765-09-3

Basic information

• Product Name: 1-Bromotridecane
• Synonyms: 1-bromo-tridecan;n-Tridecyl-1-bromide;tridecane,1-bromo-;1-BROMOTRIDECANE;TRIDECYL BROMIDE;N-TRIDECYL BROMIDE;1-Bromotridecane,99%
• CAS NO: 765-09-3
• Molecular Formula: C₁₃H₂₇Br
• Molecular Weight: 263.26
• EINECS: 212-138-0
• Product Categories: Alkyl Bromides;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes;Aliphatics;Intermediates
• Mol File: 765-09-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 4-7 °C(lit.)
• Boiling Point: 148-150 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: light yellow liquid
• Density: 1.03 g/mL at 25 °C(lit.)
• Vapor Density: 9.2 (vs air)
• Vapor Pressure: 0.00322mmHg at 25°C
• Refractive Index: n20/D 1.459(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• Stability: Stable. Incompatible with strong bases, strong oxidizing agents.
• BRN: 1739992
• CAS DataBase Reference: 1-Bromotridecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromotridecane(765-09-3)
• EPA Substance Registry System: 1-Bromotridecane(765-09-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• RTECS: YD3100000
• F: 8
• Hazardous Substances Data: 765-09-3(Hazardous Substances Data)

Usage

Chemical Properties

light yellow liquid

Uses

1-Bromotridecane is a long chain alkyl bromide with skin sensitization potency. 1-Bromotridecane may potentially enhance plant stimulator activity.

Preparation

1-Bromotridecane is prepared from 1-tridecanol.

Application

1-Bromotridecane was used in the synthesis of:tetradecanoic acid enriched with 13C at carbons 1, 3, or 6(Z)-7-henicosenePentadecanal(Z)-(2′R)-[N-carboethoxypyrrolidine]tetradec-1-ene2,3,6,7,10,11,14,15-octaalkyloxytetrabenzo[a,d,g,jlcyclododecatetraenes (CTTV-n) containing n=4-15 methylenic units in the alkyloxy substituentsCoupling reaction between the dilithio-derivative of propargyl alcohol with 1-bromotridecane in liquid ammonia gave 2-hexadecyne-1-ol.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 3405, 1979 DOI: 10.1021/jo01333a029

InChI:InChI=1/C13H27Br/c1-2-3-4-5-6-7-8-9-10-11-12-13-14/h2-13H2,1H3

Synthetic route

n-tetradecanoic acid (544-63-8) → 1-bromotridecane (765-09-3)

Conditions	Yield
With bromine; mercury(II) oxide In tetrachloromethane for 1.5h; Heating;	92%
With [bis(acetoxy)iodo]benzene; bromine In various solvent(s) for 22h; bromodecarboxylation; Heating; irradiation;	79%
(i) TlOEt, (ii) Br2; Multistep reaction;
With bromine; thallium (I) ethoxide 1.) hexane, 2.) reflux, 3 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide 2: dmap; Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt / 4 h / Reflux View Scheme

tridecan-1-ol (112-70-9) → 1-bromotridecane (765-09-3)

Conditions	Yield
With carbon tetrabromide In dichloromethane at -30 - 20℃;	88%
With hydrogen bromide at 100℃;
With hydrogen bromide

formaldehyde ditridecylacetal (68975-76-8) → 1-bromotridecane (765-09-3)

Conditions	Yield
With phosphorus pentabromide; benzene

1-tridecene (2437-56-1) → 1-bromotridecane (765-09-3)

Conditions	Yield
With hydrogen bromide; dihydrogen peroxide

1-benzamino-tridecane → 1-bromotridecane (765-09-3)

Conditions	Yield
With phosphorus pentabromide

1-tridecene (2437-56-1) + hydrogen bromide (10035-10-6, 12258-64-9) → 1-bromotridecane (765-09-3)

Conditions	Yield
in Gegenwart von Peroxyden;

formaldehyde ditridecylacetal (68975-76-8) + phosphorus pentabromide (7789-69-7) + benzene (71-43-2) → 1-bromotridecane (765-09-3)

mercury (II)-salt of/the/ myristic acid → 1-bromotridecane (765-09-3)

Conditions	Yield
With tetrachloromethane; bromine

silver salt of/the/ myristic acid → 1-bromotridecane (765-09-3)

Conditions	Yield
With bromine
With tetrachloromethane; bromine
With bromine

silver-salt of/the/ myristic acid → 1-bromotridecane (765-09-3)

Conditions	Yield
With Trichloroethylene; bromine

tetradecanoyl chloride (112-64-1) → 1-bromotridecane (765-09-3)

Conditions	Yield
With dmap; Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt for 4h; Hunsdiecker-Borodin reaction; Reflux;

undecylaldehyde (112-44-7) → 1-bromotridecane (765-09-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: dichloromethane / 20 °C 2: 10% Pd/C; hydrogen / ethanol / 20 °C 3: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C 4: carbon tetrabromide / dichloromethane / -30 - 20 °C View Scheme

(E)-Tridec-2-enoic acid ethyl ester (671787-02-3) → 1-bromotridecane (765-09-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 10% Pd/C; hydrogen / ethanol / 20 °C 2: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C 3: carbon tetrabromide / dichloromethane / -30 - 20 °C View Scheme

ethyl tridecanoate (28267-29-0) → 1-bromotridecane (765-09-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C 2: carbon tetrabromide / dichloromethane / -30 - 20 °C View Scheme

1-bromotridecane (765-09-3) + 3-(tetrahydropyran-2'-yloxy)propyne (6089-04-9) → 2-(hexadec-2-yn-1-yloxy)tetrahydro-2H-pyran (119290-95-8)

Conditions	Yield
With n-butyllithium at -30℃; for 1h;	100%
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: 1-bromotridecane In tetrahydrofuran at 20℃; for 21h;	76%
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 1-bromotridecane With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -78℃; for 24h;	60%
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium 1.) THF; Multistep reaction;
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; hexane at 0℃; Stage #2: 1-bromotridecane In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane at 40℃; for 24h;

1-bromotridecane (765-09-3) + thiourea (17356-08-0) → BrH*C14H30N2S

Conditions	Yield
In ethanol for 18h; Reflux;	100%
In ethanol for 12h; Reflux;

1-bromotridecane (765-09-3) + 2,4-bis(benzyloxy)phenol (6195-80-8) → 2,4-dibenzyloxy-1-tridecyloxybenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃;	100%

4-amino-1-benzylpiperidine (50541-93-0) + 1-bromotridecane (765-09-3) → (1-benzyl-4-piperidinyl)tridecylamine

Conditions	Yield
With triethylamine In acetonitrile for 3h; Heating;	99%

1-bromotridecane (765-09-3) + N,N-bis[3-(dimethylamino)propyl]-N',N'-dimethylpropane-1,3-diamine (33329-35-0) → C54H117N4(3+)*3Br(1-)

Conditions	Yield
In acetonitrile for 24h; Reflux;	99%

1-bromotridecane (765-09-3) + 2,4-di-(azetidin-1-yl)-6-methylpyrimidine → 2,4-di-(azetidin-1-yl)-6-tetradecylpyrimidine

Conditions	Yield
Stage #1: 2,4-di-(azetidin-1-yl)-6-methylpyrimidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.25h; Inert atmosphere; Stage #2: 1-bromotridecane In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;	98%
Stage #1: 2,4-di-(azetidin-1-yl)-6-methylpyrimidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 1-bromotridecane In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere;	98%

1-bromotridecane (765-09-3) + lithium acetylide (70277-75-7) → pentadec-1-yne (765-13-9)

Conditions	Yield
With ethylenediamine In dimethyl sulfoxide at 0 - 20℃;	97.9%
In dimethyl sulfoxide at 20℃; for 1h;	91%

1-bromotridecane (765-09-3) + methyl 4'-hydroxy-4-biphenylcarboxylate (40501-41-5) → 4'-tridecyloxy-biphenyl-4-carboxylic acid methyl ester (1439362-30-7)

Conditions	Yield
Stage #1: methyl 4'-hydroxy-4-biphenylcarboxylate With potassium carbonate; caesium carbonate In acetone for 0.0833333h; Inert atmosphere; Stage #2: 1-bromotridecane In acetone for 72h; Inert atmosphere; Reflux;	97.3%

1-bromotridecane (765-09-3) + diphenyl diselenide (1666-13-3) → Phenyl 1-tridecyl selenide

Conditions	Yield
Stage #1: diphenyl diselenide With sodium tetrahydroborate In tetrahydrofuran; ethanol Reduction; Stage #2: 1-bromotridecane In tetrahydrofuran; ethanol at 60℃; Substitution;	97%

1-bromotridecane (765-09-3) + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → ethyl 2-oxo-1-n-tridecylcyclopentanecarboxylate (1428444-37-4)

Conditions	Yield
Stage #1: 2-ethoxycarbonyl-1-cyclopentanone With potassium carbonate; potassium iodide In acetone for 0.166667h; Stage #2: 1-bromotridecane In acetone at 62℃; for 20h;	97%

3-(3,4-trihydroxyphenyl)propionic acid methyl ester (883196-20-1) + 1-bromotridecane (765-09-3) → 3-(3,4,5-tris-tridecyloxyphenyl)propionic acid methyl ester (1342314-02-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 8h; Inert atmosphere;	96%

1-bromotridecane (765-09-3) + ethylamine (75-04-7) → N-ethyltridecan-1-amine

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	96%

1-bromotridecane (765-09-3) + 5-amino-3-mercapto-4H-[1,2,4]triazole (16691-43-3) → 5-Tridecylsulfanyl-4H-[1,2,4]triazol-3-ylamine (183793-94-4)

Conditions	Yield
With triethylamine In acetonitrile for 2h; Heating;	95%

1-bromotridecane (765-09-3) + bis(p-chlorophenyl) diselenide (20541-49-5) → 4-Chlorophenyl 1-tridecyl selenide

Conditions	Yield
Stage #1: bis(p-chlorophenyl) diselenide With sodium tetrahydroborate In tetrahydrofuran; ethanol Reduction; Stage #2: 1-bromotridecane In tetrahydrofuran; ethanol at 60℃; Substitution;	95%

1-bromotridecane (765-09-3) + 4-(azetidin-1-yl)-2-cyclobutanoxy-6-methylpyrimidine → 4-(azetidin-1-yl)-2-cyclobutanoxy-6-tetradecylpyrimidine

Conditions	Yield
Stage #1: 4-(azetidin-1-yl)-2-cyclobutanoxy-6-methylpyrimidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.25h; Inert atmosphere; Stage #2: 1-bromotridecane In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;	95%
Stage #1: 4-(azetidin-1-yl)-2-cyclobutanoxy-6-methylpyrimidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 1-bromotridecane In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere;	95%

1-bromotridecane (765-09-3) + benzylamine (100-46-9) → N-benzyltridecan-1-amine

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	94%

1,3-di(4-pyridyl)propane (17252-51-6) + 1-bromotridecane (765-09-3) → C39H68N2(2+)*2Br(1-)

Conditions	Yield
In acetonitrile Reflux;	93%
In acetonitrile Reflux;	93%

1-bromotridecane (765-09-3) + (2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol (93367-10-3) → (S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)pentadecan-1-ol (1344994-22-4)

Conditions	Yield
Stage #1: 1-bromotridecane With magnesium In tetrahydrofuran Stage #2: With copper(l) cyanide In tetrahydrofuran at -20℃; for 0.5h; Stage #3: (2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol regioselective reaction; Further stages;	92%

1-bromotridecane (765-09-3) + (1R,2R)-1,2-bis((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol (22323-78-0) → 3,4-O-di-tridecyl-1,2:5,6-di-O-isopropylidene-D-mannitol

Conditions	Yield
Stage #1: (1R,2R)-1,2-bis((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol With sodium hydride In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: 1-bromotridecane In N,N-dimethyl-formamide at 20℃; for 4h;	92%

1-bromotridecane (765-09-3) + 2,4-dicyclobutanoxy-6-methylpyrimidine → 2,4-dicyclobutanoxy-6-tetradecylpyrimidine

Conditions	Yield
Stage #1: 2,4-dicyclobutanoxy-6-methylpyrimidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.25h; Inert atmosphere; Stage #2: 1-bromotridecane In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;	92%
Stage #1: 2,4-dicyclobutanoxy-6-methylpyrimidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 1-bromotridecane In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere;	92%

Pentaethylene glycol (4792-15-8) + 1-bromotridecane (765-09-3) → tridecyl pentaethylene glycol ether

Conditions	Yield
With sodium hydride In water at 66℃; for 12h; Temperature; Solvent; Cooling with ice;	91.1%

1-bromotridecane (765-09-3) + 6-mercapto-1-hexanol (1633-78-9) → 6-(tridecylthio)hexan-1-ol

Conditions	Yield
Stage #1: 6-mercapto-1-hexanol With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 1-bromotridecane In N,N-dimethyl-formamide at 65℃; for 3h;	91%

1-bromotridecane (765-09-3) + triphenylphosphine (603-35-0) → n-tridecyltriphenylphosphonium bromide (13266-02-9)

Conditions	Yield
In acetonitrile for 24h; Heating;	90%
In toluene for 26h; Inert atmosphere; Reflux;	85%
In toluene Reflux;	85%

N-methyl-N'-(2-dimethylaminoethyl)piperazine (104-19-8) + 1-bromotridecane (765-09-3) → C35H75N3(2+)*2Br(1-)

Conditions	Yield
In acetonitrile Reflux;	90%
In acetonitrile Reflux;	90%

1-bromotridecane (765-09-3) + 3-phenyl-4,5-dihydro-1H-1,2,4-triazole-5-thione (3414-94-6) → 3-phenyl-5-tridecylsulfanyl-1H-[1,2,4]triazole

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	89%

1-bromotridecane (765-09-3) + diethyl malonate (105-53-3) → diethyl 2-tridecylmalonate (41240-46-4)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 60℃; for 18h;	88%
With sodium hydride In tetrahydrofuran at 0 - 70℃; for 18.6667h; Inert atmosphere;	75%
(i) Na, (ii) /BRN= 1739992/; Multistep reaction;

1-bromotridecane (765-09-3) + tris(tert-butyldimethylsilyloxy)tris(methoxymethoxy)dehydrobenzo[12]annulene (1333499-12-9) → C69H102O9

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide at 70℃; for 5.5h; Inert atmosphere; Schlenk technique;	88%

1-bromotridecane (765-09-3) + (4R,5R)-5-benzyloxy-4-ethynyl-2,2-dimethyl-1,3-dioxane (169238-10-2) → (4R,5R)-5-benzyloxy-4-(pentadec-1-ynyl)-2,2-dimethyl-1,3-dioxane (161459-67-2)

Conditions	Yield
With n-butyllithium	87%
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 10.5h; Alkylation;	87%

Upstream product

• 68975-76-8 formaldehyde ditridecylacetal 
• 112-70-9 tridecan-1-ol 
• 2437-56-1 1-tridecene 
• 544-63-8 n-tetradecanoic acid 
• 10035-10-6 hydrogen bromide 
• 7789-69-7 phosphorus pentabromide 
• 71-43-2 benzene 
• 112-64-1 tetradecanoyl chloride 
• 112-44-7 undecylaldehyde 
• 671787-02-3 (E)-Tridec-2-enoic acid ethyl ester 
• 28267-29-0 ethyl tridecanoate 

Downstream Products

• 73491-93-7 1-tridecyl-pyridinium; bromide 
• 124114-31-4 4-ethoxycarbonyl-1-methyl-1-tridecyl-piperazinium; bromide 
• 18787-63-8 hexadecan-2-one 
• 62016-51-7 α-tridecylmalonic acid 
• 112-70-9 tridecan-1-ol 
• 765-13-9 pentadec-1-yne 
• 19484-26-5 tridecane-1-thiol 
• 929-41-9 2-n-Tridecylamino-ethanthioschwefelsaeure 
• 2765-11-9 n-pentadecanal 
• 72936-25-5 19,19-diethyl-14,24-ditridecyl-heptatriacontane-14,24-diol 
• 36588-34-8 1-Phenoxytridecan 
• 73726-85-9 (1-Phenylseleno-1-cyclopropyl)-tridecan 
• 18787-64-9 hexadecan-3-one 
• 79294-56-7 4-n-tridecyloxy-3-methoxybenzoic acid 

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