[ CAS No. 2533-69-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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

2D 3D

Structure of 2533-69-9 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 2533-69-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2533-69-9 ]

SDS Specification

Alternatived Products of [ 2533-69-9 ]

Product Details of [ 2533-69-9 ]

CAS No. :	2533-69-9	MDL No. :	MFCD00001759
Formula :	C₃H₄Cl₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OGBINJLTBZWRRB-UHFFFAOYSA-N
M.W :	176.43	Pubchem ID :	100479
Synonyms :

Calculated chemistry of [ 2533-69-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.64
TPSA :	33.08 ?2

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) :	-5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.75
Log Po/w (XLOGP3) :	2.06
Log Po/w (WLOGP) :	1.98
Log Po/w (MLOGP) :	1.27
Log Po/w (SILICOS-IT) :	1.86
Consensus Log Po/w :	1.78

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.1
Solubility :	1.4 mg/ml ; 0.00795 mol/l
Class :	Soluble
Log S (Ali) :	-2.38
Solubility :	0.73 mg/ml ; 0.00413 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.0
Solubility :	1.78 mg/ml ; 0.0101 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.73

Safety of [ 2533-69-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2533-69-9 ]

* 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 [ 2533-69-9 ]
Downstream synthetic route of [ 2533-69-9 ]

[ 2533-69-9 ] Synthesis Path-Upstream 1~1

1
[ 170487-40-8 ]
[ 2533-69-9 ]
[ 1071433-01-6 ]

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 13, p. 1661 - 1663

[ 2533-69-9 ] Synthesis Path-Downstream 1~8

1
[ 70733-25-4 ]
[ 2533-69-9 ]
[ 916060-44-1 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 4989 - 4992

2
[ 68176-57-8 ]
[ 2533-69-9 ]
5-tert-butyl-1H-benzimidazole-2-carboxylic acid [ No CAS ]

Reference： [1]Heterocycles,2006,vol. 67,p. 769 - 775

3
[ 22259-53-6 ]
[ 2533-69-9 ]
[ 60523-81-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In dimethyl sulfoxide; benzene;	EXAMPLE 1 N-(3-indolylmethyl)-trichloroacetamidine A solution of 5.72 g. (0.033 mole) of methyl trichloroacetimidate in 15 ml. of benzene is added over 15 minutes to a stirred solution of 3.18 g. (0.022 mole) of <strong>[22259-53-6]3-aminomethylindole</strong> in 25 ml. dry dimethylsulfoxide at room temperature. The mixture is stirred for 20 hours at room temperature, concentrated to dryness, and the residue taken up in warm chloroform. The chloroform solution is washed with 2 portions of water and extracted with 3 portions of dilute hydrochloric acid. The aqueous acid extracts are combined, extracted with 2 portions of chloroform and filtered. The clear aqueous filtrate is made basic with a saturated aqueous solution of sodium bicarbonate and the product extracted into 3 portions of chloroform. The combined chloroform extracts are washed with water, dried over magnesium sulfate, filtered and concentrated to dryness to afford N-(3-indolylmethyl)-trichloroacetamidine, which after crystallization from benzene/hexane has a m.p. of 135.5° to 138.5° C.

Reference： [1]Patent: US4065465,1977,A

4
[ 7474-78-4 ]
[ 2533-69-9 ]
[ 288247-71-2 ]

Yield	Reaction Conditions	Operation in experiment
42%		A round-bottom 3 neck flask was charged with <strong>[7474-78-4]3,4-diaminobenzenesulfonic acid</strong> (8.0 g, 42.5 mmol) and anhydrous MeOH (0.85 L). O-Methyl-1,1,1-trichloroacetimidat was added (2.8 mL, 3.74 g, 21.2 mmol). The resultant suspension was stirred for 24 h at ambient conditions. Additional amount of O-methyl-1,1,1-trichloroacetimidat was added (1.4 mL, 1.87 g, 10.5 mmol) after this time, then reaction mixture was stirred for 72 h days at ambient conditions, heated for 3 h at 50° C. and triethylamine (14 mL, 9.4 g, 93.5 mmol) was added. Stirring was continued at this temperature for 18 h. Then reaction mixture was cooled to 30° C., and an intensive flow of dry HCl was passed through the solution until a precipitate formed. The suspension was filtered off at 40° C., precipitate was washed with MeOH (4.x.150 mL, stirring of suspension for 10-15 min each turn) and with MeOH-HCl 3.5percent solution (100 mL, 1 h of stirring). Product 1H,1'H-2,2'-bibenzimidazole-5,5'-disulfonic acid was pale yellow or colorless, weight 3.5 g, yield 42percent. It may contain own hydrochloride as a salt. NMR1 H spectrum (Brucker Avance 300 instrument; solvent d6-dimethyl sulfoxide; delta, ppm; J, Hz): 5.27 br.s (-SO3H in exchange with H2O and NH) 7.73 m (2Ha,2Hb), 8.01 br.s (2Hx). NMR 13C{1H} spectrum (Brucker Avance 300 instrument; solvent d6-dimethyl sulfoxide; delta, ppm): 113.00, 115.41, 123.27, 136.44, 137.60, 142.24, 145.34.

Reference： [1]Patent: US2010/279122,2010,A1 .Location in patent: Page/Page column 15

5
[ 6494-19-5 ]
[ 2533-69-9 ]
[ 444731-73-1 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of <strong>[6494-19-5]6-nitro-1H-indazole</strong> (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5?10 min at 25?35 °C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16?18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 × 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0percent) as a yellow solid.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1661 - 1663

6
[ 94444-96-9 ]
[ 2533-69-9 ]
[ 541539-88-2 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of 6-nitro-1H-indazole (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5-10 min at 25-35 C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16-18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 × 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0%) as a yellow solid.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1661 - 1663

7
[ 3171-46-8 ]
[ 2533-69-9 ]
[ 1432645-36-7 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 4093 - 4103

8
[ 302800-13-1 ]
[ 2533-69-9 ]
[ 1447911-02-5 ]

Yield	Reaction Conditions	Operation in experiment
0.78 g		Example 14 4- ( ( 4-Fluorobenzyl ) oxy) -1- ( l-methyl-lH-benzimidazol-6- yl ) pyridin-2 ( 1H) -one A) 6-Bromo-l-methyl-2- (trichloromethyl ) -lH-benzimidazole A mixture of <strong>[302800-13-1]5-bromo-N-methyl-2-nitroaniline</strong> (0.65 g) , iron (0.63 g) , CaCl2 (0.62 g) , EtOH (14 ml) and water (14 ml) was heated at 70C for 3h. The inorganic material was removed by filtration, and the filtrate was concentrated. The residue was basified with saturated NaHCC>3, and extracted with EtOAc. The extract was washed with brine, dried over MgS04, and concentrated to give the title compound (0.51 g) as a brown oil. To the oil in AcOH (3 ml), methyl 2,2,2- trichloroacetimidate (0.42 ml) was added dropwise at 0C. The mixture was stirred at room temperature for 2 h. After addition of water, the precipitate was collected by filtration and washed with water to give the title compound (0.78 g) as a gray solid. XH NMR (300 MHz, CDCI3) : δ 4.09 (3H, s) , 7.46 (1H, dd, J = 1.7, 8.5 Hz), 7.58 (1H, d, J = 1.5 Hz), 7.74 (1H, d, J = 8.7 Hz).

Reference： [1]Patent: WO2013/105676,2013,A1 .Location in patent: Page/Page column 118; 119

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Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Heat of Combustion ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

Historical Records

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[ 2533-69-9 ]

Aliphatic Chain Hydrocarbons

[ 98946-18-0 ]

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Similarity: 0.79

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Chlorides

[ 98946-18-0 ]

tert-Butyl trichloroacetimidate

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[ 81927-55-1 ]

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Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
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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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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P262	Do not get in eyes, on skin, or on clothing.
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P270	Do not eat, drink or smoke when using this product.
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Code	Phrase
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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.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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[ CAS No. 2533-69-9 ] {[proInfo.proName]}

Quality Control of [ 2533-69-9 ]

Related Doc. of [ 2533-69-9 ]

Product Details of [ 2533-69-9 ]

Calculated chemistry of [ 2533-69-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2533-69-9 ]

Application In Synthesis of [ 2533-69-9 ]

[ 2533-69-9 ] Synthesis Path-Upstream 1~1

[ 2533-69-9 ] Synthesis Path-Downstream 1~8

Technical Information

Related Functional Groups of [ 2533-69-9 ]

Aliphatic Chain Hydrocarbons

Chlorides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2533-69-9 ]