[ CAS No. 2387-08-8 ] {[proInfo.proName]}

Name: 2387-08-8|4,5-Dichloro-2-methylaniline|98%
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3d Animation Molecule Structure of 2387-08-8

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Quality Control of [ 2387-08-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2387-08-8 ]

SDS Specification

Alternatived Products of [ 2387-08-8 ]

Product Details of [ 2387-08-8 ]

CAS No. :	2387-08-8	MDL No. :	MFCD11855825
Formula :	C₇H₇Cl₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QFUZJHWRUZVIOF-UHFFFAOYSA-N
M.W :	176.04	Pubchem ID :	343796
Synonyms :

Calculated chemistry of [ 2387-08-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.83
TPSA :	26.02 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) :	-5.07 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.95
Log Po/w (XLOGP3) :	3.25
Log Po/w (WLOGP) :	2.89
Log Po/w (MLOGP) :	2.99
Log Po/w (SILICOS-IT) :	2.85
Consensus Log Po/w :	2.79

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.42
Solubility :	0.0665 mg/ml ; 0.000378 mol/l
Class :	Soluble
Log S (Ali) :	-3.47
Solubility :	0.0596 mg/ml ; 0.000339 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.65
Solubility :	0.039 mg/ml ; 0.000222 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.16

Safety of [ 2387-08-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2387-08-8 ]

* 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 [ 2387-08-8 ]
Downstream synthetic route of [ 2387-08-8 ]

[ 2387-08-8 ] Synthesis Path-Upstream 1~1

1
[ 2387-08-8 ]
[ 124691-76-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: With acetic anhydride In chloroform at 0 - 20℃; Stage #2: With potassium acetate; isopentyl nitrite In chloroformReflux	Step 25 ,6-Dichloro-l H-indazolTo a solution of 4,5-dichloro-2-methylaniline (1.69 g, 9.6 mmol) in CHC1₃ (25 ml) at 0°C was slowly added acetic anhydride (2.09 ml, 22.1 mmol). The reaction mixture was warmed to room temperature and stirred for 1 h. A thick white precipitate had gradually formed. Potassium acetate (283 mg, 2.88 mmol) was added followed by slow addition of isoamyl nitrite (2.78 ml, 20.6 mmol). The reaction mixture was heated at reflux overnight. The homogeneous deep orange reaction mixture was cooled to room temperature and concentrated. Water (10 mL) was added and the mixture was reconcentrated to an orange solid. This solid was suspended in cone. HCl (15 mL) and heated at 60°C for 2 h then cooled to 0°C and neutralized with 50percent NaOH. Extracted with EtOAc, dried over MgS04 and concentrated to an orange solid. This solid was dissolved in THF/MeOH (1 :1 , 25 mL) and 10percent> NaOH (3 mL) was added. The deep maroon reaction mixture was stirred at room temperature for 5 min then neutralized with 1.0 M HCl and diluted with water. The mixture was extracted with EtOAc (2 x) then dried over MgS0₄ and concentrated. The residue was absorbed onto silica gel and purified by chromatography with 30percent to 50percent EtOAc/hexanes to afford 1.50 g (84percent) of 5, 6-dichloro-l H-indazole as a light orange solid. 1H NMR (CDC1₃, 300 MHz): ? (ppm) 8.04 (s, 1H), 7.89 (s, 1H), 7.68 (s, 1H).

Reference： [1] Patent: WO2013/30138, 2013, A1, . Location in patent: Page/Page column 188
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1966 - 1982

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[ 2387-08-8 ]

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P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
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P321
P322
P330	Rinse mouth.
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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.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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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.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Yield	Reaction Conditions	Operation in experiment
99%	With iron; ammonium chloride In tetrahydrofuran; methanol; water at 100℃; for 3h;	67.1 Step 14,5-Dichloro-2-methylanilin Example 67.2-(5 ,6-Dichloro- 1 -methyl- 1 H-indazol-3 -yl)-5H-pyrrolo [2,3 -b]pyrazine-7-carboxylic acid [(R)-2- (4-cyano-piperidin-l -yl)-l -cyclopropyl-2-oxo-ethyl]-amideStep 14,5-Dichloro-2-methylanilinTo a partial suspension of l ,2-dichloro-4-methyl-5-nitrobenzene (2.0 g, 9.71 mmol) in MeOH (25 ml), water (25 ml), and THF (10 ml) was added NH4C1 (5.19 g, 97.1 mmol) followed by iron powder (2.71 g, 48.5 mmol). The heterogeneous reaction mixture was heated at 100°C for 3 h then cooled to room temperature and filtered over a Buchner funnel, rinsing with MeOH. The filtrate was diluted with water and saturated aqueous NaHC03 then extracted with CH2CI2 (3x). The combined organics were dried over MgS04 and concentrated to afford 1.69 g (99%) of 4,5- dichloro-2-methylaniline as a white solid. 1H NMR (CDC13, 300 MHz): ? (ppm) 7.10 (s, 1H), 6.75 (s, 1H), 3.74 (br. s., 2H), 2.12 (s, 3H).
98%	With hydrazine hydrate
88%	With hydrogenchloride; tin(ll) chloride In ethanol at 20℃; for 17h;

	bei der Reduktion;
2.4 g (56%)	In titanium(III) chloride	7.B 4,5-Dichloro-2-methyl-phenylamine 6 Step B 4,5-Dichloro-2-methyl-phenylamine 6 4,5-Dichloro-2-methyl-nitrobenzene 5 (5.0 g, 24.3 mmol) was heated at 100° C. in titanium trichloride (30% in aqueous hdyrochloric acid, 25 mL) for 2 hrs., cooled to RT, the reaction solution was basified to pH 8 with 50% aqueous sodium hydroxide, then extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography using 10% ethyl acetate in hexanes to give 2.4 g (56%) of the title product. 1H NMR (400 MHz, CDCl3) δ7.09 (s, 1 H, Ar), 6.74 (s, 1 H, Ar), 3.63 (s, 2 H, NH2), 2.10 (s, 3H, CH3).

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran	III Preparation of ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate EXAMPLE III Preparation of ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate Into a nitrogen-purged round bottom flask was charged 5.53 grams (0.03 mole) of 2-methyl-4,5-dichloroaniline, 3.18 grams (0.03 mole) of triethylamine and 190 milliliters of tetrahydrofuran solvent. With vigorous stirring, a 5.55 gram (0.03 mole) portion of ethyl 1-chlorocarbonylcyclopropanecarboxylate prepared in Example XVIII was added in one portion, after which the mixture was stirred at ambient temperature for a six-hour period. A precipitate of triethylamine hydrochloride was then filtered off and the filtrate vacuum stripped to give a light yellow solid. The solid was taken up in ether and the solution water-washed, dried over magnesium sulfate, and solvent evaporated to give a yellow powder. Recrystallization from ethyl acetate-hexane gave 4.51 grams (0.01 mole) of ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate having a melting point of 105° C.-107° C. Elemental analysis of the product indicated the following: Analysis: C14 H15 Cl2 NO3 Calculated: C, 53.18; H, 4.78; N, 4.43; Found: C, 53.41; H, 4.76; N, 4.44.
	With triethylamine In tetrahydrofuran	III Preparation of ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate EXAMPLE III Preparation of ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate Into a nitrogen-purged round bottom flask was charged 5.53 grams (0.03 mole) of 2-methyl-4,5-dichloroaniline, 3.18 grams (0.03 mole) of triethylamine and 190 milliliters of tetrahydrofuran solvent. With vigorous stirring, a 5.55 gram (0.03 mole) portion of ethyl 1-chlorocarbonylcyclopropanecarboxylate prepared in Example XVIII was added in one portion, after which the mixture was stirred at ambient temperature for a six-hour period. A precipitate of triethylamine hydrochloride was then filtered off and the filtrate vacuum stripped to give a light yellow solid. The solid was taken up in ether and the solution water-washed, dried over magnesium sulfate, and solvent evaporated to give a yellow powder. Recrystallization from ethyl acetate-hexane gave 4.51 grams (0.01 mole) of ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate having a melting point of 105° C.-107° C. Elemental analysis of the product indicated the following: Analysis: C14 H15 Cl2 NO3: Calculated: C, 53.18; H, 4.78; N, 4.43. Found: C, 53.41; H, 4.76; N, 4.44.

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

[ CAS No. 2387-08-8 ] {[proInfo.proName]}

Quality Control of [ 2387-08-8 ]

Related Doc. of [ 2387-08-8 ]

Product Details of [ 2387-08-8 ]

Calculated chemistry of [ 2387-08-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2387-08-8 ]

Application In Synthesis of [ 2387-08-8 ]

[ 2387-08-8 ] Synthesis Path-Upstream 1~1

[ 2387-08-8 ] Synthesis Path-Downstream 1~29

Related Functional Groups of [ 2387-08-8 ]

Aryls

Chlorides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2387-08-8 ]