[ CAS No. 66416-72-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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2D 3D

Structure of 66416-72-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 66416-72-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 66416-72-6 ]

SDS Specification

Alternatived Products of [ 66416-72-6 ]

Product Details of [ 66416-72-6 ]

CAS No. :	66416-72-6	MDL No. :	MFCD02093764
Formula :	C₆H₅BrIN	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	HHTYEQWCHQEJNV-UHFFFAOYSA-N
M.W :	297.92	Pubchem ID :	823934
Synonyms :

Calculated chemistry of [ 66416-72-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.26
TPSA :	26.02 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.0
Log Po/w (XLOGP3) :	3.52
Log Po/w (WLOGP) :	2.64
Log Po/w (MLOGP) :	3.15
Log Po/w (SILICOS-IT) :	2.79
Consensus Log Po/w :	2.82

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.4
Solubility :	0.0119 mg/ml ; 0.00004 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.75
Solubility :	0.0529 mg/ml ; 0.000178 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.83
Solubility :	0.0441 mg/ml ; 0.000148 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.96

Safety of [ 66416-72-6 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P273-P280-P301+P310-P305+P351+P338	UN#:	2811
Hazard Statements:	H301-H315-H318-H335-H411	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 66416-72-6 ]

* 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 [ 66416-72-6 ]
Downstream synthetic route of [ 66416-72-6 ]

[ 66416-72-6 ] Synthesis Path-Upstream 1~1

1
[ 66416-72-6 ]
[ 76228-06-3 ]

Reference： [1] Synthetic Communications, 2016, vol. 46, # 15, p. 1249 - 1256

[ 66416-72-6 ] Synthesis Path-Downstream 1~6

1
[ 668970-91-0 ]
[ 66416-72-6 ]
[ 1443684-92-1 ]

Yield	Reaction Conditions	Operation in experiment
98.6%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In tetrahydrofuran; at 80℃; for 3h;	To a solution of 4-bromo-2-iodoaniline (2.5 g, 8.39 mmol, Eq: 1.00) and <strong>[668970-91-0]4-ethynyl-3,5-dimethylisoxazole</strong> (1.22 g, 10.1 mmol, Eq: 1.2) in triethylamine (16.8 ml, 8.39 mmol, Eq: 1.00) and THF (33.6 ml) was added tetrakis(triphenylphosphine)palladium (0) (485 mg, 420 μmol, Eq: 0.05) and copper (I) iodide (37.6 mg, 420 μmol, Eq: 0.05). This mixture was heated to 80 C. for 3 h, before the solvent were removed. The resulting residue was redissolved in ethyl acetate and washed with water and brine. The organic layer was dried onto silica gel and purified by flash chromatography (5-50% ethyl acetate/hexane gradient) to give 4-bromo-2-((3,5-dimethylisoxazol-4-yl)ethynyl)aniline (2.41 g, 8.28 mmol, 98.6% yield) as a brown solid.

Reference： [1]Patent: US2013/158049,2013,A1 .Location in patent: Paragraph 0262

2
[ 66416-72-6 ]
[ 100-47-0 ]
[ 1741-50-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 7271 - 7275

3
[ 66416-72-6 ]
[ 140-89-6 ]
[ 51618-30-5 ]

Yield	Reaction Conditions	Operation in experiment
78.7%	With copper(l) chloride; In N,N-dimethyl-formamide; at 110℃; for 6h;Inert atmosphere; Sealed tube;	General procedure: A 25 mL Wattecs reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium O-ethyl dithiocarbonate 2 (1.8 mmol),CuCl (0.06 mmol), and DMF (2 mL). The reaction vessel was flushed with argon three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110C for 6 h.The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, and then HCl (3 mL, 3 mol/L) was added and stirred for another 30 min. The reaction mixture solution was extracted by ethyl acetate (3 × 20 mL). Subsequently, the combined organic solutions were dried by anhydrous sodium sulfate and the target product was purified by chromatography on a silica gel column (eluent: petroleum ether/ethyl acetate) togive the corresponding pure product 3. Complete characterization characterizationof the products (all known) is found in the Supplemental Materials (Figures S1-S13).
72%	With iron(III) trifluoride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In N,N-dimethyl-formamide; at 110℃; for 18h;Inert atmosphere; Sealed tube;	General procedure: A 25 mL reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium o-ethyldithiocarbonate 2 (1.8 mmol), FeF3 (0.06 mmol), 2,2?-bis(diphenylphosphino)-1,1?-binaphthyl (0.03 mmol) and DMF (4 mL). The reaction vessel was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110 for 3 - 21 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, then 4 mL HCl (3mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by ethyl acetate (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous sodium sulfate and the target product was purified by silica gel colum chromatography (eluent: petroleum ether / ethylacetate) to give the corresponding pure product 3.

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2016,vol. 191,p. 699 - 701
[2]Synthetic Communications,2015,vol. 45,p. 2378 - 2385

4
[ 66416-72-6 ]
[ 104190-22-9 ]
1-(2-((2-amino-5-bromophenyl)ethynyl)phenyl)ethanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 9125 - 9136

5
[ 66416-72-6 ]
[ 89226-13-1 ]
tert-butyl N-[(6-bromo-1,3-benzothiazol-2-yl)methyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		CuO (0.8 g, 10.13 mmol) was added to a stirred solution of 4-bromo-2-iodo-aniline (3 g, 10.13mmol) and tert-butyl N-(2-amino-2-thioxo-ethyl)carbamate (1.92 g, 10.13 mmol) in DMF (30mL) at RT and the reaction mixture was degassed with argon for 15 mm. Then dppf (280 mg,0.50 mmol) and Pd2(dba)3 (185.4 mg, 0.20) were added to the reaction mixture and degassed with argon for further 5 mm. The reaction mixture was stirred in sealed tube at 60C for 3 h and filtered through celite pad which was washed with EtOAc (50 mL). The filtrate was washed with water (2x30 mL) and concentrated under reduced pressure. The crude compound was purified by flash chromatography eluting with 22% EtOAc in petroleum ether affording a yellow solid (5 g, 72%). M/z 343.0 (M+H).
72%		To a stirred solution of 4-bromo-2-iodo-aniline (3 g, 10.13 mmol) and tert-butyl (2-amino-2-thioxoethyl) carbamate(1.92 g, 10.13 mmol) in DMF (30 mL) was added CuO (0.8 g, 10.13 mmol) at room temperature and the reactionmixture was degassed with argon for 15 minutes. Then Dppf (280 mg, 0.50 mmol) and Pd2(dba)3 (185.4 mg, 0.20) wereadded and the resulting reaction mixture was degassed with argon for further 5 minutes. The reaction mixture was stirredin sealed tube at 60 C for 3h, and then filtered through celite pad and washed the pad with EtOAc (50 mL). The filtratewas washed with water (2x30 mL) and concentrated under reduced pressure. The crude compound was purified bysilica gel chromatography eluting with 22% EtOAc in petroleum ether affording as a yellow solid (5 g, 72%). M/z 343(M+H)+.

Reference： [1]Patent: WO2018/172423,2018,A1 .Location in patent: Page/Page column 75; 76
[2]Patent: EP3628666,2020,A1 .Location in patent: Paragraph 0093-0095

6
[ 66416-72-6 ]
[ 100-52-7 ]
[ 1741-50-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With ammonium hydroxide; 8-quinolinol; caesium carbonate; nickel dichloride; at 100℃; for 0.216667h;Sealed tube; Microwave irradiation;	General procedure: A 10 mL glass tube was charged with the appropriate 2-haloaniline(0.5 mmol), 25-28% aq NH3 (2 mL), the appropriate aldehyde(0.6 mmol), NiCl2 (11.88 mg, 0.05 mmol), quinolin-8-ol(7.258 mg, 0.05 mmol), and Cs2CO3 (325.82 mg, 1.0 mmol). Thevessel was then sealed with a septum and placed in the cavity ofa Discover microwave synthesizer (CEM Corp., Buckingham,UK), and irradiated at 130 W. The temperature was rampedfrom r.t. to the desired temperature of 100 C, then held at thistemperature for 13 min. The mixture was stirred continuouslyduring the reaction. The mixture was then allowed to cool to r.t.and the solvent was removed under reduced pressure. Theresidue was purified by column chromatography (silica gel) toafford the corresponding product. The structures of the productswere confirmed by NMR and MS spectroscopic analyses.2-Phenyl-1H-benzo[d]imidazole (2a)Light-yellow solid; yield: 89.24 mg (92%).

Reference： [1]Synlett,2018,vol. 29,p. 2722 - 2726
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 8090 - 8094

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction ? Vilsmeier-Haack Reaction

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[ 66416-72-6 ]

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Code	Phrase
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Code	Phrase
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P322
P330	Rinse mouth.
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H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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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
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H336	May cause drowsiness or dizziness
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H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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H361d	Suspected of damaging the unborn child
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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

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[ CAS No. 66416-72-6 ] {[proInfo.proName]}

Quality Control of [ 66416-72-6 ]

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Product Details of [ 66416-72-6 ]

Calculated chemistry of [ 66416-72-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 66416-72-6 ]

Application In Synthesis of [ 66416-72-6 ]

[ 66416-72-6 ] Synthesis Path-Upstream 1~1

[ 66416-72-6 ] Synthesis Path-Downstream 1~6

Technical Information

Related Functional Groups of [ 66416-72-6 ]

Aryls

Bromides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 66416-72-6 ]