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Bromoacetyl bromide

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Name

Bromoacetyl bromide

EINECS 209-923-5
CAS No. 598-21-0 Density 2.373 g/cm3
PSA 17.07000 LogP 1.30280
Solubility REACTS Melting Point 148.5°C (estimate)
Formula C2H2Br2O Boiling Point 148.5 °C at 760 mmHg
Molecular Weight 201.845 Flash Point 72 °C
Transport Information UN 2513 8/PG 2 Appearance COA
Safety 26-36/37/39-45-8-30-25 Risk Codes 34-14
Molecular Structure Molecular Structure of 598-21-0 (Bromoacetyl bromide) Hazard Symbols CorrosiveC
Synonyms

Acetyl bromide, bromo-;2-Bromoacetyl bromide;

Article Data 25

Bromoacetyl bromide Synthetic route

506-96-7

Acetyl bromide

598-21-0

2-Bromoacetyl bromide

Conditions
ConditionsYield
With bromine
593-92-0

vinylidene dibromide

598-21-0

2-Bromoacetyl bromide

Conditions
ConditionsYield
With oxygen
64-19-7

acetic acid

598-21-0

2-Bromoacetyl bromide

Conditions
ConditionsYield
With phosphorus; bromine; acetic anhydride
With phosphorus; bromine
With bromine; phosphorus tribromide at 20 - 75℃; Bromination; Hell-Vollhard-Zelinskii reaction;
With phosphorus; bromine; sodium hydroxide at 110℃; Hell-Vollard-Zelinsky halogenation; regioselective reaction;
79-08-3

bromoacetic acid

598-21-0

2-Bromoacetyl bromide

Conditions
ConditionsYield
With phosphorus tribromide
75-36-5

acetyl chloride

598-21-0

2-Bromoacetyl bromide

Conditions
ConditionsYield
With bromine at 100 - 140℃;
With bromine
7726-95-6

bromine

64-19-7

acetic acid

red phosphorus

red phosphorus

598-21-0

2-Bromoacetyl bromide

7726-95-6

bromine

64-19-7

acetic acid

red phosphorus

red phosphorus

A

79-08-3

bromoacetic acid

B

598-21-0

2-Bromoacetyl bromide

Conditions
ConditionsYield
at 100 - 105℃;
7726-95-6

bromine

64-19-7

acetic acid

phosphorus

phosphorus

A

506-96-7

Acetyl bromide

B

79-08-3

bromoacetic acid

C

598-21-0

2-Bromoacetyl bromide

593-92-0

vinylidene dibromide

air

air

598-21-0

2-Bromoacetyl bromide

593-92-0

vinylidene dibromide

oxygen

oxygen

598-21-0

2-Bromoacetyl bromide

Bromoacetyl bromide Specification

The CAS registry number of Bromoacetyl bromide is 598-21-0. The IUPAC name is 2-bromoacetyl bromide. Its EINECS registry number is 209-923-5. In addition, the molecular formula is C2H2Br2O and the molecular weight is 201.84. It is a kind of dark brown-yellow liquid and belongs to the classes of Pharmaceutical Intermediates; Organics; Acid Halides; Carbonyl Compounds; Organic Building Blocks.

Physical properties about this chemical are: (1)ACD/LogP: 1.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.32; (4)ACD/LogD (pH 7.4): 1.32; (5)ACD/BCF (pH 5.5): 5.93; (6)ACD/BCF (pH 7.4): 5.93; (7)ACD/KOC (pH 5.5): 124.42; (8)ACD/KOC (pH 7.4): 124.42; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 17.07 Å2; (13)Index of Refraction: 1.543; (14)Molar Refractivity: 26.8 cm3; (15)Molar Volume: 85 cm3; (16)Polarizability: 10.62 ×10-24cm3; (17)Surface Tension: 45.6 dyne/cm ; (18)Density: 2.373 g/cm3; (19)Flash Point: 72 °C; (20)Enthalpy of Vaporization: 38.54 kJ/mol; (21)Boiling Point: 148.5 °C at 760 mmHg; (22)Vapour Pressure: 4.21 mmHg at 25°C.

Preparation of Bromoacetyl bromide: It can be prepared from acetic acid and bromine in the presence of phosphorus. Firstly, dry the red phosphorus for 2 hours. Then mix it with glacial acetic acid. Next, add the bromine with stirring. when add half of the bromine, you should heat it immediately. After adding the bromine, heat it to 140 °C for reaction 2 hours. By means of cooling and distilling you can get the product.

Bromoacetyl bromide can be prepared from acetic acid and bromine in the presence of phosphorus

Uses of Bromoacetyl bromide: it is mainly used in medicine intermediates. And it can react with 10H-phenothiazine to get 10-bromoacetyl-10H-phenothiazine. This reaction will need reagent pyridine and solvent toluene. The reaction time is 12 hours at reaction ambient temperature. In addition, the yield is about 45%.

Bromoacetyl bromide can react with 10H-phenothiazine to get 10-bromoacetyl-10H-phenothiazine

When you are using this chemical, please be cautious about it as the following:
This chemical can react violently with water and cause burns. So you should never add water to this product.During using it, wear suitable protective clothing, gloves and eye/face protection and avoid contact with eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). What's more, you should keep container dry.

You can still convert the following datas into molecular structure:
(1)SMILES: BrC(=O)CBr
(2)InChI: InChI=1/C2H2Br2O/c3-1-2(4)5/h1H2
(3)InChIKey: LSTRKXWIZZZYAS-UHFFFAOYAE

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