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p-Bromophenoxyacetic acid

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Name

p-Bromophenoxyacetic acid

EINECS 217-530-5
CAS No. 1878-91-7 Density 1.641 g/cm3
PSA 46.53000 LogP 1.91250
Solubility N/A Melting Point 149-153 °C(lit.)
Formula C8H7BrO3 Boiling Point 337.9 °C at 760 mmHg
Molecular Weight 231.046 Flash Point 158.2 °C
Transport Information N/A Appearance White or cream crystalline powder
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 1878-91-7 (p-Bromophenoxyacetic acid) Hazard Symbols IrritantXi
Synonyms

Aceticacid, (4-bromophenoxy)- (9CI);Acetic acid, (p-bromophenoxy)- (6CI,7CI,8CI);(4-Bromophenoxy)acetic acid;2-(4-Bromophenyl)-2-hydroxyacetic acid;NSC 65085;p-Bromophenoxyacetic acid;

Article Data 50

p-Bromophenoxyacetic acid Synthetic route

106-41-2

4-bromo-phenol

79-08-3

bromoacetic acid

1878-91-7

(4-bromophenoxy)acetic acid

Conditions
ConditionsYield
With sodium hydroxide In water Reflux;95%
With sodium hydride In tetrahydrofuran for 12h; Heating;
With sodium hydroxide Heating;
122-59-8

2-phenoxyacetic acid

1878-91-7

(4-bromophenoxy)acetic acid

Conditions
ConditionsYield
With sodium hypochlorite; sodium bromide at 5 - 36℃; for 0.00666667h;94.3%
With bromine In tetrachloromethane for 12h; Heating;50%
With bromine; iodine; acetic acid

4-bromophenoxy acetic acid t-butyl ester

1878-91-7

(4-bromophenoxy)acetic acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane; water at 20℃; for 66h;91%
With trifluoroacetic acid In dichloromethane at 20℃; for 3h;
4841-23-0

(4-bromophenoxy)acetic acid methyl ester

1878-91-7

(4-bromophenoxy)acetic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol at 35℃; for 1h;87%
With Alkaline; water at 15℃; Kinetics; ΔH(excit.), ΔS(excit.), velocity const., EA; also at 10 and 20 deg C;
With lithium hydroxide monohydrate In methanol; water for 2h; Reflux;
106-41-2

4-bromo-phenol

79-11-8

chloroacetic acid

1878-91-7

(4-bromophenoxy)acetic acid

Conditions
ConditionsYield
Stage #1: chloroacetic acid With sodium hydroxide In water
Stage #2: 4-bromo-phenol With sodium hydroxide In ethanol; water at 105℃; for 5.33333h;
85%
With sodium hydroxide; bentonite In water for 0.0833333h; microwave irradiation;78%
Stage #1: chloroacetic acid With sodium hydroxide
Stage #2: 4-bromo-phenol With sodium hydroxide In ethanol; water at 105℃; for 5h;
78%
106-41-2

4-bromo-phenol

3926-62-3

sodium monochloroacetic acid

1878-91-7

(4-bromophenoxy)acetic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 105℃; for 5h;78%
Stage #1: 4-bromo-phenol With sodium hydroxide In ethanol; water at 20℃; for 0.333333h;
Stage #2: sodium monochloroacetic acid In ethanol; water at 102℃; for 5h;
76%
6964-29-0

ethyl 2-(4-bromophenoxy)acetate

1878-91-7

(4-bromophenoxy)acetic acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate; water In tetrahydrofuran at 0 - 20℃; for 4h;73%
With potassium hydroxide
With lithium hydroxide In tetrahydrofuran; water at 20℃;

benzene

A

1878-91-7

(4-bromophenoxy)acetic acid

B

591-50-4

iodobenzene

C

106262-08-2

p-bromophenyl p-bromophenoxyacetate

D

106261-96-5

p-bromophenoxymethyl p-bromophenoxyacetate

Conditions
ConditionsYield
at 200℃; for 0.5h;A 21%
B 65%
C 8%
D 49%
In various solvent(s) at 174℃; for 0.5h; Heating;A n/a
B n/a
C 20%
D 58%
2555-49-9

phenoxyacetic acid ethyl ester

1878-91-7

(4-bromophenoxy)acetic acid

Conditions
ConditionsYield
With carbon disulfide; bromine at 0℃; man destilliert den Schwefelkohlenstoff ab, kocht den Rueckstand mit Natronlauge und faellt mit Salzsaeure;
7726-95-6

bromine

7553-56-2

iodine

64-19-7

acetic acid

122-59-8

2-phenoxyacetic acid

1878-91-7

(4-bromophenoxy)acetic acid

Conditions
ConditionsYield
at 20℃;

p-Bromophenoxyacetic acid Specification

The CAS registry number of 4-Bromophenoxyacetic acid is 1878-91-7. Its EINECS registry number is 217-530-5. The IUPAC name is 2-(4-bromophenoxy)acetic acid. In addition, the molecular formula is C8H7BrO3 and the molecular weight is 231.04. It is also called aceticacid, 2-(4-bromophenoxy)-. What's more, it is a kind of white or cream crystalline powder and belongs to the classes of Drug Intermediates; Acetics acid and esters; Organic acids; Plant Growth Regulator; Auxins; Biochemistry; C8; Carbonyl Compounds; Carboxylic Acids. And it should be stored in sealed container, and placed in a cool and dry place. The storage place must stay away from oxidant.

Physical properties about this chemical are: (1)ACD/LogP: 2.37; (2)ACD/LogD (pH 5.5): -0.02; (3)ACD/LogD (pH 7.4): -1.27; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1.88; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 35.53 Å2; (12)Index of Refraction: 1.579; (13)Molar Refractivity: 46.81 cm3; (14)Molar Volume: 140.7 cm3; (15)Polarizability: 18.56 ×10-24cm3; (16)Surface Tension: 50.9 dyne/cm; (17)Density: 1.641 g/cm3; (18)Flash Point: 158.2 °C; (19)Enthalpy of Vaporization: 61.35 kJ/mol; (20)Boiling Point: 337.9 °C at 760 mmHg; (21)Vapour Pressure: 3.96E-05 mmHg at 25°C.

Preparation of 4-Bromophenoxyacetic acid: it can be prepared by phenoxyacetic acid. This reaction will need reagent Br2 and solvent CCl4. The reaction time is 12 hours by heating. The yield is about 50%.

4-Bromophenoxyacetic acid can be prepared by phenoxyacetic acid

Uses of 4-Bromophenoxyacetic acid: it can be used as plant growth regulator. And it can react with 4-Methyl-3-pentenylamine to get 2-(4-bromo-phenoxy)-N-(4-methyl-pent-3-enyl)-acetamide. This reaction will need reagent POCl3 and Et3N and solvent CH2Cl2. The yield is about 69.5%.

4-Bromophenoxyacetic acid can react with 4-Methyl-3-pentenylamine to get 2-(4-bromo-phenoxy)-N-(4-methyl-pent-3-enyl)-acetamide

When you are using this chemical, please be cautious about it as the following:
During using it, you should avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: Brc1ccc(OCC(=O)O)cc1
(2)InChI: InChI=1/C8H7BrO3/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4H,5H2,(H,10,11)
(3)InChIKey: SZEBGAQWWSUOHT-UHFFFAOYAD

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