506-59-2

Basic information

• Product Name: Dimethylamine hydrochloride
• Synonyms: hydrochloricaciddimethylamine;Methanamine,N-methyl-,hydrochloride;n-methylmethanaminehydrochloride;n-methyl-methanaminhydrochloride;DIMETHYLAMINE HCL;DIMETHYLAMINE HYDROCHLORIDE;DIMETHYLAMMONIUM CHLORIDE;METHANAMINE HYDROCHLORIDE
• CAS NO: 506-59-2
• Molecular Formula: C₂H₈N*Cl
• Molecular Weight: 81.54
• EINECS: 208-046-5
• Product Categories: Amine Salts;Nitrogen Compounds;Organic Building Blocks;amine series
• Mol File: 506-59-2.mol
• Article Data: 49

Chemical Properties

• Melting Point: 170-173 °C(lit.)
• Boiling Point: 95.79°C (rough estimate)
• Appearance: White to off-white/Crystalline Powder or Crystals
• Density: 0.8949 (rough estimate)
• Vapor Pressure: <0.1 hPa (25 °C)
• Refractive Index: 1.4202 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: soluble0.5g/10 mL
• Water Solubility: 3000 g/L (20 ºC)
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,3228
• BRN: 3589311
• CAS DataBase Reference: Dimethylamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethylamine hydrochloride(506-59-2)
• EPA Substance Registry System: Dimethylamine hydrochloride(506-59-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37-37/39-36
• WGK Germany: 1
• RTECS: IQ0220000
• F: 3-9
• TSCA: Yes
• Hazardous Substances Data: 506-59-2(Hazardous Substances Data)

Usage

Chemical Properties

white crystals

Uses

Different sources of media describe the Uses of 506-59-2 differently. You can refer to the following data:
1. Dimethylamine hydrochloride is a precursor to several industrially significant compounds.
2. As accelerator in vulcanizing rubber, tanning, manufacture of detergent soaps, or attracting boll weevils to exterminate them. As reagent for Mg.
3. Dimethylamine hydrochloride is used as an intermediate in the manufacture of pharmaceuticals like ranitidine and metformin, tramadol and amlodipine. It is used as a precursor of atrazine. It is associated with sodium acetate and used to carry out the Willgerodt- Kindler reaction to prepare amides. Its free base reacts with carbon disulfide to get dimethyldithiocarbamate which is used in rubber vulcanization. It is involved in the synthesis of dimethyl-(1-methyl-pyrrol-2-ylmethyl)-amine by reacting with 1-methyl pyrrole and formaldehyde.

Application

Dimethylamine hydrochloride is a raw material for organic synthesis. It is also used as a catalyst and magnesium reagent for acetylation analysis.Dimethylamine hydrochloride has been used in the preparation of hexamethylmelamine-methyl-14C. It has also been used to prepare the standard solution of methylamine (MA), dimethylamine (DMA), trimethylamine (TMA), and trimethylamine-N-oxide (TMAO) while determing methylamines and trimethylamine-N-oxide in particulate matter. Dimethylamine hydrochloride is used as an intermediate in the manufacture of pharmaceuticals like ranitidine and metformin, amlodipine. It is used as a precursor of atrazine. It is associated with sodium acetate and used to carry out the Willgerodt- Kindler reaction to prepare amides. Its free base reacts with carbon disulfide to get dimethyldithiocarbamate which is used in rubber vulcanization. It is involved in the synthesis of dimethyl-(1-methyl-pyrrol-2-ylmethyl)-amine by reacting with 1-methyl pyrrole and formaldehyde.

Flammability and Explosibility

Nonflammable

Purification Methods

Crystallise the salt from hot CHCl3 or absolute EtOH. It also recrystallises from MeOH/ether solution. Dry it in a vacuum desiccator over H2SO4, then P2O5. Hygroscopic. [Beilstein 4 IV 132.]

InChI:InChI=1/C2H7N.ClH/c1-3-2;/h3H,1-2H3;1H

Synthetic route

N,N'-dimethylbenzylamine (103-83-3) → N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With dichloromethane; hydrogen; palladium on activated charcoal In methanol at 20℃; for 24h; atmospheric pressure;	99%
With 1,1,2-trichloroethane; 10% palladium on activated carbon; hydrogen In methanol under 760.051 Torr; for 0.666667h; chemoselective reaction;	98%

({(CH3)2NH}2B(Cl)C6H5)(1+)*Cl(1-)=({(CH3)2NH}2B(Cl)C6H5)Cl (94947-35-0) → chloro(dimethylamino)phenylborane (1196-44-7) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
In neat (no solvent) pyrolysis from 150 to 200°C;;	A 94.1% B n/a
In neat (no solvent) pyrolysis from 150 to 200°C;;	A 94.1% B n/a

pentachloro-2H-pyrrole (57802-40-1) + N,N-Dimethyltrimethylsilylamine (2083-91-2) → N,N-dimethylammonium chloride (506-59-2) + 2.5-Bis-(dimethylamino).3.4-dichlor-azacyclopentadienyliumchlorid + 2.3.5-Tris-(dimethylamino)-4-chlor-azacyclopentadienyliumchlorid

Conditions	Yield
In tetrahydrofuran	A n/a B 91% C n/a

C6H19N4P*ClH + N,N-dimethyl-N',N''-bisphosphorous triamide (93766-28-0) → N,N-dimethylammonium chloride (506-59-2) + trisphosphonium chloride

Conditions	Yield
at 50℃; for 1h;	A 89% B 91%

pentan-1-ol (71-41-0) + N,N-Dimethylformamide Hydrochloride (3397-76-0, 100508-13-2) → 1-Chloropentane (543-59-9) + n-pentyl formate (638-49-3) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
at 100℃; for 0.833333h; Product distribution; different alcohols;	A n/a B 90% C n/a

H(C5H5)Mo(CO)2(P(OC2H5)2N(CH3)2) (93304-26-8) → H(C5H5)Mo(CO)2(P(OC2H5)2Cl) (93304-27-9) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With HCl In toluene dry gaseous HCl bubbled through soln. of educt in toluene at -20°C; elem. anal.;	A 70% B 90%

tantalum pentachloride (7721-01-9) + dimethyl amine (124-40-3) → mer,cis-[TaCl3(NMe2)2(NHMe2)] (77071-69-3) + TaCl2(N(CH3)2)3(HN(CH3)2) (77071-71-7) + (TaCl2(N(CH3)2)2(HN(CH3)2))2O (77071-70-6) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
In benzene dimethylamine added to frozen soln.TaCl5 in benzene at -178°C and slowly allowed to warm to room temp. and soln. stirred for 24 h under N2 atm.; Me2NH2Cl filtered, filtrate concd., pentane added slowly, crystals Ta(NMe2)2Cl3(HNMe2) filtered, filtrate allowed to stand for 10 days - Ta(NMe2)3Cl2(HNMe2) and (TaCl2(NMe2)2(HNMe2))2O; elem. anal.;	A 85% B 1.6% C 6.3% D n/a

dimethyl amine (124-40-3) + pentafluorophenyl dichlorophosphine (5032-91-7) → N,N-dimethylammonium chloride (506-59-2) + Bis-dimethylamino-pentafluorphenyl-phosphin (5032-95-1)

Conditions	Yield
In diethyl ether byproducts: HCl; in presence of a trap for HCl;	A n/a B 81.5%
In diethyl ether byproducts: HCl; in presence of a trap for HCl;	A n/a B 81.5%

dimethyl amine (124-40-3) + benzohydroximoyl chloride (698-16-8) → (E)-N,N-Dimethylbenzamid-oxim (65986-63-2) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
In diethyl ether for 48h; Ambient temperature;	A 80% B n/a

tetrakis(dimethylamido)diborane (1630-79-1) → dichlorobis(dimethylamino)diborane(4) (64541-76-0) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With HCl In diethyl ether	A 79.3% B n/a

bis(dimethylamino)cyclohexylphosphine(pentacarbonyl)chromium(0) (126306-16-9) → chlorodimethylaminocyclohexylphosphine(pentacarbonyl)chromium(0) (126306-27-2) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With hydrogenchloride In pentane Under stirring a strong stream of hydrogenhalogenide is bubbled for 10 min through the cooled (0°C) soln. of phosphine complex (inert atmosphere).; Solvent is evapd. at room temp. in vac., residue is digested with pentane, dialkylamminhydrohalogenide is filtered off, filtrate is dried to dryness in vac., recrystn. from pentane (-78°C), elem. anal.;	A 79% B n/a

bis(dimethylamino)phenylphosphine(pentacarbonyl)chromium(0) (72868-70-3) → chlorodimethylaminophenylphosphine(pentacarbonyl)chromium(0) (126306-23-8) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With hydrogenchloride In pentane Under stirring a strong stream of hydrogenhalogenide is bubbled for 10 min through the cooled (0°C) soln. of phosphins complex (inert atmosphere).; Solvent is evapd. at room temp. in vac., residue is digested with pentane, dialkylamminhydrohalogenide is filtered off, filtrate is dried to dryness in vac., chromy. (silica gel, pentane), elem. anal.;	A 74% B n/a

2-piperidino-2,4,4,6,6-pentacholorocyclotriphosphazatriene (3356-73-8) + dimethyl amine (124-40-3) → N,N-dimethylammonium chloride (506-59-2) + Dimethyl-((2S,6R)-2,4,4,6-tetrachloro-6-piperidin-1-yl-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinin-2-yl)-amine + Dimethyl-((2R,6R)-2,4,4,6-tetrachloro-6-piperidin-1-yl-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinin-2-yl)-amine

Conditions	Yield
In tetrahydrofuran	A n/a B 30% C 70%

penatchloromonoisopropylaminocyclotriphosphazatriene (3720-88-5) + dimethyl amine (124-40-3) → N,N-dimethylammonium chloride (506-59-2) + (2R,4R)-2,4,6,6-Tetrachloro-N-isopropyl-N',N'-dimethyl-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinine-2,4-diamine + (2R,4S)-2,4,6,6-Tetrachloro-N-isopropyl-N',N'-dimethyl-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinine-2,4-diamine

Conditions	Yield
	A n/a B 70% C 30%
at 30℃;	A n/a B 70% C 30%

Pentachlor--triphosphonitril (3998-23-0) + dimethyl amine (124-40-3) → N,N-dimethylammonium chloride (506-59-2) + (2R,4R)-N-Butyl-2,4,6,6-tetrachloro-N',N'-dimethyl-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinine-2,4-diamine + (2S,4R)-N-Butyl-2,4,6,6-tetrachloro-N',N'-dimethyl-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinine-2,4-diamine

Conditions	Yield
Thermodynamic data; Kinetics; ΔH (excit.), ΔS (excit.);	A n/a B 70% C 30%
at 30℃;	A n/a B 70% C 30%

Dibutyl-(2,4,4,6,6-pentachloro-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinin-2-yl)-amine (77215-38-4) + dimethyl amine (124-40-3) → N,N-dimethylammonium chloride (506-59-2) + (2R,4S)-N,N-Dibutyl-2,4,6,6-tetrachloro-N',N'-dimethyl-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinine-2,4-diamine + (2R,4R)-N,N-Dibutyl-2,4,6,6-tetrachloro-N',N'-dimethyl-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinine-2,4-diamine

Conditions	Yield
at 18 - 30℃;	A n/a B 30% C 70%

bis(trifluoromethyl)chlorophosphine (650-52-2) + dimethyl amine (124-40-3) → dimethylamino-bis-trifluoromethyl-phosphine (432-01-9) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
In gaseous matrix 0°C;	A 70% B n/a

N,N,N,N,N,N-hexamethylphosphoric triamide (680-31-9) + benzenesulfenyl chloride (931-59-9) → S-Phenyl benzenethiosulfonate (1212-08-4) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
In dichloromethane at 20℃; for 4h; Inert atmosphere;	A 70% B n/a

N,N,N,N,N,N-hexamethylphosphoric triamide (680-31-9) + 4-chloro-benzenesulfenyl chloride (933-01-7) → 4,4'-dichlorophenyl thiosulfonate (1146-44-7) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
In dichloromethane at 20℃; for 4h; Inert atmosphere;	A 70% B n/a

hexakis(dimethylamino)tetraborane(6) (26459-63-2) → pentakis(dimethylamino)chlorotetraborane(6) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With hydrogenchloride In diethyl ether -20°C;	A 65% B n/a

{(CH3)3Si}2NB{N(CH3)2}2 (32882-73-8) → Bis(trimethylsilyl)aminochlorodimethylaminoboran (32882-72-7) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With HCl In toluene sepn. of dimethylamine hydrochloride and toluene, distn.;	A 65% B n/a

dichloro(nitrosyl)[tris(3,5-dimethylpyrazolyl)-borato]molybdenum + dimethyl amine (124-40-3) → Mo(HB(Me2pyz)3)(NO)Cl(NMe2) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
In dichloromethane under N2 to Mo(HB(Me2pyz)3)(NO)Cl2 dissolved in dichloromethane added dimethylamine and mixt. stirred for 30 min; volume soln. reduced in vacuo, treated with Et2O, (NH2Me2)Cl filtered off, filtrate slowly evapd.; elem. anal.;	A 61% B n/a

dimethyl amine (124-40-3) + tris(dimethylamino)isothiocyanatophosphonium chloride → N,N-dimethylammonium chloride (506-59-2) + N'''-(dimethylthiocarbamoyl)hexamethylphosphorimidic triamide

Conditions	Yield
for 6h;	A n/a B 60%

(η5-chlorodivinylborane)(η5-cyclopentadienyl)cobalt (73939-32-9) + dimethyl amine (124-40-3) → (η5-(dimethylamino)divinylborane)(η5-cyclopentadienyl)cobalt (11486-73-0) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
In diethyl ether Under nitrogen, dimethylamine is bubbled through a stirred soln. of Co-complex in ether, ppt. of dimethylamine*HCl forms, addn. of amine is continued for 15 min.; Filtn., redn. of solvent under high vac., extn. with pentane, coolg. of the red soln. to -78°C, filtn., drying under high vac, elem. anal.;	A 54% B n/a

1,1,3,3-tetrakis(dimethylamino)-2-diethylaminotriborane(5) → diethylamino-tris(dimethylamino)chlorotriborane(5) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With hydrogenchloride In diethyl ether -20°C for 2 h; distn. at 78-82°C/1 Torr;	A 53% B n/a

1,1,3,3-tetrakis(dimethylamino)-2-dimethylamino-triboran(5) (26459-62-1) → tetrakis(dimethylamino)chlorotriborane(5) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With hydrogenchloride In diethyl ether -20°C; distn. at 70-72°C/1 Torr;	A 48% B n/a

pentafluorobenzenesulonyl chloride (832-53-1) + dimethyl amine (124-40-3) → 2,3,4,5,6-pentafluoro-N,N-dimethylbenzenesulfonamide (36650-05-2) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
In diethyl ether 20°C,20 h,in presence of Et3N;	A 42.5% B n/a
In diethyl ether 20°C,20 h,in presence of Et3N;	A 42.5% B n/a

boron trichloride (10294-34-5) + dimethyl amine (124-40-3) → dichlorodimethylaminoborane (1113-31-1) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
	A 35% B n/a

tetrakis(dimethylamido)diborane (1630-79-1) → tris(dimethylamino)monochlorodiborane(4) (7360-75-0) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With hydrogenchloride In diethyl ether -20°C; distn.;	A 28% B n/a
With HCl In diethyl ether -20°C; distn.;	A 28% B n/a
With HCl In diethyl ether -20°C;

bis(dimethylamino)-t-butylphosphine(pentacarbonyl)chromium(0) (126306-18-1) → chlorodimethylamino-t-butylphosphine(pentacarbonyl)chromium(0) (126289-56-3) + N,N-dimethylammonium chloride (506-59-2)

Conditions	Yield
With hydrogenchloride In pentane Under stirring a strong stream of hydrogenhalogenide is bubbled for 10 min through the cooled (0°C) soln. of phosphine complex (inert atmosphere).; Solvent is evapd. at room temp. in vac., residue is digested with pentane, dialkylamminhydrohalogenide is filtered off, filtrate is dried to dryness in vac., recrystn. from pentane (-78°C), not isolated.;	A 10% B n/a

2-methylimidazo[1,2-a]pyridine (934-37-2) + formaldehyd (50-00-0) + N,N-dimethylammonium chloride (506-59-2) → 3-<(dimethylamino)methyl>-2-methylimidazo<1,2-a>pyridine (133395-11-6)

Conditions	Yield
In methanol for 1.5h; Heating;	100%

N,N-dimethylammonium chloride (506-59-2) + 2-(methylsulfanyl)pyrimidine-5-carbaldehyde (90905-31-0) → 2-(N,N-dimethylamino)pyrimidine-5-carbaldehyde (55551-49-0)

Conditions	Yield
With sodium carbonate In ethanol Heating;	100%

N,N-dimethylammonium chloride (506-59-2) + 3-(β-D-ribofuranosyl)-7-(1,2,4-triazol-4-yl)pyrazolo<4,3-d>pyrimidine → 7-(dimethylamino)-3-(β-D-ribofuranosyl)pyrazolo<4,3-d>pyrimidine (13263-97-3)

Conditions	Yield
With pyridine at 57℃; for 22h;	100%

carbon disulfide (75-15-0) + N,N-dimethylammonium chloride (506-59-2) → sodium dimethyldithiocarbamate (128-04-1)

Conditions	Yield
With sodium hydroxide In methanol for 3h; Ambient temperature;	100%

N,N-dimethylammonium chloride (506-59-2) + 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methanesulfonyloxymethyl-5-pivaloylamino-4H-1-benzopyran-4-one (165180-39-2) → 7-dimethylaminomethyl-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pivaloylamino-4H-1-benzopyran-4-one (165180-41-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 0.75h; Ambient temperature;	100%
With sodium chloride; potassium carbonate In N-methyl-acetamide; water	100%
With sodium chloride; potassium carbonate In N-methyl-acetamide; water	100%

N,N-dimethylammonium chloride (506-59-2) + 2-naphthaloyl chloride (2243-83-6) → N,N-dimethyl-2-naphthylcarboxamide (13577-85-0)

Conditions	Yield
With sodium hydroxide In diethyl ether; water; ethyl acetate at 0℃; for 1h;	100%
With pyridine In dichloromethane for 20h; Substitution;	572 mg

N,N-dimethylammonium chloride (506-59-2) + 3-[1-(benzenesulfonyl)-1H-indol-4-yl]propionic acid ethyl ester (297751-32-7) → N,N-dimethyl-4-[1-(benzenesulfonyl)-1H-indol-4-yl]propionamide (297751-33-8)

Conditions	Yield
With trimethylaluminum In hexane; benzene for 18h; Heating;	100%
With hydrogenchloride; trimethylaluminum In benzene

N,N-dimethylammonium chloride (506-59-2) + 2-(2,5-dimethylpyrrolyl)-6-(4-(2-carboxymethyloxy)-1-naphthyl)pyridine (221087-71-4) → 2-(2,5-dimethylpyrrolyl)-6-((4-(N,N-dimethylcarboxamido)methyloxy)-1-naphthyl)pyridine (221087-73-6)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In acetonitrile at 20℃; for 80h;	100%

N,N-dimethylammonium chloride (506-59-2) + 2-(2,5-dimethylpyrrolyl)-6-[4-carboxymethoxy-5,6,7,8-tetrahydronaphthalen-1-yl]pyridine (221087-93-0) → 2-(2,5-dimethylpyrrolyl)-6-[4-(N,N-dimethylcarboxamido)methoxy-5,6,7,8-tetrahydronaphthalen-1-yl]pyridine (221087-95-2)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In acetonitrile at 20℃;	100%

N,N-dimethylammonium chloride (506-59-2) + trifluoroacetic acid (76-05-1) + 2-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-3-methyl-1-oxo-1,3,4,6-tetrahydro-2H-naphtho[1,2-f][1,4]oxazocine-7-carbonitrile (711020-56-3) → (3R)-2-[(2S)-2-(3,4-dichlorophenyl)-4-(dimethylamino)butyl]-3-methyl-1-oxo-1,3,4,6-tetrahydro-2H-naphtho[1,2-f][1,4]oxazocine-7-carbonitrile trifluoroacetate

Conditions	Yield
With sodium cyanoborohydride; acetic acid; triethylamine In methanol	100%

N,N-dimethylammonium chloride (506-59-2) + (S)-4-tert-Butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester (147471-66-7) → benzyl N-tert-butyloxycarbonyl-L-γ-glutamate α-N,N-dimethylamide (841233-80-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 20h;	100%

N,N-dimethylammonium chloride (506-59-2) + methyl (R)-2'-(((trifluoromethyl)sulfonyl)oxy)-[1,1'-binaphthalene]-2-carboxylate → (R)-2-N,N-dimethylcarbamoyl-2'-trifluoromethanesulfonyloxy-1,1'-binaphthyl

Conditions	Yield
Stage #1: N,N-dimethylammonium chloride With trimethylaluminum In toluene at 20℃; for 1h; Stage #2: 2'-trifluoromethanesulfonyloxy-[1,1']binaphthalenyl-2-carboxylic acid methyl ester In toluene for 3h; Heating; Further stages.;	100%

2-methylsulfanyl-4-(3-trifluoromethylanilino)pyrimidine-5-carboxylic acid (227449-41-4) + N,N-dimethylammonium chloride (506-59-2) → N,N-dimethyl-2-methylsulfanyl-4-(3-trifluoromethylanilino)pyrimidine-5-carboxamide (863029-03-2)

Conditions	Yield
Stage #1: 2-methylsulfanyl-4-(3-trifluoromethylanilino)pyrimidine-5-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 4h; Stage #2: N,N-dimethylammonium chloride In N,N-dimethyl-formamide at 20℃; for 14h;	100%

N,N-dimethylammonium chloride (506-59-2) + methyl 4-<<<4-<<<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrole-2-carboxylic acid (126093-01-4) → {5-[5-(5-dimethylcarbamoyl-1-methyl-1H-pyrrol-3-ylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-pyrrol-3-yl}-carbamic acid tert-butyl ester (292073-28-0)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 14h;	100%

[3-cyclohexyl-6-(methoxycarbonyl)-2-phenyl-1H-pyrrolo[2,3-b]pyridin-1-yl]acetic acid (774213-95-5) + N,N-dimethylammonium chloride (506-59-2) → methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-phenyl-1H-pyrrolo[2,3-b]pyridine-6-carboxylate (774213-96-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	100%
With N-ethyl-N,N-diisopropylamine; HATU In DMF (N,N-dimethyl-formamide) at 20℃; for 1.5h;	100%

1-(2-methoxyethyl)-2-methyl-8-phenyl-1,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxylic acid (1015174-82-9) + N,N-dimethylammonium chloride (506-59-2) → 1-(2-methoxyethyl)-N,N.2-trimethyl-8-phenyl-1,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	100%

(5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2-methyl-4,5-dihydro-1H-pyrrole-3-carboxylic acid (918650-03-0) + N,N-dimethylammonium chloride (506-59-2) → 1-tert-butyl 2-methyl (2S)-4-(dimethylcarbamoyl)-5-methyl-2,3-dihydro-1H-pyrrole-1,2-dicarboxylate

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h;	100%

4-(3-cyano-phenyl)-7-ethyl-3-(methylsulfonyl)-pyrrolo[1,2-b]pyridazine-2-carboxylic acid (728015-44-9) + N,N-dimethylammonium chloride (506-59-2) → 4-(3-cyano-phenyl)-7-ethyl-N,N-dimethyl-3-(methylsulfonyl)-pyrrolo[1,2-b]pyridazine-2-carboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 20℃; for 3h;	100%

C23H23ClN2O4 + N,N-dimethylammonium chloride (506-59-2) → 5,6-bis(4-methoxyphenyl)-4-dimethyl-carbamoyl-2-isobutyl-2H-pyridazin-3-one

Conditions	Yield
In benzene Heating / reflux;	100%

2-fluoro-5-nitrobenzonitrile (17417-09-3) + N,N-dimethylammonium chloride (506-59-2) → 2-cyano-4-nitro-N,N-dimethylaniline (17417-10-6)

Conditions	Yield
With potassium hydrogencarbonate In water; N,N-dimethyl-formamide	100%

N,N-dimethylammonium chloride (506-59-2) + N-cyanodiphenylcarbonimidate (79463-77-7) → O-phenyl-N-cyano-N',N'-dimethylurea (167494-04-4)

Conditions	Yield
In tetrahydrofuran	100%

1-N-[1-N-(3-chloropropyl)-piperidin-4-yl]-indole (170364-87-1) + N,N-dimethylammonium chloride (506-59-2) → [3-(4-Indol-1-yl-piperidin-1-yl)-propyl]-dimethylamine

Conditions	Yield
With potassium carbonate In ethanol; water	100%

2-chloro-N-{4-[(2S)-4-((1R)-1-phenylethyl)morpholin-2-yl]phenyl}acetamide + N,N-dimethylammonium chloride (506-59-2) → N2,N2-dimethyl-N1-(4-((2S)-4-((1R)-1-phenylethyl)morpholin-2-yl)phenyl)glycinamide

Conditions	Yield
With potassium carbonate In tetrahydrofuran; acetonitrile at 95℃; for 10h;	100%
With potassium carbonate In tetrahydrofuran; acetonitrile at 95℃; for 10h;	100%

4-amino-2-chloro-5-nitropyridine (2604-39-9) + N,N-dimethylammonium chloride (506-59-2) → N,N-dimethyl-5-nitropyridine-2,4-diamine (886435-69-4)

Conditions	Yield
Stage #1: 4-amino-2-chloro-5-nitropyridine; N,N-dimethylammonium chloride With triethylamine In ethanol at 85℃; for 0.166667h; Microwave irradiation; Stage #2: With sodium hydroxide In water	100%
With triethylamine In isopropyl alcohol at 100℃; for 12h;

2-methyl-8-[(5-methyl-3,4-dihydro-2H-chromen-4-yl)amino]imidazo[1,2-a]pyridine-6-carboxylic acid (928774-42-9) + N,N-dimethylammonium chloride (506-59-2) → N,N,2-trimethyl-8-[(5-methyl-3,4-dihydro-2H-chromen-4-yl)amino]imidazo[1,2-a]pyridine-6-carboxamide (950595-98-9)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 24h;	100%

dichloro(benzene)ruthenium(II) dimer (37366-09-9) + (R)-(+)-2,2’-bis(diphenylphosphino)-1,1’-binaphthalene (76189-55-4, 76189-56-5, 98327-87-8) + N,N-dimethylammonium chloride (506-59-2) → [(RuCl((C6H5)2PC10H6C10H6P(C6H5)2))2Cl3](1-)*[(CH3)2NH2](1+)=[(RuCl((C6H5)2PC10H6C10H6P(C6H5)2))2Cl3][(CH3)2NH2]

Conditions	Yield
In 1,4-dioxane (Ar); heating a soln. of ruthenium complex with ammonium salt and phosphine in dioxane at 50°C for 2 h with stirring, refluxing with stirring for 12 h; cooling, evapn.;	100%

(2,2'-bis(diphenylphosphino)-1,1'-binaphathalene)chloro(p-cymene)ruthenium chloride (130004-33-0, 145926-28-9, 376354-47-1) + N,N-dimethylammonium chloride (506-59-2) → [(RuCl((C6H5)2PC10H6C10H6P(C6H5)2))2Cl3](1-)*[(CH3)2NH2](1+)=[(RuCl((C6H5)2PC10H6C10H6P(C6H5)2))2Cl3][(CH3)2NH2]

Conditions	Yield
In tetrahydrofuran (Ar); heating a soln. of ruthenium complex with ammonium salt in THF for 6 h; evapn., washing;	100%

4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide (713530-55-3) + formaldehyd (50-00-0) + N,N-dimethylammonium chloride (506-59-2) → 5-[(dimethylamino)methyl]-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide hydrochloride (1034771-47-5)

Conditions	Yield
With triethylamine In water; isopropyl alcohol at 35 - 45℃; for 2 - 6h;	100%

4-iodobenzoic acid (619-58-9) + N,N-dimethylammonium chloride (506-59-2) → 4-iodo-N,N-dimethylbenzamide (24167-53-1)

Conditions	Yield
Stage #1: N,N-dimethylammonium chloride With triethylamine In dichloromethane for 0.5h; Stage #2: 4-iodobenzoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 8h;	100%

N-tert-butyloxycarbonyl-L-tert-leucine (62965-35-9) + N,N-dimethylammonium chloride (506-59-2) → (S)-tert-butyl 1-(dimethylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (340161-34-4)

Conditions	Yield
Stage #1: N-tert-butyloxycarbonyl-L-tert-leucine With HBTU In dichloromethane for 0.0333333h; Inert atmosphere; Stage #2: N,N-dimethylammonium chloride With N-ethyl-N,N-diisopropylamine In dichloromethane for 1.5h; Inert atmosphere;	100%
With triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Cooling with ice;	91%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h;

Upstream product

• 683-85-2 N,N-dimethylaminodichlorophosphane 
• 90993-36-5 dicyano dimethyl amino phosphine 
• 33326-14-6 cyano bis(dimethylamino) phosphine 
• 7647-01-0 hydrogenchloride 
• 3768-63-6 tetramethylsulfamide 
• 27918-31-6 pentafluorobenzenesulfenyl chloride 
• 124-40-3 dimethyl amine 
• 1066-48-4 Trifluormethyl-tetrachlor-phosphoran 
• 650-52-2 bis(trifluoromethyl)chlorophosphine 
• 18799-80-9 (CF₃)2P(S)N(CH₃)2 
• 5032-91-7 pentafluorophenyl dichlorophosphine 
• 1113-30-0 Tetramethylborazen 
• 94408-59-0 Bis(dimethylamino)dipropyldiborane 
• 4887-12-1 1,2-di-n-butyl-1,2-bis(dimethylamino) diborane 

Downstream Products

• 5435-88-1 3,4-bis-dimethylaminomethyl-2,5-dimethyl-pyrrole 
• 90607-99-1 6-dimethylaminomethyl-cyclohex-2-enone 
• 101293-72-5 5-dimethylaminomethyl-2,4-dihydroxy-benzophenone; hydrochloride 
• 52955-92-7 2-<(dimethylamino)methyl>-6-phenylcyclohexanone 
• 101729-18-4 2-dimethylaminomethyl-3-phenyl-indan-1-one 
• 1892-36-0 3-dimethylamino-1,2-bis-(4-methoxy-phenyl)-propan-1-one 
• 99188-53-1 6-dimethylaminomethyl-3-methyl-cyclohex-2-enone 
• 1467-79-4 NCNMe₂ 
• 5350-67-4 α-(dimethylamino)-propionitrile 
• 31081-14-8 N,N,N'-trimethyl-guanidine 
• 922-63-4 ethylacrolein 
• 344752-24-5 2-dimethylaminomethyl-4-methyl-cyclohexanone 
• 53921-85-0 1-cyclohexyl-3-(N,N-dimethylamino)-1-propanone 
• 13552-47-1 3-(dimethylamino)-1-(p-tolyl)propan-1-one 

Relevant articles and documents

Dihydrogen bond intermediated alcoholysis of dimethylamine-borane in nonaqueous media

Dimethylamine-borane (DMAB) acid/base properties, its dihydrogen-bonded (DHB) complexes and proton transfer reaction in nonaqueous media were investigated both experimentally (IR, UV/vis, NMR, and X-ray) and theoretically (DFT, NBO, QTAIM, and NCI). The e

The enthalpies of formation of bis(dimethylamino)cyanophosphine, (dimethylamino)dicyanophosphine, and tricyanophosphine

The standard molar enthalpies of formation at the temperature 298.15 K of 2PCN(l), (CH3)2NP(CN)2(l), and P(CN)3(cr) have been determined by reaction calorimetry as -(0.4 +/- 3.2) kJ * mol-1, (189.3 +/- 5.0) kJ * mol-1, and (373.1 +/- 6.8) kJ * mol-1, respectively.Enthalpies of vaporization have been obtained from vapour-pressure measurements for the first two compounds and the corresponding values of ΔfH0m(g)/(kJ * mol-1) derived as (54.2 +/- 3.5), (228.7 +/- 5.5), and 448.4 +/- 7.4), respectively.The values of the bond enthalpies D(P-CN) in the cyanophosphines are discussed.

Studies in Cyclophosphazenes. Part 9. Influence of the Steric Requirements of the Amino-substituents on the Rates of Amination of 2-Amino-2,4,4,6,6-pentachlorocyclotri(λ5-phosphazenes)

Measurements of the rates of amination of a number of aminopentachlorotriphosphazenes, N3P3Cl5(NRR') (R = n-Bu, R' = H; R = R'=n-Bu; R = i-Pr, R' = H; RR' = C5H10), with dimethylamine to give non-geminal disubstituted products have been made at two temperatures in tetrahydrofuran with the aim of elucidating the steric effects of the amino-substituents in these reactions.The values of the rate constants and of the activation parameters determined showed that steric effects are only very small.To resolve the conflict between these findings and others in literature in which appreciable steric influences were observed, the division of these amination reactions into three classes, each of which is affected by stric factors in its own way, is proposed.This enables much of the kinetic and preparative data on steric effects in these reactions to be rationalised in the framework of one general hypothesis.

Norbornane-2-spiro-α-cycloalkanone-α′-spiro-2″-norbornane-5,5″,6,6″-tetracarboxylic dianhydride, norbornane-2-spiro-α-cycloalkanone-α′-spiro-2″-norbornane-5,5″,6,6″-tetracarboxylic acid and ester thereof, method for producing norbornane-2-spiro-α-cycloalkanone-α′-spiro-2″-norbornane-5,5″,6,6″-tetracarboxylic dianhydride, polyimide obtained by using the same, and method for producing polyimide

A norbornane-2-spiro-α-cycloalkanone-α′-spiro-2″-norbornane-5,5″,6,6″-tetracarboxylic dianhydride represented by the following general formula (1): wherein the formula (1), n represents an integer of 0 to 12, and R1s, R2, R3 each independently represents a hydrogen atom or the like.

Nucleophilic substitution reaction at the nitrogen of arylsulfonamides with phosphide anion

A novel nucleophilic substitution reaction at the nitrogen of arylsulfonamides by means of phosphide anions has been described. This reaction allows for the efficient transformation of arylsulfonamides into synthetically valuable phosphamides, amines, and a variety of protected amines.