[ CAS No. 54029-45-7 ] {[proInfo.proName]}

Name: 54029-45-7|2-Nitro-4-thiocyanatoaniline|97%
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SKU: A185683
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Quality Control of [ 54029-45-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 54029-45-7 ]

Product Details of [ 54029-45-7 ]

CAS No. :	54029-45-7	MDL No. :	MFCD00463878
Formula :	C₇H₅N₃O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QUWHIBBGKKRYFW-UHFFFAOYSA-N
M.W :	195.20	Pubchem ID :	104677
Synonyms :

Calculated chemistry of [ 54029-45-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.14
TPSA :	120.93 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.16
Log Po/w (XLOGP3) :	1.77
Log Po/w (WLOGP) :	1.76
Log Po/w (MLOGP) :	0.75
Log Po/w (SILICOS-IT) :	-0.94
Consensus Log Po/w :	0.9

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.37
Solubility :	0.823 mg/ml ; 0.00422 mol/l
Class :	Soluble
Log S (Ali) :	-3.93
Solubility :	0.0231 mg/ml ; 0.000118 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.62
Solubility :	4.68 mg/ml ; 0.024 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	4.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.5

Safety of [ 54029-45-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 54029-45-7 ]

* 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 [ 54029-45-7 ]
Downstream synthetic route of [ 54029-45-7 ]

[ 54029-45-7 ] Synthesis Path-Upstream 1~11

1
[ 54029-45-7 ]
[ 54965-21-8 ]

Reference： [1] Patent: WO2012/70069, 2012, A2,
[2] Patent: US2013/303782, 2013, A1,
[3] Patent: CN105585533, 2016, A,

2
[ 1147550-11-5 ]
[ 88-74-4 ]
[ 54029-45-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 18, p. 2231 - 2236
[2] Journal of Organic Chemistry, 1947, vol. 12, p. 718,722
[3] Journal of Organic Chemistry, 1952, vol. 17, p. 758,761
[4] Patent: WO2012/70069, 2012, A2, . Location in patent: Page/Page column 5
[5] Chemical Communications, 2017, vol. 53, # 11, p. 1880 - 1883

3
[ 88-74-4 ]
[ 54029-45-7 ]

Yield	Reaction Conditions	Operation in experiment
504 kg	With chlorine In methanol at 10℃; for 7 h; Large scale	(a) Preparation of 2-Nitro-p-Thiocyanoaniline 2-Nitroaniline (360 kg) was treated with ammonium thiocyanate (407 kg) in methanol at room temperature. The reaction mixture was stirred and cooled to below 10° C. Chlorine gas was purged for 6 hrs and maintained for 1 hr. After completion of the reaction, water was added and stirred for 1 hr at 20° C. The reaction mass was filtered, washed with water, and dried at 80° C. Weight: 504 kg.

Reference： [1] Patent: US2013/303782, 2013, A1, . Location in patent: Paragraph 0019
[2] Patent: US4046908, 1977, A,
[3] Patent: US4076828, 1978, A,

4
[ 54029-46-8 ]
[ 54029-45-7 ]

Reference： [1] Journal of the Chemical Society, 1928, p. 1370
[2] Patent: US4072696, 1978, A,

5
[ 88-74-4 ]
[ 54029-45-7 ]

Reference： [1] Patent: US4034107, 1977, A,
[2] Patent: US4071528, 1978, A,

6
[ 540-72-7 ]
[ 88-74-4 ]
[ 54029-45-7 ]

Reference： [1] RSC Advances, 2016, vol. 6, # 107, p. 105119 - 105124

7
[ 3321-94-6 ]
[ 54029-45-7 ]
[ 54029-46-8 ]

Reference： [1] Journal of the Chemical Society, 1928, p. 1370

8
[ 2987-46-4 ]
[ 54029-45-7 ]

Reference： [1] Journal of the Chemical Society, 1928, p. 1370
[2] Journal of the Chemical Society, 1928, p. 1370

9
[ 333-20-0 ]
[ 88-74-4 ]
[ 54029-45-7 ]

Reference： [1] Pharmazie, 1948, vol. 3, p. 151

10
[ 3321-94-6 ]
[ 54029-45-7 ]

Reference： [1] Journal of the Chemical Society, 1928, p. 1370

11
[ 7726-95-6 ]
[ 1147550-11-5 ]
[ 64-19-7 ]
[ 88-74-4 ]
[ 54029-45-7 ]

Reference： [1] Journal of Organic Chemistry, 1952, vol. 17, p. 758,761
[2] Zhurnal Obshchei Khimii, 1953, vol. 23, p. 116[3] Chem.Abstr., 1954, p. 673

[ 54029-45-7 ] Synthesis Path-Downstream 1~60

1
[ 3321-94-6 ]
[ 54029-45-7 ]
[ 54029-46-8 ]

Reference： [1]Journal of the Chemical Society,1928,p. 1370

2
[ 54029-45-7 ]
[ 16671-77-5 ]

Reference： [1]Journal of the Chemical Society,1928,p. 1370

3
[ 54029-45-7 ]
[ 89642-54-6 ]

Reference： [1]Journal of Organic Chemistry,1947,vol. 12,p. 718,722

4
[ 54029-45-7 ]
[ 98436-70-5 ]

Reference： [1]Journal of the Chemical Society,1928,p. 1368

5
[ 54029-45-7 ]
4-bromo-3-nitro-phenyl thiocyanate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1952,vol. 17,p. 758,761

6
[ 54029-45-7 ]
[ 54394-37-5 ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 5905
[2]Russian Journal of Organic Chemistry,2003,vol. 39,p. 979 - 984

7
[ 54029-45-7 ]
[ 80825-28-1 ]

Reference： [1]Journal of the Chemical Society,1928,p. 1370
[2]Journal of the Chemical Society,1928,p. 1370
[3]Russian Journal of Organic Chemistry,2003,vol. 39,p. 979 - 984

8
[ 54029-46-8 ]
[ 54029-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; water;	EXAMPLE V 6 G. of 1-acetamido-2-nitro-4-thiocyanatobenzene is suspended in a mixture of 30 ml. concentrated hydrochloric acid and 30 ml. methanol, and the mixture stirred at room temperature for 24 hours. The water is added and the product isolated by filtration, yielding 1-amino-2-nitro-4-thiocyanatobenzene.

Reference： [1]Journal of the Chemical Society,1928,p. 1370
[2]Patent: US4072696,1978,A

9
[ 54029-45-7 ]
[ 98-88-4 ]
benzoic acid-(2-nitro-4-thiocyanato-anilide) [ No CAS ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 313,315
Chem.Abstr.,1956,p. 10043

10
[ 54029-45-7 ]
[ 103-71-9 ]
[ 106167-14-0 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 313,315
Chem.Abstr.,1956,p. 10043

11
[ 333-20-0 ]
[ 88-74-4 ]
[ 54029-45-7 ]

Reference： [1]Pharmazie,1948,vol. 3,p. 151

12
[ 1147550-11-5 ]
[ 88-74-4 ]
[ 54029-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine; In methanol; at 10℃; for 7h;Industry scale;	2-Nitroaniline (360 kg) was treated with ammonium thiocyanate (407 kg) in methanol at room temperature. The reaction mixture was stirred and cooled to below 10C. Chlorine gas was purged for 6 hrs and maintained for 1 hr. After completion of the reaction, water was added and stirred for 1 hr at 20C. The reaction mass was filtered, washed with water, and dried at 80C.Weight: 504 kg.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2231 - 2236
[2]Journal of Organic Chemistry,1947,vol. 12,p. 718,722
[3]Patent: WO2012/70069,2012,A2 .Location in patent: Page/Page column 5
[4]Chemical Communications,2017,vol. 53,p. 1880 - 1883

13
[ 54029-45-7 ]
[ 106-94-5 ]
[ 54393-89-4 ]

Yield	Reaction Conditions	Operation in experiment
		(0.2 mol) of pure <strong>[54029-45-7]4-thiocyanato-2-nitroaniline</strong> was charged into a reaction flask under an argon-purged nitrogen atmosphere,(0.50 mol) of a 30% sodium hydroxide solution was added dropwise at a temperature of 30 to 40 C for about 1 hour,After completion of dropwise addition, the temperature was raised to 50 C, and 32.0 g (0.26 mol) of bromopropane was added dropwise for about 0.5 hour.End to keep the insulation for 2 hours, after the end, close the N2 protection, 50-60 C layer, discard the wastewater layer, the upperRed-brown liquid, that is 4-propylthio-2-nitroaniline solution of n-propanol.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2231 - 2236
[2]Patent: CN105585533,2016,A .Location in patent: Paragraph 0040; 0041; 0042

14
[ 7726-95-6 ]
[ 1147550-11-5 ]
[ 64-19-7 ]
[ 88-74-4 ]
[ 54029-45-7 ]

Reference： [1]Journal of Organic Chemistry,1952,vol. 17,p. 758,761

Yield	Reaction Conditions	Operation in experiment
77%		EXAMPLE II Preparation of 4-thiocyano-2-nitroaniline--The experiment was conducted as in Example I except that 7.8 g of chlorine gas was bubbled into the chilled reaction mixture over a 35 minute period. After the same workup as in Example I, 16.75 g of crude dry product was obtained. This product assayed 90% giving 77% yield of 4-thiocyano-2-nitroaniline from o-nitroaniline.

16
[ 3321-94-6 ]
HNO₃+H₂SO₄ [ No CAS ]
[ 54029-45-7 ]
[ 54029-46-8 ]

Reference： [1]Journal of the Chemical Society,1928,p. 1370

17
[ 7647-01-0 ]
[ 54029-45-7 ]
[ 80825-28-1 ]

Reference： [1]Journal of the Chemical Society,1928,p. 1370

18
[ 54029-45-7 ]
alcoholic KOH-solution [ No CAS ]
[ 80825-28-1 ]

Reference： [1]Journal of the Chemical Society,1928,p. 1370

19
[ 54029-45-7 ]
[ 100-00-5 ]
[ 127923-96-0 ]

Reference： [1]Russian Journal of General Chemistry,2002,vol. 72,p. 1439 - 1443

20
[ 54029-45-7 ]
sodium 4-amino-3-nitrobenzenethiolate [ No CAS ]
[ 80825-28-1 ]

Reference： [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 979 - 984

21
[ 54029-45-7 ]
[ 100-00-5 ]
[ 101-59-7 ]
[ 1223-31-0 ]
[ 127923-96-0 ]

Reference： [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 979 - 984

22
[ 54029-45-7 ]
[ 80983-47-7 ]

Yield	Reaction Conditions	Operation in experiment
99.28%	With sodium hydroxide; for 1.5h;	19.52 g (0.10 mol) of <strong>[54029-45-7]4-thiocyano-2-nitroaniline</strong> in a container with a concentration of 4.40 g of 30% sodium hydroxide solution was reacted for 1.5 h hours, and then concentrated to obtain crystals. sodium 4-mercapto-2-nitroaniline19.08 g was obtained. The yield was 99.28% and the content was 99.86%.
96%	With potassium hydroxide; In ethanol; at 5 - 20℃; for 0.5h;	Accordingly, in some embodiments, <strong>[54029-45-7]2-nitro-4-thiocyanatoaniline</strong> (e.g., about 3.51 g, 18 mmol) is added in portions to a stirred solution of potassium hydroxide (e.g., about 6 g) in ethanol (e.g., about 100 ml) at about 5-10 C. and the mixture is stirred for about 30 min at room temperature. An about 25% aqueous solution of sulfuric acid (about 30 ml) is added until the color of the mixture changed from dark violet to bright orange. Solvents may be removed by rotary evaporation. Water (about 200 ml) is added into the mixture, and it is then extracted with ethyl acetate (e.g., about 3×60 ml). The combined organic extracts may then be washed with brine and dried over magnesium sulfate. The solution may then be filtered and the solvent removed by rotary evaporation (for example) to yield compound 1 of FIG. 3 as a red solid (e.g., about 2.94 g, 96%); mp 99-101 C. (reported in literature: 99-101 C.).

Reference： [1]Patent: CN109400537,2019,A .Location in patent: Paragraph 0053; 0054
[2]Patent: US2016/108002,2016,A1 .Location in patent: Paragraph 0060
[3]Organic and Biomolecular Chemistry,2003,vol. 1,p. 4342 - 4350
[4]RSC Advances,2016,vol. 6,p. 105119 - 105124
[5]Chemical Communications,2017,vol. 53,p. 1880 - 1883

23
[ 54029-45-7 ]
[ 78212-93-8 ]