821-10-3

Basic information

• Product Name: 1,4-Dichloro-2-butyne
• Synonyms: 1,4-DICHLORO-2-BUTYNE;1,4-dichloro-2-butyn;1,4-dichloro-but-2-yne;1,4-Dichlorobutyne;Dichlorobutyne;2-Butyne, 1,4-dichloro-;bis(chloromethyl)acetylene;1,4-Dichloro-2-butyne,99%
• CAS NO: 821-10-3
• Molecular Formula: C₄H₄Cl₂
• Molecular Weight: 122.98
• EINECS: 212-474-8
• Product Categories: Acetylenes;Functionalized Acetylenes;Alkynyl;Halogenated Hydrocarbons;Organic Building Blocks;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 821-10-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 162-165 °C
• Boiling Point: 165-168 °C(lit.)
• Flash Point: 320 °F
• Appearance: /
• Density: 1.258 g/mL at 25 °C(lit.)
• Vapor Pressure: 9.56mmHg at 25°C
• Refractive Index: n20/D 1.505(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Sensitive: Light Sensitive
• BRN: 635740
• CAS DataBase Reference: 1,4-Dichloro-2-butyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dichloro-2-butyne(821-10-3)
• EPA Substance Registry System: 1,4-Dichloro-2-butyne(821-10-3)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-40-23/24/25
• Safety Statements: 26-36-45-38-36/37/39-28A
• RIDADR: UN 2810
• WGK Germany: 3
• RTECS: ER9600000
• F: 8-10
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 821-10-3(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLORLESS TO YELLOWISH LIQUID

Uses

1,4-Dichloro-2-butyne used in the synthesis of 1,4-disubstituted 1,2,3-triazoles. Also, it is used in the approach of the 20S-camptothecin family of antitumor agents.

Safety Profile

Poison by intravenous route. When heated to decomposition it emits toxic fumes of Cl-. Probably a dangerous fKe and explosion hazard. See also ACETYLENE COMPOUNDS and CHLORINATED HYDROCARBONS, ALIPHATIC

InChI:InChI=1/C4H4Cl2/c5-3-1-2-4-6/h1,3H2

Synthetic route

1,4-dihydroxybut-2-yne (110-65-6) → 1,4-Dichloro-2-butyne (821-10-3)

Conditions	Yield
With pyridine; thionyl chloride	84%
With thionyl chloride In pyridine	82%
With pyridine; thionyl chloride at 0 - 20℃; for 2h;	56%

but-2-yne-1,4-bisoxycarbonylchloride (16669-40-2) → 1,4-Dichloro-2-butyne (821-10-3)

Conditions	Yield
With N,N-dimethyl-formamide In 1,2-dichloro-ethane at 80℃;	76%

1,4-dihydroxybut-2-yne (110-65-6) → 4-chlorobut-2-yn-1-ol (13280-07-4) + 1,4-Dichloro-2-butyne (821-10-3)

Conditions	Yield
With thionyl chloride; triethylamine In dichloromethane at 10 - 20℃;	A 54% B 18%
With pyridine; thionyl chloride In benzene at 10 - 20℃; for 6h;	A 49% B 24%
With pyridine; thionyl chloride In benzene at 0 - 20℃;	A 40% B 17%
With pyridine; thionyl chloride In benzene at 0 - 20℃;	A 35% B n/a
With pyridine; thionyl chloride In benzene 1) 10 - 20 deg C, 7 h, 2) overnight;	A 26% B 30%

pyridine (110-86-1) + 1,4-dihydroxybut-2-yne (110-65-6) + thionyl chloride (7719-09-7) → 1,4-Dichloro-2-butyne (821-10-3)

Conditions	Yield
at 10 - 20℃;

1,4-dihydroxybut-2-yne (110-65-6) + phosphorus pentachloride (10026-13-8, 874483-75-7) + benzene (71-43-2) → 1,4-Dichloro-2-butyne (821-10-3)

1,4-dihydroxybut-2-yne (110-65-6) + SOCl2 (excess) → 1,4-Dichloro-2-butyne (821-10-3)

Conditions	Yield
at 80℃;

1,4-dihydroxybut-2-yne (110-65-6) + hydrogenchloride (7647-01-0) + acetic acid (64-19-7) → (Z)-2,4-dichloro-but-2-en-1-ol (7166-52-1) + 3,4-dichloro-but-2-en-1-ol (16346-49-9) + 1,4-Dichloro-2-butyne (821-10-3)

Conditions	Yield
at 100 - 110℃;

triethylsilane (617-86-7) + 1,4-Dichloro-2-butyne (821-10-3) → 1,4-dichloro 2-triethylsilylbut-2-ene (108930-44-5)

Conditions	Yield
With dihydrogen hexachloroplatinate In tetrahydrofuran at 85℃; for 4h;	100%
With platinum(IV) oxide In toluene at 100℃; for 24h; diastereoselective reaction;	75%
dihydrogen hexachloroplatinate
With dihydrogen hexachloroplatinate at 170℃; for 1h;

Phenylselenyl chloride (5707-04-0) + 1,4-Dichloro-2-butyne (821-10-3) → (E)-2-(Phenylseleno)-1,3,4-trichlorobut-2-ene (85972-08-3)

Conditions	Yield
In acetonitrile at 25℃; for 20h;	100%

1,4-Dichloro-2-butyne (821-10-3) → 1,2,3,4,5-pentakis(chloromethyl)-5-(1'-chlorovinyl)cyclopentadiene

Conditions	Yield
With copper dichloride; palladium dichloride In butan-1-ol; benzene at 25℃; for 24h;	100%
With copper dichloride; palladium dichloride In methanol; carbon dioxide at 40℃; under 120012 Torr; for 8h;	98%

1-methyl-1H-imidazole (616-47-7) + 1,4-Dichloro-2-butyne (821-10-3) → 3,3′-(but-2-yne-1,4-diyl)bis(1-methyl-1H-imidazol-3-ium) chloride

Conditions	Yield
In neat (no solvent) Sonication;	100%
In acetonitrile at 80℃; for 24h;	86%

3-thiapentan-1,5-dithiol (3570-55-6) + 1,4-Dichloro-2-butyne (821-10-3) → 1,4,7-trithiacycloundec-9-yne (158548-70-0)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 5h;	99.7%

potassium phenyl selenide (40973-72-6) + 1,4-Dichloro-2-butyne (821-10-3) → 1,4-bis(phenylselanyl)but-2-yne (13597-13-2)

Conditions	Yield
With hydrazine hydrate; potassium hydroxide at 25℃; for 2.5h; Temperature;	99%

1,4-Dichloro-2-butyne (821-10-3) + benzenesulfenyl chloride (931-59-9) → (E)-phenyl(1,3,4-trichlorobut-2-en-2-yl)sulfane (85972-06-1)

Conditions	Yield
In acetonitrile at 25℃; for 1h;	98%
In acetonitrile at 25℃; for 3h;	98%

allyl alcohol (107-18-6) + 1,4-Dichloro-2-butyne (821-10-3) → (Z)-5,6-dichloro-4-(chloromethyl)hexa-1,4-diene

Conditions	Yield
With 1-(carboxymethyl)-3-methylimidazolium chloride; hydrogenchloride; palladium dichloride In water at 20℃; for 12h; diastereoselective reaction;	98%
With acetic acid; palladium dichloride In water at 20℃; for 6h;	91%

(2-propenyl)propanedioic acid diethyl ester (2049-80-1) + 1,4-Dichloro-2-butyne (821-10-3) → tetraethyl dodeca-1,11-dien-6-yne-4,4,9,9-tetracarboxylate (1193378-70-9)

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; Stage #2: 1,4-Dichloro-2-butyne In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃;	98%

Ph4P{MoCl(CO)3(1,10-phenanthroline)} (67870-32-0, 156926-44-2) + 1,4-Dichloro-2-butyne (821-10-3) → MoCl(CO)2(1,10-phenanthroline)(η(3)-CH2C(COCl)C=CH2) (156842-95-4)

Conditions	Yield
In water N2; stirring aq. suspn. of Mo complex with alkyne for 0.5 h; decantation, washing the residue with minimum cold water, drying at 50°C;	97.7%
In chloroform treatment of Mo-complex with excess ClCH2CCCH2Cl in CHCl3 at 20°C; high yield, elem. anal.;

1,4-Dichloro-2-butyne (821-10-3) → trans-2,3-dibromo-1,4-dichloro-2-butene (85415-22-1)

Conditions	Yield
With bromine In tetrachloromethane at 20℃; for 4h;	97%
With bromine In tetrachloromethane at 25℃; for 4h;	94%

N-allyl-o-nitrobenzenesulfonamide (65118-17-4) + 1,4-Dichloro-2-butyne (821-10-3) → N,N'-(but-2-yn-1,4-diyl)-bis-(N-allyl-2-nitrobenzenesulfonamide)

Conditions	Yield
With potassium carbonate In acetonitrile for 48h; Reflux;	97%

1,4-Dichloro-2-butyne (821-10-3) + bis(2-mercaptoethyl)ether (2150-02-9) → 1,7-dithia-4-oxa-cycloundec-9-yne (153615-60-2)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 5h;	95%

1,4-Dichloro-2-butyne (821-10-3) → (Z)-2-bromo-1,4-dichloro-2-butene

Conditions	Yield
With hydrogen bromide In acetic acid for 12h; Ambient temperature;	95%

potassium benzenemethanethiolate (61671-44-1) + 1,4-Dichloro-2-butyne (821-10-3) → 1,4-bis(benzylsulfanyl)but-2-yne (86737-77-1)

Conditions	Yield
With hydrazine hydrate; potassium hydroxide at 25℃; for 2.5h; Temperature;	95%

1,3-dimethyl-5-hydroxyuracil (20406-86-4) + 1,4-Dichloro-2-butyne (821-10-3) → 5-(4-Chloro-but-2-ynyloxy)-1,3-dimethyl-1H-pyrimidine-2,4-dione

Conditions	Yield
With potassium carbonate In acetone for 10h; Heating;	94%

water+2 + Octanethiol (111-88-6) + 1,4-Dichloro-2-butyne (821-10-3) → 1-chloro-5-thia-2-tridecyne (301648-86-2)

Conditions	Yield
With sodium methylate; sodium chloride In methanol	94%

1,4-Dichloro-2-butyne (821-10-3) → Butadiyne (460-12-8)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 70 - 75℃; into -78 deg C cooling trap;	93%
With potassium hydroxide In tetrahydrofuran; water; dimethyl sulfoxide at 95℃; for 0.25h;	90%
With potassium hydroxide Dehydrochlorination;	50%

Phenylselenyl bromide (34837-55-3) + 1,4-Dichloro-2-butyne (821-10-3) → (E)-2-(Phenylseleno)-3-bromo-1,4-dichlorobut-2-ene (85972-09-4)

Conditions	Yield
In dichloromethane at 40℃; for 120h;	93%

3,5-dichloro-6-phenyl-2(H)-1,4-oxazin-2-one (125850-00-2) + 1,4-Dichloro-2-butyne (821-10-3) → 2,6-dichloro-3,4-bis(chloromethyl)-5-phenylpyridine (163459-10-7)

Conditions	Yield
at 120℃; for 120h;	93%
at 100℃; Yield given;
at 80℃; for 240h; Diels-Alder reaction;

3,5-dichloro-2(H)-1,4-oxazin-2-one (125850-02-4) + 1,4-Dichloro-2-butyne (821-10-3) → 2,6-Dichloro-3,4-bis-chloromethyl-pyridine (182552-90-5)

Conditions	Yield
at 120℃; for 4h;	93%
In toluene for 120h; Heating;

WBrI(CO)3(NCCH3)2 (127340-84-5) + 1,4-Dichloro-2-butyne (821-10-3) → {W(μ-I)(CO)Br(NCMe)(η2-ClCH2C2CH2Cl)}2

Conditions	Yield
In dichloromethane N2-atmosphere; 1:1 molar ratio, stirring (4 h); filtration, solvent removal from filtrate (vac.), recrystn. (CH2Cl2); elem. anal.;	93%

1,4-Dichloro-2-butyne (821-10-3) + N-allyl-2-bromobenzenesulfonamide (851297-52-4) → N,N'-(but-2-yn-1,4-diyl)-bis-(N-allyl-2-bromobenzenesulfonamide)

Conditions	Yield
With potassium carbonate In acetonitrile for 48h; Reflux;	93%

tetraacetyl thioglucose (19879-84-6) + 1,4-Dichloro-2-butyne (821-10-3) → Acetic acid (2S,3S,4S,5R,6S)-3,5-diacetoxy-2-(2-oxo-propoxy)-6-[4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-but-2-ynylsulfanyl]-tetrahydro-pyran-4-yl ester (83476-61-3)

Conditions	Yield
With potassium carbonate In acetone for 1h;	92%

C7H7Se(1-)*K(1+) + 1,4-Dichloro-2-butyne (821-10-3) → 1,4-bis(benzylselanyl)but-2-yne

Conditions	Yield
With hydrazine hydrate; potassium hydroxide at 25℃; for 2.5h; Temperature;	92%

methyl 2-carbomethoxy-10-<(tetrahydro-2H-pyran-2-yl)oxy>-8-decynoate (114952-70-4) + 1,4-Dichloro-2-butyne (821-10-3) → 2-(4-Chloro-but-2-ynyl)-2-[8-(tetrahydro-pyran-2-yloxy)-oct-6-ynyl]-malonic acid dimethyl ester (114939-18-3)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 0.666667h; Heating;	91%

3,5-dichloro-6-methyl-2(H)-1,4-oxazin-2-one (125849-94-7) + 1,4-Dichloro-2-butyne (821-10-3) → 2,6-dichloro-3,4-bis(chloromethyl)-5-methylpyridine (163459-09-4)

Conditions	Yield
at 120℃; for 120h;	91%
at 100℃; Yield given;
In toluene for 120h; Heating;

dimethylmonochlorosilane (1066-35-9) + 1,4-Dichloro-2-butyne (821-10-3) → 1,4-dichloro-2-(chlorodimethyl)silyl-2-butene (99091-57-3)

Conditions	Yield
chloroplatinic acid In isopropyl alcohol	91%

2-ethynylpyridine (1945-84-2) + sodium azide + 1,4-Dichloro-2-butyne (821-10-3) → C18H14N8

Conditions	Yield
Stage #1: sodium azide; 1,4-Dichloro-2-butyne In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Stage #2: 2-ethynylpyridine With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; N,N-dimethyl-formamide at 20℃; for 17h; Inert atmosphere;	91%

tert-butylmagnesium chloride (677-22-5) + 1,4-Dichloro-2-butyne (821-10-3) → 2,3-di-tert-butyl-1,3-butadiene (3378-20-9)

Conditions	Yield
With copper(I) bromide In tetrahydrofuran at -20 - 0℃;	90%
In tetrahydrofuran	80%

Upstream product

• 110-65-6 1,4-dihydroxybut-2-yne 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 10026-13-8 phosphorus pentachloride 
• 71-43-2 benzene 
• 110-86-1 pyridine 
• 7719-09-7 thionyl chloride 
• 16669-40-2 but-2-yne-1,4-bisoxycarbonylchloride 

Downstream Products

• 51-73-0 1,4-di(pyrrolidin-1-yl)but-2-yne 
• 7498-32-0 1,4-di(piperidin-1-yl)but-2-yne 
• 53878-96-9 but-2-yne-1,4-diamine 
• 84814-02-8 4-chloro-1-(2-methylphenyloxy)but-2-yne 
• 32788-92-4 1-Phenyl-pentadiin-(2,4)-ol-⁽¹⁾ 
• 14272-28-7 1.4-Bis--but-2-in 
• 72290-54-1 N,N-bis-(4-chloro-but-2-ynyl)-4-methyl-aniline 
• 72290-52-9 N,N-bis(4'-chloro-2'-butynyl)-p-anisidine 
• 4200-28-6 1,4-Bis-(p-Methoxy-phenoxy)-but-2-in 
• 41229-90-7 1,4-Bis-(3,4-dimethylphenoxy)-2-butin 
• 4200-18-4 1,4-bis(4-methylphenoxy)-2-butyne 
• 59521-22-1 1,4-Bis-(2,4-dimethylphenoxy)-2-butin 
• 56163-31-6 1,4-Bis-(2-methylphenylthio)-2-butin 
• 108054-33-7 3-methylene-1-phenylpent-4-en-2-ol 

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