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Cas Database

104-04-1

104-04-1

Identification

  • Product Name:Acetamide,N-(4-nitrophenyl)-

  • CAS Number: 104-04-1

  • EINECS:203-169-0

  • Molecular Weight:180.163

  • Molecular Formula: C8H8N2O3

  • HS Code:29242990

  • Mol File:104-04-1.mol

Synonyms:N-Acetyl-4-nitroaniline;N-Acetyl-4-nitrobenzenamine;N-Acetyl-p-nitroaniline;NSC 1315;p-Acetamidonitrobenzene;p-Nitroacetanilide;Acetanilide,4'-nitro- (6CI,8CI);Acetanilide, p-nitro- (3CI);1-Nitro-4-acetylaminobenzene;4-(Acetylamino)nitrobenzene;N-(4-Nitrophenyl)acetamide;N-(p-Nitrophenyl)acetamide;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TCI Chemical
  • Product Description:4'-Nitroacetanilide >99.0%(GC)
  • Packaging:500g
  • Price:$ 511
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4'-Nitroacetanilide >99.0%(GC)
  • Packaging:25g
  • Price:$ 59
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4'-Nitroacetanilide for synthesis. CAS 104-04-1, chemical formula CH CONHC H -4-(NO )., for synthesis
  • Packaging:8208800025
  • Price:$ 41.2
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4'-Nitroacetanilide for synthesis. CAS 104-04-1, chemical formula CH CONHC H -4-(NO )., for synthesis
  • Packaging:8208800100
  • Price:$ 223
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4′-Nitroacetanilide for synthesis
  • Packaging:100 g
  • Price:$ 149.85
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4′-Nitroacetanilide for synthesis
  • Packaging:25 g
  • Price:$ 39.5
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Nitroacetanilide 98%
  • Packaging:5g
  • Price:$ 26.5
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  • Manufacture/Brand:Aronis compounds
  • Product Description:N-(4-nitrophenyl)acetamide
  • Packaging:10mg
  • Price:$ 20
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  • Manufacture/Brand:Aronis compounds
  • Product Description:N-(4-nitrophenyl)acetamide
  • Packaging:1mg
  • Price:$ 12
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:4'-NITROACETANILIDE 95.00%
  • Packaging:1G
  • Price:$ 1006.58
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Relevant articles and documentsAll total 229 Articles be found

Acidified, wet, silica-supported tetrabutylammonium periodate: A convenient and mild reagent for conversion of thioamides to their corresponding amides under solvent-free conditions

Nasr-Esfahani, Masoud,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Boostanifar, Mohammad Hasan

, p. 2004 - 2009 (2009)

A series of thioamides are transformed to their corresponding oxo analogues in good to excellent yields with acidified, wet, silica-supported tetrabutylammonium periodate under solvent-free conditions.

On the mechanism for the photooxidation of aromatic azides containing a secondary N–H bond: A sequence of intramolecular transformations with the formation of heterocyclic oximes

Chainikova, Ekaterina,Khursan, Sergey,Yusupova, Alfia,Lobov, Alexander,Abdullin, Marat,Safiullin, Rustam

, p. 3267 - 3271 (2018)

During the photooxidation of aromatic azides containing a secondary N–H bond at the para-position, a sequence of intramolecular transformations of nitroso oxides led to the formation of heterocyclic oximes along with the corresponding nitroso and nitro co

-

Holleman,Sluiter

, p. 210 (1906)

-

NOVEL DESULFURIZATION OF THIOCARBONYL COMPOUNDS INTO THEIR CARBONYL COMPOUNDS WITH TERTIARY BUTYL THIONITRATE

Kim, Jin Hyung,Kim, Yong Hae

, p. 1669 - 1670 (1987)

Various thiocarbonyl compounds such as thioamides, thiocarbamate, thiocarbonate, trithiocarbonate and thioketone were readily reacted with t-butyl thionitrate (t-BuSNO2) to give the corresponding carbonyl compounds in excellent yields under mild conditions.Desulfurization seems to be initiated via the selective nitrosation on the sulfur atom of thiocarbonyl group with t-BuSNO2.

-

Witt,Utermann

, (1908)

-

-

Rabiger,Joullie

, p. 1649 (1961)

-

NOVEL DESULFURIZATION OF THIOCARBONYL COMPOUNDS INTO THEIR CORRESPONDING OXO-DERIVATIVES USING A PEROXY-SULFUR INTERMEDIATE GENERATED FROM 2-NITROBENZENESULFONYL CHLORIDE AND SUPEROXIDE ANION.

Kim, Yong Hae,Chung, Bong Chul,Chang, Hae Sung

, p. 1079 - 1082 (1985)

Thiocarbonyl compounds such as substituted-thioureas, -thioamides, and -thiocarbamates were found to react with a peroxysulfur intermediate (3) which is generated by the treatment of 2-nitrobenzenesulfonyl chloride with potassium superoxide to convert into the corresponding carbonyl compounds in quantitative yield at -30 oC in acetonitrile.

Transformation of thioamide compounds to corresponding amides using 12-Tungstosilicic acid

Nasr-Esfahani, Masoud,Montazerozohori, Morteza,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Moradi, Sareh

, p. 261 - 266 (2010)

12-Tungstosilicic acid (H4SiW12O40) is applied for the conversion of a series of thioamides to their corresponding oxo analogues in excellent yields in acetonitrile. In the case of thioketones, no reaction is observed under these conditions. The reusability of the catalyst also is investigated.

Synthesis of ring-opened derivatives of triazole-containing quinolinones and their antidepressant and anticonvulsant activities

Song, Ming-Xia,Huang, Yu-Shan,Zhou, Qiu-Gui,Deng, Xian-Qing,Yao, Xiao-Dong

, (2021)

Based on the potent antidepressant and anticonvulsant activities of the triazole-containing quinolinones reported in our previous work, a series of ring-opened derivatives of them were designed, synthesized in this work. Their antidepressant and anticonvulsant activities were screened using the forced swimming test (FST) and the maximal electroshock seizure test (MES), respectively. The results showed that compounds 4a, 5a, 6c-6e, 6g-6i, and 7 led to significant reductions in the accumulated immobility time in the FST at a dose of 50 mg/kg. Especially compound 7 exhibited higher levels of efficacy than the reference standard fluoxetine in the FST and the tail suspension test. The results of an open field test excluded the possibility of central nervous stimulation of 7, which further confirmed its antidepressant effect. Meanwhile, compounds 6a-6i and 7 showed different degrees of anticonvulsant activity in mice at the doses range from 300 to 30 mg/kg in the MES. Among them, compounds 6e and 7 displayed the ED50 of 38.5 and 32.7 mg/kg in the MES, and TD50 of 254.6 and 245.5 mg/kg, respectively. No one showed neurotoxicity at the dose of 100 mg/kg. The preliminary investigation forward to their mechanism indicated that regulation of GABAergic system might contribute to their anticonvulsive and anti-depressive action.

A mild and convenient method for conversion of thioamides to their corresponding amides using acidified wet silica-supported permanganate under solvent-free conditions

Nasr-Esfahani, Masoud,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Boostanifar, Mohammad Hasan

, p. 141 - 146 (2009)

A mild and efficient method for conversion of thioamides to their corresponding amides is reported. A series of thioamides are transformed to their corresponding carbonyl compounds in good to excellent yields by acidified wet silica-supported permanganate under solid phase conditions.

Synthesis and conformational analysis of N-aryl-N-(3-thienyl)acetamides

Ito, Ai,Asami, Yuki,Asato, Marino,Fukuda, Kazuo,Yamasaki, Ryu,Okamoto, Iwao

, p. 2454 - 2458 (2018)

The cis-trans conformational equilibrium of amides is of interest because it can be used to control functional activity. Here, we designed and synthesized a series of N-(3-thienyl)amides in order to study the factors affecting their conformational equilibrium. NMR studies showed that the major conformer of N-methyl-N-(3-thienyl)amide in solution is the E-form (cis form), as is the case for N-methylacetamide. For N-aryl-N-(3-thienyl)amides bearing an N-phenyl moiety, the major conformers differ depending on not only the relative π-electron density of the N-aryl moiety, but also its size. X-ray analysis showed that their solid-state conformational preferences were similar to those in solution.

Ruthenium(III) chloride catalyzed acylation of alcohols, phenols, thiols, and amines

Kanta De, Surya

, p. 2919 - 2922 (2004)

Ruthenium(III) chloride catalyzes the acylation of a variety of phenols, alcohols, thiols, and amines under mild conditions. Some of the major advantages of this method are high yields, short reaction times, ease of operation, and compatibility with other protecting groups.

Brown,Reagan

, p. 1032 (1947)

Ortho-Selective Nitration of Acetanilides with Nitrogen Dioxide in the Presence of Ozone

Suzuki, Hitomi,Ishibashi, Taro,Murashima, Takashi,Tsukamoto, Kenkichi

, p. 6591 - 6594 (1991)

In the presence of ozone, nitrogen dioxide rapidly reacts with acetanilides ortho-selectively at low temperatures, giving a high proportion of ortho-nitro derivatives in good yields.

Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation

Bényei, Attila,Domján, Attila,Egyed, Orsolya,Gonda, Zsombor,Novák, Zoltán,Sályi, Gerg?,Tóth, Balázs L.

supporting information, (2021/11/09)

The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.

Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd&at;MCP) for chemoselective N-formylation and N-acylation of amines

Amirsoleimani, Mina,Khalilzadeh, Mohammad A.,Zareyee, Daryoush

, (2020/08/22)

Novel palladium nanoparticles stabilized by clinoptilolite as a natural inexpensive zeolite prepared and used for N-formylation and N-acylation of amines at room temperature at environmentally benign reaction conditions in good to excellent yields. Pd (II) was immobilized on the surface of clinoptilolite via facile multi-step amine functionalization to obtain a sustainable, recoverable, and highly active nano-catalyst. The structural and morphological characterizations of the catalyst carried out using XRD, FT-IR, BET and TEM techniques. Moreover, the catalyst is easily recovered using simple filtration and reused for 7 consecutive runs without any loss in activity.

An efficient, economical and eco-friendly acylation of alcohols and amines by alum doped nanopolyaniline under solvent free condition

Behera, Satyaranjan,Patra, Braja N.

, (2021/08/06)

We report acylation of alcohols and amines employing acetic acid as an acylating agent in solvent free condition by using alum doped nanopolyaniline (NDPANI) as a catalyst. This environmentally benign method does not use corrosive acid anhydrides and acid chlorides for acylation and does not produce waste product. Also, a non-toxic potash alum was used for doping of polyaniline rather than corrosive acids. The reaction conditions represent an advance over established method not only in omitting the need for expensive catalysts or solvents but also in shortening the reaction time significantly. The advantages of this catalyst are non-hazardous, cheap, reusable, easy to prepare and handling.

Synthesis of acetamides via oxidative C–C bond cleavage of ketones catalyzed by Cu-immobilized magnetic nanoparticles

Yazdani, Elahe,Pazoki, Farzane,Salamatmanesh, Arefe,Nejad, Masoume Jadidi,Miraki, Maryam Kazemi,Heydari, Akbar

, (2020/07/27)

Copper supported on magnetite nanoparticles modified with environmentally friendly ligand tricine was devised for synthesis of acetamides via C–C oxidative cleavage of ketones with amines. The catalyst was characterized using different techniques, including Fourier transform infrared, X-ray diffraction, scannin electron microscopy, vibrating sample magnetometry, thermogravimetric analysis, and energy dispersive x-ray spectroscopy. The protocol showed relatively high yields of acetamide products. Furthermore, the magnetic recovery of the catalyst rendered the overall process fast and efficient. It was used in the reaction for six consecutive cycles with negligible loss of catalytic activity. This research is the first report of application of magnetic nanocatalysts for synthesis of acetamides from ketones of low activity through a C–C bond cleavage strategy.

Process route upstream and downstream products

Process route

N-acetyl-N-phenylacetamide
1563-87-7

N-acetyl-N-phenylacetamide

o-nitroacetanilide
552-32-9

o-nitroacetanilide

2,4-dinitroacetanilide
610-53-7

2,4-dinitroacetanilide

N-(3-nitrophenyl)acetanilide
122-28-1

N-(3-nitrophenyl)acetanilide

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
Conditions Yield
bei der Nitrierung unter wechselnden Bedingungen;
4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

dimethylglyoxal
431-03-8

dimethylglyoxal

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

Conditions
Conditions Yield
With Me4NPF4; In N,N-dimethyl-formamide; Product distribution; Mechanism; electrolytic reduction at a Pt gauze electrode at a potential of -0.30 V; other supporting electrolytes;
67%
37%
Acetanilid
103-84-4

Acetanilid

2,4-dinitroacetanilide
610-53-7

2,4-dinitroacetanilide

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
Conditions Yield
at 0 ℃; bei der Verwendung hoeherer Konzentration;
N-(4-nitrophenyl)-3-oxobutanamide
4835-39-6

N-(4-nitrophenyl)-3-oxobutanamide

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2-Methyl-1H-benzimidazole
615-15-6

2-Methyl-1H-benzimidazole

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
Conditions Yield
With iron(III) chloride adsorbed on silica gel; In ethanol; for 2h; Overall yield = 88 %; Reflux;
4-nitrobenzoyl azide
2733-41-7

4-nitrobenzoyl azide

acetic anhydride
108-24-7

acetic anhydride

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

bis-N,N'-(4-nitrophenyl)urea
587-90-6

bis-N,N'-(4-nitrophenyl)urea

Conditions
Conditions Yield
With acetic acid;
acetic anhydride
108-24-7

acetic anhydride

4-Nitrophenyl isocyanate
100-28-7

4-Nitrophenyl isocyanate

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

bis-N,N'-(4-nitrophenyl)urea
587-90-6

bis-N,N'-(4-nitrophenyl)urea

Conditions
Conditions Yield
With acetic acid; benzene;
acetic anhydride
108-24-7

acetic anhydride

4-Nitrophenyl isocyanate
100-28-7

4-Nitrophenyl isocyanate

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

bis-N,N'-(4-nitrophenyl)urea
587-90-6

bis-N,N'-(4-nitrophenyl)urea

Conditions
Conditions Yield
acetic anhydride
108-24-7

acetic anhydride

4-Nitrophenyl isocyanate
100-28-7

4-Nitrophenyl isocyanate

acetic acid
64-19-7,77671-22-8

acetic acid

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

bis-N,N'-(4-nitrophenyl)urea
587-90-6

bis-N,N'-(4-nitrophenyl)urea

Conditions
Conditions Yield
2-acetyl-3-(4-nitrophenyl)isoxazol-5(2H)-one
267877-41-8

2-acetyl-3-(4-nitrophenyl)isoxazol-5(2H)-one

2-methyl-4-(4-nitro-phenyl)-oxazole
79965-75-6

2-methyl-4-(4-nitro-phenyl)-oxazole

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

4-Nitrophenylacetonitrile
555-21-5,34512-13-5,174848-08-9

4-Nitrophenylacetonitrile

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
Conditions Yield
at 500 ℃; Further Variations:; Temperatures; Product distribution;
46%
29%
18%
8%
Acetanilid
103-84-4

Acetanilid

o-nitroacetanilide
552-32-9

o-nitroacetanilide

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
Conditions Yield
With nickel ammonium sulfate; nitric acid; In chloroform; water; at 20 ℃; for 4h;
86%
14%
With bismuth (III) nitrate pentahydrate; acetic anhydride; In dichloromethane; at 23 ℃; for 3h; Solvent; Temperature; Reagent/catalyst; regioselective reaction;
81%
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide; at 20 ℃; for 6h; Ionic liquid;
71%
22%
With tert.-butylnitrite; copper(II) nitrate trihydrate; In acetonitrile; at 80 ℃; for 2h;
67%
19%
With dipotassium peroxodisulfate; silver(I) nitrite; tert.-butylnitrite; In acetonitrile; at 110 ℃; for 16h; regioselective reaction;
59%
17%
With thionyl chloride; bismuth subnitrate; In dichloromethane; at 20 ℃; for 3h;
52%
16%
With trinitratooxovanadium(V); In dichloromethane; for 0.25h; Ambient temperature;
48%
37%
With tetra-O-acetyl riboflavin; oxygen; sodium nitrite; In water; acetonitrile; at 25 ℃; for 10h; Irradiation;
28%
33%
With Nitrogen dioxide; ozone; In chloroform; for 2.5h; below 0 deg C; other acetanilides;
With oxygen; Nitrogen dioxide; ozone; In dichloromethane; at 0 ℃; for 2.5h; Product distribution; various solvents; kyodai-nitration of anilides and phenyl esters with NO2, enhanced ortho-reactivity, effect of solvents on ortho:para isomer ratios;
With chloroform; dinitrogen tetraoxide;
With Nitrogen dioxide; ozone; In chloroform; for 2.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; < 0 deg C;
With oxygen; Nitrogen dioxide; ozone; In chloroform; at 0 ℃; for 2.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With nitric acid;
With sulfuric acid; Methamphetamin; nitric acid; sodium chloride; Man laesst einige Zeit stehen und faellt dann mit Eis und Wasser;
With oxygen; Nitrogen dioxide; ozone; In chloroform; at 0 ℃; for 2.5h; Yield given. Yields of byproduct given;
With benzyltriphenylphosphonium nitrate; Methanesulfonic anhydride; at 20 ℃; for 0.166667h;
With nitric acid; phosphorus pentoxide; silica gel; at 20 ℃; for 0.0333333h; Title compound not separated from byproducts;
With nitric acid; acetic anhydride; H5PV2Mo10O40(1,11); for 9h; Title compound not separated from byproducts.; Heating;
60.3 % Chromat.
1.3 % Chromat.
With nitric acid; for 15h; Overall yield = 73 %;
With Iron(III) nitrate nonahydrate; N-hydroxyphthalimide; In 1,2-dichloro-ethane; at 50 ℃; for 10h; Reagent/catalyst; Solvent; regioselective reaction;
86 %Spectr.
7 %Spectr.
With dipotassium peroxodisulfate; sodium nitrite; In acetonitrile; at 120 ℃; for 12h; Overall yield = 59 percent; Inert atmosphere; Schlenk technique;

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