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Methyl 2-bromohexanoate

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Name

Methyl 2-bromohexanoate

EINECS 226-643-9
CAS No. 5445-19-2 Density 1.297 g/cm3
PSA 26.30000 LogP 2.11310
Solubility N/A Melting Point < -10ºC
Formula C7H13BrO2 Boiling Point 195.9 °C at 760 mmHg
Molecular Weight 209.083 Flash Point 80.6 °C
Transport Information N/A Appearance Clear, colourless liquid
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 5445-19-2 (Methyl 2-bromohexanoate) Hazard Symbols IrritantXi
Synonyms

2-Bromohexanoic acid methyl ester;Methyl 2-bromocaproate;Methyl a-bromocaproate;NSC 21976;

Article Data 16

Methyl 2-bromohexanoate Synthetic route

67-56-1

methanol

66-25-1

hexanal

A

5445-19-2

methyl 2-bromohexanoate

B

106-70-7

methyl hexanoate

Conditions
ConditionsYield
Stage #1: hexanal With ammonium cerium (IV) nitrate; lithium bromide In neat liquid
Stage #2: methanol In neat liquid at 35 - 40℃; for 3.5h;
A 80%
B 10 %Chromat.
73621-73-5

methyl 2-acetyl-2-bromohexanoate

5445-19-2

methyl 2-bromohexanoate

Conditions
ConditionsYield
With lithium perchlorate; triethylamine In diethyl ether for 5h; Ambient temperature;72%
32798-42-8

methyl α-butylacetoacetate

5445-19-2

methyl 2-bromohexanoate

Conditions
ConditionsYield
With sodium acetate; sodium bromide In methanol at 15℃; Electrochemical reaction;70%
Multi-step reaction with 2 steps
1: MgBr2, H2O2
2: 72 percent / LiClO4, Et3N / diethyl ether / 5 h / Ambient temperature
View Scheme
42768-46-7

2-bromohexanoyl chloride

5445-19-2

methyl 2-bromohexanoate

Conditions
ConditionsYield
With triethylamine; mercury In methanol; benzene69.7%
106-70-7

methyl hexanoate

5445-19-2

methyl 2-bromohexanoate

Conditions
ConditionsYield
Stage #1: methyl hexanoate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 0.583333h;
Stage #2: With N-Bromosuccinimide In tetrahydrofuran at -78 - 20℃;
51%
616-05-7

2-bromohexanoic acid

5445-19-2

methyl 2-bromohexanoate

Conditions
ConditionsYield
With diethyl ether
67-56-1

methanol

42768-46-7

2-bromohexanoyl chloride

5445-19-2

methyl 2-bromohexanoate

67-56-1

methanol

142-61-0

Hexanoyl chloride

5445-19-2

methyl 2-bromohexanoate

Conditions
ConditionsYield
(i) (bromination), (ii) /BRN= 1098229/; Multistep reaction;
106-70-7

methyl hexanoate

A

5445-19-2

methyl 2-bromohexanoate

B

41796-82-1

methyl 5-bromohexanoate

C

78019-66-6

Methyl 4-bromohexanoate

D

methyl 3-bromohexanoate

Conditions
ConditionsYield
With N-hydroxyphthalimide; bromine; nitric acid; copper diacetate In acetic acid at 80℃; for 5h; Title compound not separated from byproducts.;
106-70-7

methyl hexanoate

A

5445-19-2

methyl 2-bromohexanoate

B

14273-90-6

methyl 6-bromohexanoate

C

41796-82-1

methyl 5-bromohexanoate

D

78019-66-6

Methyl 4-bromohexanoate

E

methyl 3-bromohexanoate

Conditions
ConditionsYield
With N-bromo-N-(t-butyl)-3,5-bis(trifluoromethyl)benzamide In benzene at 20℃; for 4h; Reagent/catalyst; Sealed tube; Irradiation; Inert atmosphere; Overall yield = 56.1 %Chromat.;

Methyl 2-bromohexanoate Specification

The Methyl 2-bromohexanoate, with the CAS registry number 5445-19-2 and EINECS registry number 226-643-9, is also called hexanoic acid, 2-bromo-, methyl ester. It belongs to the product category of Acid based bromo compounds. And the molecular formula of this chemical is C7H13BrO2.

The physical properties of Methyl 2-bromohexanoate are as following: (1)ACD/LogP: 2.78; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.78; (4)ACD/LogD (pH 7.4): 2.78; (5)ACD/BCF (pH 5.5): 76.31; (6)ACD/BCF (pH 7.4): 76.31; (7)ACD/KOC (pH 5.5): 774.72; (8)ACD/KOC (pH 7.4): 774.72; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.457; (14)Molar Refractivity: 43.94 cm3; (15)Molar Volume: 161.1 cm3; (16)Polarizability: 17.42×10-24cm3; (17)Surface Tension: 32.5 dyne/cm; (18)Density: 1.297 g/cm3; (19)Flash Point: 80.6 °C; (20)Enthalpy of Vaporization: 43.2 kJ/mol; (21)Boiling Point: 195.9 °C at 760 mmHg; (22)Vapour Pressure: 0.411 mmHg at 25°C.

Uses of Methyl 2-bromohexanoate: It can react with cyclopent-2-enyl-acetone to produce 2-(2-cyclopent-2-enyl-1-hydroxy-1-methyl-ethyl)-hexanoic acid methyl ester. And the yield is about 70%. 

Methyl 2-bromohexanoate can react with cyclopent-2-enyl-acetone to produce 2-(2-cyclopent-2-enyl-1-hydroxy-1-methyl-ethyl)-hexanoic acid methyl ester

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: BrC(C(=O)OC)CCCC
(2)InChI: InChI=1/C7H13BrO2/c1-3-4-5-6(8)7(9)10-2/h6H,3-5H2,1-2H3
(3)InChIKey: YGLPDRIMFIXNBI-UHFFFAOYAZ

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