium]2[Nb6Cl18]

Conditions	Yield
for 6h; Reflux;	90%

Tetrapropylammonium chloride (5810-42-4) + dihydrogen peroxide (7722-84-1) + ortho-tungstic acid → ClH2O6W(1-)*C12H28N(1+) (1447968-67-3)

Conditions	Yield
Stage #1: dihydrogen peroxide; ortho-tungstic acid In water at 31.84℃; for 0.5h; Stage #2: Tetrapropylammonium chloride With hydrogenchloride In water at -0.16℃; for 0.666667h;	88%

Tetrapropylammonium chloride (5810-42-4) + antimony(III) chloride (10025-91-9) → tetrapropylammonium tetrachloroantimonate(III)

Conditions	Yield
In further solvent(s) solvent: 1.2-C2H4Cl2; dropwise addn. of SbCl3 soln. at room temp. with stirring; 1 h; filtration; crystn. from 1.2-C2H4Cl2 or EtOH; elem. anal.;	85%

[Mo3S4Br3((2-aminoethyl)diphenylphosphine)3]Br + Tetrapropylammonium chloride (5810-42-4) → [W3S4Cl3((2-aminoethyl)diphenylphosphine)3]Br

Conditions	Yield
In acetonitrile at 20℃; for 1h; Inert atmosphere; Schlenk technique; Reflux;	82%

Tetrapropylammonium chloride (5810-42-4) + sodium 4-styrenesulfonate (2695-37-6) → C8H7O3S(1-)*C12H28N(1+)

Conditions	Yield
In dichloromethane; water	81%

Re6Se5Cl8 + Tetrapropylammonium chloride (5810-42-4) → N(CH2CH2CH3)4(1+)*Re6Se5Cl9(1-)={N(CH2CH2CH3)4}{Re6Se5Cl9}

Conditions	Yield
In N,N-dimethyl-formamide (N2); mixture in DMF is heated at 60°C for 18 h; filtration, addn. of ether to the filtrate, after 3 d solid is washed (acetonitrile, ether), recrystn. (hot acetonitrile), elem. anal.;	80%

W6Cl18 + Tetrapropylammonium chloride (5810-42-4) → 2N(CH2CH2CH3)4(1+)*W6Cl18(2-)=(N(CH2CH2CH3)4)2W6Cl18

Conditions	Yield
With methanol In methanol addn. of a soln. of ammonium salt in methanol to a soln. of W6Cl18 in methanol; sepn. of ppt.;	80%

Re6Se6Cl6 + Tetrapropylammonium chloride (5810-42-4) → 2N(CH2CH2CH3)4(1+)*Re6Se6Cl8(2-)={N(CH2CH2CH3)4}2{Re6Se6Cl8}

Conditions	Yield
In acetonitrile (N2); mixture in acetonitrile is refluxed for 24 h; addn. of ether, solid is collected, recrystd. by ether diffusion into a soln. of DMF, after 5 d solid is collected, washed (ether), dried, elem. anal.;	78%

sodium polyselenide + Tetrapropylammonium chloride (5810-42-4) + silver nitrate → 2(CH3CH2CH2)4N(1+)*{Ag4(Se4)3}(2-) = {(CH3CH2CH2)4N}2{Ag4(Se4)3}

Conditions	Yield
In N,N-dimethyl-formamide filtering, addn. of ether, elem. anal.;	75%

1.5(CH3)2Sn(CH2)3Sn(CH3)2(2+)*Co(CN)6(3-)=[((CH3)2Sn(CH2)3Sn(CH3)2)1.5Co(CN)6] + Tetrapropylammonium chloride (5810-42-4) → (CH3)3Sn(H2O)(1+) (129732-09-8) + (C3H7)4N(1+)*((CH3)2Sn(H2O)(CH2)3Sn(CH3)2(H2O))Co(CN)6(1-)=[(C3H7)4N][((CH3)2Sn(H2O)(CH2)3Sn(CH3)2(H2O))Co(CN)6]

Conditions	Yield
In water; acetonitrile (Me2Sn(CH2)3SnMe)1.5Co(CN)6 suspended in soln. of (n-Pr)4NCl in H2O (plus a few drops of MeCN; stirred for 24 h; filtered; washed (cold H2O); dried; elem. anal.;	A n/a B 75%

phenyl trimethylsilyl selenide (33861-17-5) + Tetrapropylammonium chloride (5810-42-4) + cadmium(II) chloride (10108-64-2) → 2N(C3H7)4(1+)*Cd4(SeC6H5)6Cl4(2-)=(N(C3H7)4)2Cd4(SeC6H5)6Cl4

Conditions	Yield
In dichloromethane CdCl2, N(nPr)4Cl were dissolved in CH2Cl2, ligand was added, stirred overnight, Et2O was added; elem. anal.;	70%

Tetrapropylammonium chloride (5810-42-4) + zinc (7440-66-6) → [(C3H7)4N](1+)*[C6H5ZnCl2](1-)=[(C3H7)4N][C6H5ZnCl2] (73104-38-8)

Conditions	Yield
With C6H5Cl In acetonitrile; benzene Electrolysis; (N2); electrolysis of soln. of arylhalogenide and Pr4NBr in MeCN/benzene with Zn anode during 6 h; filtered soln. was pptd. by addn. of Et2O, ppt. washed with PE and dried; elem. anal.;	69%

Re6Se4Cl10 + Tetrapropylammonium chloride (5810-42-4) → 2N(CH2CH2CH3)4(1+)*Re6Se4O2Cl8(2-)={N(CH2CH2CH3)4}2{Re6Se4O2Cl8}

Conditions	Yield
With H2O In N,N-dimethyl-formamide (N2); mixture in DMF containing water is heated at 60°C for 18 h; filtration, addn. of ether, obtained oil is washed (acetonitrile, ether), obtained powder is dissolved in DMF, ether is diffused for 7 d, crystals are washed (ether);	66%

Re4Se4(TeCl2)4Cl8 + Tetrapropylammonium chloride (5810-42-4) + water (7732-18-5) + acetonitrile (75-05-8) → [N(C3H7)4]2[Re4Se4(acetamido)2Cl8]

Conditions	Yield
In acetonitrile reflux (1 h); filtration, concn. (in air, room temperature), dissolution (CH3CN), recrystn. (CH3CN/toluene), filtration, washing (MeOH and ether), drying; elem. anal.;	66%

Trifluoromethanesulfonyl fluoride (335-05-7) + Tetrapropylammonium chloride (5810-42-4) + methylmagnesium chloride (676-58-4) → tetrapropylammonium tris(trifluoromethanesulfonyl)methide (227098-73-9)

Conditions	Yield
Stage #1: Trifluoromethanesulfonyl fluoride; methylmagnesium chloride In tetrahydrofuran at 0 - 50℃; Inert atmosphere; Stage #2: Tetrapropylammonium chloride In tetrahydrofuran; water	62%

piperidine (110-89-4) + Tetrapropylammonium chloride (5810-42-4) + platinum(II) chloride + piperidinium (2,7-dimethoxy-9H-fluoren-9-ylidine)methanedithioate (817163-84-1) → [NPr4]2[Pt(2,7-dimethoxyfluoren-9-ylidene)methanedithiolato)2]

Conditions	Yield
In dichloromethane byproducts: colloidal Pt, piperidinium chloride; room temp.; to a suspn. of PtCl2 in CH2Cl2 were added piperidine and ammonium-compound, the soln. was filtered through Celite, dithioate was added, the mixt. was stirred for 1 h; partially evapd., the solid was filtered off, washed with CH2Cl2 and methanol, vac.-dried; elem. anal.;	60%

3,5-bis(bis[(N'-isopropylureayl)-N-ethyl]aminomethyl)-1H-pyraze (887280-12-8) + Tetrapropylammonium chloride (5810-42-4) + cobalt(II) chloride (7646-79-9) → [nPr4N]2[Co(II)2H4P(iPr)buam(μ-Cl)]

Conditions	Yield
With potassium hydride In N,N-dimethyl acetamide byproducts: KCl; (under Ar); KH in N,N-dimethylacetamide added to ligand at room temp., CoCl2 added at room temp., (CH3CH2CH2)4NCl added;	60%

3,5-bis(bis[(N'-tert-butylureayl)-N-ethyl]aminomethyl)-1H-pyraze (887280-10-6) + Tetrapropylammonium chloride (5810-42-4) + cobalt(II) chloride (7646-79-9) → [nPr4N]2[Co(II)2H4P(tBu)buam(μ-Cl)]

Conditions	Yield
With potassium hydride In N,N-dimethyl acetamide byproducts: KCl; (under Ar); KH in N,N-dimethylacetamide added to ligand at room temp., CoCl2 added at room temp., (CH3CH2CH2)4NCl added;	60%

lithium selenide (12136-60-6) + N(CH2CH2CH3)4(1+)*Re6Se5Cl9(1-)={N(CH2CH2CH3)4}{Re6Se5Cl9} + Tetrapropylammonium chloride (5810-42-4) → 2N(CH2CH2CH3)4(1+)*Re6Se6Cl8(2-)={N(CH2CH2CH3)4}2{Re6Se6Cl8}

Conditions	Yield
In tetrahydrofuran (N2); mixture is stirred for 30 min; ppt. is collected, dissolved in DMF, slow diffusion of ether for 3 d, crystals are collected;	57%

Downstream Products

• 128096-96-8 C₁₂H₂₈N⁽¹⁺⁾*C₈ClF₅N₂P^(1-) 
• 75149-54-1 tetraethylammonium pentacyanocyclopentadienide 
• 5927-80-0 bis(tetra-n-propylammonium) bis(2-mercapto-1,2-dicyanovinyl) sulfide 
• 102-69-2 tri-n-propylamine 
• 187737-37-7 propene 
• 74-98-6 propane 
• 19508-39-5 (CH₃CH₂CH₂)4N⁽¹⁺⁾*PtCl₃(P(C₆H₅)3)^(1-)=(CH₃CH₂CH₂)4N[PtCl₃(P(C₆H₅)3)] 
• 102493-30-1 (C₃H₇)4N⁽¹⁺⁾*PtCl₃(As(C₆H₅)3)^(1-)=((C₃H₇)4N)(PtCl₃(As(C₆H₅)3)) 
• 82456-81-3 N(CH₂CH₂CH₃)4⁽¹⁺⁾*Cr((C₆H₅)2AsCHCHAs(C₆H₅)2)Cl₄^(1-)=N(CH₂CH₂CH₃)4Cr((C₆H₅)2AsCHCHAs(C₆H₅)2)Cl₄ 
• 82456-81-3 tetrapropylammonium [Cr(cis-Ph₂AsCHCHAsPh₂)Cl₄] 
• 73104-38-8 [(C₃H₇)4N]⁽¹⁺⁾*[C₆H₅ZnCl₂]^(1-)=[(C₃H₇)4N][C₆H₅ZnCl₂] 
• 82469-03-2 tetra-n-propylammonium [cis-1,2-bis(diphenylphosphino)ethylene]tetrachlorochromate(III) 
• 82469-03-2 tetrapropylammonium [Cr(cis-Ph₂PCHCHPPh₂)Cl₄] 
• 82456-79-9 N(CH₂CH₂CH₃)4⁽¹⁺⁾*Cr((C₆H₅)2PCH₂CH₂P(C₆H₅)2)Cl₄^(1-)=N(CH₂CH₂CH₃)4Cr((C₆H₅)2PCH₂CH₂P(C₆H₅)2)Cl₄