[ CAS No. 78078-92-9 ] {[proInfo.proName]}

Name: 78078-92-9|2-Oxo-1,2-dihydrobenzo[cd]indole-6-sulfonyl chloride|95%
Brand: Ambeed
SKU: A390078
Rating: 92 (30 reviews)

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

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There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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Structure of 78078-92-9 * Storage: {[proInfo.prStorage]}

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For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 78078-92-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 78078-92-9 ]

SDS Specification

Alternatived Products of [ 78078-92-9 ]

Product Details of [ 78078-92-9 ]

CAS No. :	78078-92-9	MDL No. :	MFCD02732837
Formula :	C₁₁H₆ClNO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HBGOGAFJKXIXKJ-UHFFFAOYSA-N
M.W :	267.69	Pubchem ID :	3138191
Synonyms :

Calculated chemistry of [ 78078-92-9 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	66.34
TPSA :	75.38 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) :	-6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	2.11
Log Po/w (WLOGP) :	3.13
Log Po/w (MLOGP) :	1.88
Log Po/w (SILICOS-IT) :	2.72
Consensus Log Po/w :	2.27

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.29
Solubility :	0.139 mg/ml ; 0.000518 mol/l
Class :	Soluble
Log S (Ali) :	-3.32
Solubility :	0.127 mg/ml ; 0.000475 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.99
Solubility :	0.00277 mg/ml ; 0.0000104 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.04

Safety of [ 78078-92-9 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 78078-92-9 ]

* 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.

Downstream synthetic route of [ 78078-92-9 ]

[ 78078-92-9 ] Synthesis Path-Downstream 1~49

2
[ 885228-15-9 ]
[ 78078-92-9 ]
[ 1234566-94-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3518 - 3534

3
[ 1234566-90-5 ]
[ 78078-92-9 ]
[ 1234566-97-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3518 - 3534

4
[ 130-00-7 ]
[ 78078-92-9 ]

Yield	Reaction Conditions	Operation in experiment
26%	With chlorosulfonic acid;	FIGURE 72 shows the synthesis of TNF-alpha binding bifunctional molecule 4e-GN3.
	With chlorosulfonic acid; In chloroform; at 0 - 50℃; for 5.5h;	To a solution of benzo [cd]indol-2(1H)-one 2 (10g, 60mmol) in chloroform (150mL) was added batches of chlorosulfonic acid (22mL, 6.0 equiv.) at 0C for 30min. The reaction mixture was heated at 50C for 5h. The mixture was then poured into ice water and extracted with CHCl3 (100mL×3). The organic layer was washed with brine and dried over Na2SO4. The solid was filtered off, and the filtrate was concentrated under reduced pressure to afford 2-oxo-1,2-dihydrobenzo [cd]indole-6-sulfonyl chloride (10g, yield 50%). The resulting crude product was resolved in dichloromethane (100mL), then the solution was added into pyrrolidine (3.4mL, 1.2 equiv.) and N-ethyldi isopropylamine (DIPEA, 18mL, 3.0 equiv.). The reaction mixture was stirred at room temperature for 5h. After completion of the reaction as monitored by TLC, dilute HCl was added, the aqueous layer was extracted with DCM (80mL×3), and the organic layer was washed with water and brine, dried with Na2SO4, and evaporated to give 6-(pyrrolidin-1-ylsulfonyl) benzo [cd]indol-2(1H)-one 3 (9g, yield 80%). The product 3 (150mg, 0.5mmol) and sodium hydride (NaH, 36mg, 1.5mmol) were dissolved in DMF (15mL). Bromoethane (65.4mg, 0.6mmol) was added dropwise into the solution and the reaction mixture was stirred at room temperature. After completion of the reaction as monitored by TLC, the reaction mixture was extracted with ethyl acetate (10mL×2). The organic layer was washed with brine and dried over Na2SO4. The solid was filtered off, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography with petroleum ether/ethyl acetate (3/1, v/v) to yield compound 1. Under the same conditions, compounds 4-9 were obtained (for detail, see Supporting information 1 and 2). 4.2.1 1-Ethyl-6-(pyrrolidin-1-ylsulfonyl)benzo[cd]indol-2(1H)-one (1) Yellow-green solid, yield 77%, m. p. 168.1-168.9C; 1H NMR (600MHz, CDCl3) delta (ppm): 8.79 (d, J=8.4Hz, 1H), 8.16 (d, J=7.2Hz, 1H), 8.11 (d, J=7.2Hz, 1H), 7.83 (t, J=7.8Hz, 1H), 6.96 (d, J=7.8Hz, 1H), 3.99 (q, J=7.2Hz, 2H), 3.31 (t, J=6.6Hz, 4H), 1.79-1.77 (m, 4H), 1.39 (t, J=7.2Hz, 3H); 13C NMR (150MHz, CDCl3) delta (ppm): 167.6 (C=O), 143.6, 132.9 (CH), 130.4 (CH), 130.3 (CH), 127.0, 126.5, 125.8 (2C), 125.2 (CH), 103.0 (CH), 47.5 (2CH2), 35.1(CH2), 25.3 (2CH2), 13.9 (CH3); HRMS (ESI): Calcd for C17H18N2O3SNa ([M+Na]+): 353.0936, Found: 353.0932. Anal. Calcd for C17H18N2O3S: C, 61.80; H, 5.49; N, 8.48. Found: C, 61.78; H, 5.52; N, 8.49.

Reference： [1]Journal of Chemical Information and Modeling,2017,vol. 57,p. 355 - 364
[2]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3518 - 3534
[3]Patent: WO2019/199634,2019,A1 .Location in patent: Page/Page column 32
[4]ACS Medicinal Chemistry Letters,2010,vol. 1,p. 355 - 359
[5]Journal of Enzyme Inhibition and Medicinal Chemistry,2015,vol. 30,p. 126 - 132
[6]Journal of Medicinal Chemistry,2016,vol. 59,p. 1565 - 1579
[7]European Journal of Medicinal Chemistry,2018,vol. 152,p. 264 - 273

5
[ 13325-10-5 ]
[ 78078-92-9 ]
[ 1234567-15-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3518 - 3534

6
[ 2508-29-4 ]
[ 78078-92-9 ]
[ 1234567-19-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3518 - 3534

7
[ 4048-33-3 ]
[ 78078-92-9 ]
[ 1234567-23-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3518 - 3534

8
[ 53253-54-6 ]
[ 78078-92-9 ]
[ 1234567-53-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3518 - 3534

9
[ 53253-55-7 ]
[ 78078-92-9 ]
[ 1234567-56-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3518 - 3534

10
[ 78078-92-9 ]
[ 58779-63-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3518 - 3534

11
[ 78078-92-9 ]
[ 141-43-5 ]
[ 378224-70-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3518 - 3534

12
[ 104-13-2 ]
[ 78078-92-9 ]
[ 441745-43-3 ]