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2-Butyne-1,4-diol

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Name

2-Butyne-1,4-diol

EINECS 203-788-6
CAS No. 110-65-6 Density 1.181 g/cm3
PSA 40.46000 LogP -1.02560
Solubility 3740 g/L (20 °C) in water Melting Point 54 °C
Formula C4H6O2 Boiling Point 260.202 °C at 760 mmHg
Molecular Weight 86.0904 Flash Point 135.558 °C
Transport Information UN 2716 6.1/PG 3 Appearance white to light-brown solid or brownish-yellow aqueous solution
Safety 25-26-36/37/39-45-46 Risk Codes 21-23/25-34-43-48/22
Molecular Structure Molecular Structure of 110-65-6 (2-Butyne-1,4-diol) Hazard Symbols ToxicT,CorrosiveC
Synonyms

1,4-Butynediol;1,4-Dihydroxy-2-butyne;2-Butynediol;Bis(hydroxymethyl)acetylene;Butynediol;NSC 834;2-Btyne-1,4-diol;

Article Data 72

2-Butyne-1,4-diol Synthetic route

62994-00-7

(E)-2,3-diiodobut-2-ene-1,4-diol

110-65-6

1,4-dihydroxybut-2-yne

Conditions
ConditionsYield
With pyrrolidine for 15h; Sonication;100%
With tetra-(n-butyl)ammonium iodide In [(2)H6]acetone at 25℃; for 48h; Inert atmosphere; Reflux;
186697-76-7

2,3-dibromo-2(E)-butenylene diacetate

110-65-6

1,4-dihydroxybut-2-yne

Conditions
ConditionsYield
With samarium In methanol for 1h; Ambient temperature;94%
163591-85-3

1,4-bis-(tert-butyl-dimethyl-silanyloxy)-but-2-yne

110-65-6

1,4-dihydroxybut-2-yne

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In methanol for 0.5h;94%
With acetyl chloride In methanol for 0.116667h;87%
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.116667h;85%
92372-45-7

2,2'-[2-butyne-1,4-diylbis(oxy)]bis(tetrahydro-2H-pyran)

110-65-6

1,4-dihydroxybut-2-yne

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In methanol at 20℃; for 0.33h;92%
With trichloroisocyanuric acid In methanol at 20℃; for 6h;91%
With ethane-1,2-dithiol; nickel dichloride In methanol; dichloromethane at 20℃; for 0.666667h;76%

1-tert-butyldimethylsilyloxy-4-triethylsilyloxy-2-butyne

A

110-65-6

1,4-dihydroxybut-2-yne

B

86120-46-9

4-(tert-butyldimethylsilyloxy)-2-butyn-1-ol

Conditions
ConditionsYield
With MCM-41 In methanol for 4h; Ambient temperature;A 6%
B 85%
With mesoporous silica MCM-41 In methanol at 20℃; for 4h;A 6%
B 85%
1573-17-7

2-butyn-1,4-diol diacetate

A

110-65-6

1,4-dihydroxybut-2-yne

B

83466-88-0

4-acetoxy-2-butyn-1-ol

Conditions
ConditionsYield
1,3-disubstituted tetraalkyldistannoxane (X = Y = Cl) In methanol; chloroform for 24h; Ambient temperature;A 49%
B 46%
p-formaldehyde

p-formaldehyde

107-19-7

propargyl alcohol

74-86-2

acetylene

110-65-6

1,4-dihydroxybut-2-yne

Conditions
ConditionsYield
Stage #1: propargyl alcohol With potassium hydride In tetrahydrofuran at 30℃; under 759.826 Torr; for 0.25h;
Stage #2: p-formaldehyde; acetylene In tetrahydrofuran at 10℃; under 759.826 Torr; for 1.25h;
20%
110-88-3

1,3,5-Trioxan

4301-15-9

ethynyldimagnesium dibromide

110-65-6

1,4-dihydroxybut-2-yne

3234-02-4

2,3-dibromo-but-2-ene-1,4-diol

110-65-6

1,4-dihydroxybut-2-yne

Conditions
ConditionsYield
With ethanol; zinc
50-00-0

formaldehyd

107-19-7

propargyl alcohol

110-65-6

1,4-dihydroxybut-2-yne

Conditions
ConditionsYield
With copper(I) monacetylide at 100℃; under 14710.2 Torr;

2-Butyne-1,4-diol Chemical Properties

Molecular structure of 2-Butyne-1,4-diol (CAS NO.110-65-6) is:

Product Name: 2-Butyne-1,4-diol
CAS Registry Number: 110-65-6
IUPAC Name: but-2-yne-1,4-diol
Molecular Weight: 86.08924 [g/mol]
Molecular Formula: C4H6O2
XLogP3-AA: -1.1
H-Bond Donor: 2
H-Bond Acceptor: 2 
EINECS: 203-788-6
Melting Point: 54 °C 
Refractive index: 1.4804
Storage temp.: Refrigerator
Water Solubility: 3740 g/L (20 ºC)
Stability: Stable. Highly flammable solid. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, strong acids, strong bases.  
Surface Tension: 60.086 dyne/cm
Density: 1.181 g/cm3
Flash Point: 135.558 °C
Enthalpy of Vaporization: 57.827 kJ/mol
Boiling Point: 260.202 °C at 760 mmHg
Vapour Pressure: 0.002 mmHg at 25°C
Product Categories: Pharmaceutical Intermediates;Acetylenes;Acetylenic Alcohols & Their Derivatives;Alkynes;Internal;Organic Building Blocks

2-Butyne-1,4-diol Uses

 2-Butyne-1,4-diol (CAS NO.110-65-6) is a precursor to 1,4-butanediol.It can be used in the manufacture of plant protection agents, pesticides, textile additives, corrosion inhibitors, platicizers, synthetic resins, and polyurethanes.Also it is the major raw material of vitamin B6. And it is also used for brightening, preserving, and inhibiting nickel plating. 2-Butyne-1,4-diol (CAS NO.110-65-6) produced is consumed in the manufacture of butanediol and butenediol. It undergoes the usual reactions of primary alcohols that contribute to its use as a chemical intermediate. Because of its rigid, linear structure, many reactions forming cyclic products from butanediol or cis-butenediol give only polymers with butynediol. Both hydroxyl groups can be esterified normally, and the monoesters are readily prepared as mixtures with diesters and unesterified butynediol, but care must be taken in separating them because the monoesters disproportionate easily.
The hydroxyl groups can be alkylated with the alkylating agents, although a reverse treatment is used to obtain aryl ethers; for example; treatment of butynediol toluene sulfonate or dibromobutyne with a phenol gives the corresponding ether. Reactions of 2-Butyne-1,4-diol with alkylene oxides give ether alcohols.
In the presence of acid catalysts, 2-Butyne-1,4-diol and aldehydes or acetals give polymeric acetals, useful intermediates for acetylenic polyurethanes suitable for high-energy solid propellants.
HOCH2C≡CCH2OH → HO(CH2C≡CCH2OCH2O)nH
Electrolytic oxidation gives acetylene dicarboxylic acid (2-butyne-dioic acid) in good yields. It can be hydrogenated partway to butenediol (HOCH2CH=CHCH2OH) or completely to butanediol(HOCH2CH2CH2CH2OH).

2-Butyne-1,4-diol Production

 2-Butyne-1,4-diol (CAS NO.110-65-6) was first synthesized in 1906 by reaction of acetylene bis(magnesium bromide) with paraformaldehyde.
    HC≡CH + 2HCH=O → HOCH2C≡CCH2OH
All manufacturers of butynediol(110-65-6) use this formaldehyde ethynylation process, and yields of butynediol may be in excess of 90 percent, in addition to 4 to 5% propargyl alcohol.
          HC≡CH + HCH=O → HC≡CH2OH

2-Butyne-1,4-diol Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 75mg/kg (75mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
guinea pig LD50 oral 130mg/kg (130mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BLOOD: OTHER CHANGES
Hygiene and Sanitation Vol. 33(1-3), Pg. 41, 1968.
mouse LCLo inhalation 150mg/m3/2H (150mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

BLOOD: HEMORRHAGE
Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 7, Pg. 13, 1965.
mouse LD50 oral 105mg/kg (105mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BLOOD: OTHER CHANGES
Hygiene and Sanitation Vol. 33(1-3), Pg. 41, 1968.
rabbit LD50 oral 150mg/kg (150mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BLOOD: OTHER CHANGES
Hygiene and Sanitation Vol. 33(1-3), Pg. 41, 1968.
rat LCLo inhalation 150mg/m3/2H (150mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

BLOOD: HEMORRHAGE
Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 7, Pg. 13, 1965.
rat LD50 intraperitoneal 52435ug/kg (52.435mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 26, Pg. 597, 1974.
rat LD50 oral 105mg/kg (105mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BLOOD: OTHER CHANGES
Hygiene and Sanitation Vol. 33(1-3), Pg. 41, 1968.

2-Butyne-1,4-diol Safety Profile

A poison by ingestion. A skin sensitizer upon long or repeated contact. Moderately explosive. When heated to decomposition it emits acrid smoke and fumes and may explode. Explosive reaction with traces of alkalies, alkali earth hydroxides, halide salts, strong acids, mercury salts + strong acids. See also ACETYLENE COMPOUNDS and ALKYNES.
Heating with strongly alkaline materials should be avoided.
Butynediol(110-65-6) is corrosive and irritates the skin and eyes. 
Hazard Codes: ToxicT,CorrosiveC
Risk Statements: 21-23/25-34-43-48/22 
R21:Harmful in contact with skin. 
R23/25:Toxic by inhalation and if swallowed. 
R34:Causes burns. 
R43:May cause sensitization by skin contact. 
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed.
Safety Statements: 25-26-36/37/39-45-46 
S25:Avoid contact with eyes. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S46:If swallowed, seek medical advice immediately and show this container or label.
RIDADR: UN 2716 6.1/PG 3
WGK Germany: 2
RTECS: ES0525000
F: 23-10
HazardClass: 6.1
PackingGroup: III
HS Code: 29053980

2-Butyne-1,4-diol Specification

 2-Butyne-1,4-diol , its cas register number is 110-65-6. It also can be called 1,4-Dihydroxy-2-butyne ; BOZ ; 2-Butyne-1,4-diol .It is a white to light-brown solid or brownish-yellow aqueous solution. Its solid sinks and mixes with water.And it is more difficult to polymerize than propargyl alcohol, but it cyclotrimerizes to hexamethylolbenzene (benzenehexamethanol) with a nickel carbonyl-phosphine catalyst or a rhodium chloride-arsine catalyst.

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