99-90-1 Usage
Chemical Properties
white to light yellow crystals. soluble in alcohol, ether, glacial acetic acid, benzene, carbon disulfide and petroleum ether, insoluble in water. Easy to volatilize with water vapor.
Uses
Different sources of media describe the Uses of 99-90-1 differently. You can refer to the following data:
1. 4'-Bromoacetophenone is an important organic synthesis intermediate, widely used in synthetic medicine, pesticides, dyes, flavors and fragrances, perfumes, Intermediates of Liquid Crystals etc.
2. Labeled 4?-Bromoacetophenone possess activity against positive phototaxis of Chlamydomonas cells. A fundamental starting material for organic synthesis.
Preparation
4'-Bromoacetophenone is synthesized by the reaction of bromobenzene and acetic anhydride in the presence of aluminum trichloride. Add bromobenzene and dry carbon disulfide into the reactor, put in powdered anhydrous aluminum trichloride, heat until it starts to reflux, stop heating, add acetic anhydride dropwise, and then reflux for 1 hour after adding, steam out carbon disulfide, and put it while it is still hot. The reactant was poured into the hydrochloric acid ice-water mixture, filtered to dryness, and distilled under reduced pressure to obtain p-bromoacetophenone.
Synthesis Reference(s)
The Journal of Organic Chemistry, 51, p. 5400, 1986 DOI: 10.1021/jo00376a064Tetrahedron Letters, 26, p. 4657, 1985 DOI: 10.1016/S0040-4039(00)98778-1
Purification Methods
Crystallise it from EtOH, MeOH or from pet ether (b 80-100o). [Tanner J Org Chem 52 2142 1987, Beilstein 7 IV 647.]
Check Digit Verification of cas no
The CAS Registry Mumber 99-90-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 9 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 99-90:
(4*9)+(3*9)+(2*9)+(1*0)=81
81 % 10 = 1
So 99-90-1 is a valid CAS Registry Number.
99-90-1Relevant articles and documents
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Bothner-By
, p. 3293,3294 (1955)
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Visible light-mediated, high-efficiency oxidation of benzyl to acetophenone catalyzed by fluorescein
Geng, Haoxing,Liu, Xin,Zhu, Qing
supporting information, (2021/12/20)
An environmentally friendly aerobic oxidation of benzyl C(sp3)-H bonds to ketones via selective oxidation catalysis was developed. Fluorescein is an efficient photocatalyst with excellent chemical selectivity. The reaction has a wide substrate scope, and a successful gram-scale experiment demonstrated its potential industrial utility.
Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy
Zhong, Jing,Zhou, Wuxin,Yan, Xufei,Xia, Ying,Xiang, Haifeng,Zhou, Xiangge
supporting information, p. 1372 - 1377 (2022/02/23)
A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.