3-CHLORO-3-METHYL-1-BUTYNE Chemical Properties

Melting point:

-61 °C (lit.)

Boiling point:

73-75 °C (lit.)

Density 

0.913 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.418(lit.)

Flash point:

40 °F

storage temp. 

2-8°C

solubility 

Chloroform, Hexane (Slightly)

form 

Liquid

color 

Clear colorless to straw

Specific Gravity

0.91

InChI

InChI=1S/C5H7Cl/c1-4-5(2,3)6/h1H,2-3H3

InChIKey

QSILYWCNPOLKPN-UHFFFAOYSA-N

SMILES

C#CC(Cl)(C)C

CAS DataBase Reference

1111-97-3(CAS DataBase Reference)

EPA Substance Registry System

1-Butyne, 3-chloro-3-methyl- (1111-97-3)

Safety Information

Hazard Codes 

F,Xn,Xi

Risk Statements 

11-20/21/22

Safety Statements 

16-26-36

RIDADR 

UN 1993 3/PG 2

WGK Germany 

3

TSCA 

TSCA listed

HazardClass 

3

PackingGroup 

II

HS Code 

29032990

Storage Class

3 - Flammable liquids

Hazard Classifications

Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Flam. Liq. 2

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-CHLORO-3-METHYL-1-BUTYNE Usage And Synthesis

Chemical Properties

Clear colorless to straw colored liquid

Uses

3-Chloro-3-methyl-1-butyne was used in preparation of:

• series of benzo[b]pyrano[2,3-i]xanthen-6-ones and benzo[b]pyrano[3,2-h]xanthen-7-ones
• 6-hydroxy-3,3-dimethyl-3H,7H-benzo[a]pyrano[3,2-h]xanthen-7-one
• 5-hydroxy-2,2-dimethyl-2H,6H-benzo[a]pyrano[2,3-i]xanthen-6-one
• 3,3-dimethyl-3Hbenzofuro[3,2-f][1]-benzopyran

Uses

3-Chloro-3-methyl-1-butyne is a propargyl chloride used to alkylate methanol, ethanol, ammonia and amines to the corresponding propargylic ether and amines.

Synthesis

The process is shown in Figure 1. First, the chlorination reactor was turned on and a reflux condensing unit was installed. The reaction vessel was cooled to 10 °C, followed by the sequential addition of concentrated hydrochloric acid, zinc chloride and polyethylene glycol 600. 2-methyl-3-butyn-2-ol was mixed with sulphuric acid and slowly added dropwise to the reaction vessel when the reactor temperature dropped to 0 °C. The reaction temperature was maintained at 0 °C for 2 hours. After the dropwise addition was completed, the reaction temperature was maintained between 0 and 5°C for 2 hours. Upon completion of the reaction, the mixture was transferred to a washing kettle for washing. This was followed by stirring and standing for layering. After separation of the aqueous layer, the organic layer was transferred to the extraction kettle. After filtration and drying, 3-chloro-3-methyl-1-butyne was obtained (95% yield, 99% purity).

References

[1] Patent: CN107903181, 2018, A. Location in patent: Paragraph 0007-0008; 0036-0040; 0054; 0058
[2] Chemistry - A European Journal, 2005, vol. 11, # 1, p. 308 - 320
[3] Chemical Communications, 2013, vol. 49, # 39, p. 4346 - 4348
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1996, vol. 38, # 12, p. 1077 - 1081
[5] European Journal of Organic Chemistry, 2014, vol. 2014, # 36, p. 8029 - 8034

3-CHLORO-3-METHYL-1-BUTYNE(1111-97-3)Related Product Information

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