22661-87-6

Basic information

• Product Name: Methylguanidine hydrochloride
• Synonyms: N-METHYLGUANIDINE HYDROCHLORIDE;1-METHYLGUANIDINIUM HYDROCHLORIDE;METHYLGUANIDINE HYDROCHLORIDE;GUANIDINE, METHYL-, HYDROCHLORIDE;EINECS 245-147-3;1-METHYLGUANIDINE HYDROCHLORIDE 98+%;1-Methylguanidine hydrochloride;1-Methylguanidine/hydrochloride,(1:x)
• CAS NO: 22661-87-6
• Molecular Formula: C₂H₇N₃*ClH
• Molecular Weight: 109.56
• EINECS: 245-147-3
• Product Categories: Guanidines;Nitrogen Compounds;Organic Building Blocks
• Mol File: 22661-87-6.mol
• Article Data: 4

Chemical Properties

• Appearance: White to off-white/Powder
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility: Soluble in water (50 mg/ml - clear, colorless to light yellow solution).
• Sensitive: Hygroscopic
• Stability: Hygroscopic
• CAS DataBase Reference: Methylguanidine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Methylguanidine hydrochloride(22661-87-6)
• EPA Substance Registry System: Methylguanidine hydrochloride(22661-87-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• RTECS: MF3990000
• Hazardous Substances Data: 22661-87-6(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Uses

N-Methylguanidine is an alkylated guanidine which shows inhibitory action against trypsin catalysis. N-Methylguanidine inhibited metabolism of certain hepatic drugs that was mediated by cytochrome P 450 protein in human liver microsome and hepatocyte.

InChI:InChI=1/C2H7N3.ClH/c1-2(3)5-4;/h5H,1,3-4H2;1H

Synthetic route

methylamine hydrochloride (593-51-1) + N-Cyanoguanidine (127099-85-8, 780722-26-1) → 1-methylguanidine hydrochloride (22661-87-6)

Conditions	Yield
	64%
In methanol at 180℃; for 3h;

(E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (67751-23-9) + 1-methylguanidine hydrochloride (22661-87-6) → 4-(dimethoxymethyl)-N-methylpyrimidin-2-amine (180869-38-9)

Conditions	Yield
With sodium In ethanol for 3h; Heating / reflux;	100%
With sodium hydroxide

1-methylguanidine hydrochloride (22661-87-6) + 5-Dimethylamino-3-oxo-4-penten-2-one-3-dimethylketal (106157-94-2) → [4-(1,1-dimethoxy-ethyl)-pyrimidin-2-yl]-methyl-amine

Conditions	Yield
With ethanol; sodium for 4h; Heating / reflux;	100%
With sodium In ethanol for 4 - 6.5h; Heating / reflux;	100%
With sodium In ethanol for 4h; Heating / reflux;	100%

1-(3-bromo-4-fluorophenyl)-2-(4-methoxy-3-methylphenyl)ethane-1,2-dione (1202708-26-6) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-(3-bromo-4-fluorophenyl)-5-(4-methoxy-3-methylphenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one (872041-81-1)

Conditions	Yield
With sodium carbonate In 1,4-dioxane; ethanol; water at 70℃; for 5h;	99%
Stage #1: 1-(3-bromo-4-fluorophenyl)-2-(4-methoxy-3-methylphenyl)ethane-1,2-dione; 1-methylguanidine hydrochloride In 1,4-dioxane; ethanol at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With sodium carbonate In 1,4-dioxane; ethanol; water at 85℃; for 0.75h; Inert atmosphere;	90%

1-(3-bromophenyl)-2-(4-(difluoromethoxy)-3-methylphenyl)ethane-1,2-dione (1062613-90-4) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-(3-bromophenyl)-5-(4-(difluoromethoxy)-3-methylphenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one (1062604-64-1)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 80℃; for 2h;	98.3%

1-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-2-(3-(5-fluoropent-1-ynyl)phenyl)ethane-1,2-dione (1062617-07-5) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-4-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-4-(3-(5-fluoropent-1-ynyl)phenyl)-1-methyl-1H-imidazol-5(4H)-one (1062609-15-7)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 16h;	98%

1-methylguanidine hydrochloride (22661-87-6) + 1-phenyl-5-(1-benzoyl-2-dimethylaminovinyl)-1H-tetrazole → Methyl-[4-phenyl-5-(1-phenyl-1H-tetrazol-5-yl)-pyrimidin-2-yl]-amine

Conditions	Yield
With sodium ethanolate In ethanol for 2h; Heating;	97%

1-methylguanidine hydrochloride (22661-87-6) + 5-(2-Dimethylamino-1-trifluoracetyl-vinyl)-1-phenyl-1H-tetrazol → Methyl-[5-(1-phenyl-1H-tetrazol-5-yl)-4-trifluoromethyl-pyrimidin-2-yl]-amine

Conditions	Yield
With sodium ethanolate In ethanol for 2h; Heating;	96%

1-[4-(difluoromethoxy)phenyl]-2-phenylethane-1,2-dione + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-[4-(difluoromethoxy)phenyl]-3-methyl-5-phenyl-3,5-dihydro-4H-imidazol-4-one

Conditions	Yield
With sodium carbonate In 1,4-dioxane; ethanol; water at 95℃; for 3h;	94%
With sodium carbonate In 1,4-dioxane; ethanol; water at 95℃; for 3h;	94%

3-bromo-4'-methoxy-benzil (860599-82-2) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-(3-bromo-phenyl)-5-(4-methoxy-phenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one (937374-15-7)

Conditions	Yield
Stage #1: 3-bromo-4'-methoxy-benzil; 1-methylguanidine hydrochloride In 1,4-dioxane; ethanol; water; acetonitrile at 20℃; for 0.25h; Stage #2: With sodium carbonate In 1,4-dioxane; ethanol; water at 85℃; for 0.75h;	94%

1-methylguanidine hydrochloride (22661-87-6) + methyl 1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4,5-dicarboxylate (66657-09-8) → 4,5-dihydro-8H-6-(N-methyl)amino-1-(β-D-ribofuranosyl)imidazo[4,5-e][1,3]diazepine-4,8-dione

Conditions	Yield
Stage #1: 1-methylguanidine hydrochloride With sodium methylate In methanol for 0.5h; Stage #2: methyl 1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4,5-dicarboxylate With sodium methylate In methanol at 20℃;	93%

1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione (114433-94-2) + 1-methylguanidine hydrochloride (22661-87-6) → 4-(4-fluoro phenyl)-6-isopropyl-N-methyl-pyrimidin-2-amine (1031246-31-7)

Conditions	Yield
With potassium hydroxide In isopropyl alcohol Temperature; Reflux;	93%
With potassium hydroxide In acetone Temperature; Concentration; Reflux;	93%
With potassium hydroxide In isopropyl alcohol Solvent; Reflux;	93%
Stage #1: 1-methylguanidine hydrochloride With sodium In isopropyl alcohol at 82℃; for 2.5h; Stage #2: 1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione In isopropyl alcohol at 82℃; for 11h;	65%
Stage #1: 1-methylguanidine hydrochloride With sodium isopropylate In isopropyl alcohol at 82℃; for 2.5h; Stage #2: 1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione In isopropyl alcohol at 82℃; for 11h;	65%

3-[2-(4-Difluoromethoxy-phenyl)-2-oxo-acetyl]-benzaldehyde + 1-methylguanidine hydrochloride (22661-87-6) → 3-{2-amino-4-[4-(difluoromethoxy)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}benzaldehyde (931429-87-7)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 15.5h;	93%

2-Acetyl-7-methoxytropone (72030-45-6) + 1-methylguanidine hydrochloride (22661-87-6) → 4-acetyl-2-methylaminocycloheptimidazole (143769-47-5)

Conditions	Yield
In ethanol for 3h; Heating;	91%

1-(2-chloropyridin-3-yl)-3-dimethylaminopropenone (166196-84-5) + 1-methylguanidine hydrochloride (22661-87-6) → 4-(2-chloropyridin-3-yl)-N-methylpyrimidin-2-amine (870221-22-0)

Conditions	Yield
Stage #1: 1-methylguanidine hydrochloride With sodium methylate In methanol for 0.5h; Stage #2: 1-(2-chloropyridin-3-yl)-3-dimethylaminopropenone In methanol at 50℃; for 23h;	90%

chloro(2,2':6',2''-terpyridine)platinum(II) chloride dihydrate + 1-methylguanidine hydrochloride (22661-87-6) → {(Pt(2,2':6',2''-terpyridine))2(methylguanidine)}Cl4 + {Pt(2,2':6',2''-terpyridine)(methylguanidine)}Cl2

Conditions	Yield
In water Pt-complex, the guanidine in H2O kept at 80°C, 5d, pH adjusted to ca 8.0 with NaOH; chromy. (CM52 cation exchanger; elution: potassium phosphate buffer pH7.0 at 4°C);	A 90% B 10%

(E)-1-(2-(4-(tert-b utyl)phenyl)-4-methylthiazol-5-yl)-3-(dimethylamino)prop-2-en-1-one + 1-methylguanidine hydrochloride (22661-87-6) → 4-(2-(4-(tert-butyl)phenyl)-4-methylthiazol-5-yl)-N-methylpyrimidin-2-amine

Conditions	Yield
With potassium carbonate In ethanol for 8h; Reflux;	89%

1-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-2-(3-(4-methoxybut-1-ynyl)phenyl)ethane-1,2-dione (1062616-96-9) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-4-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-4-(3-(4-methoxybut-1-ynyl)phenyl)-1-methyl-1H-imidazol-5(4H)-one (1062608-84-7)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 16h;	88%

1-(4-(difluoromethoxy)-3-methylphenyl)-2-phenylethane-1,2-dione (1062613-70-0) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-[4-(difluoromethoxy)-3-methylphenyl]-3-methyl-5-phenyl-3,5-dihydro-4H-imidazol-4-one (1062604-38-9)

Conditions	Yield
With sodium carbonate In ethanol at 80℃;	86%

N-Boc-N-methyl-dehydroalanine methyl ester (56776-34-2) + 1-methylguanidine hydrochloride (22661-87-6) → (2-amino-1-methyl-4-oxo-1,4,5,6-tetrahydro-pyrimidin-5-yl)-methyl-carbamic acid tert-butyl ester (601507-04-4)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	85%

1-(4-Difluoromethoxy-phenyl)-2-[3-(1-fluoro-pent-4-enyl)-phenyl]-ethane-1,2-dione (1065168-04-8) + 1-methylguanidine hydrochloride (22661-87-6) → 2-Amino-5-(4-difluoromethoxy-phenyl)-5-[3-(1-fluoro-pent-4-enyl)-phenyl]-3-methyl-3,5-dihydro-imidazol-4-one (1065165-18-5)

Conditions	Yield
With sodium carbonate In 1,4-dioxane; ethanol; water at 95℃; for 3h;	85%

1-methylguanidine hydrochloride (22661-87-6) + 1,1,5,5-tetraethyl-3-fluoro-1,5-diazapentadienium iodide → (5-Fluoro-pyrimidin-2-yl)-methyl-amine

Conditions	Yield
With sodium methylate In methanol; acetonitrile at 70 - 75℃; for 3h;	84%

1-(4-Difluoromethoxy-phenyl)-2-{3-[3-(2-fluoro-ethyl)-cyclobutyl]-phenyl}-ethane-1,2-dione (1065168-72-0) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-[4-(difluoromethoxy)phenyl]-5-{3-[3-(2-fluoroethyl)cyclobutyl]phenyl}-3-methyl-3,5-dihydro-4H-imidazol-4-one (1065166-21-3)

Conditions	Yield
With sodium carbonate In ethanol at 89℃; for 16h;	84%

(E)-3-(dimethylamino)-2-(3-nitrophenoxy)prop-2-enenitrile + 1-methylguanidine hydrochloride (22661-87-6) → N2-methyl-5-(3-nitrophenoxy)pyrimidine-2,4-diamine

Conditions	Yield
With potassium carbonate In butan-1-ol at 100℃; for 2h;	84%

1-(3-bromo-phenyl)-2-(3-cyclopropyl-4-difluoromethoxy-phenyl)-ethane-1,2-dione (1062616-71-0) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-(3-bromo-phenyl)-5-(3-cyclopropyl-4-difluoromethoxy-phenyl)-3-methyl-3,5-dihydro-imidazol-4-one (1062608-28-9)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 16h;	83%

1-(4-(difluoromethoxy)phenyl)-2-(3-(furan-2-ylmethyl)phenyl)ethane-1,2-dione (1065169-59-6) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(2-furylmethyl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (1065166-87-1)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 16h;	83%

1-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-2-(3-(3-hydroxy-3-methylbut-1-ynyl)phenyl)ethane-1,2-dione (1062616-91-4) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-4-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-4-(3-(3-hydroxy-3-methylbut-1-ynyl)phenyl)-1-methyl-1H-imidazol-5(4H)-one (1062608-70-1)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 16h;	82%

1,2-bis(3-cyclopropyl-4-(difluoromethoxy)phenyl)ethane-1,2-dione (1062617-20-2) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-4,4-bis(3-cyclopropyl-4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one (1062609-29-3)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 85℃; for 14h;	82%

1-methylguanidine hydrochloride (22661-87-6) + benzil (134-81-6) → 2-amino-3-methyl-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one (26975-80-4)

Conditions	Yield
With potassium carbonate at 90℃; for 2h; Inert atmosphere;	82%

1-methylguanidine hydrochloride (22661-87-6) → methyl guanidinium borohydride

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;	81%

1-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-2-(4-fluoro-3-(3-fluoropropoxy)phenyl)ethane-1,2-dione (1062614-25-8) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-4-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-4-(4-fluoro-3-(3-fluoropropoxy)phenyl)-1-methyl-1H-imidazol-5(4h)-one (1062605-70-2)

Conditions	Yield
With sodium carbonate In ethanol at 90℃; for 3h;	80%

Upstream product

• 593-51-1 methylamine hydrochloride 
• 127099-85-8 N-Cyanoguanidine 

Downstream Products

• 180869-38-9 4-(dimethoxymethyl)-N-methylpyrimidin-2-amine 
• 918487-89-5 2-amino-5-(4-bromo-3-fluoro-phenyl)-5-(1-ethyl-5-methanesulfonyl-1H-pyrrol-3-yl)-3-methyl-3,5-dihydro-imidazol-4-one 

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