• Name

  4-Hydroxymethyl-5-methylimidazole

• EINECS 249-740-8
• CAS No. 29636-87-1
• Article Data18
• CAS DataBase
• Density 1.231 g/cm³
• Solubility almost transparency
• Melting Point 136°C
• Formula C5H8 N2 O
• Boiling Point 389.1 °C at 760 mmHg
• Molecular Weight 112.131
• Flash Point 189.1 °C
• Transport Information
• Appearance White and light brown Crystalsl Powder
• Safety 26-36/37/39
• Risk Codes 36/37/38
• Molecular Structure
• Hazard Symbols R36/37/38:Irritating to eyes, respiratory system and skin.;
• Synonyms 1H-Imidazole-4-methanol,5-methyl- (9CI); Imidazole-4(or 5)-methanol, 5(or 4)-methyl- (7CI);Imidazole-4-methanol, 5-methyl- (8CI); 4-(Hydroxymethyl)-5-methyl-1H-imidazole;4-(Hydroxymethyl)-5-methylimidazole; 4-Methyl-5-(hydroxymethyl)imidazole;4-Methyl-5-imidazolemethanol; 5-(Hydroxymethyl)-4-methylimidazole;5-Methyl-1H-imidazole-4-methanol; 5-Methyl-4-imidazolemethanol
• PSA 48.91000
• LogP 0.21040

Synthetic route

51605-32-4

Ethyl 5-Methyl-4-imidazolecarboxylate

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 4h; Reflux;	89%
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating;	55%

50-00-0

formaldehyd

51605-32-4

Ethyl 5-Methyl-4-imidazolecarboxylate

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

Conditions

Conditions	Yield
With sodium hydroxide In water for 0.5h; Heating;	68%

5-methylimidazole-4-carboxylic acid sodium salt

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

Conditions

Conditions	Yield
With sodium hydroxide; formaldehyd In water	65%

50-00-0

formaldehyd

822-36-6

4-Methylimidazole

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

Conditions

Conditions	Yield
In water at 40℃;

51605-32-4

ethyl 4(5)-methylimidazole-5(4)-carboxylate

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; ethanol

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

(5-methyl-1H-imidazol-4-yl)methyl nitrate

Conditions

Conditions	Yield
With acetic anhydride; sodium nitrite In methanol at 10 - 20℃; for 3.5h;	92%

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

68282-53-1

5-methyl-4-formylimidazole

Conditions

Conditions	Yield
With manganese(IV) oxide In tetrahydrofuran for 3h; Oxidation; Heating;	85%

68-11-1

mercaptoacetic acid

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

112528-37-7

[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]acetic acid

Conditions

Conditions	Yield
In acetic acid for 24h; Reflux;	82%

67-56-1

methanol

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

78892-68-9

5-methyl-4-imidazole carboxylic acid methyl ester

Conditions

Conditions	Yield
With manganese(IV) oxide; sodium cyanide at 20℃; for 20h; Oxidation; esterification;	70%

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

51605-33-5

4-chloromethyl-5-methyl-imidazole hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride at 100℃; for 0.5h;	67%

122852-75-9

2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

122852-42-0

alosetron

Conditions

Conditions	Yield
With methanesulfonic acid In 1-methyl-pyrrolidin-2-one at 20 - 135℃; for 21h; Schlenk technique; Inert atmosphere;	58%

24544-04-5

2,6-diisopropylbenzenamine

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

4(5)-methyl-5(4)-(2,6-diisopropylphenylimino)methylimidazole

Conditions

Conditions	Yield
Stage #1: 4(5)-methyl-5(4)-hydroxymethylimidazole With manganese(IV) oxide In ethanol for 12h; Reflux; Stage #2: 2,6-diisopropylbenzenamine With toluene-4-sulfonic acid In ethanol for 6h; Reflux;	50%

76-83-5

trityl chloride

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

106147-84-6

4-Hydroxymethyl-5-methyl-1-(triphenylmethyl)imidazole

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature;	10%
With triethylamine In N,N-dimethyl-formamide
With triethylamine In N-methyl-acetamide; methanol-dichloromethane; ethanol; water

540-63-6

ethane-1,2-dithiol

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

100442-40-8

1,6-bis(5-methyl-4-imidazolyl)-2,5-dithiahexane

Conditions

Conditions	Yield
With acetic acid Heating;

106-45-6

para-thiocresol

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

119827-28-0

5-methyl-4-(4'-methylphenylmercaptomethyl)imidazole

Conditions

Conditions	Yield
With acetic acid Heating;

100-53-8

phenylmethanethiol

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

119827-22-4

5-methyl-4(benzylmercaptomethyl)-imidazole

Conditions

Conditions	Yield
With acetic acid Heating;

75-08-1

ethanethiol

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

119827-24-6

5-methyl-4-(ethylmercaptomethyl)imidazole

Conditions

Conditions	Yield
With acetic acid Heating;

109-80-8

1.3-propanedithiol

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

91631-43-5

1,7-bis(5-methyl-4-imidazolyl)-2,6-dithiaheptane

Conditions

Conditions	Yield
With acetic acid Heating;

41563-69-3

1,3-bis(mercaptomethyl)benzene

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

1,3-bis(3'-(5''-methyl-4''-imidazolyl)-2'-thia-1'-propyl)benzene

Conditions

Conditions	Yield
With acetic acid Heating;

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

2302-39-8

4,5-dimethylimidazole

Conditions

Conditions	Yield
Ambient temperature;

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

69395-89-7

5-methyl-4-chloromethyl imidazole

Conditions

Conditions	Yield
With thionyl chloride

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

4(5)-(carboxymethyl)-5(4)-methylimidazole hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: SOCl2 2.1: dimethylsulfoxide / 20 °C 3.1: aq. HBr / 1.5 h / Heating 3.2: HCl / ethanol / 2.5 h / Heating 3.3: 291 mg / aq. HCl / 5 h / 50 °C View Scheme

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

51667-66-4

4(5)-(cyanomethyl)-5(4)-methylimidazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 2: dimethylsulfoxide / 20 °C View Scheme
Multi-step reaction with 2 steps 1: SOCl2 2: dimethylsulfoxide View Scheme

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

500782-84-3

C42H45N5O4S

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: Et3N / dimethylformamide 2: 80 percent / SOCl2 / dimethylformamide; CH2Cl2 / 0.25 h / 0 °C 3: 70 percent / NaH / tetrahydrofuran 4: 98 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure 5: 86 percent / CH2Cl2 / 5 h / 0 - 20 °C View Scheme

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

501010-07-7

C23H31N5O4S

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: Et3N / dimethylformamide 2: 80 percent / SOCl2 / dimethylformamide; CH2Cl2 / 0.25 h / 0 °C 3: 70 percent / NaH / tetrahydrofuran 4: 98 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure 5: 86 percent / CH2Cl2 / 5 h / 0 - 20 °C 6: 88 percent / TFA; triethylsilane / CH2Cl2 / 1 h / 20 °C View Scheme

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

C22H29N5O4S

Conditions

Conditions

Yield

Multi-step reaction with 7 steps 1: Et3N / dimethylformamide 2: 80 percent / SOCl2 / dimethylformamide; CH2Cl2 / 0.25 h / 0 °C 3: 70 percent / NaH / tetrahydrofuran 4: 98 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure 5: 86 percent / CH2Cl2 / 5 h / 0 - 20 °C 6: 88 percent / TFA; triethylsilane / CH2Cl2 / 1 h / 20 °C 7: 85 percent / aq. NaOH / methanol / 1 h / 20 °C View Scheme

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

500782-85-4

C43H47N5O4

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: Et3N / dimethylformamide 2: 80 percent / SOCl2 / dimethylformamide; CH2Cl2 / 0.25 h / 0 °C 3: 70 percent / NaH / tetrahydrofuran 4: 98 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure 5: 85 percent / CH2Cl2 / 5 h / 0 - 20 °C View Scheme

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

501010-09-9

C24H33N5O4

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: Et3N / dimethylformamide 2: 80 percent / SOCl2 / dimethylformamide; CH2Cl2 / 0.25 h / 0 °C 3: 70 percent / NaH / tetrahydrofuran 4: 98 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure 5: 85 percent / CH2Cl2 / 5 h / 0 - 20 °C 6: 88 percent / TFA; triethylsilane / CH2Cl2 / 1 h / 20 °C View Scheme

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

C23H31N5O4

Conditions

Conditions

Yield

Multi-step reaction with 7 steps 1: Et3N / dimethylformamide 2: 80 percent / SOCl2 / dimethylformamide; CH2Cl2 / 0.25 h / 0 °C 3: 70 percent / NaH / tetrahydrofuran 4: 98 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure 5: 85 percent / CH2Cl2 / 5 h / 0 - 20 °C 6: 88 percent / TFA; triethylsilane / CH2Cl2 / 1 h / 20 °C 7: 85 percent / aq. NaOH / methanol / 1 h / 20 °C View Scheme

29636-87-1

4(5)-methyl-5(4)-hydroxymethylimidazole

500782-86-5

C42H45N5O4

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: Et3N / dimethylformamide 2: 80 percent / SOCl2 / dimethylformamide; CH2Cl2 / 0.25 h / 0 °C 3: 70 percent / NaH / tetrahydrofuran 4: 98 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure 5: 80 percent / CH2Cl2 / 5 h / 0 - 20 °C View Scheme

4-Hydroxymethyl-5-methylimidazole Chemical Properties