5699-40-1

Basic information

• Product Name: N-ACETYLGUANIDINE
• Synonyms: 1-ACETYLGUANIDINE;N-ACETYLGUANIDINE;N-(aminoiminomethyl)acetamide;2-Acetylguanidine;1-Acetylguanidine,99%;1-Acetylguanidne;Monoacetyl guanidine;N-(Carbamimidoyl)acetamide
• CAS NO: 5699-40-1
• Molecular Formula: C₃H₇N₃O
• Molecular Weight: 101.10718
• EINECS: 227-180-5
• Product Categories: Guanidines;Nitrogen Compounds;Organic Building Blocks
• Mol File: 5699-40-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 181-183 °C(lit.)
• Boiling Point: 238.7oC at 760mmHg
• Flash Point: 98.2oC
• Appearance: White to off-white/Powder
• Density: 1.34g/cm3
• Vapor Pressure: 0.0418mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: pK1: 8.23(+1) (25°C)
• CAS DataBase Reference: N-ACETYLGUANIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYLGUANIDINE(5699-40-1)
• EPA Substance Registry System: N-ACETYLGUANIDINE(5699-40-1)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5699-40-1(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Uses

1-Acetylguanidine may be used in the preparation of:4-[5-(3-fluorophenyl)furan-2-yl]-2-acetylamino-5-methylimidazolenovel series of amino-protected 6-alkyl-, 6-aryl-, 6-heteroaryl- and 5,6-fused-cycloalkane 4-trifluoromethyl-2-acetylaminopyrimidinesnew series of protected 6-alkyl- and 6-aryl-2-acetylamino-4(3H)-pyrimidinones4-trifluoromethyl-6-(2,2-dimethoxyethyl)-2-acetylaminopyrimidine

General Description

1-Acetylguanidine is a guanidine derivative.

InChI:InChI=1/C3H7N3O/c1-2(7)6-3(4)5/h1H3,(H4,4,5,6,7)/p+1

Synthetic route

guanidine carbonate + ethyl acetate (141-78-6) → acetylguanidine (5699-40-1)

Conditions	Yield
With sodium In ethanol at 40 - 60℃;	57%

ethanol (64-17-5) + N,N'-diacetyl-guanidine (81256-27-1) → acetylguanidine (5699-40-1)

guanidine nitrate (113-00-8) + ethyl acetate (141-78-6) → acetylguanidine (5699-40-1)

C19H19N3O5 (1610517-96-8) → acetylguanidine (5699-40-1)

Conditions	Yield
With 10 wt% Pd(OH)2 on carbon; hydrogen In tetrahydrofuran; ethanol at 20℃; under 760.051 Torr; for 16h;

acetylguanidine (5699-40-1) + 3-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-1-bromo-butan-2-one (476623-19-5) → acetic acid 3-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-2-oxo-butyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 23℃; for 48h;	95%

tetrafluoroboric acid diethyl ether complex + acetylguanidine (5699-40-1) → acylguanidinium tetrafluoroborate

Conditions	Yield
In methanol at 20℃;	94%

acetylguanidine (5699-40-1) + 1-[1-(benzenesulfonyl)-1H-indol-3-yl]-2-bromoethan-1-one (332135-64-5) → N-{5-[1-(benzenesulfonyl)-1H-indol-3-yl]-1H-imidazol-2-yl}acetamide

Conditions	Yield
In N,N-dimethyl-formamide at 40℃; for 96h;	92%

(E)-1,1,1-Trifluoro-4-methoxy-4-(4-methoxy-phenyl)-but-3-en-2-one + acetylguanidine (5699-40-1) → 4-trifluoromethyl-6-(4-methoxyphenyl)-2-acetylaminopyrimidine (1020541-03-0)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	85%

acetylguanidine (5699-40-1) + 4-(p-bromophenyl)-1,1,1-trifluoro-4-methoxy-3-buten-2-one → 4-trifluoromethyl-6-(4-bromophenyl)-2-acetylaminopyrimidine (1020541-02-9)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	85%

acetylguanidine (5699-40-1) + 1,3-diphenyl-propen-3-one (614-47-1) → N-(4,6-diphenylpyrimidin-2-yl)acetamide (58413-41-5)

Conditions	Yield
Stage #1: 1,3-diphenyl-propen-3-one With sulfur In dimethyl sulfoxide at 20℃; Sealed tube; Stage #2: acetylguanidine In dimethyl sulfoxide at 40℃; for 12h; Sealed tube;	84%

acetylguanidine (5699-40-1) + 1-(4-amino-3,5-dichlorophenyl)-2-bromoethan-1-one (37148-47-3) → N-(4-(4-amino-3,5-dichlorophenyl)-1H-imidazol-2-yl)acetamide

Conditions	Yield
In acetonitrile at 100℃; for 3h;	81%
In acetonitrile at 100℃; for 3h;	81%

(E)-4-(4-Chloro-phenyl)-1,1,1-trifluoro-4-methoxy-but-3-en-2-one + acetylguanidine (5699-40-1) → 4-trifluoromethyl-6-(4-chlorophenyl)-2-acetylaminopyrimidine (1020541-01-8)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	80%

acetylguanidine (5699-40-1) + 4-methoxy-4-phenyl-1,1,1-trifluorobut-3-en-2-one → 4-trifluoromethyl-6-phenyl-2-acetylaminopyrimidine (1020540-98-0)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	80%

acetylguanidine (5699-40-1) + 2-bromo-1-(4-chlorophenyl)-1-propanone (877-37-2) → N-(5-(4-chlorophenyl)-4-methyl-1H-imidazol-2-yl)acetamide

Conditions	Yield
In acetonitrile at 70℃; for 20h;	80%

1-(benzo[1,3]dioxol-5-yl)-2-bromo-2-(6-methylpyridin-2-yl)ethanone (752260-31-4) + acetylguanidine (5699-40-1) → N-[4-(benzo[1,3]dioxol-5-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl]acetamide (945244-83-7)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 96h;	79%

acetylguanidine (5699-40-1) + 2-bromo-4'-fluoroacetophenone (403-29-2) → N-(4-(4-fluorophenyl)-1H-imidazol-2-yl)acetamide (910443-44-6)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 0.333333h; Microwave irradiation;	79%
In acetonitrile at 40℃; for 1h; microwave irradiation;

acetylguanidine (5699-40-1) + 4,6,6-trimethoxy-1,1,1-trifluorohex-3-en-2-one (1140485-84-2) → 4-trifluoromethyl-6-(2,2-dimethoxyethyl)-2-acetylaminopyrimidine (1482520-18-2)

Conditions	Yield
In acetonitrile at 85℃; for 24h;	76%

acetylguanidine (5699-40-1) + 1,1,1-trifluoro-4-methoxy-4-(4-methylphenyl)-3-buten-2-one → 4-trifluoromethyl-6-(4-methylphenyl)-2-acetylaminopyrimidine (1020540-99-1)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	72%

acetylguanidine (5699-40-1) + (R,E)-6-(2-bromo-4-fluorophenyl)-3-(1-hydroxyethylidene)piperidine-2,4-dione (1177369-31-1) → (R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one (934344-61-3)

Conditions	Yield
With pyrrolidine In ethanol at 160℃; for 0.166667h; microwave irradiation;	72%

4-(4-biphenyl)-1,1,1-trifluoro-4-methoxybut-3-en-2-one (868662-39-9) + acetylguanidine (5699-40-1) → 4-trifluoromethyl-6-biphenyl-2-acetylaminopyrimidine (1020541-07-4)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	70%

acetylguanidine (5699-40-1) + 2-(4-bromo-3-oxobutyl)isoindoline-1,3-dione (51132-00-4) → N-<5-<2-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)ethyl>-1H-imidazol-2-yl>acetamide (160072-65-1)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 100h;	70%

acetylguanidine (5699-40-1) + α-bromoacetophenone (70-11-1) → 2-amino-4-phenyl-1H-imidazole hemisulfate

Conditions	Yield
Stage #1: acetylguanidine; α-bromoacetophenone Stage #2: With sulfuric acid; water	68%
Stage #1: acetylguanidine; α-bromoacetophenone In acetonitrile at 80℃; for 9h; Stage #2: With sulfuric acid In acetonitrile for 4h; pH=2; Temperature;	16%

acetylguanidine (5699-40-1) + 1,1,1-trifluoro-4-methoxypent-3-en-2-one (135351-20-1, 102145-82-4) → 4-trifluoromethyl-6-methyl-2-acetylaminopyrimidine (1020540-97-9)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	67%

acetylguanidine (5699-40-1) + C19H23BrF2O (1223104-88-8) → C22H28BrF2N3O (1223105-02-9)

Conditions	Yield
With sodium carbonate In acetonitrile for 4h; Reflux;	67%

acetylguanidine (5699-40-1) + 1-[1-(benzenesulfonyl)-1H-indol-3-yl]-2-bromobutan-1-one → N-{5-[1-(benzenesulfonyl)-1H-indol-3-yl]-4-ethyl-1H-imidazol-2-yl}acetamide

Conditions	Yield
In N,N-dimethyl-formamide at 40℃; for 96h;	67%

acetylguanidine (5699-40-1) + α-bromoacetophenone (70-11-1) → N-[1-(2-oxo-2-phenylethyl)-4-phenyl-1H-imidazol-2-yl]acetamide

Conditions	Yield
In acetonitrile at 80℃; for 8h; Temperature; Time; Solvent; Concentration;	65.9%

acetylguanidine (5699-40-1) + α-bromoacetophenone (70-11-1) → N-<4(5)-Phenyl-1H-imidazol-2-yl>acetamide (160041-64-5)

Conditions	Yield
In acetonitrile at 100℃; for 3h;	64%
In acetonitrile at 100℃; for 3h;	64%
In N,N-dimethyl-formamide at 20℃; for 3.5h; Time; Temperature; Solvent; Concentration;	60%
In N,N-dimethyl-formamide at 0 - 20℃; for 15h;	54%

tert-butyl 4-((dimethylamino)methylene)-3,5-dioxopiperidine-1-carboxylate (478623-90-4) + acetylguanidine (5699-40-1) → C9H10N4O2 + 1,1-dimethylethyl 2-(acetylamino)-5,8-dihydro-5-oxo-pyrido[3,4-d]pyrimidine-7(6H)-carboxylate (478628-60-3)

Conditions	Yield
In toluene for 1.5h; Heating / reflux;	A 63% B 11%

2-trifluoroacetyl-1-methoxycycloheptene (881020-28-6) + acetylguanidine (5699-40-1) → 4-trifluoromethyl-6,7,8,9-tetrahydro-5H-cyclohepta[d]-2-acetylaminopyrimidine (1020541-12-1)

Conditions	Yield
With boron trifluoride diethyl etherate In methanol; isopropyl alcohol at 80 - 85℃; for 20h;	62%

acetylguanidine (5699-40-1) + 2-Bromo-1-[(1S,3R)-3-(3-chloro-phenyl)-2,2-dimethyl-cyclopropyl]-propan-1-one → C17H20ClN3O

Conditions	Yield
In DMF (N,N-dimethyl-formamide) for 72h;	61%

C38H52BrN4O10P (877069-01-7) + acetylguanidine (5699-40-1) → C41H56N7O10P

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 120h;	57%

2-ethoxythiocarbonyl-pyrrolidine-1-carboxylic acid benzyl ester (888314-27-0) + acetylguanidine (5699-40-1) → 2-(N'-acetyl-guanidinocarbothioyl)-pyrrolidine-1-carboxylic acid benzyl ester (888314-29-2)

Conditions	Yield
Stage #1: acetylguanidine With sodium hydride In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: 2-ethoxythiocarbonyl-pyrrolidine-1-carboxylic acid benzyl ester In tetrahydrofuran at 0 - 20℃; for 12.5h; Stage #3: With acetic acid In water pH=3;	56%

acetylguanidine (5699-40-1) + 1,1,1-trifluoro-4-(4-fluorophenyl)-4-methoxybut-3-en-2-one → 4-trifluoromethyl-6-(4-fluorophenyl)-2-acetylaminopyrimidine (1020541-00-7)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	55%

Upstream product

• 64-17-5 ethanol 
• 81256-27-1 N,N'-diacetyl-guanidine 
• 113-00-8 guanidine nitrate 
• 141-78-6 ethyl acetate 
• 1610517-96-8 C₁₉H₁₉N₃O₅ 
• 81256-27-1 diacetylguanidine 

Downstream Products

• 542-02-9 2-methyl-4,6-diamino-1,3,5-triazine 
• 102589-26-4 N-acetyl-N'-(4-nitro-benzenesulfonyl)-guanidine 
• 27182-54-3 5-phenyl-1,2,4-thiadiazol-3-amine 
• 57083-86-0 3-Amino-5-pentyl-1,2,4-thiadiazol 
• 27182-58-7 5-benzyl-[1,2,4]thiadiazol-3-ylamine 
• 40639-97-2 N-<4,5-Dimethyl-1H-imidazol-2-yl>acetamide 
• 160041-64-5 N-<4(5)-Phenyl-1H-imidazol-2-yl>acetamide 
• 160072-51-5 N-<4(5)-Methyl-4(5)-phenyl-1H-imidazol-2-yl>acetamide 
• 40639-93-8 N‐(4,5,6,7‐tetrahydro‐1H‐benzo[d]imidazol‐2‐yl)acetamide 
• 160072-52-6 N-<4(5)-Diphenyl-1H-imidazol-2-yl>acetamide 
• 189131-47-3 N-(acetylamidino)-N'-(2,3,5-tri-O-benzoyl-β-D-ribosyl)urea 
• 436091-30-4 N-(5-{1-[7-methoxy-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-ethyl}-1H-imidazol-2-yl)-acetamide 
• 852446-91-4 carbonic acid 4-[2-(2-acetylamino-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-ethyl]-phenyl ester tert-butyl ester 

Relevant articles and documents

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