[ CAS No. 37067-95-1 ] {[proInfo.proName]}

Name: 37067-95-1|2-Iodo-1-methyl-1H-imidazole|97%
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SKU: A254101
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2D 3D

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Quality Control of [ 37067-95-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 37067-95-1 ]

SDS Specification

Alternatived Products of [ 37067-95-1 ]

Product Details of [ 37067-95-1 ]

CAS No. :	37067-95-1	MDL No. :	MFCD00661606
Formula :	C₄H₅IN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BKRACZNEJSCZML-UHFFFAOYSA-N
M.W :	208.00	Pubchem ID :	335835
Synonyms :

Calculated chemistry of [ 37067-95-1 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.21
TPSA :	17.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.07 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.54
Log Po/w (XLOGP3) :	0.7
Log Po/w (WLOGP) :	1.02
Log Po/w (MLOGP) :	0.59
Log Po/w (SILICOS-IT) :	1.43
Consensus Log Po/w :	1.06

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.1
Solubility :	1.66 mg/ml ; 0.00796 mol/l
Class :	Soluble
Log S (Ali) :	-0.65
Solubility :	46.4 mg/ml ; 0.223 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.75
Solubility :	3.67 mg/ml ; 0.0177 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Safety of [ 37067-95-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 37067-95-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 37067-95-1 ]
Downstream synthetic route of [ 37067-95-1 ]

[ 37067-95-1 ] Synthesis Path-Upstream 1~2

1
[ 616-47-7 ]
[ 37067-95-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With 4-(3-methylimidazolium)butanesulfonate; iodine In water at 20℃; for 2 h; Sealed tube; Green chemistry	General procedure: To a mixture of 2-phenylimidazo[1,2-a]pyridine (1a, 39 mg, 0.2 mmol), molecular I₂ (50 mg, 1 equiv), and 4-(3-methylimidazolium)butane-1-sulfonate (I, 9 mg, 20 molpercent) in a sealed tube was added water (2 mL) and the mixture was stirred at r.t. for 2 h. After completion of the reaction (TLC), the mixture was extracted with EtOAc (20 mL). The organic phase was dried (anhyd Na₂SO₄) and concentrated under reduced pressure give the crude residue which was purified by column chromatography (silica gel, 60–120 mesh, petroleum ether/EtOAc, 9:1) to afford 2a as a white solid: yield: 58 mg (91percent); mp 132–134 °C.
55%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.0833333 h; Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 20℃; for 0.333333 h;	a) Synthesis of 2-iodine-1-methyl-imidazol 7.97 ml (100.0 mmol) 1-methyl-imidazol was dissolved in THF (100 ml) and cooled to -78° C. 40 ml (2.5 M in hexane, 100 mmol) BuLi was added in drops at this temperature. After the end of addition, heating was performed for 5 min to 0° C., followed immediately by cooling to -78° C. A solution of 27.9 g (110.0 mmol) iodine (I₂) in THF (60 ml) was added in drops at this temperature and stirring was performed for 20 min at RT. Quenching was subsequently performed with a 5percent aq. Na₂S₂O₃ sol (120 ml) and extraction with DCM (4*50 ml). The collected organic phases were dried over MgSO₄, filtered and concentrated in a vacuum. 11.5 g (55.2 mmol, 55percent) 2-iodine-1-methyl-imidazol was obtained by crystallisation of the residue from diethylether.

Reference： [1] Organic Letters, 2014, vol. 16, # 12, p. 3244 - 3247
[2] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 20, p. 2774 - 2781
[3] Organic Letters, 2003, vol. 5, # 18, p. 3209 - 3212
[4] Journal of Organometallic Chemistry, 2007, vol. 692, # 1-3, p. 635 - 644
[5] Synthesis (Germany), 2016, vol. 48, # 22, p. 4009 - 4015
[6] Chemical Communications, 2016, vol. 52, # 28, p. 4983 - 4986
[7] Patent: US2008/261996, 2008, A1, . Location in patent: Page/Page column 45
[8] Polish Journal of Chemistry, 1981, vol. 55, # 7/8, p. 1659 - 1665
[9] Tetrahedron, 1997, vol. 53, # 21, p. 7237 - 7254
[10] Chemical Communications, 2004, # 11, p. 1306 - 1307
[11] CrystEngComm, 2013, vol. 15, # 47, p. 10157 - 10160

2
[ 616-47-7 ]
[ 37067-95-1 ]
[ 86026-81-5 ]

Yield	Reaction Conditions	Operation in experiment
35%	With 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; potassium <i>tert</i>-butylate In toluene at 20℃; for 3 h;	1-methylimidazole (1 mmol, 82.1 mg),Perfluoro iodobutane (3.1 mmol, 1072 mg) was placed in a 10 mL round bottom flask.Potassium tert-butoxide (2.2 mmol, 246.9 mg) was addedAnd 5mL of toluene, stirring at room temperature for 3 hours,TLC monitored the endpoint of the reaction.After the toluene was removed by rotary evaporation, the mixture was washed with water and extracted with dichloromethane. The organic phase was collected and dried. The dichloromethane was removed by rotary evaporation to give a crude product.The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (ratio by volume = 15:1).The product 1 was obtained: 2-iodo-1-methylimidazole (white solid, 72 mg, 35percent).Product 2: 2,5-diiodo-1-methylimidazole (white solid, 210 mg, 63percent)

Reference： [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 6, p. 886 - 890
[2] Patent: CN107501023, 2017, A, . Location in patent: Paragraph 0039; 0040
[3] Tetrahedron Letters, 2010, vol. 51, # 41, p. 5423 - 5425

[ 37067-95-1 ] Synthesis Path-Downstream 1~58

1
[ 5799-76-8 ]
[ 37067-95-1 ]
[ 51245-50-2 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1973,vol. 22,p. 2582 - 2584
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1973,vol. 22,p. 2638 - 2640

2
[ 616-47-7 ]
[ 37067-95-1 ]
[ 1066-54-2 ]
[ 115563-46-7 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 5571

3
[ 616-47-7 ]
[ 37067-95-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With 4-(3-methylimidazolium)butanesulfonate; iodine; In water; at 20℃; for 2h;Sealed tube; Green chemistry;	General procedure: To a mixture of 2-phenylimidazo[1,2-a]pyridine (1a, 39 mg, 0.2 mmol), molecular I2 (50 mg, 1 equiv), and 4-(3-methylimidazolium)butane-1-sulfonate (I, 9 mg, 20 mol%) in a sealed tube was added water (2 mL) and the mixture was stirred at r.t. for 2 h. After completion of the reaction (TLC), the mixture was extracted with EtOAc (20 mL). The organic phase was dried (anhyd Na2SO4) and concentrated under reduced pressure give the crude residue which was purified by column chromatography (silica gel, 60-120 mesh, petroleum ether/EtOAc, 9:1) to afford 2a as a white solid: yield: 58 mg (91%); mp 132-134 C.
55%		a) Synthesis of 2-iodine-1-methyl-imidazol 7.97 ml (100.0 mmol) 1-methyl-imidazol was dissolved in THF (100 ml) and cooled to -78 C. 40 ml (2.5 M in hexane, 100 mmol) BuLi was added in drops at this temperature. After the end of addition, heating was performed for 5 min to 0 C., followed immediately by cooling to -78 C. A solution of 27.9 g (110.0 mmol) iodine (I2) in THF (60 ml) was added in drops at this temperature and stirring was performed for 20 min at RT. Quenching was subsequently performed with a 5% aq. Na2S2O3 sol (120 ml) and extraction with DCM (4*50 ml). The collected organic phases were dried over MgSO4, filtered and concentrated in a vacuum. 11.5 g (55.2 mmol, 55%) 2-iodine-1-methyl-imidazol was obtained by crystallisation of the residue from diethylether.

Reference： [1]Organic Letters,2014,vol. 16,p. 3244 - 3247
[2]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 2774 - 2781
[3]Chemistry - A European Journal,2019,vol. 25,p. 7480 - 7484
[4]Organic Letters,2003,vol. 5,p. 3209 - 3212
[5]Journal of Organometallic Chemistry,2007,vol. 692,p. 635 - 644
[6]Chemical Communications,2018,vol. 54,p. 5319 - 5322
[7]Synthesis,2016,vol. 48,p. 4009 - 4015
[8]Chemical Communications,2016,vol. 52,p. 4983 - 4986
[9]Angewandte Chemie - International Edition,2019,vol. 58,p. 18424 - 18428
Angew. Chem.,2019,vol. 58,p. 18595 - 18599,5
[10]Patent: US2008/261996,2008,A1 .Location in patent: Page/Page column 45
[11]Polish Journal of Chemistry,1981,vol. 55,p. 1659 - 1665
[12]Tetrahedron,1997,vol. 53,p. 7237 - 7254
[13]Chemical Communications,2004,p. 1306 - 1307
[14]CrystEngComm,2013,vol. 15,p. 10157 - 10160

4
[ 37067-95-1 ]
[ 536-74-3 ]
[ 111600-87-4 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 5320 - 5334
[2]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 823 - 828

5
[ 37067-95-1 ]
[ 37570-94-8 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 3209 - 3212
[2]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 823 - 828
[3]Chemical Communications,2004,p. 1306 - 1307
[4]Organic and Biomolecular Chemistry,2009,vol. 7,p. 2214 - 2222

6
[ 37067-95-1 ]
[ 86026-83-7 ]

Reference： [1]Polish Journal of Chemistry,1981,vol. 55,p. 1659 - 1665

7
[ 37067-95-1 ]
[ 86026-84-8 ]

Reference： [1]Polish Journal of Chemistry,1981,vol. 55,p. 1659 - 1665

8
[ 37067-95-1 ]
[ 13369-86-3 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 1781 - 1786

9
[ 591-50-4 ]
[ 37067-95-1 ]
[ 3475-07-8 ]