926-57-8

Basic information

• Product Name: 1,3-DICHLORO-2-BUTENE
• Synonyms: 1,3-dichlorobutylene;2-Butene, 1,3-dichloro-;2-Butene,1,3-dichloro-;1,3-DICHLORO-2-BUTENE;1,3-Dichloro-2-butene isomers;1,3-dichloro-2-butene, cis + trans;1,3-Dichlor-2-butene;Isomerengemisch
• CAS NO: 926-57-8
• Molecular Formula: C₄H₆Cl₂
• Molecular Weight: 125
• EINECS: 213-138-3
• Mol File: 926-57-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: -27.02°C (estimate)
• Boiling Point: 125-129 °C
• Flash Point: 33 °C
• Appearance: /
• Density: 1.16
• Vapor Pressure: 11.2mmHg at 25°C
• Refractive Index: 1.469-1.473
• Storage Temp.: 0-6°C
• Water Solubility: Insoluble in water
• Sensitive: Moisture Sensitive
• BRN: 906754
• CAS DataBase Reference: 1,3-DICHLORO-2-BUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DICHLORO-2-BUTENE(926-57-8)
• EPA Substance Registry System: 1,3-DICHLORO-2-BUTENE(926-57-8)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20-10
• Safety Statements: 37/39-26
• RIDADR: 1993
• RTECS: EM4760000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 926-57-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 1039, 1949 DOI: 10.1021/ja01171a076

InChI:InChI=1/C4H6Cl2/c1-4(6)2-3-5/h2H,3H2,1H3/b4-2+

Synthetic route

3-buten-1-yne (689-97-4) → chloroprene (126-99-8) + 1,3-dichloro-2-butene (926-57-8)

Conditions	Yield
With hydrogenchloride; ammonium chloride; copper(l) chloride at 30℃;
With hydrogenchloride; ammonium chloride; copper(l) chloride at 30℃;
With hydrogenchloride; ammonium chloride; copper(l) chloride at 30℃;

2-bromo-1,3-butadiene (1822-86-2) → 1,3-dichloro-2-butene (926-57-8)

Conditions	Yield
With hydrogenchloride; ammonium chloride; hydroquinone; copper(l) chloride

3-chloro-2-butenyl bromide (51430-83-2) → 1,3-dichloro-2-butene (926-57-8)

Conditions	Yield
With hydrogenchloride; ammonium chloride; copper(l) chloride

chloroprene (126-99-8) → 1,3-dichloro-2-butene (926-57-8)

Conditions	Yield
With hydrogenchloride; ammonium chloride; hydroquinone; copper(l) chloride

phosphorus pentachloride (10026-13-8, 874483-75-7) + methyl vinyl ketone (78-94-4) → 1,3-dichloro-2-butene (926-57-8)

Conditions	Yield
Kuehlung in Eis-Kochsalz-Mischung;

hydrogenchloride (7647-01-0) + ammonium chloride + chloroprene (126-99-8) + CuCl → 1,3-dichloro-2-butene (926-57-8)

3-buten-1-yne (689-97-4) + hydrogenchloride (7647-01-0) + ammonium chloride + CuCl → 1,3-dichloro-2-butene (926-57-8)

Conditions	Yield
bei hoeheren Temperaturen oder hoeherer HCl-Konzentration;
bei hoeheren Temperaturen oder hoeherer HCl-Konzentration;

3-buten-1-yne (689-97-4) + hydrogenchloride (7647-01-0) + ammonium chloride + CuCl → chloroprene (126-99-8) + 1,3-dichloro-2-butene (926-57-8)

3-α-Naphthylpropargylpyrrolidine (125014-55-3) + 1,3-dichloro-2-butene (926-57-8) → 1-((Z)-3-Chloro-but-2-enyl)-1-(3-naphthalen-1-yl-prop-2-ynyl)-pyrrolidinium; chloride

Conditions	Yield
In acetonitrile	100%

1-(3-(naphthalen-1-yl)prop-2-ynyl)piperidine (125014-56-4) + 1,3-dichloro-2-butene (926-57-8) → 1-((Z)-3-Chloro-but-2-enyl)-1-(3-naphthalen-1-yl-prop-2-ynyl)-piperidinium; chloride

Conditions	Yield
In acetonitrile	100%

4-(3-(naphthalen-1-yl)prop-2-ynyl)morpholine (125014-57-5) + 1,3-dichloro-2-butene (926-57-8) → 4-((Z)-3-Chloro-but-2-enyl)-4-(3-naphthalen-1-yl-prop-2-ynyl)-morpholin-4-ium; chloride

Conditions	Yield
In acetonitrile	100%

dimethyl-3-α-naphthylpropargylamine (97289-01-5) + 1,3-dichloro-2-butene (926-57-8) → ((Z)-3-Chloro-but-2-enyl)-dimethyl-(3-naphthalen-1-yl-prop-2-ynyl)-ammonium; chloride

Conditions	Yield
In acetonitrile	100%

3-(diethylamino)-1-(naphthalen-1-yl)propyne (97289-02-6) + 1,3-dichloro-2-butene (926-57-8) → ((Z)-3-Chloro-but-2-enyl)-diethyl-(3-naphthalen-1-yl-prop-2-ynyl)-ammonium; chloride

Conditions	Yield
In acetonitrile	100%

1,3-dichloro-2-butene (926-57-8) + 4-benzyloxy-2-(tert-butyloxycarbonylamino)-1-iodo-5,6,7,8-tetrahydronaphthalene (452921-69-6) → (4-benzyloxy-1-iodo-5,6,7,8-tetrahydro-naphthalen-2-yl)-(3-chloro-but-2-enyl)-carbamic acid tert-butyl ester (452921-85-6)

Conditions	Yield
Stage #1: 4-benzyloxy-2-(tert-butyloxycarbonylamino)-1-iodo-5,6,7,8-tetrahydronaphthalene With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,3-dichloro-2-butene In N,N-dimethyl-formamide at 20℃; for 14h; Further stages.;	99%

tert-butyl (4-(benzyloxy)-1-iodonaphthalen-2-yl)carbamate (161646-53-3) + 1,3-dichloro-2-butene (926-57-8) → (E/Z)-2-amino-4-benzyloxy-N-(tert-butyloxycarbonyl)-N-(3-chloro-2-butenyl)-1-iodonaphthalene

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;	98%

p-bis(3-piperidinopropyl-1-yl)benzene (7119-44-0) + 1,3-dichloro-2-butene (926-57-8) → p-bis{[N-(3-chlorobuten-2-yl)piperidino]propyn-1-yl}benzene dichloride

Conditions	Yield
In acetonitrile; benzene at 20℃; for 72h;	97%

p-bis(3-morpholinopropyn-1-yl)benzene (7119-40-6) + 1,3-dichloro-2-butene (926-57-8) → p-bis{[N-(3-chlorobuten-2-yl)morpholinio]propyn-1-yl}benzene dichloride

Conditions	Yield
In acetonitrile; benzene at 20℃; for 72h;	97%

1,4-bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]benzene + 1,3-dichloro-2-butene (926-57-8) → p-bis{[N-(3-chlorobuten-2-yl)pyrrolidino]propyn-1-yl}benzene dichloride

Conditions	Yield
In acetonitrile; benzene at 20℃; for 72h;	97%

indole-2,3-dione (91-56-5) + 1,3-dichloro-2-butene (926-57-8) → 1-((Z)-3-Chloro-but-2-enyl)-1H-indole-2,3-dione (86106-82-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h;	96%

3-methyl-1-(phenylsulfonyl)but-2-ene (15874-80-3) + 1,3-dichloro-2-butene (926-57-8) → ((E)-7-Chloro-2-methyl-octa-2,6-diene-4-sulfonyl)-benzene (62692-34-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -70℃;	96%

N-tert-butoxycarbonyl-4-benzyloxy-6-cyano-1-bromo-2-naphthylamine (1262394-22-8) + 1,3-dichloro-2-butene (926-57-8) → (E/Z)-2-amino-4-benzyloxy-1-bromo-N-tert-butoxycarbonyl-N-(3-chlorobut-2-enyl)-6-cyanonaphthalene

Conditions	Yield
Stage #1: N-tert-butoxycarbonyl-4-benzyloxy-6-cyano-1-bromo-2-naphthylamine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Stage #2: 1,3-dichloro-2-butene In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	96%

1,3-dichloro-2-butene (926-57-8) → (E,Z)-3-chloro-but-2-enyliodide (54201-06-8)

Conditions	Yield
With sodium iodide In acetone at 20℃; for 0.333333h;	95%
With sodium iodide In acetonitrile for 1h;	80%
With sodium iodide In acetone
With sodium iodide In N,N-dimethyl-formamide for 6h; Ambient temperature;	3.7 g

2-butyl-4-chloro-6-fluoro-5-methoxyindan-1-one (371757-71-0) + 1,3-dichloro-2-butene (926-57-8) → (S)-9a-butyl-8-chloro-6-fluoro-7-methoxy-1,2,9,9a-tetrahydrofluoren-3-one + (R)-9a-butyl-8-chloro-6-fluoro-7-methoxy-1,2,9,9a-tetrahydrofluoren-3-one

Conditions	Yield
Stage #1: 2-butyl-4-chloro-6-fluoro-5-methoxyindan-1-one; 1,3-dichloro-2-butene With sodium hydroxide In toluene at 10℃; for 30h; Stage #2: With sulfuric acid In water; toluene at 0 - 65℃; Further stages. Title compound not separated from byproducts.;	A 95% B n/a

1,3-dichloro-2-butene (926-57-8) → 3-chloro-2-buten-1-ol (37428-46-9, 37428-53-8, 40605-42-3)

Conditions	Yield
With water; sodium carbonate at 89 - 98℃; for 8h;	94.2%
With sodium carbonate for 3h; Heating;	63%

1,3-dichloro-2-butene (926-57-8) → 1,2,3,3-tetrachlorobutane (13138-51-7) + 1,2,2,3,4-pentachlorobutane (2431-52-9)

Conditions	Yield
With chlorine at 75℃; for 0.66h;	A 94% B 8%
With chlorine at -20℃; for 11h;	A 10% B 90%

5-fluoro-2-propyl-indan-1-one + 1,3-dichloro-2-butene (926-57-8) → 2-((E)-3-Chloro-but-2-enyl)-5-fluoro-2-propyl-indan-1-one

Conditions	Yield
With N-[4-(trifluoromethyl)benzyl]cinchoninium bromide In sodium hydroxide; toluene at 20℃;	94%

diphenylphosphane (829-85-6) + 1,3-dichloro-2-butene (926-57-8) → 3-chloro-1-(diphenylphosphino)-2-butene (129145-76-2)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 1h; Ambient temperature;	92.3%

2-propylindan-1-one (92013-10-0) + 1,3-dichloro-2-butene (926-57-8) → 2-((E)-3-Chloro-but-2-enyl)-2-propyl-indan-1-one

Conditions	Yield
With N-[4-(trifluoromethyl)benzyl]cinchoninium bromide In sodium hydroxide; toluene at 20℃;	92%

C15H22N2 (1285636-78-3) + 1,3-dichloro-2-butene (926-57-8) → C18H28ClN

Conditions	Yield
Stage #1: C15H22N2 With lithium dihydronaphthylide radical In tetrahydrofuran at -40℃; for 0.666667h; Inert atmosphere; Stage #2: 1,3-dichloro-2-butene In tetrahydrofuran at -40 - 20℃; for 16h; Inert atmosphere;	92%

5-methyl-indole-2,3-dione (608-05-9) + 1,3-dichloro-2-butene (926-57-8) → 1-((Z)-3-Chloro-but-2-enyl)-5-methyl-1H-indole-2,3-dione (86106-83-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h;	91%

5-chloro-2-propyl-indan-1-one + 1,3-dichloro-2-butene (926-57-8) → 5-Chloro-2-((E)-3-chloro-but-2-enyl)-2-propyl-indan-1-one

Conditions	Yield
With N-[4-(trifluoromethyl)benzyl]cinchoninium bromide In sodium hydroxide; toluene at 20℃;	90%

5-methyl-2-propyl-indan-1-one + 1,3-dichloro-2-butene (926-57-8) → 2-((E)-3-Chloro-but-2-enyl)-5-methyl-2-propyl-indan-1-one

Conditions	Yield
With N-[4-(trifluoromethyl)benzyl]cinchoninium bromide In sodium hydroxide; toluene at 20℃;	88%

(1S,3aS,7aS)-1-(1,1-dimethylethoxy)octahydro-7a-methyl-5H-inden-5-one (59974-82-2, 61490-25-3, 61490-26-4, 80374-04-5, 53662-92-3) + 1,3-dichloro-2-butene (926-57-8) → (1S,3aS,6R,7aS)-6-(3-chloro-2-butenyl)-1-(1,1-dimethylethoxy)octahydro-7a-methyl-5H-inden-5-one (944796-95-6)

Conditions	Yield
Stage #1: (1S,3aS,7aS)-1-(1,1-dimethylethoxy)octahydro-7a-methyl-5H-inden-5-one With potassium hexamethylsilazane In tetrahydrofuran; toluene for 0.5h; Stage #2: 1,3-dichloro-2-butene With triethyl borane; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at -78 - 20℃; Further stages.;	88%

Bis(phenylethinyl)magnesium (6928-78-5) + 1,3-dichloro-2-butene (926-57-8) → 1-phenyl-5-chlorohex-4-en-1-yne (115198-06-6)

Conditions	Yield
copper(l) chloride In tetrahydrofuran at 40℃; for 4h;	87%

5-Methoxy-2-propyl-indan-1-one (101375-37-5) + 1,3-dichloro-2-butene (926-57-8) → 2-((E)-3-Chloro-but-2-enyl)-5-methoxy-2-propyl-indan-1-one

Conditions	Yield
With N-[4-(trifluoromethyl)benzyl]cinchoninium bromide In sodium hydroxide; toluene at 20℃;	86%

NH-pyrazole (288-13-1) + 1,3-dichloro-2-butene (926-57-8) → (E)-1-(3-chlorobut-2-en-1-yl)-1H-pyrazole + C7H9ClN2

Conditions	Yield
With 4-methylmorpholine N-oxide; sodium hydroxide In water at 50℃; for 3.5h; Reagent/catalyst; Green chemistry;	A 84% B n/a

1,3-dichloro-2-butene (926-57-8) → methylphosphonic acid dichloroanhydride (676-97-1) + 1,2-dichloroethyl phosphorodichloridate (34838-28-3) + acetyl chloride (75-36-5) + chloromethylphosphonic dichloride (1983-26-2) + phosphoryl chloride

Conditions	Yield
With oxygen; phosphorus trichloride at -10 - 10℃; Product distribution; Mechanism;	A n/a B 80% C n/a D n/a E n/a
With oxygen; phosphorus trichloride at -10 - 10℃; Title compound not separated from byproducts;	A n/a B 80% C n/a D n/a E n/a
With oxygen; phosphorus trichloride at -10 - 10℃;	A n/a B 80% C n/a D n/a E n/a

diheptinylmagnesium (105826-09-3) + 1,3-dichloro-2-butene (926-57-8) → (E)-2-Chloro-undec-2-en-5-yne (115198-07-7)

Conditions	Yield
copper(l) chloride In tetrahydrofuran at 40℃; for 4h;	73%

Upstream product

• 126-99-8 chloroprene 
• 689-97-4 3-buten-1-yne 
• 7647-01-0 hydrogenchloride 
• 10026-13-8 phosphorus pentachloride 
• 78-94-4 methyl vinyl ketone 
• 51430-83-2 3-chloro-2-butenyl bromide 
• 1822-86-2 2-bromo-1,3-butadiene 

Downstream Products

• 100792-54-9 5-(3-chloro-but-2-enyl)-5-cyclohexyl-barbituric acid 
• 10561-01-0 4-(3-chloro-but-2-enyl)-1,2-diphenyl-pyrazolidine-3,5-dione 
• 939-60-6 2-(3¹-chloro-2¹-butenyl)-1-cyclohexanone 
• 99191-48-7 (3-chloro-but-2-enyl)-cyclohexyl-amine 
• 100129-40-6 N-(3-chloro-but-2-enyl)-p-anisidine 
• 51637-56-0 (3-chloro-but-2-enyl)-phenyl sulfide 
• 4071-75-4 2-Methyl-2-(3-chloro-2-butenyl)cyclohexanone 
• 28066-56-0 4-(3-chloro-but-2-enyl)-anisole 
• 100141-27-3 N-ethyl-N-(3-chloro-but-2-enyl)-aniline 
• 105902-41-8 3-chloro-1-(2,4-dimethyl-phenyl)-but-2ξ-ene 
• 99359-66-7 N-(3-chloro-but-2-enyl)-aniline 
• 92295-01-7 N,N-bis-(3-chloro-but-2-enyl)-aniline 
• 28066-57-1 2-(3-chloro-but-2-enyl)-anisole 
• 67894-91-1 1-(3-chlor-2-buten-1-yl)-2-hydroxy-cyclohexancarbonsaeureaethylester