2491-06-7

Basic information

• Product Name: N,N-Dimethylglycine hydrochloride
• Synonyms: n,n-dimethyl-glycinhydrochloride;n-methylsarcosinehydrochloride;N,N-DIMETHYLAMINOACETIC ACID HYDROCHLORIDE;N,N-DIMETHYL-GLY-OH HCL;N,N-DIMETHYLGLYCINE HCL;N,N-DIMETHYLGLYCINE HYDROCHLORIDE;DMG HYDROCHLORIDE;DIMETHYLGLYCINE HCL
• CAS NO: 2491-06-7
• Molecular Formula: C₄H₉NO₂*ClH
• Molecular Weight: 139.58
• EINECS: 219-648-2
• Mol File: 2491-06-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 189-194 °C(lit.)
• Boiling Point: 175.2 °C at 760 mmHg
• Flash Point: 59.8 °C
• Appearance: White/Crystalline Powder
• Density: 1.069g/cm3
• Vapor Pressure: 0.556mmHg at 25°C
• Storage Temp.: Store below +30°C.
• Water Solubility: 100 g/L (20 ºC)
• Sensitive: Hygroscopic
• Merck: 14,3244
• BRN: 3910578
• CAS DataBase Reference: N,N-Dimethylglycine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethylglycine hydrochloride(2491-06-7)
• EPA Substance Registry System: N,N-Dimethylglycine hydrochloride(2491-06-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 2
• RTECS: MB9995000
• TSCA: Yes
• Hazardous Substances Data: 2491-06-7(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

N,N-Dimethylglycine (DMG) is a natural N-methylated glycine that is used in comparative analysis with other N-methylated glycines such as sarcosine and βine. Used in the development of glycine-based ionic liquids and emulsifiers. Also it is potentially useful as a biomarker of protein degradation in COPD patients. DMG is used as a substrate to identify, differentiate and characterize amino acid methyltransferase(s).

Flammability and Explosibility

Notclassified

InChI:InChI=1/C4H9NO2.ClH/c1-5(2)3-4(6)7;/h3H2,1-2H3,(H,6,7);1H

Synthetic route

N,N-dimethylglycine methyl ester (7148-06-3) → N,N-dimethylglycine hydrochoride (2491-06-7)

Conditions	Yield
With hydrogenchloride for 24h; Heating;	99%

dimethyl amine (124-40-3) + chloroacetic acid (79-11-8) → N,N-dimethylglycine hydrochoride (2491-06-7)

Conditions	Yield
Stage #1: dimethyl amine; chloroacetic acid In water at 25 - 55℃; for 11h; Stage #2: With hydrogenchloride In water at 40℃;

dimethylaminoacetic acid (1118-68-9) → N,N-dimethylglycine hydrochoride (2491-06-7)

Conditions	Yield
With hydrogenchloride In ethanol; water; acetone

N,N-dimethylglycine hydrochoride (2491-06-7) + benzylamine (100-46-9) → N-benzyl-2-(dimethylamino)acetamide (76733-71-6)

Conditions	Yield
With 4-methyl-morpholine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Inert atmosphere;	98%

1,2:5,6-bis-O-(1-methylethylidene)-4-O-Val-3-O-methyl-D-chiro-inositol + N,N-dimethylglycine hydrochoride (2491-06-7) → 1,2:5,6-bis-O-(1-methylethylidene)-4-O-{[2-(dimethylamino)acetamido]-Val}-3-O-methyl-D-chiro-inositol

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃;	96%

C22H34N4O3 (233684-38-3) + N,N-dimethylglycine hydrochoride (2491-06-7) → C26H41N5O4 (233684-39-4)

Conditions	Yield
With triethylamine; diethyl dicarbonate In dichloromethane at 20℃; for 13h;	95%

N,N-dimethylglycine hydrochoride (2491-06-7) + C31H52O → C35H59NO2

Conditions	Yield
With pyridine; 2-chloro-1,3-dimethylimidazolinium chloride In dichloromethane at 20℃; for 96h; Esterification;	92%

C26H25N3O4S + N,N-dimethylglycine hydrochoride (2491-06-7) + isobutyl chloroformate (543-27-1) → C31H33N3O6S + C30H32N4O5S

Conditions	Yield
Stage #1: N,N-dimethylglycine hydrochoride With triethylamine In dichloromethane; butan-1-ol at 20℃; for 1h; Inert atmosphere; Stage #2: isobutyl chloroformate In dichloromethane; butan-1-ol at -15℃; for 2h; Inert atmosphere; Stage #3: C26H25N3O4S In dichloromethane; butan-1-ol at 20℃; for 19h; Inert atmosphere;	A 91% B 6%

6-bromo-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one + copper(I) iodide (7681-65-4) + N,N-dimethylglycine hydrochoride (2491-06-7) + phenol (108-95-2) → 1'-pentyl-6-phenoxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one (912668-11-2)

Conditions	Yield
With caesium carbonate In 1,4-dioxane	87%

N,N-dimethylglycine hydrochoride (2491-06-7) + benzyl alcohol (100-51-6) → 2-(dimethylamino)acetic acid benzyl ester (30379-57-8)

Conditions	Yield
With 4-methyl-morpholine; dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; Inert atmosphere;	87%

(3R,4R)-3,4-bis((9Z,12Z)-octadec-9,12-dienyloxy)pyrrolidine (1346224-49-4) + N,N-dimethylglycine hydrochoride (2491-06-7) → (3R,4R)-1-(2-(dimethylamino)acetyl)-3,4-bis((9Z,12Z)-octadec-9,12-dienyloxy)pyrrolidine (1346224-72-3)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 1.5h;	86.8%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 1.5h;	86.8%

N,N-dimethylglycine hydrochoride (2491-06-7) + n-tetradecanoic acid (544-63-8) → calcium(II) N,N-dimethylglycine tetradecanoate

Conditions	Yield
Stage #1: N,N-dimethylglycine hydrochoride With sodium hydroxide In ethanol at 20℃; for 0.5h; Stage #2: n-tetradecanoic acid With calcium hydroxide In ethanol at 20℃; for 4h;	84.33%

N,N-dimethylglycine hydrochoride (2491-06-7) → N,N-dimethylaminoacetyl chloride hydrochloride (60853-81-8)

Conditions	Yield
With thionyl chloride at 78℃; for 0.5h;	84%
With phosphorus pentachloride	82%
With oxalyl dichloride In dichloromethane at 20℃; for 2h;

N,N-dimethylglycine hydrochoride (2491-06-7) → calcium(II) N,N-dimethylglycine sulfate

Conditions	Yield
Stage #1: N,N-dimethylglycine hydrochoride With sodium hydroxide In ethanol at 20℃; for 0.5h; Stage #2: With sulfuric acid; calcium hydroxide In ethanol at -20 - 20℃; for 4h;	83.67%

N,N-dimethylglycine hydrochoride (2491-06-7) + 1,8,17,24-tetraoxa-33,34,35,36-tetrakis(hydroxymethyl)<8.8>(1,4)naphthalenophane (80594-03-2) → 1,8,17,24-tetraoxa-33,34,35,36-tetrakis(N,N-dimethylglycyloxymethyl)<8.8>(1,4)naphthalenophane (80594-02-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In pyridine for 4h; Ambient temperature;	82%

N,N-dimethylglycine hydrochoride (2491-06-7) + C-acridin-4-yl-methylamine; hydrochloride → N-acridin-4-ylmethyl-2-dimethylaminoacetamide

Conditions	Yield
Stage #1: C-acridin-4-yl-methylamine; hydrochloride With ammonia In water Stage #2: N,N-dimethylglycine hydrochoride With benzotriazol-1-ol; triethylamine In dichloromethane for 48h;	80%

N,N-dimethylglycine hydrochoride (2491-06-7) + Tocopherol (59-02-9) → d-α-tocopheryl N,N-dimethylaminoacetate hydrochloride

Conditions	Yield
With dicyclohexyl-carbodiimide In pyridine for 24h; Ambient temperature;	79%

3,5-seco-4-nor-cholestane-5-one-3-ol (14291-31-7) + N,N-dimethylglycine hydrochoride (2491-06-7) → C30H53NO3 (878193-63-6)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;	78%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;	78%

Capadenoson + dimethylaminoacetic acid (1118-68-9) + N,N-dimethylglycine hydrochoride (2491-06-7) → 2-(4-{2-({[2-(4-Chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-3,5-dicyano-6-[(N,N-dimethylglycyl)-amino]pyridin-4-yl}phenoxy)ethyl N,N-dimethylglycinate (1112459-44-5)

Conditions	Yield
Stage #1: Capadenoson; N,N-dimethylglycine hydrochoride With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In dichloromethane Reflux; Stage #2: dimethylaminoacetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In dichloromethane Reflux; Stage #3: With sodium hydrogencarbonate In dichloromethane	78%

N,N-dimethylglycine hydrochoride (2491-06-7) → calcium(II) N,N-dimethylglycine phosphate

Conditions	Yield
With phosphoric acid; sodium hydroxide; calcium hydroxide In ethanol at 20℃; for 4h;	77.53%

WSC.HCl + 2-aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one + N,N-dimethylglycine hydrochoride (2491-06-7) → 2-(N,N-Dimethylglycyl)aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one.HCl (156935-37-4)

Conditions	Yield
With benzotriazol-1-ol In N-methyl-acetamide	77%

2,5-bis-[5-{2-(N-hydroxyamidino)-pyridyl}]selenophene (1143621-30-0) + N,N-dimethylglycine hydrochoride (2491-06-7) → 2,5-bis-[5-{2-N-(N,N-dimethylaminoacetoxyamidino)-pyridyl}]selenophene (1143621-33-3)

Conditions	Yield
Stage #1: N,N-dimethylglycine hydrochoride With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 60℃; for 2h; Stage #2: 2,5-bis-[5-{2-(N-hydroxyamidino)-pyridyl}]selenophene In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	77%

N,N-dimethylglycine hydrochoride (2491-06-7) + 1,4-bis(propynyloxy)-2,3-bis(hydroxymethyl)naphthalene (80593-97-1) → 1,4-bis(propynyloxy)-2,3-bis(N,N-dimethylglycyloxymethyl)naphthalene (80593-96-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 5h; Ambient temperature;	76%

Gly-OBz (1738-68-7) + N,N-dimethylglycine hydrochoride (2491-06-7) → benzyl 2-(2-(dimethylamino)acetamido)acetate (1227930-08-6)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide at 20℃; for 16h;	76%

4-acetaminophenol (103-90-2) + N,N-dimethylglycine hydrochoride (2491-06-7) → 4-acetamidophenyl 2-(dimethylamino)acetate hydrochloride (1314962-36-1)

Conditions	Yield
With pyridine; dicyclohexyl-carbodiimide at 20℃;	75%

C26H25N3O4S + N,N-dimethylglycine hydrochoride (2491-06-7) → C30H32N4O5S

Conditions	Yield
Stage #1: C26H25N3O4S; N,N-dimethylglycine hydrochoride In methanol at 0℃; for 1h; Inert atmosphere; Stage #2: With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In methanol at 20℃; for 38h; Inert atmosphere;	75%

cholesterol (57-88-5) + N,N-dimethylglycine hydrochoride (2491-06-7) → cholesteryl 2-(dimethylamino)acetate (123191-82-2)

Conditions	Yield
Stage #1: cholesterol; N,N-dimethylglycine hydrochoride With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	74.6%
Stage #1: cholesterol; N,N-dimethylglycine hydrochoride With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

N,N-dimethylglycine hydrochoride (2491-06-7) + toluene-4-sulfonic acid (104-15-4) → calcium(II) N,N-dimethylglycine p-toluenesulfonate

Conditions	Yield
Stage #1: N,N-dimethylglycine hydrochoride With sodium hydroxide In ethanol at 20℃; for 0.5h; Stage #2: toluene-4-sulfonic acid With calcium hydroxide In ethanol at 20℃; for 4h;	74.23%

N,N-dimethylglycine hydrochoride (2491-06-7) + (2E)-but-2-enedioic acid (110-17-8) + zinc(II) hydroxide → copper(II) N,N-dimethylglycine fumarate

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 4h;	73.06%

N,N-dimethylglycine hydrochoride (2491-06-7) + acridin-4-ylmethanol (620612-16-0) → acridin-4-ylmethyl 2-(N,N-dimethylamino)acetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In acetone at 20℃; for 96h;	73%

N,N-dimethylglycine hydrochoride (2491-06-7) + FR901469 hydrochloride → C75H123N15O24

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	72%

5-(2-benzyl-2H-indazol-6-yl)-7-morpholin-2-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (937042-71-2) + N,N-dimethylglycine hydrochoride (2491-06-7) → 5-(2-benzyl-2H-indazol-6-yl)-7-{4-[(dimethylamino)acetyl]morpholin-2-yl}pyrrolo[2,1-f][1,2,4]triazin-4-amine

Conditions	Yield
With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In tetrahydrofuran at 20℃; for 1h;	71%

Upstream product

• 1118-68-9 dimethylaminoacetic acid 
• 124-40-3 dimethyl amine 
• 79-11-8 chloroacetic acid 
• 7148-06-3 N,N-dimethylglycine methyl ester 

Downstream Products

• 1266180-70-4 C₁₄H₂₀N₄O₃ 
• 59660-95-6 dimethylaminoacetyl chloride hydrochloride 
• 741706-84-3 5α,10β,15α,20β-tetrakis(2-(N,N-dimethylaminoacetamido)phenyl)porphyrinatoiron(III) chloride 
• 1432617-49-6 C₂₂H₂₂NOPS 
• 30379-57-8 2-(dimethylamino)acetic acid benzyl ester 
• 76733-71-6 N-benzyl-2-(dimethylamino)acetamide 
• 294193-71-8 N,N-dimethyl-glycine-(3-nitro-anilide) 

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