629-04-9

Basic information

• Product Name: 1-Bromoheptane
• Synonyms: Heptyl bromide;NSC 7315
• CAS NO: 629-04-9
• Molecular Formula: C₇H₁₅Br
• Molecular Weight: 179.098
• EINECS: 211-068-8
• Mol File: 629-04-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: -58℃
• Boiling Point: 178.7 °C at 760 mmHg
• Flash Point: 60.6 °C
• Appearance: Colorless liquid
• Density: 1.14 g/cm³
• Vapor Pressure: 1.32mmHg at 25°C
• Refractive Index: 1.449
• Water Solubility: insoluble
• CAS DataBase Reference: 1-Bromoheptane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromoheptane(629-04-9)
• EPA Substance Registry System: 1-Bromoheptane(629-04-9)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37:
• Safety Statements: S26:; S37/39:
• PackingGroup: III
• Hazardous Substances Data: 629-04-9(Hazardous Substances Data)

Usage

General Description

1-Bromoheptane is a chemical compound with the molecular formula C7H15Br. It is a colorless liquid with a strong, unpleasant odor. 1-Bromoheptane is primarily used as a chemical intermediate in the manufacture of pharmaceuticals and other organic compounds. It is also used as a solvent, a surfactant, and an intermediate in the synthesis of other chemicals. 1-Bromoheptane is highly flammable and may cause skin and eye irritation upon contact. It should be handled and stored with care to prevent accidents and exposure to its harmful effects.

InChI:InChI=1/C7H15Br/c1-2-3-4-5-6-7-8/h2-7H2,1H3

Synthetic route

1-Heptene (592-76-7) → 1-Bromoheptane (629-04-9)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); hydrogen bromide In toluene at 0℃; for 2h; Reagent/catalyst; Solvent;	95%
With hexane; hydrogen bromide at -15 - -10℃; im Dunkeln;
With tetrachloromethane; hydrogen bromide at -15 - -10℃; im Dunkeln;

n-heptan1ol (111-70-6) → 1-Bromoheptane (629-04-9)

Conditions	Yield
With toluene-4-sulfonic acid; 1-(1-methylethyl)-3-methylimidazolium bromide at 200℃; under 10343 Torr; for 0.05h; microwave irradiation;	95%
With oxalyl dichloride; Tropone; tetrabutylammomium bromide In dichloromethane at 20℃; for 12h; Inert atmosphere;	79%
With phosphorus tribromide

heptyl 4-methylbenzenesulfinate (89149-55-3) → 1-Bromoheptane (629-04-9) + n-heptan1ol (111-70-6) + 1,2-dibromoheptane (42474-21-5) + toluene-p-sulfonyl bromide (1950-69-2)

Conditions	Yield
With bromine In chloroform for 2.5h; Ambient temperature;	A 89 % Chromat. B 3 % Chromat. C 1 % Chromat. D 94%

N-n-heptyl-N'-tosylhydrazine (86724-18-7) → 1-Bromoheptane (629-04-9) + 1,2-dibromoheptane (42474-21-5) + toluene-p-sulfonyl bromide (1950-69-2)

Conditions	Yield
With bromine In chloroform for 2.5h; Ambient temperature;	A 59 % Chromat. B 8 % Chromat. C 93%

heptanethiol (1639-09-4) → 1-Bromoheptane (629-04-9)

Conditions	Yield
With Silphos; bromine In acetonitrile for 0.75h; Heating;	90%

methoxymethyl heptyl ether (71739-40-7) → 1-Bromoheptane (629-04-9)

Conditions	Yield
With phosphotungstic acid; tetrabutylammomium bromide at 130 - 142℃; for 0.0333333h; Microwave irradiation; Ionic liquid; chemoselective reaction;	90%
With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0666667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;	83%

ethoxymethyl heptyl ether (1058649-58-3) → 1-Bromoheptane (629-04-9)

Conditions	Yield
With phosphotungstic acid; tetrabutylammomium bromide at 130 - 142℃; for 0.0333333h; Microwave irradiation; Ionic liquid; chemoselective reaction;	88%
With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0666667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;	82%

1-fluoroheptane (661-11-0) → 1-Bromoheptane (629-04-9)

Conditions	Yield
With hydrogen bromide at 130℃; for 8h;	87%
Multi-step reaction with 2 steps 1: 12 N HCl / 105 °C 2: 84 percent / 47percent aq. HBr / 20 h / 130 °C View Scheme

1-Chloroheptane (629-06-1) → 1-Bromoheptane (629-04-9)

Conditions	Yield
With hydrogen bromide at 130℃; for 20h;	84%

1-Heptene (592-76-7) → 1-Bromoheptane (629-04-9) + 2-bromoheptane (1974-04-5)

Conditions	Yield
With hydrogen bromide In hexane at -33.1 - 26.9℃; for 48h; Mechanism; Product distribution; other solvents;

N-n-heptyl-N'-tosylhydrazine (86724-18-7) → 1-Bromoheptane (629-04-9) + 2-bromoheptane (1974-04-5) + n-heptan1ol (111-70-6) + 1,2-dibromoheptane (42474-21-5) + toluene-p-sulfonyl bromide (1950-69-2)

Conditions	Yield
With bromine In chloroform for 2.5h; Mechanism; Product distribution; Ambient temperature; Several primary hydrazine were studied. Primary hydrazines gave preferably monobromides.;

1-fluoroheptane (661-11-0) → 1-Bromoheptane (629-04-9) + 2-bromoheptane (1974-04-5)

Conditions	Yield
With boron tribromide In hexane at 0℃; for 0.0833333h; Yield given. Title compound not separated from byproducts;

tetrachloromethane (56-23-5) + 1-Heptene (592-76-7) + hydrogen bromide (10035-10-6, 12258-64-9) → 1-Bromoheptane (629-04-9)

Conditions	Yield
at -15 - 0℃; in einer peroxydfreier Loesung unter Ausschluss von Feuchtigkeit, Luft und Licht;

1-Heptene (592-76-7) + hexane (110-54-3) + hydrogen bromide (10035-10-6, 12258-64-9) → 1-Bromoheptane (629-04-9)

Conditions	Yield
at -15 - 0℃; in einer peroxydfreier Loesung unter Ausschluss von Feuchtigkeit, Luft und Licht;

1-Heptene (592-76-7) + hydrogen bromide (10035-10-6, 12258-64-9) + acetic acid (64-19-7) → 1-Bromoheptane (629-04-9)

Conditions	Yield
at -15 - 0℃; in einer peroxydfreier Loesung unter Ausschluss von Feuchtigkeit, Luft und Licht;

tetrachloromethane (56-23-5) + Octanoic acid (124-07-2) + bromine (7726-95-6) → 1-Bromoheptane (629-04-9)

Conditions	Yield
Reaktion des Quecksilbersalzes;
Reaktion des Silbersalzes;
Reaktion des Quecksilbersalzes;
Reaktion des Silbersalzes;

Octanoic acid (124-07-2) + bromine (7726-95-6) + CS2 → 1-Bromoheptane (629-04-9)

Conditions	Yield
Reaktion des Silbersalzes;
Reaktion des Quecksilbersalzes;
Reaktion des Quecksilbersalzes;
Reaktion des Silbersalzes;

mercury (I)-caprylate → 1-Bromoheptane (629-04-9)

Conditions	Yield
With tetrachloromethane; bromine
With tetrachloromethane; bromine

mercury (II)-caprylate → 1-Bromoheptane (629-04-9)

Conditions	Yield
With carbon disulfide; bromine
With carbon disulfide; bromine

potassium caprylate → 1-Bromoheptane (629-04-9)

Conditions	Yield
With tetrachloromethane; bromine
With tetrachloromethane; bromine

silver octanoate → 1-Bromoheptane (629-04-9)

Conditions	Yield
With tetrachloromethane; bromine

tetrachloromethane (56-23-5) + bromine (7726-95-6) + potassium octanoate (764-71-6) → 1-Bromoheptane (629-04-9)

bromine (7726-95-6) + potassium octanoate (764-71-6) + CS2 → 1-Bromoheptane (629-04-9)

n-heptane (142-82-5) → 4-bromoheptane (998-93-6) + 1-Bromoheptane (629-04-9) + 3-bromoheptane (116435-51-9, 1974-05-6, 116724-27-7) + 2-bromoheptane (1974-04-5)

Conditions	Yield
With bromine; sodium t-butanolate In cyclohexane Heating; Title compound not separated from byproducts;

n-heptan1ol (111-70-6) → 1-Bromoheptane (629-04-9) + diheptyl ether (629-64-1)

Conditions	Yield
Stage #1: n-heptan1ol With N,N-dimethylthiourea In dichloromethane at 20℃; Stage #2: With N-Bromosuccinimide In dichloromethane at 20℃; for 12h;	A 58 %Chromat. B 29 %Chromat.

1-Bromoheptane (629-04-9) → 1-azidoheptane (44961-22-0)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 80℃;	100%
With sodium azide; Aliquat 336 In formamide at 100℃; Rate constant; Product distribution; further solvent;	99%
With sodium azide; Aliquat 336 In formamide at 100℃;	99%

4,5-bis(benzoylthio)-1,3-dithiole-2-thione (68494-08-6) + 1-Bromoheptane (629-04-9) → C17H30S5 (160627-51-0)

Conditions	Yield
Stage #1: 4,5-bis(benzoylthio)-1,3-dithiole-2-thione With sodium methylate In methanol for 1h; Inert atmosphere; Stage #2: 1-Bromoheptane In methanol at 78℃; for 5h; Inert atmosphere;	100%

1-Bromoheptane (629-04-9) + 1,4-bis(tert-butoxycarbonylmethyl)-1,4,7-triazacyclononane (174137-97-4) → C25H49N3O4 (1428255-39-3)

Conditions	Yield
With potassium carbonate In acetonitrile for 96h;	100%

4-iodopyrazole (3469-69-0) + 1-Bromoheptane (629-04-9) → 1-heptyl-4-iodo-1H-pyrazole

Conditions	Yield
Stage #1: 4-iodopyrazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Schlenk technique; Stage #2: 1-Bromoheptane In tetrahydrofuran at 0 - 20℃; Schlenk technique;	100%

1-Bromoheptane (629-04-9) + 2-Iodophenol (533-58-4) → 1-(heptyloxy)-2-iodobenzene (1410158-61-0)

Conditions	Yield
Stage #1: 2-Iodophenol With potassium carbonate In N,N-dimethyl-formamide for 0.166667h; Stage #2: 1-Bromoheptane In N,N-dimethyl-formamide at 20℃;	100%

1-Bromoheptane (629-04-9) + (2S,3S)-3-((2-bromo-5-fluoro-6-(thiophen-2-yl)pyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2-carboxylic acid → (2S,3S)-heptyl 3-((2-bromo-5-fluoro-6-(thiophen-2-yl)pyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	100%

1-Bromoheptane (629-04-9) + C99H104N4O6 → C106H118N4O6

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydroxide In water; toluene at 50℃;	100%

1-Bromoheptane (629-04-9) + triphenylphosphine (603-35-0) → triphenylheptylphosphonium bromide (13423-48-8)

Conditions	Yield
In acetonitrile for 24h; Addition; Heating;	99%
In toluene for 48h; Reflux;	96%
In toluene for 48h; Reflux;	96%

1-Bromoheptane (629-04-9) + 4-Iodophenol (540-38-5) → (1-(heptyloxy)-4-iodobenzene) (116223-56-4)

Conditions	Yield
With potassium carbonate In acetonitrile Williamson synthesis; Reflux;	99%
Stage #1: p-Iodophenol With potassium carbonate In N,N-dimethyl-formamide for 0.166667h; Stage #2: 1-Bromoheptane In N,N-dimethyl-formamide at 20℃;	99%
With potassium hydroxide In acetone for 24h; Reflux;	94%

1-Bromoheptane (629-04-9) + trimethylstannane (1631-73-8) → n-heptane (142-82-5) + n-butyltrimethyltin (1527-99-7)

Conditions	Yield
With n-butyllithium In hexane n-BuLi (1.50 mmol, 2.40 M soln. in hexane) added to soln. of TMTH (1.50 mmol) in hexane under Ar, stirred for 3 h at room temp., 1-bromoheptane (1.50 mmol) added, heated to reflux for 2 h; analyzed by GC;	A 7% B 99%
With n-butyllithium In hexane 1-bromoheptane (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 5 min, quenched with water; analyzed by GC;	A 98% B 93%
With n-butyllithium In hexane to 1-bromoheptane (2.20 mmol) and TMTH (2.20 mmol) in hexane at 0°C under Ar added n-BuLi (2.20 mmol, in hexane) in four 0.55-mmol increments, stirred for 5 min; various product ratio (yields) for various amounts of n-BuLi increments added; analyzed by GC;

1-Bromoheptane (629-04-9) + (R)-propylene oxide (15448-47-2) → (R)-decan-2-ol (1120-06-5, 33758-16-6, 74742-10-2, 33758-15-5)

Conditions	Yield
Stage #1: 1-Bromoheptane With methylmagnesium bromide; magnesium In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: (R)-propylene oxide With dilithium tetrachlorocuprate(II) In tetrahydrofuran at -78 - 20℃; for 1.5h; Inert atmosphere; Stage #3: With water; ammonium chloride In tetrahydrofuran Inert atmosphere; Cooling with ice;	99%

1-Bromoheptane (629-04-9) + 3-Iodophenol (626-02-8) → 1-(heptyloxy)-3-iodobenzene

Conditions	Yield
Stage #1: 3-Iodophenol With potassium carbonate In N,N-dimethyl-formamide for 0.166667h; Stage #2: 1-Bromoheptane In N,N-dimethyl-formamide at 20℃;	99%

1-Bromoheptane (629-04-9) + 2,4-bis(benzyloxy)phenol (6195-80-8) → 2,4-dibenzyloxy-1-heptyloxybenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃;	99%

1-Bromoheptane (629-04-9) + methyl 4-hydroxy-3,5-bis((3,7-(rac)-dimethyloctyl)oxy)benzoate → methyl 3,5-bis((3,7-(rac)-dimethyloctyl)oxy)-4-(heptyloxy)benzoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 4h; Williamson Ether Synthesis; Inert atmosphere;	99%

1-Bromoheptane (629-04-9) + 4-Hydroxyacetophenone (99-93-4) → 4'-heptyloxyacetophenone (37062-61-6)

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; for 9h;	98%
In acetonitrile Inert atmosphere; Reflux;	90%
With potassium carbonate

1-Bromoheptane (629-04-9) + ethyl 3-hydroxy-2-pyridineacetate (2584-12-5) → ethyl 3-n-heptyloxy-2-pyridineacetate (99156-25-9)

Conditions	Yield
With sodium In ethanol; dimethyl sulfoxide Ambient temperature;	98%

(RS)-5,6'-dihydroxy-2,2'-spirobiindan-1,1'-dione (867296-84-2) + 1-Bromoheptane (629-04-9) → (RS)-5,6'-diheptyloxy-2,2'-spirobiindan-1,1'-dione (867296-86-4)

Conditions	Yield
With potassium carbonate In acetone for 16h; Heating;	98%

1-Bromoheptane (629-04-9) + 3-bromo-4-hydroxybenzylaldehyde (2973-78-6) → 3-bromo-4-heptyloxybenzaldehyde (100792-27-6)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 50℃; for 8h; Inert atmosphere;	98%

1-Bromoheptane (629-04-9) + vanillin (121-33-5) → 4-(heptyloxy)-3-methoxybenzaldehyde (5438-59-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;	98%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;

1-Bromoheptane (629-04-9) + 2-ethoxy-7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid methyl ester (526221-05-6) → methyl 2-ethoxy-7-(heptyloxy)benzo[d][1,3]dioxole-5-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 4h; Williamson Ether Synthesis; Inert atmosphere;	98%

6-bromo-naphthalen-2-ol (15231-91-1) + 1-Bromoheptane (629-04-9) → 2-bromo-6-(heptyloxy)naphthalene (155378-37-3)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 75℃; for 3h;	97%
Stage #1: 6-bromo-naphthalen-2-ol With potassium hydroxide In N,N-dimethyl-formamide; benzene Stage #2: 1-Bromoheptane In N,N-dimethyl-formamide; benzene Heating;	87%
With potassium tert-butylate In dimethyl sulfoxide for 0.25h;
With potassium hydroxide In acetonitrile

4-bromo-phenol (106-41-2) + 1-Bromoheptane (629-04-9) → 4-n-heptyloxybromobenzene (123732-04-7)

Conditions	Yield
With potassium carbonate In acetone for 48h; Heating;	97%
With potassium hydroxide In N,N-dimethyl-formamide; benzene for 6h; Heating;	95%
With potassium carbonate In N,N-dimethyl-formamide at 90℃;	93%

1-Bromoheptane (629-04-9) + 2,3-difluorophenol (6418-38-8) → 2,3-difluoro-4-(heptyloxy)benzene (122265-84-3)

Conditions	Yield
With potassium carbonate In butanone Heating / reflux;	97%
With potassium carbonate In ethyl acetate Heating;	90%
With potassium carbonate In acetone for 48h; Alkylation; Heating;
With potassium hydroxide In ethanol
With sodium hydroxide In dimethyl sulfoxide

1-Bromoheptane (629-04-9) + 4-cyanophenol (767-00-0) → 4-(heptyloxy)benzonitrile (29147-88-4)

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux; Inert atmosphere;	97%
With potassium carbonate In cyclohexanone for 24h; Heating;	73%

1-Bromoheptane (629-04-9) + N-allyloxycarbonyl-2-nitrobenzenesulfonamide (90916-29-3) → C17H24N2O6S (245364-53-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; Alkylation;	97%

1-Bromoheptane (629-04-9) + methyl 4-hydroxylbenzoate (99-76-3) → 4-heptyloxybenzoic acid methyl ester (67399-84-2)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone at 60℃;	97%
With potassium carbonate; potassium iodide In acetone for 6h; Reflux;	93%
With potassium hydroxide In N,N-dimethyl-formamide at 50℃; for 6h;	88%

1-Bromoheptane (629-04-9) + diphenyl diselenide (1666-13-3) → n-heptyl phenyl selenide (76376-91-5)

Conditions	Yield
With ruthenium trichloride; zinc In N,N-dimethyl-formamide at 100℃; for 1h;	97%
With zinc In N,N-dimethyl-formamide at 100℃; for 2h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	95%
Stage #1: diphenyl diselenide With sodium tetrahydroborate In ethanol for 0.5h; Cooling with ice; Stage #2: 1-Bromoheptane In ethanol at 20℃; for 2h; Cooling with ice;

tricyclohexyltin hydride (6056-50-4) + 1-Bromoheptane (629-04-9) → (cyclo-C6H11)3SnC4H9 (7067-44-9) + n-heptane (142-82-5)

Conditions	Yield
With n-butyllithium In hexane 1-bromoheptane (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 15 min, quenched with water; analyzed by GC;	A n/a B 97%

1-Bromoheptane (629-04-9) + (1S)-2-(benzyloxy)-1-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol (1310460-70-8) → 1-O-benzyl-2-O-(hept-1-yl)-3,4-O-isopropylidene-D-erythritol (1392477-93-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;	97%

1-Bromoheptane (629-04-9) → diheptyldisulfide (10496-16-9)

Conditions	Yield
With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate In water at 25℃; for 1h;	96%
With potassium sulfide; nickel(II) chloride hexahydrate; acetylacetone; potassium hydroxide In water; N,N-dimethyl-formamide at 110℃; for 6h;	93%
With morpholinium morpholine-1-carbodithioate; copper(l) chloride; potassium hydroxide In water; N,N-dimethyl-formamide at 110℃; for 20h; Green chemistry;	83%

Upstream product

• 592-76-7 1-Heptene 
• 111-70-6 n-heptan1ol 
• 661-11-0 1-fluoroheptane 
• 629-06-1 1-Chloroheptane 
• 89149-55-3 heptyl 4-methylbenzenesulfinate 
• 56-23-5 tetrachloromethane 
• 10035-10-6 hydrogen bromide 
• 110-54-3 hexane 
• 64-19-7 acetic acid 
• 1639-09-4 heptanethiol 
• 71739-40-7 methoxymethyl heptyl ether 
• 1058649-58-3 ethoxymethyl heptyl ether 
• 142-82-5 n-heptane 
• 7726-95-6 bromine 

Downstream Products

• 154845-73-5 4-heptyloxy-benzoic acid ethyl ester 
• 1078-71-3 heptylbenzene 
• 860564-37-0 2-heptyloxy-benzophenone 
• 40481-07-0 3-carbamoyl-1-heptyl-pyridinium; bromide 
• 112-23-2 n-heptyl formate 
• 57792-33-3 heptyl-o-tolyl ether 
• 26981-81-7 N,N-diethylheptylamine 
• 1639-09-4 heptanethiol 
• 40814-21-9 Ethyl-2-S-n-Heptylmercaptoacetat 
• 1114-73-4 2-cyano-nonanoic acid ethyl ester 
• 75681-68-4 4-heptylamino-benzoic acid ethyl ester 
• 100243-38-7 2-heptyloxy-benzoic acid amide 
• 16519-20-3 benzyl hept-1-yl ether 
• 74051-28-8 3endo-benziloyloxy-8anti-heptyl-8syn-methyl-nortropanium; bromide 

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