4549-33-1

Basic information

• Product Name: 1,9-DIBROMONONANE
• Synonyms: 1,9-Dibromnonan;1,9-dibromo-nonan;Nonane,1,9-dibromo-;1,9-DIBROMONONANE;NONAMETHYLENE BROMIDE;NONAMETHYLENE DIBROMIDE;1 9-DIBROMONONANE 97% (GC);1,9-Dibromononane,97%
• CAS NO: 4549-33-1
• Molecular Formula: C₉H₁₈Br₂
• Molecular Weight: 286.05
• EINECS: 224-913-0
• Product Categories: Bromine Compounds;alpha,omega-Bifunctional Alkanes;alpha,omega-Dibromoalkanes;Monofunctional & alpha,omega-Bifunctional Alkanes
• Mol File: 4549-33-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: -2 °C
• Boiling Point: 285-288 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.407 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00453mmHg at 25°C
• Refractive Index: n20/D 1.496(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1737598
• CAS DataBase Reference: 1,9-DIBROMONONANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,9-DIBROMONONANE(4549-33-1)
• EPA Substance Registry System: 1,9-DIBROMONONANE(4549-33-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4549-33-1(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

Uses

1,9-Dibromononane is a useful research chemical compound.

InChI:InChI=1/C9H18Br2/c10-8-6-4-2-1-3-5-7-9-11/h1-9H2

Synthetic route

1,9-Nonanediol (3937-56-2) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
With carbon tetrabromide; Cu(tmp)(BINAP)BF4; sodium bromide In N,N-dimethyl-formamide for 24h; Appel Halogenation; UV-irradiation; Inert atmosphere;	99%
With water; hydrogen bromide
With hydrogen bromide

2-(9-bromononyloxy)tetrahydropyran (55695-90-4) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
With tetrabutylammomium bromide; dichloromethylenedimethyliminium chloride In dichloromethane at 0℃;	96%

9-bromononan-1-ol (55362-80-6) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
Stage #1: 9-bromononan-1-ol With N,N-dimethylthiourea In dichloromethane at 20℃; Stage #2: With N-Bromosuccinimide In dichloromethane at 20℃; for 20h;	88%

tert-butyl-[9-(4-methoxy-benzyloxy)-nonyloxy]-dimethyl-silane → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 30℃; for 2h;	85%

tert-butyl-[9-(4-methoxy-benzyloxy)-nonyloxy]-diphenyl-silane → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 30℃; for 2h;	82%

1,9-Nonanediol (3937-56-2) → 9-bromononan-1-ol (55362-80-6) + 1,9-Dibromononane (4549-33-1)

Conditions	Yield
With hydrogen bromide at 60℃; for 72h;	A 80% B n/a
With hydrogen bromide at 150℃;

9-(4-methoxybenzyloxy)nonan-1-ol (267005-80-1) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 30℃; for 1.5h;	80%

1,9-dimethoxynonane (91337-21-2) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
With hydrogen bromide at 100℃;

1,9-Nonanediol (3937-56-2) → 1,9-Dibromononane (4549-33-1) + bis-(9-bromo-nonyl)-ether (855751-72-3)

Conditions	Yield
With hydrogen bromide at 130℃;

Dimethyl azelate (1732-10-1) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
(i) LiAlH4, (ii) aq. HBr; Multistep reaction;
Multi-step reaction with 2 steps 1: sodium; absolute alcohol 2: hydrogen bromide / 150 °C View Scheme
Multi-step reaction with 2 steps 1: sodium; isoamyl alcohol 2: hydrogen bromide / 150 °C View Scheme
Multi-step reaction with 2 steps 1: sodium; isoamyl alcohol 2: hydrogen bromide / 150 °C View Scheme

bis-(9-bromo-nonyl)-ether (855751-72-3) + hydrogen bromide (10035-10-6, 12258-64-9) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
at 120 - 125℃; mit viel bei 0grad gesaettigter Verbindung;

nonanediol-(1.9)-diphenyl ether → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
With hydrogen bromide

1,9-Nonanediol (3937-56-2) + hydrogen bromide (10035-10-6, 12258-64-9) → 1,9-Dibromononane (4549-33-1) + bis-(9-bromo-nonyl)-ether (855751-72-3)

Conditions	Yield
at 130℃;

1,9-diphenoxy-nonane + hydrogen bromide (10035-10-6, 12258-64-9) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
at 165 - 170℃; im geschlossenen Rohr;

azelaic acid (123-99-9) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid 2: sodium; isoamyl alcohol 3: hydrogen bromide / 150 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid 2: sodium; isoamyl alcohol 3: hydrogen bromide / 150 °C View Scheme
Multi-step reaction with 2 steps 1: (i) (esterification), (ii) LiAlH4 2: aq. HBr View Scheme

1,7-dibromoheptane (4549-31-9) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether; magnesium 2: hydrobromic acid / 100 °C View Scheme
Multi-step reaction with 4 steps 1: aq. ethanol / 36 h / Heating 2: H2SO4 / 10 h / Heating 3: LiAlH4 / diethyl ether / 0.5 h 4: HBr, H2SO4 / 6 h / Heating View Scheme

diethyl azelate (624-17-9) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium; alcohol 2: hydrogen bromide / 150 °C View Scheme
Multi-step reaction with 2 steps 1: sodium; alcohol 2: hydrogen bromide / 150 °C View Scheme
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether / 0.5 h 2: HBr, H2SO4 / 6 h / Heating View Scheme

nonanedinitrile (1675-69-0) → 1,9-Dibromononane (4549-33-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2SO4 / 10 h / Heating 2: LiAlH4 / diethyl ether / 0.5 h 3: HBr, H2SO4 / 6 h / Heating View Scheme

1,9-Dibromononane (4549-33-1) + 2-ethoxy-7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid methyl ester (526221-05-6) → dimethyl 7,7'-(nonane-1,9-diylbis(oxy))bis(2-ethoxybenzo[d][1,3]dioxole-5-carboxylate)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; Inert atmosphere;	100%

1-phenylphospholane (3302-87-2) + 1,9-Dibromononane (4549-33-1) → 1,9-bis(phenylphospholanium)nonane dibromide

Conditions	Yield
In acetonitrile at 80℃; for 48h; Inert atmosphere; Schlenk technique;	99%

1-methyl-1H-imidazole (616-47-7) + 1,9-Dibromononane (4549-33-1) → 1,9-bis(3-methylimidazolium-1-yl)nonane dibromide

Conditions	Yield
In acetonitrile at 20℃; for 168h;	98%
at 20℃; for 5h;
In acetonitrile Reflux;
at 20℃;

betacarboline (244-63-3) + 1,9-Dibromononane (4549-33-1) → 2-[9-(β-carboline-2-ium-2-yl)nonyl]-β-carboline-2-ium dibromide

Conditions	Yield
In N,N-dimethyl-formamide Reflux; Inert atmosphere;	98%

1,9-Dibromononane (4549-33-1) + N,N-dimethyl-N-(3-phthalimidopropyl)amine (13474-65-2) → 9-bromo-N-[3-(1,3-dioxoisoindolin-2-yl)propyl]-N,N-dimethylnonan-1-aminium bromide

Conditions	Yield
In acetonitrile for 72h; Reflux;	98%

1,9-Dibromononane (4549-33-1) + 2-(3-(dimethylamino)-2,2-dimethylpropyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (505059-19-8) → 9-bromo-N-[3-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-2,2-dimethylpropyl]-N,N-dimethylnonan-1-aminium bromide

Conditions	Yield
In acetonitrile for 5h; Reflux;	97%

1,9-Dibromononane (4549-33-1) + C76H105N17O21Se2 → C85H123N17O21Se2

Conditions	Yield
With DL-dithiothreitol In aq. phosphate buffer; N,N-dimethyl-formamide at 22℃; for 1h; pH=7;	97%

1,9-Dibromononane (4549-33-1) → 1,9-diazidononane (98954-92-8)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 60℃; for 10h;	96%
With sodium azide In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere;	95%
With sodium azide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	86%
With methanol; sodium azide
With sodium azide In water at 120 - 140℃; Microwave irradiation;

1,9-Dibromononane (4549-33-1) + para-bromobenzenethiol (106-53-6) → 1,9-bis[(4-bromophenyl)thio]nonane

Conditions	Yield
With potassium carbonate In acetonitrile for 18h; Williamson Ether Synthesis; Reflux;	96%

(R)-(-)-3-[(R)-2-hydroxy-2-cyclopentyl-2-phenylethoxy]-1-azabicyclo[2.2.2]octane + 1,9-Dibromononane (4549-33-1) → (R)-(-)-3-[(R)-2-hydroxy-2-cyclopentyl-2-phenylethoxy]-1-(9-bromononyl)-1-azoniabicyclo[2.2.2]octane bromide

Conditions	Yield
In ethanol at 20℃; for 18h;	95.4%

1,9-Dibromononane (4549-33-1) → 1,9-diiodononane (24613-65-8)

Conditions	Yield
With sodium iodide In acetone at 20℃; for 24h; Darkness;	95%

1,9-Dibromononane (4549-33-1) + bromopentene (1119-51-3) → 14-bromo-1-tetradecene (74646-31-4)

Conditions	Yield
Stage #1: bromopentene With iodine; magnesium In tetrahydrofuran at 50℃; for 4h; Inert atmosphere; Stage #2: 1,9-Dibromononane With 1-methyl-pyrrolidin-2-one; dilithium tetrachlorocuprate(II) In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;	95%

1,9-Dibromononane (4549-33-1) + 9-(3-chlorobenzyl)-β-carboline-3-carboxylic acid (1427019-68-8) → 1,9-bis[9-(3-chlorobenzyl)-β-carboline-3-carboxylic acid]nonanediyl ester (1427019-03-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6 - 10h;	94%

1,9-Dibromononane (4549-33-1) + C21H33BrO7 → C30H51BrO7

Conditions	Yield
Stage #1: C21H33BrO7 With tert.-butyl lithium In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: 1,9-Dibromononane In tetrahydrofuran at -14 - 20℃; for 12h; Inert atmosphere;	94%
Stage #1: C21H33BrO7 With tert.-butyl lithium In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: 1,9-Dibromononane In tetrahydrofuran at -14 - 20℃; for 12h; Inert atmosphere; Schlenk technique;	1.77 g

1,9-Dibromononane (4549-33-1) + 1-benzylphospholane → 2Br(1-)*C31H48P2(2+)

Conditions	Yield
In acetonitrile at 80℃; for 48h; Inert atmosphere; Schlenk technique;	93%

NH-pyrazole (288-13-1) + 1,9-Dibromononane (4549-33-1) → 1,9-bis(pyrazol-1-yl)nonane

Conditions	Yield
Stage #1: NH-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 0.5h; Stage #2: 1,9-Dibromononane In dimethyl sulfoxide at 80℃; for 4.5h; Cooling;	93%
Stage #1: NH-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 0.5h; Stage #2: 1,9-Dibromononane In dimethyl sulfoxide at 80℃; for 4.5h;	93%

quinoline (91-22-5) + 1,9-Dibromononane (4549-33-1) → 1,1'-non-1,9-diyl-bis(quinolinium) dibromide

Conditions	Yield
at 65℃; for 24h;	92%
With ethanol
at 65℃; for 24h;
In acetonitrile at 70℃;

Ethyl 4-nitropyrrole-2-carboxylate (5930-92-7) + 1,9-Dibromononane (4549-33-1) → C23H32N4O8

Conditions	Yield
With potassium carbonate In acetone at 65℃; for 18h;	92%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1,9-Dibromononane (4549-33-1) → 1-Azo-4-(9'-{1''-azonia-4''-azobicyclo[2.2.2]octyl}-1'-nonyl)bicyclo[2.2.2]octane dibromide

Conditions	Yield
In acetonitrile at 20℃; for 24h;	92%
In acetonitrile for 120h; Alkylation; Heating;	88%
In acetonitrile at 80℃;

isoquinoline (119-65-3) + 1,9-Dibromononane (4549-33-1) → 1,9-bis(isoquinolin-2-ium)nonane dibromide

Conditions	Yield
at 65℃; for 24h;	92%
In N,N-dimethyl-formamide at 70℃;	54%
In acetonitrile	30%
at 65℃; for 24h;
In N,N-dimethyl-formamide at 70℃;

1,9-Dibromononane (4549-33-1) + triphenylphosphine (603-35-0) → 9-Bromononyltriphenylphosphonium bromide

Conditions	Yield
In toluene at 120℃; for 10h;	91%
In toluene at 110℃; for 24h;

1,9-Dibromononane (4549-33-1) + triethyl phosphite (122-52-1) → diethyl (9-bromononyl)phosphonate

Conditions	Yield
for 0.0833333h; Irradiation;	91%
at 140℃;	90%

3,5-dimethyl-1H-pyrazole (67-51-6) + 1,9-Dibromononane (4549-33-1) → 1,9-bis(3,5-dimethylpyrazol-1-yl)nonane

Conditions	Yield
Stage #1: 3,5-dimethyl-1H-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 0.5h; Stage #2: 1,9-Dibromononane In dimethyl sulfoxide at 80℃; for 4.5h; Cooling;	91%
Stage #1: 3,5-dimethyl-1H-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 0.5h; Stage #2: 1,9-Dibromononane In dimethyl sulfoxide at 80℃; for 4.5h;	91%

3-Methylpyridine (108-99-6) + 1,9-Dibromononane (4549-33-1) → bPiNB

Conditions	Yield
at 65℃; for 24h;	90%
at 65℃; for 24h;
for 24h;

n-octyne (629-05-0) + 1,9-Dibromononane (4549-33-1) → 1-Bromoheptadec-10-yne (151329-54-3)

Conditions	Yield
Stage #1: n-octyne With n-butyllithium In tetrahydrofuran; hexane at -25℃; for 1h; Stage #2: 1,9-Dibromononane With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -25 - 20℃; for 14.5h;	90%

1,9-Dibromononane (4549-33-1) + meta-hydroxybenzaldehyde (100-83-4) → C23H28O4 (1042251-70-6)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;	90%
With tetrabutylammonium sulfate; sodium hydroxide In water for 7h; Reflux;

3,6-epoxy-1,2,3,6-tetrahydrophthalimide (6253-28-7, 19878-26-3, 42074-03-3) + 1,9-Dibromononane (4549-33-1) → C25H30N2O6 (1449656-06-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere;	90%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere;	77.45%

1,9-Dibromononane (4549-33-1) + subergorgic acid (84607-62-5, 97718-45-1, 110043-85-1, 113429-19-9) → C24H37BrO3

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 12h; Inert atmosphere;	90%

Upstream product

• 91337-21-2 1,9-dimethoxynonane 
• 3937-56-2 1,9-Nonanediol 
• 55695-90-4 2-(9-bromononyloxy)tetrahydropyran 
• 855751-72-3 bis-(9-bromo-nonyl)-ether 
• 10035-10-6 hydrogen bromide 
• 55362-80-6 9-bromononan-1-ol 
• 1675-69-0 nonanedinitrile 
• 123-99-9 azelaic acid 
• 267005-80-1 9-(4-methoxybenzyloxy)nonan-1-ol 
• 1732-10-1 Dimethyl azelate 
• 624-17-9 diethyl azelate 
• 4549-31-9 1,7-dibromoheptane 

Downstream Products

• 505-52-2 brassylic acid 
• 102471-17-0 1,9-bis-(4-nitro-phenoxy)-nonane 
• 82275-87-4 N-(9-bromo-nonyl)-toluene-4-sulfonamide 
• 53596-82-0 9-bromononyl acetate 
• 4944-60-9 1,9-nonanediol diacetate 
• 3489-28-9 1,9-nonandithiol 
• 132568-33-3 p-hydroxyphenyl 9-bromononyl ether 
• 121315-90-0 4,4'-bis-ethoxycarbonyl-1,1'-dimethyl-4,4'-diphenyl-dodecahydro-1,1'-nonanediyl-bis-azepinium; dibromide 
• 5226-70-0 1,9-Bis-(m-nitrophenoxy)-nonan 
• 5226-67-5 1,9-Bis-(2-chlor-4-nitrophenoxy)-nonan 
• 94261-59-3 2-Amino-11-benzylmercapto-undecylsaeure 
• 143142-19-2 C₂₃H₂₈O₂S₂ 
• 88847-24-9 4,4'-Di-aethoxycarbonyl-α,ω-diphenoxy-nonan 
• 79557-82-7 1-[4-(9-Bromo-nonyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone 

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