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Basic Information
CAS No.: 536-38-9
Name: 4-Chloro-2'-bromoacetophenone
Article Data: 164
Molecular Structure:
Molecular Structure of 536-38-9 (4-Chloro-2'-bromoacetophenone)
Formula: C8H6BrClO
Molecular Weight: 233.492
Synonyms: Acetophenone,2-bromo-4'-chloro- (6CI,7CI,8CI);1-(4-Chlorophenyl)-2-bromo-1-ethanone;2-Bromo-1-(4-chlorophenyl)-1-ethanone;2-Bromo-4'-chloroacetophenone;2-Bromo-p-chloroacetophenone;2'-Bromo-4-chloroacetophenone;4-Chloro-a-bromoacetophenone;4-Chloro-w-bromoacetophenone;4'-Chloro-2-bromoacetophenone;4'-Chlorophenacyl bromide;Bromomethyl4-chlorophenyl ketone;Bromomethyl p-chlorophenyl ketone;NSC 8452;p-(Bromoacetyl)chlorobenzene;p-Chloro-w-bromoacetophenone;p-Chlorophenacyl bromide;a-Bromo-4-chloroacetophenone;w-Bromo-p-chloroacetophenone;
EINECS: 208-631-5
Density: 1.598 g/cm3
Melting Point: 95-99 °C
Boiling Point: 289.7 °C at 760 mmHg
Flash Point: 129 °C
Solubility: Insoluble in water.
Appearance: crystalline powder
Hazard Symbols: CorrosiveC
Risk Codes: 34-22-36
Safety: 26-36/37/39-45-27
Transport Information: UN 3261 8/PG 2
PSA: 17.07000
LogP: 2.91760
Synthetic route
99-91-2

para-chloroacetophenone

536-38-9

4-chlorobenzoylmethyl bromide

Conditions
ConditionsYield
With pyridinium hydrobromide perbromide; acetic acid at 20℃; for 18h;99%
With bromine In acetic acid98%
With hydrogen bromide; bromine; acetic acid In water at 0 - 20℃;98.67%
33491-03-1

1-(bromoethynyl)-4-chlorobenzene

536-38-9

4-chlorobenzoylmethyl bromide

Conditions
ConditionsYield
With water; copper(II) acetate monohydrate; trifluoroacetic acid at 70℃; for 6h; chemoselective reaction;93%
With water In 1,2-dichloro-ethane at 20℃; for 14h;92%
With tetrafluoroboric acid; water In 2,2,2-trifluoroethanol at 80℃; for 2h;91%
99-91-2

para-chloroacetophenone

A

13651-12-2

2,2-dibromo-1-(4-chlorophenyl)ethanone

B

536-38-9

4-chlorobenzoylmethyl bromide

Conditions
ConditionsYield
With N-Bromosuccinimide; silica gel In methanol for 0.316667h; Reflux; chemoselective reaction;A n/a
B 91%
With trimethylsilyl bromide; potassium nitrate In dichloromethane at 20℃; for 20h;A n/a
B 72%
With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 24h;A n/a
B 89 % Spectr.
With ammonium metavanadate; aluminum tri-bromide; oxygen In acetonitrile at 80℃; for 18h;A 27 %Spectr.
B 70 %Spectr.
With copper(ll) bromide In chloroform; ethyl acetate for 5h; Reflux;
89220-51-9

α-bromomethyl-4-chlorostyrene

536-38-9

4-chlorobenzoylmethyl bromide

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate; C65H77N5O4S2; oxygen In 1,2-dichloro-ethane at 75℃; under 760.051 Torr; for 24h; Green chemistry; chemoselective reaction;91%

1,1-dibromo-1-(4'-chlorophenyl)ethane

A

89619-10-3

1-(1-bromovinyl)-4-chlorobenzene

B

536-38-9

4-chlorobenzoylmethyl bromide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 90℃; Inert atmosphere;A 91%
B n/a
1073-67-2

4-vinylbenzyl chloride

536-38-9

4-chlorobenzoylmethyl bromide

Conditions
ConditionsYield
With dipotassium peroxodisulfate; potassium bromide In water at 60℃; for 12h; Green chemistry;90%
With tris(2,2'-bipyridyl)ruthenium dichloride; Bromoform; [bis(acetoxy)iodo]benzene In 1,4-dioxane at 20℃; for 8h; Reagent/catalyst; Irradiation;88%
With hydrogen bromide; oxygen In water; ethyl acetate for 5h; Irradiation;84%
89619-10-3

1-(1-bromovinyl)-4-chlorobenzene

536-38-9

4-chlorobenzoylmethyl bromide

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen In ethylene dibromide at 75℃; under 760.051 Torr; for 16h; Solvent; Green chemistry; chemoselective reaction;89%
2040-38-2

<1-(4-Chlor-phenyl)-ethyl>-benzylether

536-38-9

4-chlorobenzoylmethyl bromide

Conditions
ConditionsYield
With p-nitrobenzenesulfonamide; hydrogen bromide; oxygen; sodium nitrite In water; acetonitrile at 0 - 60℃; under 760.051 Torr; for 24.5h;88%
3282-33-5

1-(4-chlorophenyl)-2-diazoethanone

536-38-9

4-chlorobenzoylmethyl bromide

Conditions
ConditionsYield
With ferric(III) bromide; silica gel In dichloromethane at 20℃; for 0.166667h;85%
873-73-4

4-n-chlorophenylacetylene

536-38-9

4-chlorobenzoylmethyl bromide

Conditions
ConditionsYield
With N,N'-ethylenethiourea; 1,3-dibromo-5,5-dimethylhydantoin; water In acetone at 45℃;84%
Stage #1: 4-n-chlorophenylacetylene With methanol; gold(III) chloride; silver(I) triflimide In 1,4-dioxane at 45℃;
Stage #2: With N-Bromosuccinimide In 1,4-dioxane regioselective reaction;
75%
Multi-step reaction with 2 steps
1: dibromamine-T; water / acetone / 0.17 h
2: water; sodium sulfite / acetone; ethyl acetate / 20 °C
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    4-Chloro-2'-bromoacetophenone Chemical Properties Melting point 93-96 °C(lit.) Boiling point 186°C (rough estimate) density 1.5624 (rough estimate) refractive index 1.5963 (estimate) storage temp. Keep Cold form Cr

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Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Specification

The IUPAC name of p-Chlorophenacyl bromide is 2-bromo-1-(4-chlorophenyl)ethanone. With the CAS registry number 536-38-9 and EINECS 208-631-5, it is also named as 2-Bromo-4'-chloroacetophenone. The product's categories are Aromatic Acetophenones & Derivatives (substituted); Aromatics Compounds; Aromatics; Acetophenone Series. It is crystalline powder which is lachrymatory, toxic and flammable. When heated to decomposition it emits toxic vapors of Br and Cl. So the storage environment should be well-ventilated, low-temperature and dry.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.88; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.88; (4)ACD/LogD (pH 7.4): 2.88; (5)ACD/BCF (pH 5.5): 90.2; (6)ACD/BCF (pH 7.4): 90.2; (7)ACD/KOC (pH 5.5): 873.24; (8)ACD/KOC (pH 7.4): 873.24; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.584; (13)Molar Refractivity: 48.9 cm3; (14)Molar Volume: 146 cm3; (15)Polarizability: 19.38×10-24 cm3; (16)Surface Tension: 45.9 dyne/cm; (17)Enthalpy of Vaporization: 52.91 kJ/mol; (18)Vapour Pressure: 0.00216 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 2; (21)Exact Mass: 231.929055; (22)MonoIsotopic Mass: 231.929055; (23)Topological Polar Surface Area: 17.1; (24)Heavy Atom Count: 11; (25)Complexity: 141.

Preparation of p-Chlorophenacyl bromide: It can be obtained by the reaction of chlorobenzene and bromoacetyl chloride in the presence of alchlor. Or it can be produced by the bromination of parachloroacetophenone.

Uses of p-Chlorophenacyl bromide: It is used as intermediate in organic synthesis. It also can react with 2-methyl-pyridine to get 1-(4-chloro-phenacyl)-2-methyl-pyridinium; bromide. This reaction needs solvent ethanol by cooling. The yield is 72%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes. And it can cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C(c1ccc(Cl)cc1)CBr
2. InChI:InChI=1/C8H6BrClO/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4H,5H2
3. InChIKey:FLAYZKKEOIAALB-UHFFFAOYAA

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral > 2gm/kg (2000mg/kg)   Medicina Experimentalis. Vol. 11, Pg. 137, 1964.