33036-62-3

Basic information

• Product Name: 4-Bromo-1-butanol
• Synonyms: TETRAMETHYLENE BROMOHYDRIN;4-BROMO-1-BUTANOL;4-bromobutan-1-ol;4-Bromobutanol;1-BROMO-4-BUTANOL;4-Bromo-1-butenol;4-Bromo-1-butanol (contains varying amounts of Tetrahydrofuran);4-BROMO-1-BUTANOL, 85+%
• CAS NO: 33036-62-3
• Molecular Formula: C₄H₉BrO
• Molecular Weight: 153.02
• EINECS: 251-355-5
• Product Categories: omega-Bromoalkanols;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides
• Mol File: 33036-62-3.mol
• Article Data: 70

Chemical Properties

• Boiling Point: 56-58
• Flash Point: 7 °C
• Appearance: Yellow/Liquid
• Density: 1.68
• Vapor Pressure: 0.142mmHg at 25°C
• Refractive Index: 1.5035
• Storage Temp.: −20°C
• PKA: 14.98±0.10(Predicted)
• Water Solubility: insoluble
• Sensitive: Moisture & Light Sensitive
• BRN: 1839430
• CAS DataBase Reference: 4-Bromo-1-butanol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-1-butanol(33036-62-3)
• EPA Substance Registry System: 4-Bromo-1-butanol(33036-62-3)

Safety Data

• Hazard Codes: F,Xi,Xn
• Statements: 11-36/37/38-22
• Safety Statements: 26-37/39-16
• RIDADR: UN 1987 3/PG 2
• WGK Germany: 3
• F: 8-10
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 33036-62-3(Hazardous Substances Data)

Usage

Description

4-Bromo-1-butanol can be prepared by azeotropic distillation of butane-1,4-diol with 47% HBr with a yield of about 65%.1 4-Bromo-1-butanol can be used to prepare 2-(4-bromo-butoxy)-tetrahydro-pyran by reacting with 3,4-dihydro-2H-pyran in the presence of amberlyst 15 and the menstruum hexane.1 It reacts with dihydropyran to prepare tetrahydropyranyl ethers.2

Chemical Properties

Clear colorless to brown liquid

Uses

4-Bromo-1-butanol is used to prepare 2-(4-bromo-butoxy)-tetrahydro-pyran by reacting with 3,4-dihydro-2H-pyran in the presence of amberlyst 15 as a catalyst. It reacts with dihydropyran to prepare tetrahydropyranyl ethers.

InChI:InChI=1/C4H9BrO/c5-3-1-2-4-6/h6H,1-4H2

Synthetic route

tetrahydrofuran (109-99-9) → 4-Bromo-1-butanol (33036-62-3)

Conditions	Yield
With dimethylboron bromide; triethylamine In dichloromethane at 0℃; for 2h;	100%
With sulfuric acid; hydrogen bromide	90%
With tetrabutylammomium bromide; hydrogen bromide In water for 0.0833333h; Microwave irradiation;	81%

bromobutyric acid (2623-87-2) → 4-Bromo-1-butanol (33036-62-3)

Conditions	Yield
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 complex	86%

4-Bromobutyl acetate (4753-59-7) → 4-Bromo-1-butanol (33036-62-3)

Conditions	Yield
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;

tetrahydrofuran (109-99-9) + methyl p-propanoylbenzoate (17745-40-3) → 4-Bromo-1-butanol (33036-62-3) + methyl 4-(2-bromopropanoyl)benzoate (58764-22-0)

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

4-Bromo-butyric acid 6-nitro-benzotriazol-1-yl ester (121335-12-4) → 4-Bromo-1-butanol (33036-62-3)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0 - 5℃; for 1.5h;	82%

Butane-1,4-diol (110-63-4) → 4-Bromo-1-butanol (33036-62-3)

Conditions	Yield
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%

methanol (67-56-1) + bromobutyric acid (2623-87-2) → 4-Methoxy-1-bromobutane (4457-67-4) + 4-Bromo-1-butanol (33036-62-3)

Conditions	Yield
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%

tetrahydrofuran (109-99-9) + n-octyl acetate (112-14-1) + carbon monoxide (201230-82-2) → 1,4-dibromo-butane (110-52-1) + 4-Bromo-1-butanol (33036-62-3) + C13H25BrO3 + C15H27BrO4 (1352810-79-7)

Conditions	Yield
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%

Methyl 4-bromobutyrate (4897-84-1) → 4-Bromo-1-butanol (33036-62-3) + butan-1-ol (71-36-3)

Conditions	Yield
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%

bromobutyric acid (2623-87-2) + isopropyl alcohol (67-63-0) → 4-Bromo-1-butanol (33036-62-3) + 1-bromo-4-isopropoxybutane (51748-44-8)

Conditions	Yield
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-hydroxybutyl octyl sulfoxide (7333-16-6) → 1-bromo-octane (111-83-1) + 4-Bromo-1-butanol (33036-62-3) + octyl cyclobutyl sulfonium bromide + 4-bromobutyl octyl sulfone (80623-45-6)

Conditions	Yield
With bromine In acetonitrile at -25℃; for 2h; Further byproducts given;	A n/a B n/a C 24% D 46%

4-hydroxybutyl octyl sulfoxide (7333-16-6) → 1-bromo-octane (111-83-1) + 4-Bromo-1-butanol (33036-62-3) + 4-hydroxybutanesulfinyl bromide + octanesulfinyl bromide + octane-1-sulfonyl bromide + octyl cyclobutyl sulfonium bromide

Conditions	Yield
With bromine In acetonitrile at -25℃; for 2h; Product distribution;	A n/a B n/a C n/a D n/a E n/a F 24%

2-bromoethanol (540-51-2) → 4-Bromo-1-butanol (33036-62-3)

Conditions	Yield
	21%

tetrahydrofuran (109-99-9) + 2-phenylethanol (60-12-8) → (±)-2-phenethoxytetrahydrofuran (52767-51-8) + 4-Bromo-1-butanol (33036-62-3) + 2-(4-bromobutoxy)tetrahydrofuran

Conditions	Yield
With Bromotrichloromethane at 60℃; Product distribution; Further Variations:; Reagents; Alkylation;	A 8% B n/a C n/a

Methyl 4-bromobutyrate (4897-84-1) → 4-Bromo-1-butanol (33036-62-3)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

methyl p-propanoylbenzoate (17745-40-3) → 4-Bromo-1-butanol (33036-62-3) + methyl 4-(2-bromopropanoyl)benzoate (58764-22-0)

Conditions	Yield
With 2-pyrrolidinon; pyrrolidone hydrotribromide In tetrahydrofuran at 50℃; for 3h;

2-pyrrolidinon (616-45-5) + pyrrolidone hydrotribromide + methyl p-propanoylbenzoate (17745-40-3) → 4-Bromo-1-butanol (33036-62-3) + methyl 4-(2-bromopropanoyl)benzoate (58764-22-0)

Conditions	Yield
Stage #1: 2-pyrrolidinon; pyrrolidone hydrotribromide; methyl p-propanoylbenzoate In tetrahydrofuran at 50℃; for 3h; Stage #2: With sodium disulfite In tetrahydrofuran; diethyl ether; water

2-pyrrolidinon (616-45-5) + pyrrolidone hydrotribromide + methyl p-propanoylbenzoate (17745-40-3) → 4-Bromo-1-butanol (33036-62-3) + methyl 4-(2-bromopropanoyl)benzoate (58764-22-0)

Conditions	Yield
In tetrahydrofuran at 50℃; for 3h;	A 4 %Spectr. B 91 %Spectr.

4-bromoethylbutanoate (2969-81-5) → 4-Bromo-1-butanol (33036-62-3)

Conditions	Yield
With dimethylsulfide borane complex In 2-methyltetrahydrofuran at 90℃; under 7500.75 Torr; for 0.333333h; Inert atmosphere; Flow reactor;

4-Bromo-1-butanol (33036-62-3) → 4-(nitrooxy)butyl bromide (146563-40-8)

Conditions	Yield
With sulfuric acid; nitric acid at 0℃; for 1h;	100%
With sulfuric acid; nitric acid In dichloromethane at -5 - 5℃; for 2 - 5h;	96%
With sulfuric acid; nitric acid In dichloromethane at -5 - 5℃; for 2 - 5h;	96%

4-Bromo-1-butanol (33036-62-3) + (S)-N-(benzyloxycarbonyl)valine (1149-26-4) → 4-hydroxybutyl ((benzyloxy)carbonyl)-L-valinate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 8h;	100%

3,4-dihydro-2H-pyran (110-87-2) + 4-Bromo-1-butanol (33036-62-3) → 4-bromo-1-(2-tetrahydropyranyloxy)butane (31608-22-7)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 24h;	99%
With toluene-4-sulfonic acid In diethyl ether for 1h; Ambient temperature;	96%
With pyridinium p-toluenesulfonate In dichloromethane	95%

4-Bromo-1-butanol (33036-62-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (4-bromobutoxy)-tert-butyldimethylsilane (89043-32-3)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 3h; Inert atmosphere;	95%
With 1H-imidazole In dichloromethane	92%
Stage #1: 4-Bromo-1-butanol With 1H-imidazole In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	91.3%

4-Bromo-1-butanol (33036-62-3) → C8H18O2S

Conditions	Yield
With sodium sulfide at 140℃; for 12h; Inert atmosphere;	95%

4-Bromo-1-butanol (33036-62-3) + Ethyl nipecotate (71962-74-8) → ethyl 1-(4-hydroxybutyl)piperidine-3-carboxylate

Conditions	Yield
With potassium carbonate; sodium iodide In neat (no solvent) at 0 - 20℃; for 48h; Darkness;	95%

4-Bromo-1-butanol (33036-62-3) + tert-butylchlorodiphenylsilane (58479-61-1) → (4-bromobutoxy)(tert-butyl)diphenylsilane (125010-58-4)

Conditions	Yield
With 1H-imidazole In dichloromethane at 0 - 20℃; for 9h;	94%
With dmap; triethylamine In dichloromethane at 25℃; for 12h;	72%
With 1H-imidazole In tetrahydrofuran at 20℃; for 72h; Inert atmosphere;	31%
With 1H-imidazole In N,N-dimethyl-formamide at 0℃;

succinic acid (110-15-6) + 4-Bromo-1-butanol (33036-62-3) → bis(4-bromobutyl) succinate (100525-08-4)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 16h; Reflux; Dean-Stark;	94%

indole (120-72-9) + 4-Bromo-1-butanol (33036-62-3) → 1-(4-hydroxybutyl)-1H-indole

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 5h;	93%

Sesamol (533-31-3) + 4-Bromo-1-butanol (33036-62-3) → 4-(3,4-methylenedioxyphenoxy)butyl bromide (56219-41-1)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; Inert atmosphere;	92%

4-Bromo-1-butanol (33036-62-3) + allylmagnesium bromide (2622-05-1) → 6-hepten-1-ol (4117-10-6)

Conditions	Yield
With dilithium tetrachlorocuprate In tetrahydrofuran at 20℃; for 15h;	90%

1-biphenyl-4-yl-1H-imidazole + 4-Bromo-1-butanol (33036-62-3) → C19H21N2O(1+)*Br(1-)

Conditions	Yield
Stage #1: 1-biphenyl-4-yl-1H-imidazole In toluene at 85℃; for 6h; Stage #2: 4-Bromo-1-butanol In toluene at 20℃; for 48h;	90%

4-Bromo-1-butanol (33036-62-3) + (2R,3R,4R)-3,4-Dibenzyloxy-2-(benzyloxymethyl)pyrrolidine (135791-03-6) → (2R,3R,4R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-1-[(3-hydroxy)propyl]-1H-pyrrolidine

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 72h;	88%

4-Bromo-1-butanol (33036-62-3) + phenol (108-95-2) → 4-phenoxybutan-1-ol (1927-71-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h; Inert atmosphere;	88%

4-Bromo-1-butanol (33036-62-3) + 5,5'-(2,2'-bipyridine)diacid chloride (82799-91-5) → bis(4-bromobutyl) 2,2'-bipyridine-5,5'-dicarboxylate (1364123-13-6)

Conditions	Yield
With triethylamine In dichloromethane Reflux;	87%

Dimethoxymethane (109-87-5) + 4-Bromo-1-butanol (33036-62-3) → 1-bromo-4-(methoxymethoxy)butane (34508-57-1)

Conditions	Yield
With phosphorus pentaoxide In dichloromethane Ambient temperature;	86%

4-Bromo-1-butanol (33036-62-3) + N,3,5-trimethyladamantan-1-amine (41100-49-6) → 4-((3,5-dimethyladamantan-1-yl)amino)butan-1-ol (937670-71-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;	86%

memantine hydrochloride + 4-Bromo-1-butanol (33036-62-3) → 4-(((1r,3R,5S,7r)-3,5-dimethyladamantan-1-yl)amino)butan-1-ol

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h; Sealed tube;	86%

4-Bromo-1-butanol (33036-62-3) + 5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) → C16H20BrNO3S

Conditions	Yield
With triethylamine In chloroform at 20℃; for 4h; Time; Inert atmosphere;	86%

2-[2-(allyloxy)-5-hydroxyphenyl]-1H-isoindole-1,3(2H)-dione (865716-50-3) + 4-Bromo-1-butanol (33036-62-3) → C21H20BrNO4

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; PPh3-polymer supported In tetrahydrofuran at 20℃; for 12h; Mitsunobu reaction;	85%

triisopropylsilyl chloride (13154-24-0) + 4-Bromo-1-butanol (33036-62-3) → C13H29BrOSi

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 4h;	85%

4-Bromo-1-butanol (33036-62-3) + N-methyl-4-(4-(2-(piperazin-1-yl)ethyl)phenyl)thiazol-2-amine → 4-(4-((4-(2-(methylamino)thiazol-4-yl)phen)thyl)piperazin-1-yl)butan-1-ol

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 100℃; for 3h;	85%

4-Bromo-1-butanol (33036-62-3) + N-pentyl imidazole (19768-54-8) → 3-(4-hydroxybutyl)-1-pentyl-1H-imidazol-3-ium bromide

Conditions	Yield
In toluene at 100℃; for 0.333333h; Sealed tube; Microwave irradiation;	85%

4-Bromo-1-butanol (33036-62-3) + 12-hydroxy-2,2-dimethyl-3,4-dihydro-2H,6H-pyrano[3,2-b]xanthen-6-one (1241391-92-3) → 3,4-dihydro-12-O-(4'-hydroxybutyl)-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 24h;	83.4%

4-Bromo-1-butanol (33036-62-3) → 4-azido-1-butanol (54953-78-5)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 70℃; for 24h;	83%
With sodium azide In dimethyl sulfoxide for 2.5h; Ambient temperature;	67%
With sodium azide In water; acetone Inert atmosphere;	60%

Upstream product

• 109-99-9 tetrahydrofuran 
• 4897-84-1 Methyl 4-bromobutyrate 
• 110-63-4 Butane-1,4-diol 
• 4753-59-7 4-Bromobutyl acetate 
• 7333-16-6 4-hydroxybutyl octyl sulfoxide 
• 121335-12-4 4-Bromo-butyric acid 6-nitro-benzotriazol-1-yl ester 
• 2623-87-2 bromobutyric acid 
• 60-12-8 2-phenylethanol 
• 17745-40-3 methyl p-propanoylbenzoate 
• 616-45-5 2-pyrrolidinon 
• 2969-81-5 Ethyl 4-bromobutyrate 
• 540-51-2 2-bromoethanol 
• 112-14-1 n-octyl acetate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 31608-22-7 4-bromo-1-(2-tetrahydropyranyloxy)butane 
• 69775-78-6 1-bromo-4-tert-butoxybutane 
• 18292-36-9 1-bromo-4-((trimethylsilyl)oxy)butane 
• 103935-49-5 4-bromobutanol-1-trifluoromethanesulfonate 
• 603132-71-4 N-benzyl-N'-bromobutyl-N'-tert-butoxycarbonyl sulfamide 
• 23243-48-3 di(4-hydroxybutyl) diselenide 
• 110798-26-0 1-bromo-4-tosyloxybutane 
• 1007556-29-7 C₁₆H₁₇ClFN₅O 
• 1007556-32-2 C₁₆H₁₇Cl₂N₅O 
• 157245-85-7 4-(3-bromophenoxy)-butan-1-ol 
• 1112986-10-3 4-[(3-bromophenyl)sulfonyl]butan-1-ol 
• 540-51-2 2-bromoethanol 
• 169138-21-0 6,6-diphenyl-5-hexene-1-ol 
• 52096-24-9 1-n-butylpyrazole 

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