4'-Bromoacetanilide

Base Information

• Chemical Name: 4'-Bromoacetanilide
• CAS No.: 103-88-8
• Molecular Formula: C8H8BrNO
• Molecular Weight: 214.062
• Hs Code.: 29242998
• European Community (EC) Number: 203-154-9
• NSC Number: 105442,8048
• UNII: 4KB44F25A3
• DSSTox Substance ID: DTXSID6059283
• Nikkaji Number: J37.694I
• Wikidata: Q27259868
• ChEMBL ID: CHEMBL59019
• Mol file: 103-88-8.mol

Synonyms:4'-Bromoacetanilide;103-88-8;N-(4-Bromophenyl)acetamide;4-BROMOACETANILIDE;p-Bromoacetanilide;Acetamide, N-(4-bromophenyl)-;Bromoanilide;Bromoantifebrin;Antisepsin;Asepsin;N-Acetyl-4-bromoaniline;p-Bromo-N-acetanilide;1-Bromo-4-acetamidobenzene;Acetanilide, p-bromo-;Acetanilide, 4'-bromo-;4-Bromo acetanilide;USAF DO-40;N-(4-Bromo-phenyl)-acetamide;C8H8BrNO;N-Acetyl-p-bromoaniline;monobromoacetanilide;NSC 105442;EINECS 203-154-9;N-(p-Bromophenyl)acetamide;BRN 2208091;UNII-4KB44F25A3;AI3-01799;4KB44F25A3;1-(N-Acetylamino)-4-bromobenzene;MFCD00000092;NSC-105442;4 inverted exclamation mark -Bromoacetanilide;WLN: ER DMV1;Bromoanalide;p-Bromacetanilid;p-Bromoacetanalide;4'-bromacetanilid;4`-Bromacetanilide;4'-bromoacetoanilide;4/'-Bromoacetanilide;4\'-Bromoacetanilide;Maybridge4_002362;4-Bromoacetanilide, 98%;SCHEMBL9674;NCIOpen2_007075;N-(4-bromophenyl)-acetamide;CHEMBL59019;F1962-0210;Acetamide, N-(p-bromophenyl)-;P-BROMOACETANILIDE [MI];DTXSID6059283;NSC8048;HMS1527L08;AMY24793;NSC-8048;STR01944;NSC105442;STL089501;AKOS000201828;4'-Bromo-2'-methylacetanilide, 99%;4-(ACETYLAMINO)-1-BROMOBENZENE;NCGC00176635-01;AC-18809;SY049651;TS-03575;B0534;CS-0076525;FT-0617847;EN300-15537;10.14272/MSLICLMCQYQNPK-UHFFFAOYSA-N;D71238;10.14272/MSLICLMCQYQNPK-UHFFFAOYSA-N.1;AG-205/03191041;doi:10.14272/MSLICLMCQYQNPK-UHFFFAOYSA-N;doi:10.14272/MSLICLMCQYQNPK-UHFFFAOYSA-N.1;W-108835;BRD-K54936524-001-01-0;BRD-K54936524-001-02-8;Q27259868;Z27786822;IJX

Chemical Property of 4'-Bromoacetanilide

Chemical Property:

• Appearance/Colour: white to light beige crystalline solid
• Melting Point: 165-169 °C(lit.)
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 353.4 °C at 760 mmHg
• PKA: 14.25±0.70(Predicted)
• Flash Point: 167.6 °C
• PSA: 29.10000
• Density: 1.543 g/cm³
• LogP: 2.48050
• Storage Temp.: Store below +30°C.
• Solubility.: alcohol: moderately soluble
• Water Solubility.: Insoluble
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 212.97893
• Heavy Atom Count: 11
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

4'-Bromoacetanilide >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1=CC=C(C=C1)Br
• Description: 4'-Bromoacetanilide is a Pale yellow crystals or powdery crystals.Melting point 168℃, relative density 1.717.Soluble in benzene, chloroform, ethyl acetate, slightly soluble in alcohol, slightly soluble in hot water, insoluble in cold water. It can be used as reparation of 4'-Bromoacetanilide from Acetanilide.Principle: Aromatic compounds can be conveniently brominated by the use of brominating agent, which is normally a solution of bromine in acetic acid. Bromination of activated aromatic compounds usually give 2, 4, 6-tribromo derivatives while moderately activating group like anilide give preferably the para bromo product.
• Uses: 4'-Bromoacetanilide can be used as an intermediate in organic synthesis. 4'-Bromoacetanilide is used as an internal standard for phenylurea and the respective metabolic products in oysters. It has also been used as a reagent in the production of a new ligand to form a coordination compex between gadolinium(III) and T=titanium(IV) oxide. It was used in the synthesis of new ligand for anchoring Gd(III) chelates onto TiO2 surface. 4-Bromoacetanilide was used as internal standard in determination of several phenylurea and triazine herbicides and their transformation products in oyster. It was used in the synthesis of new ligand for anchoring Gd(III) chelates onto TiO2 surface.

Technology Process of 4'-Bromoacetanilide

There total 125 articles about 4'-Bromoacetanilide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Acetanilid (103-84-4) → 4-bromoacetanilide (103-88-8)

Guidance literature:

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 4,4'-dimethoxyphenyl disulfide; In acetonitrile; at 20 ℃; for 0.166667h; Reagent/catalyst;

DOI:10.1021/acs.joc.9b00769

Reference yield: 100.0%

acetic anhydride (108-24-7) + 4-bromo-aniline (106-40-1) → 4-bromoacetanilide (103-88-8)

Guidance literature:

With cadmium(II) oxide; at 80 ℃; for 0.166667h; Neat (no solvent); Microwave irradiation;

Reference yield: 99.0%

N-Bromosuccinimide (128-08-5) + Acetanilid (103-84-4) → 4-bromoacetanilide (103-88-8)

Guidance literature:

In acetonitrile; at 20 ℃; for 0.0666667h; Flow reactor; UV-irradiation;

DOI:10.1071/CH20372

upstream raw materials:

tetrachloromethane

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

Acetanilid

ethanol

Downstream raw materials:

N-(4-phenylsulfanyl)phenyl acetamide

1-(4'-bromophenyl)-5-methyl-1H-tetrazole

acetic acid-(4-bromo-N-nitroso-anilide)

N-acetylsulfanilic acid

Refernces

• 1、 Paul,Sudalai,Daniel,Srinivasan. "Ultrasound promoted bromination of activated arenes with N-bromosuccinimide". . p. 2401 - 2405. Retrieved 1995.
• 2、 Taub,Hino. "-". . p. 263,264. Retrieved 1960.
• 3、 Koo, Bon-Suk,Kim, Eun-Hoo,Lee, Kee-Jung. "Bromodecarbonylation and bromodecarboxylation of electron-rich benzaldehydes and benzoic acids with oxone and sodium bromide". . p. 2275 - 2286. Retrieved 2002.
• 4、 Zhang, Xinglu,Liu, Zhiqiang,Gao, Yu,Li, Feng,Tian, Yaming,Li, Chunju,Jia, Xueshun,Li, Jian. "Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent". . p. 272 - 277. Retrieved 2018.
• 5、 Narender,Srinivasu,Kulkarni,Raghavan. "Liquid phase regioselective bromination of aromatic compounds over HZSM-5 catalyst". . p. 3669 - 3675. Retrieved 2000.
• 6、 Shi, Yao,Ke, Zhihai,Yeung, Ying-Yeung. "Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics". . p. 4448 - 4452. Retrieved 2018.
• 7、 Bisarya,Rao. "A new mild and selective reagent for nuclear bromination". . p. 779 - 788. Retrieved 1993.
• 8、 Khazaei, Ardeshir,Manesh, Abbas Amini,Safi, Vahid Reza. "Regioselective synthesis of para-bromo aromatic compounds". . p. 559 - 562. Retrieved 2005.
• 9、 Koo, Bon-Suk,Lee, Chang Keun,Lee, Kee-Jung. "Oxidation of benzyl alcohols with Oxone and sodium bromide". . p. 2115 - 2123. Retrieved 2002.
• 10、 Wippert, Nicolai A.,Jung, Nicole,Br?se, Stefan. "Synthesis of Arylamides via Ritter-Type Cleavage of Solid-Supported Aryltriazenes". . p. 568 - 572. Retrieved 2019.