[ CAS No. 1865-09-4 ] {[proInfo.proName]}

Name: 1865-09-4|Ethyl 1H-benzo[d]imidazole-2-carboxylate|98%
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SKU: A107432
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2D 3D

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Quality Control of [ 1865-09-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1865-09-4 ]

SDS Specification

Alternatived Products of [ 1865-09-4 ]

Product Details of [ 1865-09-4 ]

CAS No. :	1865-09-4	MDL No. :	MFCD00721392
Formula :	C₁₀H₁₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NMYSVCYIPOCLEC-UHFFFAOYSA-N
M.W :	190.20	Pubchem ID :	12436923
Synonyms :

Calculated chemistry of [ 1865-09-4 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.2
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.18
TPSA :	54.98 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.59
Log Po/w (XLOGP3) :	1.81
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	1.2
Log Po/w (SILICOS-IT) :	2.17
Consensus Log Po/w :	1.7

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.44
Solubility :	0.695 mg/ml ; 0.00365 mol/l
Class :	Soluble
Log S (Ali) :	-2.58
Solubility :	0.496 mg/ml ; 0.00261 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.39
Solubility :	0.0768 mg/ml ; 0.000404 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.81

Safety of [ 1865-09-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1865-09-4 ]

* 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 [ 1865-09-4 ]
Downstream synthetic route of [ 1865-09-4 ]

[ 1865-09-4 ] Synthesis Path-Upstream 1~21

1
[ 1865-09-4 ]
[ 4856-97-7 ]

Reference： [1] Synthesis, 1984, vol. NO. 4, p. 356 - 358

2
[ 148-79-8 ]
[ 5805-52-7 ]
[ 1865-09-4 ]

Reference： [1] Australian Journal of Chemistry, 1982, vol. 35, # 4, p. 775 - 784

3
[ 64-17-5 ]
[ 148-79-8 ]
[ 5805-52-7 ]
[ 1865-09-4 ]

Reference： [1] Australian Journal of Chemistry, 1982, vol. 35, # 4, p. 775 - 784

4
[ 2849-93-6 ]
[ 64-17-5 ]
[ 1865-09-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	Heating / reflux	1 H-Benzimidazole-2-carboxylic acid (500 tng, 3.08 mmol) was suspended in EtOH (5 mL), treated with thionyl chloride (1.12 mL, 15.4 mmol), and heated to reflux overnight. The reaction mixture was concentrated in vacuo, yielding 644 mg (99percent) of the crude product.
99%	Heating / reflux	1 H-Benzimidazole-2-carboxylic acid (500 mg, 3.08 mmol) was suspended in EtOH (5 ml_), treated with thionyl chloride (1.12 ml_, 15.4 mmol), and heated to reflux overnight. The reaction mixture was concentrated in vacuo, yielding 644 mg (99percent) of the crude product. ¹H NMR (400 MHz, CD₂CI₂) δ 1.32 (t, 3H), 4.38 (q, 2H), 7.30 (m, 2H), 7.63 (m, 2H).
99%	Heating / reflux	1 H-Benzimidazole-2-carboxylic acid (500 tng, 3.08 mmol) was suspended in EtOH (5 mL), treated with thionyl chloride (1.12 mL, 15.4 mmol), and heated to reflux overnight. The reaction mixture was concentrated in vacuo, yielding 644 mg (99percent) of the crude product.

82%

for 24 h; Reflux

General procedure: A suspension of the appropriate acid 17d-e (1 eq, 12.7 mmol) in EtOH (21 ml) was treated dropwise with SOCl2 (3 eq) under ice cooling, then heated to reflux over night. The solution was then concentrated in vacuum, treated with EtOH (3x20 mL) and n-hexane (3x20 mL)and dried under vacuum to give the pure title compound.

Reference： [1] Patent: WO2006/91506, 2006, A2, . Location in patent: Page/Page column 42
[2] Patent: WO2006/49681, 2006, A2, . Location in patent: Page/Page column 40
[3] Patent: WO2006/121588, 2006, A2, . Location in patent: Page/Page column 46
[4] Patent: WO2006/121860, 2006, A2, . Location in patent: Page/Page column 46
[5] Patent: WO2006/121904, 2006, A1, . Location in patent: Page/Page column 46
[6] European Journal of Medicinal Chemistry, 2018, vol. 149, p. 56 - 68
[7] Phosphorus, Sulfur and Silicon and the Related Elements, 2013, vol. 188, # 11, p. 1564 - 1575

5
[ 1330785-75-5 ]
[ 1865-09-4 ]

Reference： [1] Organic Letters, 2011, vol. 13, # 18, p. 4914 - 4917
[2] Advanced Synthesis and Catalysis, 2011, vol. 353, # 14-15, p. 2795 - 2804

6
[ 924-44-7 ]
[ 95-54-5 ]
[ 1865-09-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 48, p. 11687 - 11695

7
[ 95-54-5 ]
[ 95-92-1 ]
[ 1865-09-4 ]

Reference： [1] Combinatorial Chemistry and High Throughput Screening, 2014, vol. 17, # 7, p. 630 - 638

8
[ 3624-90-6 ]
[ 1865-09-4 ]

Reference： [1] Organic Letters, 2011, vol. 13, # 18, p. 4914 - 4917
[2] Advanced Synthesis and Catalysis, 2011, vol. 353, # 14-15, p. 2795 - 2804

9
[ 124-63-0 ]
[ 144167-25-9 ]
[ 1865-09-4 ]
[ 144167-32-8 ]

Reference： [1] Tetrahedron, 1992, vol. 48, # 30, p. 6335 - 6360
[2] Tetrahedron, 1992, vol. 48, # 30, p. 6335 - 6360

10
[ 144167-25-9 ]
[ 1865-09-4 ]

Reference： [1] Tetrahedron, 1992, vol. 48, # 30, p. 6335 - 6360

11
[ 95-54-5 ]
[ 1865-09-4 ]

Reference： [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 14-15, p. 2795 - 2804
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2013, vol. 188, # 11, p. 1564 - 1575

12
[ 480-96-6 ]
[ 1865-09-4 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 1, p. 165 - 169

13
[ 4856-97-7 ]
[ 1865-09-4 ]

Reference： [1] Phosphorus, Sulfur and Silicon and the Related Elements, 2013, vol. 188, # 11, p. 1564 - 1575

14
[ 480-96-6 ]
[ 1099-45-2 ]
[ 1865-09-4 ]
[ 108047-49-0 ]

Reference： [1] Tetrahedron, 1986, vol. 42, # 13, p. 3631 - 3636

15
[ 144167-33-9 ]
[ 1865-09-4 ]
[ 34851-26-8 ]

Reference： [1] Tetrahedron, 1992, vol. 48, # 30, p. 6335 - 6360
[2] Tetrahedron, 1992, vol. 48, # 30, p. 6335 - 6360

16
[ 64-17-5 ]
[ 107997-49-9 ]
[ 1865-09-4 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1986, vol. 328, # 4, p. 515 - 521

17
[ 148-79-8 ]
[ 5805-52-7 ]
[ 1865-09-4 ]

Reference： [1] Australian Journal of Chemistry, 1982, vol. 35, # 4, p. 775 - 784

18
[ 5436-00-0 ]
[ 1865-09-4 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1986, vol. 328, # 4, p. 515 - 521

19
[ 64-17-5 ]
[ 148-79-8 ]
[ 5805-52-7 ]
[ 1865-09-4 ]

Reference： [1] Australian Journal of Chemistry, 1982, vol. 35, # 4, p. 775 - 784

20
[ 64-17-5 ]
[ 3584-65-4 ]
[ 1865-09-4 ]
[ 82775-87-9 ]

Reference： [1] Australian Journal of Chemistry, 1982, vol. 35, # 4, p. 775 - 784

21
[ 1865-09-4 ]
[ 7181-87-5 ]

Reference： [1] Polish Journal of Chemistry, 1984, vol. 58, # 1-3, p. 149 - 156

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Yield	Reaction Conditions	Operation in experiment
81%	With hydrazine hydrate; In ethanol;Reflux;	General procedure: The appropriate aryl-ester 18a-e (1 eq), was added of EtOH (2.22 ml*mmol/eq) followed by hydrazine monohydrate (3 eq). The solution was refluxed overnight, then cooled to room temperature. The precipitate obtained was filtered and washed with cold EtOH and n-hexane to give the pure product.
80%	With hydrazine hydrate; In ethanol; for 3h;Reflux;	A mixture of <strong>[1865-09-4]ethyl 1H-benzo[d]imidazole-2-carboxylate</strong> (1, 3.80 g, 20 mmol), and hydrazine monohydrate (3 mL, 61.5 mmol) in EtOH (5 mL) was refluxed for 3 h. After cooling the formed precipitate was filtered off, washed with water (5 x 10 mL) dried and used without further purification. Yield 80%. Mp 240-242 C (lit. [25] 217-219). IR: 3321, 3265, 3066, 1661, 1609 cm-1. 1H-NMR: delta 4.62(s, 2H, NH2), 7.28 (m, 2H, Ar), 7.53 (d, J = 8.0 Hz, 1H, Ar), 7.70 (d, J = 8.0 Hz, 1H, Ar), 10.14 (s, 1H, NH),13.20 (s, 1H, NH). ESI-MS m/z 177 (M + H)+. Anal. Calcd for C8H8N4O: C, 54.54; H, 4.58; N, 31.80.Found: C, 54.57; H, 4.57; N, 31.76.
72%	With hydrazine hydrate; In ethanol; for 6h;Reflux;	General procedure: Hydrazine hydrate (1 g, 20 mmol) was added to a solution of 1b (1.00g, 21 mmol) in EtOH (40 mL) at ambient temperature. The reaction was refluxed for 6 h and concentrated under reduced pressure. The reaction mixture was extracted with EtOAc followed by extraction with brine. The organic phase was dried over Na2SO4 overnight and the solvent was removed in vacuo. The crude product was purified by silica gel column chromatography to yield the target product 1d (yield: 73%). 1HNMR (300 MHz, DMSO-d6 ) delta 12.66 (s, 1H), 8.12 (dd, J = 7.5, 1.9 Hz, 2H), 7.81-7.65 (m, 3H), 7.62 (s, 1H), 4.41 (q, J = 7.1 Hz, 2H), 1.35 (t, J = 7.1 Hz, 3H).

89%	With thionyl chloride; In ethanol;Reflux;	Example 314 5-(2-(difluoromethyl)-6-methylpyridin-4-yl)-4-(4-fluorophenyl)-6-((l -methyl- 177- benzo\|i/\|imidazol-2-yl)methoxy)pyrimidin-2-amine [00596] Step 1: ethyl 1 //-benzol i/\|imidazole-2-carhoxylate [00597] A solution of 1 //-benzo\|c/\|imidazole-2-carboxylic acid (500 mg, 3.08 mmol), thionyl chloride (1836 mg, 15.43 mmol) in CH3CH2OH (5 mL) was stirred under refluxing overnight. After cooling, the reaction mixture was concentrated in vacuo to get crude ethyl 1H- benzol c/\|imidazole-2-carboxylate (520 mg, 89%) as yellow solid. ES-MS (m/z): [M+l]+ = 191.2.
82%	With thionyl chloride; for 24h;Reflux;	General procedure: A suspension of the appropriate acid 17d-e (1 eq, 12.7 mmol) in EtOH (21 ml) was treated dropwise with SOCl2 (3 eq) under ice cooling, then heated to reflux over night. The solution was then concentrated in vacuum, treated with EtOH (3x20 mL) and n-hexane (3x20 mL)and dried under vacuum to give the pure title compound.
70%	With thionyl chloride; at 0℃; for 12h;Reflux;	A solution of compound 2c (1g, 6.2 mmol) in CH3CH2OH (10 mL) was dropwise added SOCl2 at 0 C. After adding dropwise, the resulting solution was refluxed for 12 h and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to yield the target product 2d. (yield:70%).

Yield	Reaction Conditions	Operation in experiment
38%		NaH (504 mg of a 60% suspension in mineral oil, 1.07 mmol) was suspended in dry DMF (1.5 ml_). Ethyl 1 H-benzimidazole-2-carboxylate (170 mg, 0.89 mmol) was added, and the solution was allowed to stir at it for 1 h. 1 ,2-Dibromoethane (0.23 ml_, 2.7 mmol) was added, and the solution was heated to 50C overnight. The reaction mixture was diluted with water and extracted with EtOAc. The organic extracts were dried over Na2SO4, concentrated in vacuo, and purified by Biotage column chromatography (15% EtOAc/hexanes), yielding 100 mg (38%) of the desired product. 1H NMR (400 MHz, CD2CI2) delta 1.48 (t, 3H), 3.80 (t, 2H), 4.50 (q, 2H), 5.02 (t, 2H), 7.39 (t, 1H), 7.45 (t, 1H), 7.53 (d, 1 H), 7.87 (d, 1 H).
38%		NaH (504 mg of a 60% suspension in mineral oil, 1.07 mmol) was suspended in dry DMF (1.5 mL). Ethyl 1 H-benzimidazole-2-carboxylate (170 mg, 0.89 mmol) was added, and the solution was allowed to stir at rt for 1 h. 1 ,2-dibromoethane (0.23 mL, 2.7 mmol) was added, and the solution was heated to 50C overnight. The reaction mixture was diluted with water and extracted with EtOAc. The organic extracts were dried over Na2SO4, concentrated in vacuo, and purified by Biotage column chromatography (15% EtOAc/hexanes), yielding 100 mg (38%) of the desired product.

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

Yield	Reaction Conditions	Operation in experiment
99%	With thionyl chloride;Heating / reflux;	1 H-Benzimidazole-2-carboxylic acid (500 tng, 3.08 mmol) was suspended in EtOH (5 mL), treated with thionyl chloride (1.12 mL, 15.4 mmol), and heated to reflux overnight. The reaction mixture was concentrated in vacuo, yielding 644 mg (99%) of the crude product.
99%	With thionyl chloride;Heating / reflux;	1 H-Benzimidazole-2-carboxylic acid (500 mg, 3.08 mmol) was suspended in EtOH (5 ml_), treated with thionyl chloride (1.12 ml_, 15.4 mmol), and heated to reflux overnight. The reaction mixture was concentrated in vacuo, yielding 644 mg (99%) of the crude product. 1H NMR (400 MHz, CD2CI2) delta 1.32 (t, 3H), 4.38 (q, 2H), 7.30 (m, 2H), 7.63 (m, 2H).
99%	With thionyl chloride;Heating / reflux;	1 H-Benzimidazole-2-carboxylic acid (500 tng, 3.08 mmol) was suspended in EtOH (5 mL), treated with thionyl chloride (1.12 mL, 15.4 mmol), and heated to reflux overnight. The reaction mixture was concentrated in vacuo, yielding 644 mg (99%) of the crude product.

[ CAS No. 1865-09-4 ] {[proInfo.proName]}

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[ 1865-09-4 ] Synthesis Path-Upstream 1~21

[ 1865-09-4 ] Synthesis Path-Downstream 1~87

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Esters

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Benzimidazoles

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[ 1865-09-4 ]

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[ 1865-09-4 ]