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Cas Database

115-19-5

115-19-5

Identification

  • Product Name:3-Butyn-2-ol, 2-methyl-

  • CAS Number: 115-19-5

  • EINECS:204-070-5

  • Molecular Weight:84.1179

  • Molecular Formula: C5H8O

  • HS Code:29052990

  • Mol File:115-19-5.mol

Synonyms:2-Propyn-1-ol,1,1-dimethyl- (7CI);(1-Hydroxy-1-methylethyl)acetylene;1,1-Dimethyl-2-propyn-1-ol;1,1-Dimethyl-2-propynol;1,1-Dimethylpropargylalcohol;2-Ethynyl-2-propanol;2-Hydroxy-2-methyl-3-butyne;2-Methyl-2-hydroxy-3-butyne;2-Methyl-3-butyn-2-ol;2-Methyl-3-butyne-2-ol;2-Propyne-1,1,1-triol;3-Hydroxy-3-methyl-1-butyne;3-Methyl-1-butyn-3-ol;3-Methyl-3-hydroxy-1-butyne;3-Methyl-3-hydroxybutyne;AB 32;AB 32 (alcohol);Dimethylacetylenecarbinol;Dimethylacetylenylcarbinol;Dimethylethynylcarbinol;Dimethylethynylmethanol;Ethynyldimethylcarbinol;Mebynol;NSC 523;a,a-Dimethylpropargyl alcohol;3-Methyl butynol;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH302 Harmful if swallowed H318 Causes serious eye damage

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. In case of skin contact Rinse skin with plenty of water or shower. In case of eye contact Rinse with plenty of water (remove contact lenses if easily possible). If swallowed Rinse mouth. Contact will cause eye and skin irritation. Vapor exposure may cause eye and respiratory tract irritation. (USCG, 1999)

  • Fire-fighting measures: Suitable extinguishing media Fire Extinguishing Agents Not to Be Used: Water. Fire Extinguishing Agents: Dry chemical, alcohol foam or carbon dioxide. (USCG, 1999) Special Hazards of Combustion Products: Irritating and toxic gases, such as carbon dioxide and carbon monoxide, may be produced in fire. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from strong oxidants, acids and copper. Cool.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Product Description:2-Methyl-3-butyne-ol for synthesis. CAS 115-19-5, pH 7 (H O, 20 °C)., for synthesis
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Relevant articles and documentsAll total 38 Articles be found

-

Becker

, p. 2647 (1977)

-

-

Campbell,Campbell,Eby

, p. 2882 (1938)

-

-

Davis,Hurd

, p. 3284,3287 (1955)

-

-

Lespieau

, (1928)

-

The role of potassium cation in the Favorskii ethynylation of acetone: Effekt of dibenzo-18-crown-6

Trofimov,Nosyreva,Mal'kina

, p. 1254 - 1259 (2005)

Macrocyclic polyether dibenzo-18-crown-6 possessing a specific affinity for potassium cation inhibits ethynylation of acetone with acetylene in the presence of KOH according to Favorskii. The inhibition becomes stronger in the presence of the complex dibenzo-18-crown-6·KOH·MeOH as catalyst (both in excess acetone and in DMSO). The effect does not originate from deactivation of acetone, for its aldol-like condensation is accelerated in the presence of both dibenzo-18-crown-6 and its complex (the selectivity of ethynylation sharply falls down). Thus, apart from the high basicity of the medium, activation of acetylene due to complex formation with potassium cation plays an important role in the Favorskii ethynylation of ketones.

Modified copolymers of bifunctional vinyl ethers with methyl vinyl sulfide as active matrices of solid superbases

Trofimov,Morozova,Mikhaleva,Markova,Tatarinova,Henkelmann

, p. 2111 - 2116 (2008)

Reactive linear and crosslinked copolymers of diethylene glycol divinyl ether and ethylene glycol vinyl glycidyl ether with methyl vinyl sulfide have been synthesized in the presence of 2,2′-azobis(isobutyronitrile) (2%, 60 °C, 45-55 h) in ~53% yield. The hydrolyzed at the residual vinyloxy and epoxy groups and oxidized at the methylthio groups copolymers upon treatment with KOH afford alkoxide (complex) and crown-like superbases. They are capable of catalyzing the acetone ethynylation, as well as the prototropic isomerization of methyl propargyl ether to allenyl methyl ether and vinylation of ethylene and diethylene glycols with acetylene.

-

Carothers,Coffman

, p. 4071,4074 (1932)

-

Enantio- And Diastereodivergent Construction of 1,3-Nonadjacent Stereocenters Bearing Axial and Central Chirality through Synergistic Pd/Cu Catalysis

Huo, Xiaohong,Ma, Shengming,Xiao, Junzhe,Zhang, Jiacheng,Zhang, Wanbin,Zhao, Ling

supporting information, p. 12622 - 12632 (2021/08/31)

In contrast to the widely explored methods for the asymmetric synthesis of molecules bearing a single stereocenter or adjacent stereocenters, the concurrent construction of 1,3-stereogenic centers in an enantio- and diastereoselective manner remains a challenge, especially in acyclic systems. Herein, we report an enantio- and diastereodivergent construction of 1,3-nonadjacent stereocenters bearing allenyl axial and central chirality through synergistic Pd/Cu-catalyzed dynamic kinetic asymmetric allenylation with racemic allenylic esters. The protocol is suitable for a wide range of substrates including the challenging allenylic esters with less sterically bulky substituents and provided chiral allenylic products bearing 1,3-nonadjacent stereocenters with high levels of enantio- and diastereoselectivities (up to >20:1 dr and >99% ee). Furthermore, several representative transformations involving axial-to-central chirality transfer were conducted, affording useful structural motifs containing nonadjacent stereocenters in a diastereodivergent manner.

Separation method of 2-methyl-3-butyn-2-ol

-

Paragraph 0082-0093; 0158-0160, (2020/11/01)

The invention belongs to the technical field of acetylene alcohol production, and particularly relates to a separation method of 2-methyl-3-butyn-2-ol, which comprises the following steps: pretreatinga reaction solution containing 2-methyl-3-butyn-2-ol to remove unreacted acetone and contained salt from the reaction solution to obtain a 2-methyl-3-butyn-2-ol crude product, with the content of 2,5-dimethyl-3-hexyn-2,5-diol in the reaction solution containing 2-methyl-3-butyn-2-ol being not higher than 0.1 wt%; separating and purifying the 2-methyl-3-butyn-2-ol crude product by virtue of membrane separation treatment and reduced pressure distillation treatment, so as to obtain a 2-methyl-3-butyn-2-ol product. According to the method disclosed by the invention, water in the product can be removed and the content of the 2,5-dimethyl-3-hexyn-2,5-diol can be reduced under the condition that the investment and the energy consumption are reduced, so that the 2-methyl-3-butyn-2-ol with relatively high purity and conversion rate is obtained.

Synthetic method of 3-methoxy-3-methylbutyne

-

Paragraph 0012-0020, (2019/11/28)

The invention discloses a synthetic method of 3-methoxy-3-methylbutyne. The method comprises the following steps: using acetone and acetylene as starting raw materials, firstly synthesizing 3-methylbutyn-3-ol, and performing a reaction on the 3-methylbutyn-3-ol and dimethyl sulfate to obtain the 3-methoxy-3-methylbutyne. According to the synthetic method of the 3-methoxy-3-methylbutyne provided bythe invention, the raw materials used in the synthetic method have a low price and low costs and are easy to obtain, the synthetic method has a short synthetic route, a high yield, and high chemicalpurity of the obtained product, no special production equipment is needed in all reactions, and the obtained intermediate and the final product do not need to be treated by column chromatography and crystallization purification.

Base-Catalyzed Borylation/B-O Elimination of Propynols and B2pin2 Delivering Tetrasubstituted Alkenylboronates

Kuang, Zhijie,Chen, Haohua,Yan, Jianxiang,Yang, Kai,Lan, Yu,Song, Qiuling

supporting information, p. 5153 - 5157 (2018/09/12)

An efficient approach to tetrasubstituted alkenylboronates via a cascade borylation/B-O elimination of propynols and B2pin2 was disclosed. A series of tetrasubstituted alkenylboronates were readily furnished with this strategy in good yields, with further transformations leading to tetrasubstituted alkenes and β-diketones demonstrating the synthetic potential of the alkenylboronates constructed by this strategy as versatile intermediates in organic synthesis.

Method for efficiently preparing alkynol

-

Paragraph 0036; 0037; 0038; 0039; 0040; 0041; 0042, (2018/12/14)

The invention relates to a method for efficiently preparing alkynol, belongs to the field of preparation of chemical intermediates and chemicals, and particularly relates to a preparation method of alkynol. The preparation method comprises the following steps that 1, alkali metal is added into an anhydrous alcohols solvent; an alcohol-alkali metal solution is prepared; 2, a compound I is added into the alcohol-alkali metal solution; uniform stirring is performed; cooling is performed to be 0 DEG C or below; 3, acetylene is introduced through being metered at normal pressure; alkynol is obtained; 4, the alkynol solution after reaction is neutralized by ammonium chloride and a same alcohol mixed suspension system; 5, the neutralized mixed suspension system is filtered; after alcohols are recovered from filter liquid, reduced pressure distillation is performed to obtain an alkynol product. The method overcomes the defect that under the existing harsh reaction conditions of high pressure,liquid ammonia and the like, the solid potassium hydroxide feeding difficulty is avoided; under the ordinary pressure condition, the ketone compounds are converted into alkynol at high conversion rate. The method has the advantages of high conversion rate, simple process and good product purity.

Process route upstream and downstream products

Process route

3-chloro-3-methylbut-1-yne
1111-97-3

3-chloro-3-methylbut-1-yne

water
7732-18-5

water

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

2-methylbut-1-en-3-yne
78-80-8

2-methylbut-1-en-3-yne

Conditions
Conditions Yield
at 80 - 90 ℃;
water
7732-18-5

water

1-chloro-3-methyl-buta-1,2-diene
27822-67-9

1-chloro-3-methyl-buta-1,2-diene

4-chloro-2-methyl-1,3-butadiene
51034-46-9

4-chloro-2-methyl-1,3-butadiene

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

prop-1-yne
74-99-7

prop-1-yne

Conditions
Conditions Yield
3-chloro-3-methylbut-1-yne
1111-97-3

3-chloro-3-methylbut-1-yne

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

2,2-dimethylbicyclo<3.2.1>oct-6-en-3-one
22940-29-0

2,2-dimethylbicyclo<3.2.1>oct-6-en-3-one

3-Chlor-4,4-dimethylbicyclo<3.2.1>octa-2,6-dien
65404-99-1

3-Chlor-4,4-dimethylbicyclo<3.2.1>octa-2,6-dien

4-(1,1-Dimethyl-2-propinyl)-2-cyclopenten-1-ol
344257-36-9

4-(1,1-Dimethyl-2-propinyl)-2-cyclopenten-1-ol

propargyl alcohol
107-19-7

propargyl alcohol

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

Conditions
Conditions Yield
With potassium hydroxide; silver trifluoroacetate; In pentane; at 0 ℃; Mechanism;
acetone
67-64-1

acetone

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

Conditions
Conditions Yield
With sodium; In methanol; at 0 - 5 ℃; for 1h; Solvent; Reagent/catalyst; Autoclave; Inert atmosphere; Large scale;
99.2%
acetylene; With sodium amide; In ammonia; at -50 ℃; for 0.5h;
acetone; at -50 - 25 ℃;
87.9%
acetylene; With potassium hydroxide monohydrate; In dimethyl sulfoxide; at 10 - 15 ℃; for 7h;
acetone; In dimethyl sulfoxide; at 10 - 15 ℃; for 9h; Temperature;
82%
With potassium hydroxide; In dimethyl sulfoxide; at 15 - 17 ℃; for 1h;
77%
With tetra(n-butyl)ammonium hydroxide; In water; dimethyl sulfoxide; at 5 ℃; for 1h;
72%
With potassium hydroxide; In dimethyl sulfoxide; at 11 - 13 ℃; for 9h;
62%
With sodium hydroxide; ethene; tetrabutylammomium bromide; In toluene; for 8h; Ambient temperature;
55%
With water; copper(I) monacetylide; calcium carbonate; at 95 - 100 ℃; unter Druck;
With alkaline solution; at 100 ℃; under 14710.2 - 18387.7 Torr;
With alkali hydroxide;
With 2-butoxyethyl 2-ethoxyethyl ether; sodium 2-ethoxyethoxide; at -5 ℃;
With diethyl ether; alkali hydroxide;
With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, hexane, 0 deg C to room temperature;
at -20 ℃; beim Behandeln von Acetylennatrium;
at -20 ℃; beim Behandeln von Natriumcarbid;
With potassium hydroxide; ammonia; In ethanol; at 20 ℃;
acetylene; With potassium hydroxide; In dimethyl sulfoxide;
acetone; In dimethyl sulfoxide; toluene; for 72h;
With potassium tert-butylate; In tetrahydrofuran; at 0 ℃;
acetylene; With ethylmagnesium bromide; In tetrahydrofuran; at 0 - 25 ℃; for 1.16667h;
acetone; In tetrahydrofuran; at 23 - 25 ℃; for 5h;
With ammonia; potassium hydroxide; at 15 ℃; for 2.5h; under 9750.98 Torr;
at -20 ℃; beim Behandeln von Acetylennatrium;
at -20 ℃; beim Behandeln von Natriumcarbid;
With diethyl ether; alkali hydroxide;
With ammonia; magnesium sulfate; sodium hydroxide; In water; at -20 - 10 ℃; for 1h; Reagent/catalyst; Autoclave;
polymethyl(3-hydroxy-3-methyl-1-butynyl)siloxane

polymethyl(3-hydroxy-3-methyl-1-butynyl)siloxane

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 12h;
99%
acetone
67-64-1

acetone

acetylenemagnesium bromide
4301-14-8

acetylenemagnesium bromide

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

Conditions
Conditions Yield
In tetrahydrofuran; Heating;
47%
acetone; acetylenemagnesium bromide; In tetrahydrofuran; at 0 - 20 ℃;
With ammonium chloride; In tetrahydrofuran; water;
In tetrahydrofuran; at -10 - 20 ℃;
In tetrahydrofuran; at 23 - 25 ℃; for 4h; Inert atmosphere;
In tetrahydrofuran; at -10 - 20 ℃; for 2.25h; Inert atmosphere;
In tetrahydrofuran; at 20 ℃; for 4h; Cooling with ice; Schlenk technique; Inert atmosphere;
In tetrahydrofuran; at 0 - 20 ℃; for 4h; Inert atmosphere;
acetone
67-64-1

acetone

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

2,5-dihydroxy-2,5-dimethyl-3-hexyne
142-30-3

2,5-dihydroxy-2,5-dimethyl-3-hexyne

Conditions
Conditions Yield
With potassium hydride; In tetrahydrofuran; at 30 ℃; for 2.25h; under 759.826 Torr;
91%
7%
acetone; acetylene; With potassium 2-methylpropan-2-olate; In xylene; at 28 - 35 ℃; for 1h;
With water;
With phosphoric acid; Product distribution / selectivity;
90%
2.3%
acetone; acetylene; With potassium 2-methylpropan-2-olate; In xylene; at 10 - 20 ℃; for 1h;
With water;
With phosphoric acid; Product distribution / selectivity;
79%
3%
potassium 2-methylpropan-2-olate; In tetrahydrofuran; xylene; at 30 ℃; for 2.25h; under 759.826 Torr;
56%
19%
With potassium hydroxide; diethyl ether; at 9 - 15 ℃;
With potassium hydroxide; at 100 ℃; under 14710.2 - 16181.2 Torr;
With ammonia; sodium acetylide;
in Gegenwart eines sauren Anionen-Austauschers;
With potassium hydroxide; sodium hydroxide; Dimethoxymethane; at 0 ℃;
With potassium hydroxide; at 6 ℃; under 2574.3 Torr;
C<sub>12</sub>H<sub>13</sub>F<sub>3</sub>O<sub>2</sub>Se

C12H13F3O2Se

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

Conditions
Conditions Yield
With 1,4-diaza-bicyclo[2.2.2]octane; In benzene; at 95 ℃; for 2h; Yield given;
2-methyl-3-butyn-2-ol 1-ethoxyethyl ether
39807-00-6

2-methyl-3-butyn-2-ol 1-ethoxyethyl ether

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

Conditions
Conditions Yield
With N,4-dimethyl-N-vinylbenzenesulfonamide; picAuCl2(III); In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;
60%
acetone
67-64-1

acetone

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

Conditions
Conditions Yield
With diethyl ether; sodium amide; at -10 ℃; folgendes Einleiten von Acetylen bei derselben Temperatur;

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