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4-Bromo-1-butanol

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Name

4-Bromo-1-butanol

EINECS 251-355-5
CAS No. 33036-62-3 Density 1.454 g/cm3
PSA 20.23000 LogP 1.15380
Solubility insoluble Melting Point N/A
Formula C4H9BrO Boiling Point 190.9 °C at 760 mmHg
Molecular Weight 153.019 Flash Point 92.1 °C
Transport Information UN 1987 3/PG 2 Appearance Clear colorless to brown liquid
Safety 26-37/39-16 Risk Codes 11-36/37/38-22
Molecular Structure Molecular Structure of 33036-62-3 (4-Bromo-1-butanol) Hazard Symbols FlammableF,HarmfulXn,IrritantXi
Synonyms

1-Bromo-4-butanol;1-Bromo-4-hydroxybutane;4-Bromobutan-1-ol;4-Bromobutanol;Tetramethylene bromohydrin;

Article Data 76

4-Bromo-1-butanol Synthetic route

109-99-9

tetrahydrofuran

33036-62-3

4-Bromo-1-butanol

Conditions
ConditionsYield
With dimethylboron bromide; triethylamine In dichloromethane at 0℃; for 2h;100%
With sulfuric acid; hydrogen bromide90%
With tetrabutylammomium bromide; hydrogen bromide In water for 0.0833333h; Microwave irradiation;81%
2623-87-2

bromobutyric acid

33036-62-3

4-Bromo-1-butanol

Conditions
ConditionsYield
Stage #1: bromobutyric acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: With sodium tetrahydroborate; water In tetrahydrofuran at 0℃; for 0.5h;
99%
Stage #1: bromobutyric acid With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.166667h;
Stage #2: With sodium tetrahydroborate In water; ethyl acetate at 0℃; for 0.366667h;
92%
With dimethylsulfide borane complex86%
4753-59-7

4-Bromobutyl acetate

33036-62-3

4-Bromo-1-butanol

Conditions
ConditionsYield
With sulfuric acid In ethanol for 1h; Heating;96%
With Amberlite IR-120 (H+ form) In methanol at 22℃; for 16h;
With sulfuric acid In methanol for 40h; Ambient temperature;
With sulfuric acid In methanol for 48h; Yield given;
With methanol; sulfuric acid for 1h; Heating;
109-99-9

tetrahydrofuran

17745-40-3

methyl p-propanoylbenzoate

A

33036-62-3

4-Bromo-1-butanol

B

58764-22-0

methyl 4-(2-bromopropanoyl)benzoate

Conditions
ConditionsYield
With 2-pyrrolidinon In tetrahydrofuran at 50℃; for 3h;A 4%
B 91%
121335-12-4

4-Bromo-butyric acid 6-nitro-benzotriazol-1-yl ester

33036-62-3

4-Bromo-1-butanol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 0 - 5℃; for 1.5h;82%
110-63-4

Butane-1,4-diol

33036-62-3

4-Bromo-1-butanol

Conditions
ConditionsYield
With tetrabutylammomium bromide; hydrogen bromide In water for 0.0833333h; Microwave irradiation;77.4%
With hydrogen bromide In water; benzene Reflux; Dean-Stark apparatus;68%
With hydrogen bromide In water; benzene for 12h; Reflux;68%
67-56-1

methanol

2623-87-2

bromobutyric acid

A

4457-67-4

4-Methoxy-1-bromobutane

B

33036-62-3

4-Bromo-1-butanol

Conditions
ConditionsYield
Stage #1: bromobutyric acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: methanol With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 0.5h;
A 22%
B 75%
109-99-9

tetrahydrofuran

112-14-1

n-octyl acetate

201230-82-2

carbon monoxide

A

110-52-1

1,4-dibromo-butane

B

33036-62-3

4-Bromo-1-butanol

C

C13H25BrO3

D

1352810-79-7

C15H27BrO4

Conditions
ConditionsYield
Stage #1: n-octyl acetate; carbon monoxide With 2AlBr3*CBr4 In dibromomethane at -20 - 20℃; under 750.075 Torr; for 3h;
Stage #2: tetrahydrofuran In dibromomethane at -20 - 0℃; for 20h; regioselective reaction;
A n/a
B n/a
C n/a
D 72%
4897-84-1

Methyl 4-bromobutyrate

A

33036-62-3

4-Bromo-1-butanol

B

71-36-3

butan-1-ol

Conditions
ConditionsYield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene; Petroleum ether 1.) 10-20 deg C, 2.) room temperature, 10 min;A 60%
B 16%
2623-87-2

bromobutyric acid

67-63-0

isopropyl alcohol

A

33036-62-3

4-Bromo-1-butanol

B

51748-44-8

1-bromo-4-isopropoxybutane

Conditions
ConditionsYield
Stage #1: bromobutyric acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: isopropyl alcohol With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 0.5h;
A 50%
B 25%

4-Bromo-1-butanol Specification

The 4-Bromo-1-butanol, with the cas registry number 33036-62-3 and EINECS registry number 251-355-5, has the systematic name of 4-bromobutan-1-ol. It belongs to the following product categories: omega-Bromoalkanols; omega-Functional Alkanols, Carboxylic Acids, Amines & Halides. And the molecular formula of the chemical is C4H9BrO.

The characteristics of this chemical are as followings: (1)ACD/LogP: 0.81; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.81; (4)ACD/LogD (pH 7.4): 0.81; (5)ACD/BCF (pH 5.5): 2.43; (6)ACD/BCF (pH 7.4): 2.43; (7)ACD/KOC (pH 5.5): 65.75; (8)ACD/KOC (pH 7.4): 65.75; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.479; (14)Molar Refractivity: 29.84 cm3; (15)Molar Volume: 105.2 cm3; (16)Polarizability: 11.83×10-24cm3; (17)Surface Tension: 37.3 dyne/cm; (18)Density: 1.453 g/cm3; (19)Flash Point: 92.1 °C; (20)Enthalpy of Vaporization: 49.71 kJ/mol; (21)Boiling Point: 190.9 °C at 760 mmHg; (22)Vapour Pressure: 0.142 mmHg at 25°C.

Preparation of 4-Bromo-1-butanol: This chemical can be prepared by butane-1,4-diol. The reaction will need reagent 48% hydrobromic acid, and the menstruum benzene. The reaction time is 24 hours with heating, and the yield is about 65%. 

Uses of 4-Bromo-1-butanol: It can react with 3,4-dihydro-2H-pyran to produce 2-(4-bromo-butoxy)-tetrahydro-pyran. This reaction will need reagent Amberlyst 15, and the menstruum hexane. The reaction time is 3 hours with temperature of 25°C.

When you are using this chemical, please be cautious about it as the following: Firstly, it is highly flammable. Secondly, it is harmful if swallowed. And what's more, it irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Keep away from sources of ignition; Wear suitable protective gloves and eye/face protection; In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. 

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: BrCCCCO
(2)InChI: InChI=1/C4H9BrO/c5-3-1-2-4-6/h6H,1-4H2
(3)InChIKey: SIJLYRDVTMMSIP-UHFFFAOYAK

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