[ CAS No. 127-68-4 ] {[proInfo.proName]}

Name: 127-68-4|Sodium 3-nitrobenzenesulphonate|98%
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Quality Control of [ 127-68-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 127-68-4 ]

SDS Specification

Alternatived Products of [ 127-68-4 ]

Product Details of [ 127-68-4 ]

CAS No. :	127-68-4	MDL No. :	MFCD00007490
Formula :	C₆H₄NNaO₅S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LJRGBERXYNQPJI-UHFFFAOYSA-M
M.W :	225.15	Pubchem ID :	31389
Synonyms :

Calculated chemistry of [ 127-68-4 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.27
TPSA :	111.4 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-10.01
Log Po/w (XLOGP3) :	0.01
Log Po/w (WLOGP) :	1.58
Log Po/w (MLOGP) :	0.07
Log Po/w (SILICOS-IT) :	-1.87
Consensus Log Po/w :	-2.04

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.43
Solubility :	8.42 mg/ml ; 0.0374 mol/l
Class :	Very soluble
Log S (Ali) :	-1.9
Solubility :	2.83 mg/ml ; 0.0126 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.13
Solubility :	16.5 mg/ml ; 0.0735 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.46

Safety of [ 127-68-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P261-P272-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P333+P313	UN#:	N/A
Hazard Statements:	H319-H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 127-68-4 ]

* 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.

Upstream synthesis route of [ 127-68-4 ]
Downstream synthetic route of [ 127-68-4 ]

[ 127-68-4 ] Synthesis Path-Upstream 1~11

1
[ 615-36-1 ]
[ 127-68-4 ]
[ 16567-18-3 ]

Reference： [1] Organometallics, 2014, vol. 33, # 13, p. 3523 - 3534

2
[ 4053-44-5 ]
[ 127-68-4 ]
[ 2598-30-3 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1958, vol. 291, p. 493,502

3
[ 88-74-4 ]
[ 127-68-4 ]
[ 607-35-2 ]

Yield	Reaction Conditions	Operation in experiment
44%	With sulfuric acid In water; glycerolReflux	A mixture was prepared to which 47 g of H₂SO₄, 20 ml of H₂O, 23.4 g (0.104 mol) of sodium 3-nitrobenzene sulfonate, and 22 ml of glycerol were added in that order. It was warmed gently until forming a solution, and 11 g 2-nitroaniline 1c (0.08 mol) was added in portions. The mixture was refluxed for 5 h. After cooling to room temperature, the mixture was poured into 600 ml H₂O under ice bath, adjusted to pH 6-7 with aqueous ammonia, and suction-filtered. The cake was dried and purified with chromatography (EA:PE=1:5). A yellow solid 2c 6.177 g was given in 44percent. (0089) 1H NMR (300 MHz, CDCl3) δ 9.09 (dd, J=1.8 Hz, 4.5 Hz, 1H), 8.28 (dd, J=1.8 Hz, 8.4 Hz, 1H), 8.05 (d, J=9 Hz, 2H), 7.66-7.55 (m, 2H).

Reference： [1] Patent: US2017/29452, 2017, A1, . Location in patent: Paragraph 0087-0089

4
[ 127-68-4 ]
[ 98-18-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 28 - 33

5
[ 1824-81-3 ]
[ 127-68-4 ]
[ 1569-16-0 ]

Yield	Reaction Conditions	Operation in experiment
25.9%	With ferrous(II) sulfate heptahydrate; sulfuric acid; boric acid In water; glycerol at 0 - 135℃; for 4 h;	Sodium-3-nitrobenzenesulfonate (17.5 g, 77.7 mmol), boric acid (2.4 g, 38.8 mmol), and ferrous sulfate heptahydrate (1.4 g, 0.5 mmol) were added to 23.1 mL of 98percent sulfuric acid. After cooling to 0 °C, glycerol (12.5 mL), 2-amino-6-methylpyridine (4.3 g, 40.0 mmol), and hot water (50 °C, 22.5 mL) were slowly added to above mixture. The reaction solution was refluxed for 4 h at 135 °C and cooled to room temperature. 40percent water solution of NaOH was used to mediate pH to 7 and chloroform was used to extract the product. The organic phase was concentrated in vacuum to give the crude product and the final product was obtained by column chromatography (200-300 mesh, 3/1 ethyl acetate/petroleum ether) (3.0 g, 25.9percent yield). Characterization of 2-methyl-1,8-naphthyridine: HRMS (EI) m/z: calcd for C₉H₉N₂ [M+H]⁺, 145.0766; found, 145.0768. ¹H NMR (400 MHz; CDCl₃; TMS) 9.08 (d, 1H), 8.13-8.16 (m, 1H), 8.08 (d, 1H), 7.43-7.45 (m, 1H), 7.28 (d, H), 2.82 (s, 3H). ¹³C NMR: δ_C (100 MHz, CDCl₃): 163.1, 160.0, 153.3, 136.9, 136.7, 123.0, 121.4, 120.8, 25.7.

Reference： [1] Tetrahedron, 2014, vol. 70, # 3, p. 658 - 663

6
[ 127-68-4 ]
[ 25742-87-4 ]
[ 25823-52-3 ]

Reference： [1] Patent: WO2010/5876, 2010, A2, . Location in patent: Page/Page column 61

7
[ 452-58-4 ]
[ 127-68-4 ]
[ 17965-82-1 ]

Reference： [1] Patent: EP3401309, 2018, A1,

8
[ 98-95-3 ]
[ 127-68-4 ]

Yield	Reaction Conditions	Operation in experiment
98.4%	Stage #1: at 120℃; for 5 h; Stage #2: With sodium carbonate In water at 20℃;	1) Add 246g (2.0mol) of nitrobenzene and 139g (1.2mol) of chlorosulfonic acid to a 500mL four-necked flask equipped with a thermometer, mechanical agitation and exhaust gas absorption device, stir and raise the temperature to 120 °C.The sulfonation reaction was carried out for 3 hours.The hydrogen chloride gas generated during the reaction is introduced into 200 mL of deionized water through a tail gas absorption device, and finally obtained in a hydrogen chloride aqueous solution.The mass concentration of hydrogen chloride was 17.5percent.2), after the end of the above reaction, cool to room temperature,Add 500 mL of water and 63.6 g (0.6 mol) of sodium carbonate and stir.Allow to stand and make the oil moisture layer.Among them, the oil layer is washed three times with water (500mL × 3),The mixture was dried with 35 g of molecular sieve to obtain 95 g of a nitrobenzene recovery liquid.The content is 99.3percent.The aqueous layer solution is dried by a spray drying device (atomization speed 15-20 mL/min, inlet temperature 300 °C, outlet temperature 100 °C),266 g of sodium nitrobenzenesulfonate was obtained as a dry product, and the content was 99.0percent.The yield was 98.4percent (based on the consumption of nitrobenzene).

Reference： [1] Patent: CN108997175, 2018, A, . Location in patent: Paragraph 0046-0059; 0062-0066

9
[ 6641-02-7 ]
[ 127-68-4 ]
[ 90-60-8 ]

Reference： [1] Chemische Berichte, 1941, vol. 74, p. 1729,1734

10
[ 127-68-4 ]
[ 121-52-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 28 - 33

11
[ 367-24-8 ]
[ 127-68-4 ]
[ 220513-46-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: With sulfuric acid; glycerol In water at 85 - 133℃;	Intermediate 16-Bromo-8-fluoroquinoline A solution of concentrated sulphuric acid (63 ml, 820 mmol) in water (49.4 ml) was treated with sodium 3-nitro-benzenesulfonate (commercially available, for example, from Aldrich) (47.9 g, 213 mmol) and glycerol (commercially available, for example, from Fluka and/or Aldrich) (52 ml, 720 mmol) to give a thick grey suspension. This was heated to 110° C. (internal temperature was 85° C.). 4-Bromo-2-fluoroaniline (commercially available, for example, from Fluorochem and/or Aldrich) (38 g, 200 mmol) was added over 10 min in portions, during which the internal temperature rose to 95° C. The reaction was heated to 140° C. (internal temperature was 133° C.) and stirred overnight. The reaction mixture was cooled and then poured into water (1000 ml) and basified to pH 7 with aqueous ammonia (0.88 s.g, approximately 190 ml). The brown precipitate that formed was collected by filtration and partially dried. This solid (63 g) was loaded onto a column of silica (1500 ml) and eluted with EtOAc to give the title compound as a light brown solid (43.8 g, 97percent). LCMS RT=2.87 min, ES+ve m/z 226/228 [M+H]⁺.

Reference： [1] Patent: US2009/270355, 2009, A1, . Location in patent: Page/Page column 21

[ 127-68-4 ] Synthesis Path-Downstream 1~88

1
[ 91-04-3 ]
[ 127-68-4 ]
[ 7310-95-4 ]

Reference： [1]Patent: DE580981,1932,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 20,p. 533

2
[ 75959-08-9 ]
[ 127-68-4 ]
[ 951-06-4 ]

Reference： [1]Chemische Berichte,1962,vol. 95,p. 2395 - 2402

3
[ 4053-44-5 ]
[ 127-68-4 ]
[ 2598-30-3 ]

Reference： [1]Archiv der Pharmazie,1958,vol. 291,p. 493,502

4
[ 22471-02-9 ]
[ 127-68-4 ]
[ 1927-94-2 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1941,vol. <2> 158,p. 245,250

5
[ 83-80-7 ]
[ 127-68-4 ]
[ 128-66-5 ]

Reference： [1]Patent: US2238180,1938,

6
[ 4397-13-1 ]
[ 127-68-4 ]
[ 24623-61-8 ]

Reference： [1]Monatshefte fur Chemie,1948,vol. 79,p. 26,36

7
[ 6641-02-7 ]
[ 127-68-4 ]
[ 90-60-8 ]

Reference： [1]Chemische Berichte,1941,vol. 74,p. 1729,1734

8
[ 10496-92-1 ]
[ 127-68-4 ]
[ 1666-03-1 ]

Reference： [1]Monatshefte fur Chemie,1949,vol. 80,p. 359,363

9
[ 14519-99-4 ]
[ 127-68-4 ]
[ 54674-91-8 ]

Reference： [1]Monatshefte fur Chemie,1949,vol. 80,p. 634,638

10
[ 1717-59-5 ]
[ 127-68-4 ]
[ 75-46-7 ]
[ 120608-91-5 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 3023 - 3027

11
[ 1779-49-3 ]
[ 127-68-4 ]
[ 119907-88-9 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 2580 - 2586

12
[ 127-68-4 ]
[ 3814-18-4 ]

Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 4701 - 4704

13
[ 127-68-4 ]
[ 65185-90-2 ]

Reference： [1]Bulletin de la Societe Chimique de France,1991,p. 214 - 221

14
[ 127-68-4 ]
[ 19396-84-0 ]

Reference： [1]Bulletin de la Societe Chimique de France,1988,p. 59 - 66

15
[ 33786-89-9 ]
[ 56-81-5 ]
[ 127-68-4 ]
5-Chloro-1,7-phenanthroline [ No CAS ]

Reference： [1]Biological and pharmaceutical bulletin,2003,vol. 26,p. 448 - 452

16
[ 66671-82-7 ]
[ 127-68-4 ]
5-methoxy-4,7-phenanthroline hydrogen sulfate [ No CAS ]

Reference： [1]Dalton Transactions,2006,p. 1060 - 1072

17
[ 452-83-5 ]
[ 127-68-4 ]
[ 917251-76-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In water; glycerol; at 140℃; for 2h;	Example 1; Preparation of 6-methoxy-8-[4-(l-(5-fluoro)-qumolin-8-yl-piperidin-4-yI)-piperazin-l- ylj-quinoine (Form A)Step 1: 5-Fluoro-8 chloroquinolineTo a mixture of (5.0 g) 2-chloro-5-fluoroaniline (commercially available, 6.0 g), glycerol (6.0 g) and wi-nitrobenzene sulfonic acid sodium salt (11.0 g), was added 20 mL of 70 % sulfuric acid dropwise. The reaction temperature was raised to 140 C for 2 h. The mixture was then cooled, poured on ice water and filtered through celite. The filtrate was neutralized with NaOH and extracted with CH2CI2. The combined organic layers were dried over anhydrous MgSO4 and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using 100% CH2Cl2 to give 3.7 g of the desired product of a yellow solid; MP = 74-76C; MS (ES) m/z (relative intensity): 182 (M+H)+ (100).

Reference： [1]Patent: WO2007/146116,2007,A2 .Location in patent: Page/Page column 27

18
S-difluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium tetrafluoroborate [ No CAS ]
[ 127-68-4 ]
[ 120608-91-5 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1863 - 1866

19
[ 127-68-4 ]
3-(4-cyano-3-hydroxy-isothiazol-5-ylamino)-benzenesulfonamide [ No CAS ]