3923-79-3

Basic information

• Product Name: 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one
• Synonyms: 4,5-Dihydroxy-1,3-dimethylimidazolidin-2-on;1,3-Dimethyl-4,5-dihydroxyethyleneurea;4,5-dihydroxy-1,3-dimethyl-2-Imidazolidinone;1,3-Dimethyl-4,5-dihydroxy-2-imidazolinone;1,3-Dimethyl-4,5-dihydroxyimidazolidine-2-one;4,5-Dihydroxy-1,3-dimethyl-2-imidazolidone;2-Imidazolidinone, 4,5-dihydroxy-1,3-dimethyl-;1,3-Dimethyl-4,5-dihydroxy-2-imidazolidinone
• CAS NO: 3923-79-3
• Molecular Formula: C₅H₁₀N₂O₃
• Molecular Weight: 146.14
• EINECS: 223-496-2
• Mol File: 3923-79-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 132-134℃
• Boiling Point: 300.7°C at 760 mmHg
• Flash Point: 135.7°C
• Appearance: /
• Density: 1.442
• Vapor Pressure: 0.000108mmHg at 25°C
• Refractive Index: 1.579
• PKA: 13.99±0.40(Predicted)
• Water Solubility: 1000g/L at 20℃
• CAS DataBase Reference: 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one(3923-79-3)
• EPA Substance Registry System: 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one(3923-79-3)

Safety Data

• Hazardous Substances Data: 3923-79-3(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C5H10N2O3/c1-6-3(8)4(9)7(2)5(6)10/h3-4,8-9H,1-2H3

Synthetic route

1,1-Dimethylurea (598-94-7) → 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3)

Conditions	Yield
In methanol	83%

Glyoxal (131543-46-9) + N,N'-Dimethylurea (96-31-1) → 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3)

Conditions	Yield
With hydrogenchloride In water at 60℃; for 4h; pH=3;
With triethylamine In water at 25 - 35℃; pH=9;
In water at 50℃; for 4h; pH=4;
With triethylamine In water at 25 - 35℃; for 16h;

4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
sulfuric acid In 1,3-dimethyl-2-imidazolidinone at 150℃; for 2h; Product distribution / selectivity;	100%
In water at 80 - 90℃; pH=1;
With sodium hydrogencarbonate In water at 60℃; for 4h;	115 mg
With sulfuric acid In water at 95 - 100℃; for 6h;	161 g

thiosemicarbazide (79-19-6) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 5,7-dimethyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-one + 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
With hydrogenchloride In methanol at 80℃; for 1h;	A 96% B n/a

thiosemicarbazide (79-19-6) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → (4aRS,7aSR)-5,7-dimethyl-3-thioxooctahydroimidazo[4,5-e]-1,2,4-triazin-6-one

Conditions	Yield
With hydrogenchloride In methanol for 0.5h; Heating;	94%

N'-cyclohexylurea (698-90-8) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 4,5-bis(3-cyclohexylureido)-1,3-dimethyl-imidazolidin-2-one

Conditions	Yield
With hydrogenchloride at 80℃; for 1h; pH=1;	92%

p-toluene sulfinic acid (536-57-2) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → trans-4-hydroxy-1,3-dimethyl-5-(p-tolylsulfonyl)-2-imidazolidinone

Conditions	Yield
In water Ambient temperature;	90.5%

thiosemicarbazide (79-19-6) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,5-bis(3-thiosemicarbazido)imidazolidin-2-one + 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
With hydrogenchloride In water at 80℃; for 1h; pH=2;	A 90% B n/a

p-toluene sulfinic acid (536-57-2) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4-(p-tolylsulfonyl)-2-imidazolinone

Conditions	Yield
In water for 0.5h; Heating;	88.6%

toluene-4-sulfonamide (70-55-3) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → N-[1,3-Dimethyl-2-oxo-imidazolidin-(4E)-ylidene]-4-methyl-benzenesulfonamide

Conditions	Yield
With hydrogenchloride In methanol at 60 - 70℃; for 0.5h;	83%

benzenesulfonamide (98-10-2) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → N-[1,3-Dimethyl-2-oxo-imidazolidin-(4E)-ylidene]-benzenesulfonamide

Conditions	Yield
With hydrogenchloride In methanol at 60 - 70℃; for 0.5h;	82%

(S)-1-sec-butyl-3-methylurea (1404101-01-4) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → (S)-(+)-2-sec-butyl-4,6,8-trimethylglycoluril (1404101-10-5)

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol for 2h; Reflux;	80%

(R)-1-sec-butyl-3-methylurea (1404101-02-5) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → (R)-(-)-2-sec-butyl-4,6,8-trimethylglycoluril (1404101-11-6)

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol for 2h; Reflux;	80%

1-aminoguanidine hydrochloride (1937-19-5) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 4-(guanidinoimino)-1,3-dimethylimidazolidin-2-one hydrochloride

Conditions	Yield
Stage #1: 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one With hydrogenchloride In methanol at 60℃; Stage #2: 1-aminoguanidine hydrochloride In methanol at 70 - 75℃; for 1h;	78%

1,1-dimethylethylurea (1118-12-3) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → C10H18N4O2 + 4,5-bis(3-tert-butylureido)-1,3-dimethyl-imidazolidin-2-one + 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
With hydrogenchloride at 80℃; for 1h; pH=1;	A 77% B 10% C n/a

4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) + 1-cyclohexyl-3-methylurea (39804-96-1) → 8-cyclohexyl-2,4,6-trimethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

Conditions	Yield
With hydrogenchloride In water for 1h; Heating;	72%

1-(pyrimidin-2-yl)urea (33561-08-9) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,5-bis[3-(2-pyrimidinyl)ureido]imidazolidin-2-one

Conditions	Yield
With hydrogenchloride at 80℃; for 1h; pH=1;	70%

4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → trans-4,5-diazido-1,3-dimethylimidazolidin-2-one

Conditions	Yield
With hydrogenchloride; sodium azide for 120h;	67%

N-tert-Butyl-N'-methylharnstoff (25347-94-8) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 2-tert-butyl-4,6,8-trimethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione (71540-86-8)

Conditions	Yield
With hydrogenchloride In water for 1h; Heating;	65%

thiosemicarbazide (79-19-6) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 5,7-dimethyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-one + 1,3-dimethyl-4,5-bis(3-thiosemicarbazido)imidazolidin-2-one

Conditions	Yield
With hydrogenchloride In ethanol; water at 50℃; for 1.2h; Reflux;	A 65% B 17%

1-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]-3-methylurea + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]-4,6,8-trimethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

Conditions	Yield
With hydrogenchloride In water for 1h; Heating;	61%

N,N'-diethylurea (623-76-7) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,6-diethyl-tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

Conditions	Yield
Heating;	60%

N-methyl-N'-propylurea (38014-52-7) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 2,4,6-trimethyl-8-propyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

Conditions	Yield
With hydrogenchloride In water for 1h; Heating;	59%

1-aminoguanidine hydrochloride (1937-19-5) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,5-bis(3-guanidinioamino)imidazolidin-2-one dihydrochloride

Conditions	Yield
Stage #1: 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one With hydrogenchloride In water at 80℃; Stage #2: 1-aminoguanidine hydrochloride In water at 80℃; for 1h;	57%
With hydrogenchloride In methanol at 70 - 75℃; for 1h;

N-carbamoylglycine (462-60-2) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → rac-(1S,5S)-(6,8-dimethyl-3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]octan-2-yl)acetic acid

Conditions	Yield
With hydrogenchloride In water at 85℃; for 2h; pH=3;	55%
With hydrogenchloride In water at 85℃; for 3h; pH=1;

Benzenesulfinic acid (618-41-7) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4-phenylsulfonyl-2-imidazolinone

Conditions	Yield
In water Heating;	53.5%

N,N'-dimethylsulfamide (22504-72-9) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 2,4,6,8-tetramethyl-3-thia-2,4,6,8-tetraazabicyclo[3.3.0]octan-7-one 3,3-dioxide

Conditions	Yield
With hydrogenchloride at 80 - 90℃; for 1h; pH=1;	53%

imidazolidone (120-93-4) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,5-bis(2-oxoimidazolidin-1-yl)imidazolidin-2-one + 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
With hydrogenchloride In water for 1.5h; pH=1; Heating;	A 53% B n/a
With hydrogenchloride for 1.5h; pH=1 - 2; Heating;	A 53% B n/a

N,N-diethylurea (634-95-7) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 1,3-dimethyl-4,5-bis(3,3-diethyllureido)imidazolidin-2-one + 1,3-dimethylimidazolidine-2,4-dione (24039-08-5)

Conditions	Yield
With hydrogenchloride at 60 - 70℃; for 1h; pH=1;	A 53% B n/a

methanesulfonamide (3144-09-0) + 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → N-[1,3-Dimethyl-2-oxo-imidazolidin-(4E)-ylidene]-methanesulfonamide

Conditions	Yield
With hydrogenchloride In methanol at 60 - 70℃; for 0.5h;	50%

4,5-dihydroxy-1,3-dimethylimidazolidin-2-one (3923-79-3) → 6,8-dimethyl-3-thia-2,4,6,8-tetraazabicyclo[3.3.0]octan-7-one 3,3-dioxide (327040-82-4)

Conditions	Yield
With SULFAMIDE In water at 60℃; for 0.5h; pH=5 - 6;	49%

Upstream product

• 131543-46-9 Glyoxal 
• 96-31-1 N,N'-Dimethylurea 
• 598-94-7 1,1-Dimethylurea 

Downstream Products

• 185011-09-0 1,3-dimethyl-4-phenylsulfonyl-2-imidazolinone 
• 504-07-4 5,6-dhydrouracil 
• 1255948-99-2 (E)-4-(benzylideneamino)-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 
• 1418275-10-1 (E)-4-[(2-hydroxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 
• 1418275-11-2 (E)-4-(4-fluorobenzylidene)-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 
• 1418275-12-3 (E)-4-[(2-hydroxy-3-methoxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 
• 1418275-13-4 (E)-4-[(5-chloro-2-hydroxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 
• 1418275-14-5 (E)-4-[(5-bromo-2-hydroxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 

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