109-64-8

Basic information

• Product Name: 1,3-Dibromopropane
• Synonyms: ,’-Dibromopropane;,-Dibromopropane;1,3-dibromo-propan;1,3-Dibrompropan;1,3-Propylenebromide;CH2BrCH2CH2Br;Dibromo-1,3 propane;omega,omega’-dibromopropane
• CAS NO: 109-64-8
• Molecular Formula: C₃H₆Br₂
• Molecular Weight: 201.89
• EINECS: 203-690-3
• Product Categories: Organics;DIBROMOALKANE;alpha,omega-Bifunctional Alkanes;alpha,omega-Dibromoalkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;Aliphatics;Enzyme substrates
• Mol File: 109-64-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: −34 °C(lit.)
• Boiling Point: 167 °C(lit.)
• Flash Point: 54 °C
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.989 g/mL at 25 °C(lit.)
• Vapor Density: 7 (vs air)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.524(lit.)
• Storage Temp.: 2-8°C
• Solubility: 1.68g/l
• Water Solubility: 1.7 g/L (30 ºC)
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases. Flammable.
• Merck: 14,9713
• BRN: 635662
• CAS DataBase Reference: 1,3-Dibromopropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dibromopropane(109-64-8)
• EPA Substance Registry System: 1,3-Dibromopropane(109-64-8)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 10-22-38-51/53-36/37/38
• Safety Statements: 16-26-36-61-24/25
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 2
• RTECS: TX8575000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 109-64-8(Hazardous Substances Data)

Usage

Chemical Properties

1,3-Dibromopropane is a colourless to slightly yellow liquid with sweet odor. soluble in ether, acetone and chloroform, insoluble in water. Decomposes when exposed to heat for a long time and is partially converted to 1,2-dibromopropane. Boiling with water produces propylene glycol. It is used substrate specificity of haloalkane dehalogenases.

Uses

1,3-Dibromopropane is used to prepare C3-bridged compounds through C-N coupling reactions. It is used in the preparation of 2,3,4,5-tetrahydro-7,7-diphenylimidazo- [2,1-b]-thiazine-6(7H)-one by reacting with potassium salt of 5,5-diphenyl-2-thiohydantoin.

General Description

1,3-Dibromopropane is a dihalogenated propane. It undergoes reduction catalyzed by electrogenerated solution-phase nickel(I) salen and nickel(I) salen confined in a polymer film on the surface of a carbon electrode to afford cyclopropane and propylene, respectively.

Hazard

Colorless liquid; sweet odor. Insoluble in water; soluble in organic solvents. Combustible.

Synthesis

1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide. It can derived from the reaction of propylene glycol with brominated hydrochloric acid.

Purification Methods

1,3-Dibromopropane [109-64-8] M 201.9, f -34.4o, b 63 -63.5o/26mm, 76 -77o/40mm, 9 0o/80mm, 165o/atm, d 4 1.977, n 1.522. Wash the dibromide with dilute aqueous Na2CO3, then water. Dry and fractionally distil it under reduced pressure. [Beilstein 1 IV 216.]

InChI:InChI=1/C3H6Br2/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3

Synthetic route

3-ethoxy-1-propanol (111-35-3) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
With sulfuric acid; hydrogen bromide for 10h; Heating;	91%

1,3-bis(trimethylsiloxy)propane (17887-80-8) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
With Tri-n-butylfluorphosphoniumbromid In benzene at 20℃; for 24h;	76%

trimethylene oxide (503-30-0) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
With hydrogen bromide at 100℃;

1,2-Dibromopropane (78-75-1) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
at 240 - 250℃; beim Erhitzen im Rohr;

1,2-Dibromopropane (78-75-1) → 2,2-dibromopropane (594-16-1) + 1,3-dibromo-propane (109-64-8)

Conditions	Yield
beim Erhitzen;

propane (74-98-6) → 1,2-Dibromopropane (78-75-1) + propyl bromide (106-94-5) + 1,3-dibromo-propane (109-64-8) + isopropyl bromide (75-26-3)

Conditions	Yield
at 300 - 330℃; Bromierung; weitere Produkte: 2.2-Dibrom-propan, Tribrompropan und Tetrabrompropan;

1,3-Dichloropropane (142-28-9) → 1,3-chlorobromopropane (109-70-6) + 1,3-dibromo-propane (109-64-8)

Conditions	Yield
With ethyl bromide; aluminum tri-bromide at 2 - 5℃;

ethanol (64-17-5) + 1,3-chlorobromopropane (109-70-6) → 1,3-Dichloropropane (142-28-9) + 1,3-dibromo-propane (109-64-8)

1,3-chlorobromopropane (109-70-6) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
With aluminium trichloride; hydrogen bromide

diacetyl peroxide (110-22-5) + allyl bromide (106-95-6) → 1-butylene (106-98-9) + methyl bromide (74-83-9) + 5-bromo-4-(bromomethyl)pent-1-ene (157556-86-0) + 1,3-dibromo-propane (109-64-8)

Conditions	Yield
at 90℃; entstehen noch 1.5-Dibrom-2-brommethyl-pentan(?) und CO2;

allyl bromide (106-95-6) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
With hydrogen bromide at -78℃; Irradiation.im UV-Licht; bei Sauerstoffausschluss;
With hydrogen bromide; oxygen
With hydrogen bromide; dibenzoyl peroxide

allyl bromide (106-95-6) → 1,2-Dibromopropane (78-75-1) + 1,3-dibromo-propane (109-64-8)

Conditions	Yield
With hydrogen bromide at 100℃;

ethene (74-85-1) + 1,2-dibromomethane (74-95-3) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
With water; dibenzoyl peroxide at 100℃; under 228007 - 257428 Torr;

trimethyleneglycol (504-63-2) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
With hydrogen bromide at 100℃;
With triphenyl phosphite; bromine
With hydrogen bromide

1,3-Dichloropropane (142-28-9) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
With Aliquat 336; lithium bromide at 98℃; for 6h;	92 % Chromat.

1,3-chlorobromopropane (109-70-6) → 1,2-Dichloropropane (26198-63-0, 78-87-5) + 1,2-Dibromopropane (78-75-1) + 1,3-Dichloropropane (142-28-9) + allyl bromide (106-95-6) + 1,3-dibromo-propane (109-64-8) + 3-chloroprop-1-ene (107-05-1)

Conditions	Yield
aluminum oxide at 160℃; Mechanism; Product distribution; different temperature;

trimethylene oxide (503-30-0) + hydrogen bromide (10035-10-6, 12258-64-9) → 1,3-dibromo-propane (109-64-8)

hydrogen bromide (10035-10-6, 12258-64-9) + 3-phenoxypropyl bromide (588-63-6) → 1,3-dibromo-propane (109-64-8)

bromine (7726-95-6) + cyclopropane (75-19-4) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
im Sonnenlicht;

ethanol (64-17-5) + bromine (7726-95-6) + cyclopropane (75-19-4) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
at 20℃; Irradiation;

hydrogen bromide (10035-10-6, 12258-64-9) + allyl bromide (106-95-6) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
at -78℃; bei Einw. von UV-Licht;
at 25℃; bei Einw. von UV-Licht;

bromine (7726-95-6) + cyclopropane (75-19-4) + isopentyl nitrite (110-46-3) → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
at 20℃; Irradiation;

bromopropyl-phenyl ether → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
With hydrogen bromide beim Erhitzen im Rohr;

hydrogen bromide (10035-10-6, 12258-64-9) + allyl bromide (106-95-6) + cobalt → 1,3-dibromo-propane (109-64-8)

hydrogen bromide (10035-10-6, 12258-64-9) + allyl bromide (106-95-6) + iron → 1,3-dibromo-propane (109-64-8)

hydrogen bromide (10035-10-6, 12258-64-9) + allyl bromide (106-95-6) + nickel → 1,3-dibromo-propane (109-64-8)

bromine (7726-95-6) + cyclopropane (75-19-4) + oxygen → 1,3-dibromo-propane (109-64-8)

Conditions	Yield
at 20℃; Irradiation;

hydrogen bromide (10035-10-6, 12258-64-9) + allyl bromide (106-95-6) + oxygen → 1,3-dibromo-propane (109-64-8)

hydrogen bromide (10035-10-6, 12258-64-9) + allyl bromide (106-95-6) + peroxidene → 1,3-dibromo-propane (109-64-8)

1-Methylpyrrolidine (120-94-5) + 1,3-dibromo-propane (109-64-8) → 1-(3-bromopropyl)-1-methylpyrrolidin-1-ium bromide (3722-27-8)

Conditions	Yield
Reflux;	100%
at 20℃; for 48h; Darkness;	92%
With benzene
In acetone at 20℃; for 168h; Darkness;

triphenylphosphine (603-35-0) + 1,3-dibromo-propane (109-64-8) → 3-bromopropyltriphenylphosphonium bromide (3607-17-8)

Conditions	Yield
In toluene at 110℃; for 16h;	100%
In toluene for 24h; Reflux;	99%
In toluene Inert atmosphere; Reflux;	98%

ethyl N-hydroxylcarbamate (589-41-3) + 1,3-dibromo-propane (109-64-8) → N-(ethoxycarbonyl)isoxazolidine (54020-55-2)

Conditions	Yield
With sodium t-butanolate In tert-butyl alcohol at 65℃; for 6h; cyclocondensation;	100%
With potassium hydroxide In ethanol for 2h; Heating;	85%
With potassium hydroxide

1,3-dibromo-propane (109-64-8) → 1,3-diazido-propane (100910-72-3)

Conditions	Yield
With sodium azide In dimethyl sulfoxide at 20℃;	100%
With sodium azide In water; N,N-dimethyl-formamide at 80℃; for 20h;	97%
With sodium azide In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere;	90%

1,3-dibromo-propane (109-64-8) + Diethyl methylmalonate (609-08-5) → heptane-2,2,6,6-tetracarboxylic acid tetraethyl ester (33524-34-4)

Conditions	Yield
With sodium ethanolate In ethanol at 24℃; Substitution; Heating;	100%
(i) NaH, benzene, (ii) /BRN= 635662/; Multistep reaction;

[2,2]bipyridinyl (366-18-7) + 1,3-dibromo-propane (109-64-8) → 6H-7,8-dihydropyrido<1,2-a:2,1-c><1,4>diazepine-5,9-diium dibromide (2895-98-9)

Conditions	Yield
In acetone Heating;	100%
for 12h; Reflux;	90%
In acetonitrile

7-hydroxy-2H-chromen-2-one (93-35-6) + 1,3-dibromo-propane (109-64-8) → 7-(3-bromopropoxy)−2H-chromen-2-one (69150-28-3)

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	100%
With potassium carbonate In acetonitrile Reflux;	86.9%
With potassium carbonate In acetone Reflux;	79%

2,3:7,6-bis(2',3'-quinolino)tetracyclo<6.3.0.04,11.05,9>undecane (113258-55-2) + 1,3-dibromo-propane (109-64-8) → 1',1''-trimethylene-2,3:7,6-bis(2,',3'-quinolino)tetracyclo<6.3.0.04,11.05,9>undecane dibromide (131251-79-1)

Conditions	Yield
at 120℃; for 36h;	100%

1,3-dibromo-propane (109-64-8) + 4-methyl-4'-<2-(1H-pyrrol-1-yl)ethyl>-2,2'-bipyridine (104119-85-9) → 4-methyl-4'-<2-(1H-pyrrol-1-yl)ethyl>-N,N'-(trimethylene)-2,2'-bipyridinium dibromide

Conditions	Yield
at 100℃; for 24h;	100%

p-Chlorothiophenol (106-54-7) + 1,3-dibromo-propane (109-64-8) → (3-bromopropyl)(4-chlorophenyl)sulfane (27983-06-8)

Conditions	Yield
With potassium carbonate In acetone at 80℃; for 48h;	100%
With potassium carbonate; potassium iodide In acetone at 20℃;	56.3%
With potassium carbonate In acetonitrile at 70℃; for 16h;	40%

benzoimidazole (51-17-2) + 1,3-dibromo-propane (109-64-8) → 1,3-bis(N-benzimidazolyl)propane (39677-02-6)

Conditions	Yield
Stage #1: benzoimidazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: 1,3-dibromo-propane In tetrahydrofuran; mineral oil for 6h; Reflux; Inert atmosphere;	100%
Stage #1: benzoimidazole With sodium hydride In tetrahydrofuran at 0℃; Stage #2: 1,3-dibromo-propane In tetrahydrofuran	85%
	81%

1,3-dibromo-propane (109-64-8) + C39H50O5Si (206259-62-3) → [2-(4-{1-[4-(3-bromo-propoxy)-phenyl]-1-methyl-ethyl}-phenoxy)-1-(4-{1-[4-(3-bromo-propoxy)-phenyl]-1-methyl-ethyl}-phenoxymethyl)-ethoxy]-tert-butyl-dimethyl-silane (206259-63-4)

Conditions	Yield
With potassium carbonate In acetone Etherification;	100%

carbon disulfide (75-15-0) + 1,3-dibromo-propane (109-64-8) + acetylacetone (123-54-6) → 3‐(1,3-dithiane-2-yl)pentane-2,4-dione (55727-23-6)

Conditions	Yield
With potassium carbonate	100%
Stage #1: carbon disulfide; acetylacetone With tetrabutylammomium bromide; potassium carbonate In water at 20℃; Stage #2: 1,3-dibromo-propane In water at 20℃; for 8h;	92%
With potassium carbonate In N,N-dimethyl-formamide for 7h;	74%

2-mercaptoethylamine hydrochloride (156-57-0) + 1,3-dibromo-propane (109-64-8) → 3,7-dithianonane-1,9-diamine (57383-24-1)

Conditions	Yield
With sodium methylate In methanol at 40℃; for 10h; Inert atmosphere;	100%
With sodium methylate In methanol at 40℃; for 10h;	100%
With sodium methylate In methanol at 40℃; for 10h;	100%
With sodium hydrogencarbonate In ethanol for 3h; Substitution; Heating;
Stage #1: 2-mercaptoethylamine hydrochloride; 1,3-dibromo-propane With sodium methylate In methanol at 40℃; for 10h; Stage #2: With sodium hydroxide In water at 20℃; for 10h;

(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal (140647-02-5) + 1,3-dibromo-propane (109-64-8) → 1,1'-<<(propane-1,3-diyl)dioxy>bis<(2-nitro-5-methoxy-1,4-phenylene)carbonyl>>bis (140658-46-4)

Conditions	Yield
With potassium carbonate In acetone for 48h; Etherification; Heating;	100%
With potassium carbonate In acetone Heating;	93%

1,3-dibromo-propane (109-64-8) + methyl-(2S)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxylate (175409-49-1) → C31H36N4O14 (169258-71-3)

Conditions	Yield
With potassium carbonate In acetone for 48h; Heating;	100%

1,3-dibromo-propane (109-64-8) + 1-[2-(pyridin-2-ylamino)ethyl]-1H-pyridin-2-one (420807-07-4) → 1-[2-(2-oxo-2H-pyridin-1-yl)ethyl]-1,2,3,4-tetrahydropyrido[1,2-a]pyrimidin-5-ylium bromide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine for 18h; Heating;	100%

1,3-dibromo-propane (109-64-8) + 1-[2-(5-chloropyridin-2-ylamino)ethyl]-4-methyl-1H-pyridin-2-one (420807-11-0) → 7-chloro-1-[2-(4-methyl-2-oxo-2H-pyridin-1-yl)ethyl]-1,2,3,4-tetrahydropyrido[1,2-a]pyrimidin-5-ylium bromide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine for 18h; Heating;	100%

1,3-dibromo-propane (109-64-8) + C48H38N4O6P(1+)*F6P(1-) → bis(3-bromopropyloxy)[tetra-meso-(4-methoxyphenyl)porphyrinato]phosphorus(V) hexafluorophosphate

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 24h; Heating;	100%

1-methyl-1H-imidazole (616-47-7) + 1,3-dibromo-propane (109-64-8) → 1,1'-(propane-1,3-diyl)bis(3-methyl-1H-imidazol-3-ium) dibromide

Conditions	Yield
In tetrahydrofuran at 100℃;	100%
In methanol at 0 - 55℃; for 64h; Inert atmosphere;	98%
In acetonitrile at 20℃; for 168h;	97%

[1-(3-hydroxypropyl)imidazolidin-2-ylidene]methanesulfonylacetonitrile (904677-19-6) + 1,3-dibromo-propane (109-64-8) → [1-(3-bromopropyl)-3-(3-hydroxypropyl)imidazolidin-2-ylidene]methanesulfonylacetonitrile (904677-20-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 23h;	100%

3-isopropyl-7-ethyl-3,7-dihydropurine-2,6-dione + 1,3-dibromo-propane (109-64-8) → 1-(3-bromopropyl)-7-ethyl-3-isopropyl-3,7-dihydropurine-2,6-dione

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 100℃; for 3h;	100%

1,10-Phenanthroline (66-71-7) + 1,3-dibromo-propane (109-64-8) → 6,7-dihydro-5H-[1,4]diazepino[1,2,3,4-l,m,n][1,10]phenanthroline-4,8-diium dibromide (15302-99-5)

Conditions	Yield
In chlorobenzene at 70 - 120℃;	100%
In nitrobenzene at 120℃;	100%
for 12h; Reflux;	99%

4-Trifluoromethoxyphenol (828-27-3) + 1,3-dibromo-propane (109-64-8) → 1-(3-(4-trifluoromethoxy)phenoxy)propyl bromide (102793-82-8)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water at 70℃; for 48h;	100%
With potassium carbonate In N,N-dimethyl-formamide	60%

2-(Boc-amino)-3-methylphenol (177342-60-8) + 1,3-dibromo-propane (109-64-8) → [2-(3-bromo-propoxy)-6-methyl-phenyl]-carbamic acid tert-butyl ester (1070972-64-3)

Conditions	Yield
With potassium carbonate In acetonitrile at 55℃; for 2.5h;	100%

1,3-dibromo-propane (109-64-8) + (+)-(aR)-7,7'-dihydroxy-8,8'-biquinolyl (914288-77-0, 914288-78-1, 829666-42-4) → C21H16N2O2 (1062259-41-9)

Conditions	Yield
Stage #1: (-)-(aS)-7,7'-dihydroxy-8,8'-biquinolyl With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.416667h; Williamson synthesis; Stage #2: 1,3-dibromo-propane In N,N-dimethyl-formamide at 20℃; for 47h; Williamson synthesis;	100%

1-phenylphospholane (3302-87-2) + 1,3-dibromo-propane (109-64-8) → 1,3-bis(phenylphospholanium)propane dibromide

Conditions	Yield
In acetonitrile at 60℃; for 48h; Inert atmosphere;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1,3-dibromo-propane (109-64-8) → 1,1''-(propane-1,3-diyl)bis(1,4-diazabicyclo[2.2.2]-octan-1-ium)dibromide (97497-67-1)

Conditions	Yield
In methanol at 20℃; for 24h;	100%
In methanol at 20℃; for 20h;	97%
In acetonitrile at 20℃; for 24h;	74%

1-Butylimidazole (4316-42-1) + 1,3-dibromo-propane (109-64-8) → 1,3-bis(3-butylimidazolium-1-yl)propane dibromide

Conditions	Yield
In tetrahydrofuran at 100℃;	100%
In acetonitrile for 72h; Reflux;	86%
In acetonitrile at 20℃; for 24h; Reflux;	85%

(2S)-N-benzyl-2-(1H-imidazol-1-yl)-2,3-dimethylbutanamide (1234494-18-8) + 1,3-dibromo-propane (109-64-8) → 3,3'-(1,3-propanediyl)bis(1-{(1S)-1-[(benzylamino)carbonyl]-1,2-dimethylpropyl}-3H-imidazol-1-ium) dibromide

Conditions	Yield
In toluene; acetonitrile at 100℃; Inert atmosphere;	100%

Upstream product

• 74-85-1 ethene 
• 74-95-3 1,1-dibromomethane 
• 111-35-3 3-ethoxy-1-propanol 
• 10035-10-6 hydrogen bromide 
• 588-63-6 3-phenoxypropyl bromide 
• 7726-95-6 bromine 
• 75-19-4 cyclopropane 
• 64-17-5 ethanol 
• 106-95-6 allyl bromide 
• 110-46-3 isopentyl nitrite 
• 591-87-7 Allyl acetate 
• 74-96-4 ethyl bromide 
• 7727-15-3 aluminium bromide 
• 142-28-9 1,3-Dichloropropane 

Downstream Products

• 5721-43-7 hexahydro-pyrazolo[1,2-a]pyridazine 
• 3661-15-2 octahydro-pyridazino[1,2-a]pyridazine 
• 14208-07-2 [1,1'-(propane-1,3-diyl)-bis(pyridinium)] dibromide 
• 6270-87-7 Trimethylenbis-2,2'-isochinolindibromid 
• 78186-39-7 2-{3-[4-(hydroxyimino-methyl)-pyridinio]-propyl}-isoquinolinium; dibromide 
• 7702-61-6 3,12-dioxa-6,9-diazonia-dispiro[5.2.5.3]heptadecane; dibromide 
• 342786-08-7 3,3'-diphenyl-2,3,2',3'-tetrahydro-2,2'-propanediyl-bis-phthalazine-1,4-dione 
• 33952-37-3 N,N'-di-p-tolyl-propanediyldiamine 
• 3722-80-3 1,3-bis(4-formylphenoxy)propane 
• 483342-82-1 N¹,N³-bis(4-chlorophenyl)propane-1,3-diamine 
• 7216-18-4 3,4-dihydro-2H-benzo[b][1,4]dioxepine 
• 42397-72-8 1,3-bis(2-hydroxyphenoxy)propane 
• 59400-11-2 1,3-bis(2'-carboxyphenylamine)propane 
• 14002-33-6 bis-(3-hydroxypropyl)amine 

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