(2-Butyl-5-chloro-1H-imidazol-4-yl)methanol supplier

Name
(2-Butyl-5-chloro-1H-imidazol-4-yl)methanol
EINECS
CAS No. 79047-41-9
Article Data12
CAS DataBase
Density 1.236 g/cm³
Solubility
Melting Point 147-151 °C(lit.)
Formula C₈H₁₃ClN₂O
Boiling Point 407.7 °C at 760 mmHg
Molecular Weight 188.657
Flash Point 200.4 °C
Transport Information
Appearance white crystalline solid
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Butyl-4-chloro-5-(hydroxymethyl)imidazole;2-Butyl-5-chloro-1H-imidazole-4-methanol;2-n-Butyl-4-chloro-5-(hydroxymethyl)imidazole;5-Chloro-2-butyl-imidazole-4-methanol;
PSA 48.91000
LogP 1.89800

Synthetic route

: 83857-96-9
2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 2h;	90%
With hydrogen; magnesium In methanol at 20℃; under 258.574 - 413.718 Torr; for 0.583333h;

: 679412-76-1
5-benzyloxymethyl-2-butyl-4-chloro-1H-imidazole

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
With methanesulfonic acid In chloroform at 20℃; for 1h;	90%

: 68283-19-2
2-butyl-5-hydroxymethyl-1H-imidazole

A: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

B: 2-butyl-4,5-dichloroimidazole

Conditions

Conditions	Yield
With N-chloro-succinimide In tetrahydrofuran	A 65% B 10%

: 123-91-1
1,4-dioxane

: 136317-69-6
2-n-butyl-4,5-di-(hydroxymethyl)-1H-imidazole

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
With N-chloro-succinimide In ethanol	51%

: sodium dichloroisocyanurate dihydrate

: 136317-69-6
2-n-butyl-4,5-di-(hydroxymethyl)-1H-imidazole

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
In 1,4-dioxane; ethanol	50%

: 68283-19-2
2-butyl-5-hydroxymethyl-1H-imidazole

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
With N-chloro-succinimide
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran; acetonitrile / 2 h / 0 °C 2: 1.) NCS, 2.) Zn, AcOH / 1.) THF, acetonitrile, from -5 deg C to 0 deg C, 0.75 h, 2.) frp, -5 deg C to 0 deg C, 1.5 h View Scheme
With N-chloro-succinimide In water; ethyl acetate

: 153258-24-3
2-Butyl-5-trimethylsilanyloxymethyl-1H-imidazole

A: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

B: 2-Butyl-4,5-dichloro-4-trimethylsilanyloxymethyl-4H-imidazole

Conditions

Conditions	Yield
With N-chloro-succinimide; acetic acid; zinc 1.) THF, acetonitrile, from -5 deg C to 0 deg C, 0.75 h, 2.) frp, -5 deg C to 0 deg C, 1.5 h; Yield given. Multistep reaction. Title compound not separated from byproducts;

: 679412-75-0
N-(2-benzyloxy-1-cyanoethyl)pentanamide

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / CCl4; PPh3 / acetonitrile / 4 h / 45 °C 2: 90 percent / methanesulfonic acid / CHCl3 / 1 h / 20 °C View Scheme

: 57246-71-6
methyl pentanimidate

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaOH / H2O; methanol; toluene 1.2: 55 percent / POCl3 / toluene / 2 h / 100 °C 2.1: 90 percent / NaBH4 / methanol / 2 h / 20 °C View Scheme

: 148990-06-1
ethyl 2-butyl-1H-imidazole-4(5)carboxylate

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / DIBAL / toluene 2: NCS View Scheme

: 540-67-0
ethyl methyl ether

: 68283-19-2
2-butyl-5-hydroxymethyl-1H-imidazole

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
With N-chloro-succinimide In tetrahydrofuran; diethyl ether	16 g (52%)

: 2893-78-9
sode de l'acide trichloroisocyanurique

: 136317-69-6
2-n-butyl-4,5-di-(hydroxymethyl)-1H-imidazole

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
In 1,4-dioxane; ethanol

: 128-09-6
N-chloro-succinimide

: 68283-19-2
2-butyl-5-hydroxymethyl-1H-imidazole

A 2-butyl-4,5-10 dichloroimidazole: 2-butyl-4,5-10 dichloroimidazole

B: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
In tetrahydrofuran; 2-methoxy-ethanol; water

...Expand

: 109-86-4
2-methoxy-ethanol

: 68283-19-2
2-butyl-5-hydroxymethyl-1H-imidazole

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
With N-chloro-succinimide In 1,4-dioxane; water; ethyl acetate

(NH4)2 Ce(NO3)6: (NH4)2 Ce(NO3)6

: 75-09-2
dichloromethane

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 83857-96-9
2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde

Conditions

Conditions	Yield
With potassium hydroxide In water; acetic acid	92%
In water; acetic acid

...Expand

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 109-77-3
malononitrile

: 2-amino-4-(2-butyl-4-chloro-1H-imidazol-5-yl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile

Conditions

Conditions	Yield
With dimethyl sulfoxide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 9h;	81%

...Expand

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 18162-48-6
tert-butyldimethylsilyl chloride

: 137582-52-6
2-butyl-4-chloro-5-[(t-butyldimethylsilyloxy)methyl]imidazole

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 3.5h; Ambient temperature;	80%

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 133051-88-4
N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole

: 133909-99-6
2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h;	80%

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 135-19-3
β-naphthol

: 109-77-3
malononitrile

: 2-amino-4-(2-butyl-4-chloro-1H-imidazol-5-yl)-4H-benzo[g]chromene-3-carbonitrile

Conditions

Conditions	Yield
With dimethyl sulfoxide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 12h;	79%

...Expand

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 83857-96-9
2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In acetic acid at 25℃; for 3h;	77%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; iodine; sodium hydrogencarbonate In water; toluene at 20℃; for 16h;	690 mg
With oxygen; Pt/Bi on graphite In methanol at 60℃; under 2250.23 Torr; for 6h; Product distribution; Further Variations:; Reagents;
With manganese dioxide In dichloromethane	12.81 g (86%)

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 109-77-3
malononitrile

: 108-46-3
recorcinol

: 2-amino-4-(2-butyl-4-chloro-1H-imidazol-5-yl)-7-hydroxy-4H-chromene-3-carbonitrile

Conditions

Conditions	Yield
With dimethyl sulfoxide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 14h;	74%

...Expand

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 114772-54-2
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile

: 114772-55-3
2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

Conditions

Conditions	Yield
Stage #1: 2-n-butyl-4-chloro-5-hydroxymethylimidazole With sodium methylate In N,N-dimethyl-formamide at 25℃; for 0.5h; Stage #2: 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile In N,N-dimethyl-formamide at 20℃; for 24h;	40%
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Multistep reaction;

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 138459-24-2
methyl 4'-(bromomethyl)-3'-fluorobiphenyl-2-carboxylate

: 138459-25-3
methyl 3'-fluoro-4'-<<2-butyl-4-chloro-5-(hydroxymethyl)-1H-imidazol-1-yl>methyl>biphenyl-2-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;	30%

: 67-56-1
methanol

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 124750-71-6
2-butyl-4-chloro-1H-imidazole-5-carboxylic acid,methyl ester

Conditions

Conditions	Yield
With manganese(IV) oxide; sodium cyanide; acetic acid 1.) THF; Multistep reaction;

: 623-24-5
1,4-bis(bromomethyl)benzene

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

A: [1-(4-Bromomethyl-benzyl)-2-butyl-5-chloro-1H-imidazol-4-yl]-methanol

B: [3-(4-Bromomethyl-benzyl)-2-butyl-5-chloro-3H-imidazol-4-yl]-methanol

Conditions

Conditions	Yield
With sodium methylate 1.) methanol, 0 deg C, 2.) DMF, 25 deg C; Multistep reaction;

...Expand

: 56358-46-4
6-bromomethyl-2-naphthalenecarbonitrile

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

A: 135943-07-6
6-(2-Butyl-5-chloro-4-hydroxymethyl-imidazol-1-ylmethyl)-naphthalene-2-carbonitrile

B: 135943-02-1
2-n-butyl-4-chloro-5-(hydroxymethyl)-1-<(2-cyanonaphthalen-6-yl)methyl>imidazole

Conditions

Conditions	Yield
With sodium hydride 1.) DMF, 25 deg C, 1 h, 2.) DMF, RT, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 51359-78-5
4-(bromomethyl)benzaldehyde

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

A: 125665-59-0
4-(2-Butyl-5-chloro-4-hydroxymethyl-imidazol-1-ylmethyl)-benzaldehyde

B: 114773-11-4
1-(4-formylbenzyl)-2-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Conditions	Yield
With sodium methylate 1.) methanol, 0 deg C, 2.) DMF, 25 deg C; Multistep reaction;

...Expand

: 114772-37-1
methyl 4'-(bromomethyl)-[1,1'-biphenyl]-3-carboxylate

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 114772-41-7
2-butyl-1-<(3'-carbomethoxybiphenyl-4-yl)methyl>-4-chloro-5-(hydroxymethyl)imidazole

Conditions

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) 40 deg C, 4 h; Yield given. Multistep reaction;

: 114772-96-2
methyl 2-[4-(bromomethyl)benzoyl]benzoate

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 114772-97-3
2-butyl-1-<4-(2-carbomethoxybenzoyl)benzyl>-4-chloro-5-(hydroxymethyl)imidazole

Conditions

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) 40 deg C, 4 h; Yield given. Multistep reaction;

: 30087-38-8
methyl 2-[4-(bromomethyl)phenoxy]benzoate

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 114772-89-3
2-butyl-4-chloro-1-[4-(2-carbomethoxyphenoxy)benzyl]-5-hydroxymethylimidazole

Conditions

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) 40 deg C, 4 h; Multistep reaction;

: 2-(4-Bromomethyl-phenylsulfanyl)-benzoic acid methyl ester

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 2-[4-(2-Butyl-4-chloro-5-hydroxymethyl-imidazol-1-ylmethyl)-phenylsulfanyl]-benzoic acid methyl ester

Conditions

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) 40 deg C, 4 h; Multistep reaction;

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 128577-47-9
methyl 4-(bromomethyl)-3-fluorobenzoate

: 138459-26-4
4-(2-Butyl-4-chloro-5-hydroxymethyl-imidazol-1-ylmethyl)-3-fluoro-benzoic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 114772-39-3
4'-bromomethyl-2-nitrobiphenyl

: 124750-43-2
2-butyl-4-chloro-5-(hydroxymethyl)-1-<(2'-nitrobiphenyl-4-yl)methyl>imidazole

Conditions

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Multistep reaction;

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 114772-38-2
Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

: 114772-43-9
2-butyl-4-chloro-5-hydroxymethyl-1-[(2'-methoxycarbonyl-1,1'-biphenyl-4-yl)methyl]-1H-imidazole

Conditions

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Yield given. Multistep reaction;

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 2-(4-Bromomethyl-phenyl)-furan-3-carboxylic acid ethyl ester

: 2-[4-(2-Butyl-4-chloro-5-hydroxymethyl-imidazol-1-ylmethyl)-phenyl]-furan-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Multistep reaction;

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 134360-53-5
methyl 4'-methyl-2',6'-dimethoxy<1,1'-biphenyl>-2-carboxylate

A: 134360-55-7
4'-<<2-butyl-4-chloro-5-(hydroxymethyl)-1H-imidazolyl>methyl>-2',6'-dimethoxy<1,1'-biphenyl>-2-carboxylic acid methyl ester

B: 134360-56-8
4'-<<2-butyl-4-(hydroxymethyl)-5-chloro-1H-imidazolyl>methyl>-2',6'-dimethoxy<1,1'-biphenyl>-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 5-(4'-Bromomethyl-biphenyl-2-yl)-3H-[1,2,3]triazole-4-carbonitrile

: 125573-80-0
2-butyl-4-chloro-1-<<2'-(5-cyano-1,2,3-triazol-4-yl)biphenyl-4-yl>methyl>-5-(hydroxymethyl)imidazole

Conditions

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Multistep reaction;

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 133051-88-4
N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole

A: 133909-99-6
2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol

B: {2-Butyl-5-chloro-1-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-imidazol-4-yl}-methanol

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Product distribution; Ambient temperature; various ratios of reagents;
With potassium carbonate In N,N-dimethyl-formamide Ambient temperature;

...Expand

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 3-(4'-Bromomethyl-biphenyl-2-yl)-5-trifluoromethyl-4-trityl-4H-[1,2,4]triazole

: {2-Butyl-5-chloro-3-[2'-(5-trifluoromethyl-4-trityl-4H-[1,2,4]triazol-3-yl)-biphenyl-4-ylmethyl]-3H-imidazol-4-yl}-methanol

Conditions

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Multistep reaction;

(2-Butyl-5-chloro-1H-imidazol-4-yl)methanol Specification

The (2-Butyl-5-chloro-1H-imidazol-4-yl)methanol, with the CAS registry number 79047-41-9, has the systematic name of (2-butyl-4-chloro-1H-imidazol-5-yl)methanol. For being a kind of white crystalline solid, its product categories are including Heterocyclic Compounds; Heterocycles; Halogenated Heterocycles; Heterocyclic Building Blocks; Imidazoles; ImidazolesBuilding Blocks.

The physical properties of this chemical are as follows: (1)ACD/LogP: 1.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.37; (4)ACD/LogD (pH 7.4): 1.41; (5)ACD/BCF (pH 5.5): 6.29; (6)ACD/BCF (pH 7.4): 6.97; (7)ACD/KOC (pH 5.5): 125.92 ; (8)ACD/KOC (pH 7.4): 139.7; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 27.05 ; (13)Index of Refraction: 1.554; (14)Molar Refractivity: 48.93 cm³; (15)Molar Volume: 152.5 cm³; (16)Polarizability: 19.4×10^-24 cm³; (17)Surface Tension: 50.4 dyne/cm; (18)Density: 1.236 g/cm³; (19)Flash Point: 200.4 °C; (20)Enthalpy of Vaporization: 69.55 kJ/mol; (21)Boiling Point: 407.7 °C at 760 mmHg; (22)Vapour Pressure: 2.23E-07 mmHg at 25°C.

When you are dealing with this chemical, you should be much more cautious. For being among the irritant chemicals, it is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

In addition, you could convert the following datas into the molecular structure:
(1)SMILES:Clc1nc(nc1CO)CCCC
(2)InChI:InChI=1/C8H13ClN2O/c1-2-3-4-7-10-6(5-12)8(9)11-7/h12H,2-5H2,1H3,(H,10,11)
(3)InChIKey:DXSZKDOOHOBZMT-UHFFFAOYAN

Product Name

(2-Butyl-5-chloro-1H-imidazol-4-yl)methanol

Synthetic route

(2-Butyl-5-chloro-1H-imidazol-4-yl)methanol Specification

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