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[ CAS No. 105942-09-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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

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Chemical Structure| 105942-09-4

Chemical Structure| 105942-09-4

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Quality Control of [ 105942-09-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 105942-09-4 ]

SDS Specification

Alternatived Products of [ 105942-09-4 ]

Product Citations

Product Details of [ 105942-09-4 ]

CAS No. :	105942-09-4	MDL No. :	MFCD07368341
Formula :	C₈H₅BrFN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZESZAIOGACKOMB-UHFFFAOYSA-N
M.W :	214.03	Pubchem ID :	2783149
Synonyms :

Calculated chemistry of [ 105942-09-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.95
TPSA :	23.79 ?2

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) :	-5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.04
Log Po/w (XLOGP3) :	2.3
Log Po/w (WLOGP) :	2.86
Log Po/w (MLOGP) :	2.67
Log Po/w (SILICOS-IT) :	3.22
Consensus Log Po/w :	2.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.95
Solubility :	0.238 mg/ml ; 0.00111 mol/l
Class :	Soluble
Log S (Ali) :	-2.44
Solubility :	0.782 mg/ml ; 0.00365 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.03
Solubility :	0.0202 mg/ml ; 0.0000942 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.11

Safety of [ 105942-09-4 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501	UN#:	3261
Hazard Statements:	H302-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 105942-09-4 ]

* 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.

Downstream synthetic route of [ 105942-09-4 ]

[ 105942-09-4 ] Synthesis Path-Downstream 1~4

1
[ 6070-59-3 ]
[ 105942-09-4 ]
[ 1355158-68-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	Step 2 : tert-butyl 2-[(4-cyano-2-fluorobenzyl) amino]-3-methylbutanoateTo a stirred solution of <strong>[6070-59-3]tert-butyl 2-amino-3-methylbutanoate</strong> (8.5 g, 0.05 mol)in dry DMF (50 mL) under nitrogen, was added 4-cyano-2-fluoro-benzyl bromide (FluoroChem Ltd, 9.4 g, 0.044 mol) and NaHC03 (10.2 g, 0.12 mol). The resulting mixture was stirred at RT for 16 h. Water (70 mL) was added and the desired product was extracted with ethyl acetate (2x100 mL). The organic layer was washed with water (3x100 mL) and the solvent was dried over Na2S04 and concentrated under vacuum. The resulted residue was purified by column chromatography using petroleum ether/ ethyl acetate as eluent, affording of the title compound as colorless liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.77 (d, J = 10.2 Hz, 1 H), 7.67 (t, J = 1 .5 Hz, 1 H), 3.85-3.79 (m, 2H), 2.72 (m, 1 H), 2.49 (m, 1 H), 1.81 (m, 1 H), 1.37(s, 9H), 0.86 (m, 6H).
	With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	Step 1: 1- tert-butyl 2-[(4-cyano-2-fluorobenzyl)amino]-3-methylbutanoateTo a stirred solution of <strong>[6070-59-3]tert-butyl 2-amino-3-methylbutanoate</strong> (Bachem, 6.3 g, 0.036 mol) in dry DMF (50 mL) under nitrogen, was added 4-cyano-2-fluoro- benzyl bromide (6.2 g, 0.029 mol) and NaHC03 (6.09g, 0.073 mol). The resulting mixture was stirred for 16 h at RT. Water (70 mL) was added and extracted with ethyl acetate (2x100 mL). The organic layer was washed with water (3x100mL) and the solvent was dried over Na2S04 and concentrated under vacuum. The resulted residue was purified by column chromatography using petroleum ether/ ethyl acetate as eluent, affording the title compound as colorless liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.78 (d, J = 10.2 Hz, 1 H), 7.67 (t, J = 1.5 Hz, 2H) 3.81 (m, 2H), 2.71 (m, 1 H), 2.49 (m 1 H), 1 .81 (m, 1 H), 1 .37 (s, 9H), 0.88-0.84 (m, 6H).

Reference： [1]Patent: WO2012/4287,2012,A1 .Location in patent: Page/Page column 75
[2]Patent: WO2012/4287,2012,A1 .Location in patent: Page/Page column 88

2
[ 6070-59-3 ]
[ 105942-09-4 ]
[ 1355158-74-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 70℃; for 16h;Inert atmosphere;	Step 1: tert-butyl 2-[(4-cyano-2-fluorobenzyl)amino]-2-methylpropanoateTo a stirred solution of tert-butyl 2-amino-2-methylpropanoate (Bachem, 7.9 g, 0.05 mol) in dry DMF (50 mL) under nitrogen, was added 4-cyano-2-fluoro benzyl bromide (10.6 g, 0.05 mol) and NaHC03 (8.3 g, 0.099 mol) as a solid. The reaction mixture was stirred for 16 h at 70C. Water (70 mL) was added and extracted with ethyl acetate (100 mL). The organic layer was washed with water (3x100 mL) and the solvent was dried over Na2S04 and concentrated under vacuum. The residue was purified by column chromatography using silica gel (60-120 mesh) and petroleum ether/ ethyl acetate as eluent, affording the title compound as colourless liquid. 1H NMR (DMSO-de, 400 MHz) δ 7.78 (d, J = 10.0 Hz, 1 H), 7.71 -7.65 (m, 2H), 3.69 (d, J = 6.9 Hz, 2H), 2.55 (s, 1 H), 1 .44 (s, 9H), 1 .19 (s, 6H).

Reference： [1]Patent: WO2012/4287,2012,A1 .Location in patent: Page/Page column 88-89

3
[ 50595-15-8 ]
[ 105942-09-4 ]
tert-butyl [(4-cyano-2-fluorobenzyl)oxy]acetate [ No CAS ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 688 - 714

4
[ 118469-15-1 ]
[ 105942-09-4 ]
3-fluoro-4-((5-fluoro-2-methyl-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 16℃; for 16.0h;	(0621) A mixture of 4-(bromomethyl)-3-fluorobenzonitrile (499 mg, 2.33 mmol) and 5-fluoro-2- methyl-1H-benzo[d]imidazole (350 mg, 2.33 mmol) in DMF (15 mL) was stirred at 16 C for 16 h. The mixture was washed with water (50 mL) and extracted with EtOAc (3 x 30 mL). The collected organic layers were washed with brine (30 mL) and dried over anhydrous Na2SO4. The mixure was filtered and the filtrate was concentrated to get the crude product. The crude product was purified by reverse-phase Prep-HPLC (preparative HPLC on a GILSON 281 instrument fitted with Phenomenex Synergi C18 250x21.2mmx4um using water and acetonitrile as the eluents. Mobile phase A: water, mobile phase B: acetonitrile (containing: 0.1%TFA-ACN). Gradient: 35-65%, 0-10 min; 100% B, 10.5-12.5min; 5% B, 13-15min) to give 3-fluoro-4-((5- fluoro-2-methyl-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile as an oil. ESI-MS m/z [M + H]+ : 284.0.

Reference： [1]Patent: WO2017/222951,2017,A1 .Location in patent: Page/Page column 85

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blaise Reaction ? Blanc Chloromethylation ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? 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 ? Preparation of Aldehydes and Ketones ? 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 ? Ritter Reaction ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Thorpe-Ziegler Reaction ? Vilsmeier-Haack Reaction

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Ghs Precautionary Statements

Precautionary Statements-General
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P103	Read label before use
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Code	Phrase
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P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
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P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
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P304	IF INHALED:
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P306	IF ON CLOTHING:
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P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
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P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P372	Explosion risk in case of fire.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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H201	Explosive; mass explosion hazard
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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
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H331	Toxic if inhaled
H332	Harmful if inhaled
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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
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

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