[ CAS No. 16309-45-8 ] {[proInfo.proName]}

Name: 16309-45-8|4-(4-Nitrophenoxy)benzoic acid|98%
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SKU: A721902
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Quality Control of [ 16309-45-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 16309-45-8 ]

CAS No. :	16309-45-8	MDL No. :	MFCD00429494
Formula :	C₁₃H₉NO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XTVBFFGZCMYUJX-UHFFFAOYSA-N
M.W :	259.21	Pubchem ID :	292066
Synonyms :

Safety of [ 16309-45-8 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P362+P364-P403+P233-P501	UN#:	3077
Hazard Statements:	H315-H318-H335-H411	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 16309-45-8 ]

* 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.

Downstream synthetic route of [ 16309-45-8 ]

[ 16309-45-8 ] Synthesis Path-Downstream 1~47

1
[ 67-56-1 ]
[ 16309-45-8 ]
[ 21120-78-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride

Reference： [1]Haeussermann; Bauer [Chemische Berichte, 1896, vol. 29, p. 2084][Chemische Berichte, 1897, vol. 30, p. 738 Anm. 2]

2
[ 3402-74-2 ]
[ 16309-45-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridine; potassium permanganate; sodium hydroxide In water at 100℃; for 10.5h; Reflux;
	With sodium dichromate; sulfuric acid; acetic acid
	With chromium(VI) oxide; acetic acid

	With nitric acid at 185 - 190℃;
	With potassium dichromate; sulfuric acid In water

Reference： [1]Xia, Lianlian; Zhai, Xuejiao; Xiong, Xuhai; Chen, Ping [RSC Advances, 2014, vol. 4, # 9, p. 4646 - 4655]
[2]Brewster; Slocombe [Journal of the American Chemical Society, 1945, vol. 67, p. 562]
[3]Horii [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1937, vol. 57, p. 298,305; dtsch. Ref. S. 124, 125][Chemisches Zentralblatt, 1937, vol. 108, # II, p. 3311]
[4]Mironov,G.S. et al. [Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 127 - 130][Zhurnal Organicheskoi Khimii, 1973, vol. 9, # 1, p. 128 - 132]
[5]Li, Yingjun; Yu, Yang; Jin, Kun; Gao, Lixin; Luo, Tongchuan; Sheng, Li; Shao, Xin; Li, Jia [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4125 - 4128]

3
[ 50961-54-1 ]
[ 16309-45-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium dichromate; sulfuric acid

Reference： [1]Suter; Oberg [Journal of the American Chemical Society, 1931, vol. 53, p. 1566,1568]

4
[ 16309-45-8 ]
[ 28999-69-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; tin
	With hydrogen
	With hydrogen In ethanol	66 Example 66; General synthesis of 9.3; To a stirred solution of compound 9.1 (1 equivalent) in ethanol was added 10 % palladium on carbon (0.5 equivalent by weight). The resulting mixture was stirred under hydrogen atmosphere (balloon pressure) overnight. The reaction mixture was filtered through celite and concentrated in vacuo to give compound 9.2 as a solid which was used without purification.

Reference： [1]Haeussermann; Bauer [Chemische Berichte, 1896, vol. 29, p. 2084][Chemische Berichte, 1897, vol. 30, p. 738 Anm. 2]
[2]Mironov,G.S. et al. [Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 127 - 130][Zhurnal Organicheskoi Khimii, 1973, vol. 9, # 1, p. 128 - 132]
[3]Current Patent Assignee: ARETE THERAPEUTICS - WO2008/116145, 2008, A2 Location in patent: Page/Page column 106

5
[ 16309-45-8 ]
[ 24477-91-6 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride at 60℃;
	With thionyl chloride
	With thionyl chloride; N,N-dimethyl-formamide In toluene for 4h; Reflux;

Reference： [1]Nemleva, S. A.; Ivanova, V. M.; Vulakh, E. L.; Gitis, S. S. [Journal of general chemistry of the USSR, 1983, vol. 53, # 11, p. 2258 - 2262][Zhurnal Obshchei Khimii, 1983, vol. 53, # 11, p. 2505 - 2510]
[2]Suter; Oberg [Journal of the American Chemical Society, 1931, vol. 53, p. 1566,1568]
[3]Gargano, Emanuele Marco; Perspicace, Enrico; Carotti, Angelo; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W. [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 1, p. 21 - 24]

Yield	Reaction Conditions	Operation in experiment
	Reduktion (katalytisch, polarographisch) (Kinetik), Geschw.-Konstante;

Yield	Reaction Conditions	Operation in experiment
	/BRN= 2988592/;
	4'-Dimethylcarbamoy-4-nitro-diphenylaether <H2SO4>;
	(yield)87percent;

	4-Hydroxy-benzoesaeure, KJ, K2CO3, DMF, 1-Chlor-4-nitro-benzol;
	4-(p-Nitrophenoxy)-benzaldehyd, Ag2O;
	p-Hydroxybenzoesaeure, KOH, Cu, p-Chlornitrobenzol, dann HCl;
	/BRN= 53667/, HNO3, 185grad-190grad;
	p-Chlornitrobenzol, p-Hydroxybenzoesaeure;
	entspr. Acetylverb., HOBr;

Yield	Reaction Conditions	Operation in experiment
	With water; calcium chloride

9
[ 100-00-5 ]
[ 16309-45-8 ]

Yield	Reaction Conditions	Operation in experiment
	at 160℃; anschliessend Erhitzen des Reaktionsprodukts auf 235grad;

Reference： [1]Haeussermann; Bauer [Chemische Berichte, 1896, vol. 29, p. 2084][Chemische Berichte, 1897, vol. 30, p. 738 Anm. 2]

10
[ 350-46-9 ]
[ 16309-45-8 ]

Yield	Reaction Conditions	Operation in experiment
	With copper at 200℃;

Reference： [1]Rarick; Brewster; Dains [Journal of the American Chemical Society, 1933, vol. 55, p. 1289]

11
[ 16309-45-8 ]
[ 7803-57-8 ]
[ 100-16-3 ]
[ 99-96-7 ]

Reference： [1]Ikawa [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 457,459][Chem.Abstr., 1956, p. 2480]

12
[ 100-02-7 ]
[ 1194-02-1 ]
[ 6508-04-9 ]
[ 17076-68-5 ]
[ 16309-45-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 52 % Chromat. 2: 8.6 % Chromat. 3: 5.8 % Chromat.	With potassium carbonate In dimethyl sulfoxide for 0.166667h; Heating; microwave irradiation;

Reference： [1]Li, Feng; Meng, Qingqing; Chen, Huansheng; Li, Zhiming; Wang, Quanrui; Tao, Fenggang [Synthesis, 2005, # 8, p. 1305 - 1313]

13
[ 100-00-5 ]
[ 16309-45-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 170 °C / Erhitzen des Reaktionsgemisches auf 190-200grad 2: sodium dichromate; sulfuric acid
	Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 120 °C 1.2: Heating 2.1: sodium hydroxide; pyridine; potassium permanganate / water / 10.5 h / 100 °C / Reflux
	Multi-step reaction with 2 steps 1: 6 h / Heating 2: potassium dichromate; sulfuric acid / water

Reference： [1]Suter; Oberg [Journal of the American Chemical Society, 1931, vol. 53, p. 1566,1568]
[2]Xia, Lianlian; Zhai, Xuejiao; Xiong, Xuhai; Chen, Ping [RSC Advances, 2014, vol. 4, # 9, p. 4646 - 4655]
[3]Li, Yingjun; Yu, Yang; Jin, Kun; Gao, Lixin; Luo, Tongchuan; Sheng, Li; Shao, Xin; Li, Jia [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4125 - 4128]

14
[ 16309-45-8 ]
4-(4-Aminophenoxy)benzoylchlorid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂ / Raney-Ni 2: SOCl₂

Reference： [1]Mironov,G.S. et al. [Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 127 - 130][Zhurnal Organicheskoi Khimii, 1973, vol. 9, # 1, p. 128 - 132]

15
[ 100-00-5 ]
[ 99-96-7 ]
[ 16309-45-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In dimethyl sulfoxide at 80℃; for 1h; Sonication;	Diaryl ethers (general procedure). General procedure: i. A mixture of compound 2a,b (6 mmol), 4a-d (6 mmol), and K2CO3 (9 mmol or 18 mmol for 5c) in DMSO (25 mL) was stirred for 5 h (for 5a), 4 h (for 5b and 5d), 4.35 h (for 5c), and 8 h (for 5f) at 80 °C. After cooling, the mixture was poured into water, filtered, dried, and recrystallized from alcohol. ii. A mixture of compound 2a-c (6 mmol), 4a-e (6 mmol), or 1 (3 mmol) and K2CO3 (9 mmol or 18 mmol for 5c) in DMSO (25 mL) was subjected to ultrasound irradiation at 80 °C for 1 h (for 3a,b, 5a-d), 6 h (for 5e), and 2 h (for 3c, 5f). After cooling, the mixture was poured into water, filtered, dried, and recrystallized from alcohol.
	With sodium methylate In dimethyl sulfoxide	63.a a a 4-(4-Nitrophenoxy)benzoic Acid Following the general procedure of J. Polym. Sci., Polym. Chem. Ed. (1980), 18(10). 3069-80, 4-hydroxybenzoic acid, 1-chloro-4-nitro-benzene and sodium methoxide were heated in DMSO at 130° C. to afford the title compound.

Reference： [1]Begunov; Valyaeva; Belyaev; Dobretsova [Russian Chemical Bulletin, 2015, vol. 64, # 8, p. 1971 - 1974][Izv. Akad. Nauk, Ser. Khim., 2015, # 8, p. 1971 - 1974,4]
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - US6518267, 2003, B1

16
[ 16309-45-8 ]
[ 26506-91-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: polyphosphoric acid (PPA) / 6 h / 120 °C 2: hydrazine hydrate; pyrographite; iron(III) chloride / 2-methoxy-ethanol / 11 h / 110 °C / Inert atmosphere

Reference： [1]Xia, Lianlian; Zhai, Xuejiao; Xiong, Xuhai; Chen, Ping [RSC Advances, 2014, vol. 4, # 9, p. 4646 - 4655]

17
[ 16309-45-8 ]
[ 1425504-87-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: polyphosphoric acid (PPA) / 6 h / 120 °C 2: hydrazine hydrate; pyrographite; iron(III) chloride / 2-methoxy-ethanol / 11 h / 110 °C / Inert atmosphere 3: acetone / 9 h / 20 °C 4: triethylamine; acetic anhydride; sodium acetate / acetone / 6 h / Reflux

Reference： [1]Xia, Lianlian; Zhai, Xuejiao; Xiong, Xuhai; Chen, Ping [RSC Advances, 2014, vol. 4, # 9, p. 4646 - 4655]

18
[ 16309-45-8 ]
[ 1425504-86-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: polyphosphoric acid (PPA) / 6 h / 120 °C 2: hydrazine hydrate; pyrographite; iron(III) chloride / 2-methoxy-ethanol / 11 h / 110 °C / Inert atmosphere 3: acetone / 9 h / 20 °C

Reference： [1]Xia, Lianlian; Zhai, Xuejiao; Xiong, Xuhai; Chen, Ping [RSC Advances, 2014, vol. 4, # 9, p. 4646 - 4655]

19
[ 16309-45-8 ]
[ 636-97-5 ]
[ 26506-90-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	With polyphosphoric acid (PPA) at 120℃; for 6h;

Reference： [1]Xia, Lianlian; Zhai, Xuejiao; Xiong, Xuhai; Chen, Ping [RSC Advances, 2014, vol. 4, # 9, p. 4646 - 4655]

20
[ 106-44-5 ]
[ 16309-45-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 120 °C 1.2: Heating 2.1: sodium hydroxide; pyridine; potassium permanganate / water / 10.5 h / 100 °C / Reflux

Reference： [1]Xia, Lianlian; Zhai, Xuejiao; Xiong, Xuhai; Chen, Ping [RSC Advances, 2014, vol. 4, # 9, p. 4646 - 4655]

21
[ 1192-96-7 ]
[ 16309-45-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 6 h / Heating 2: potassium dichromate; sulfuric acid / water