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1,4-Butane sultone

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1,4-Butane sultone Basic information

Product Name:
1,4-Butane sultone
Synonyms:
  • 1,4-butylenesulfone
  • 1,4-Butylsultone
  • 1,4-BUTANE SULTONE, 99+%
  • 1,4-Bs1,4-ButaneSultone
  • 2,2-Dioxide-1,2-oxathiane
  • δ-Valerosultone
  • 1,4-Butane
  • 4-hydroxy-1-butanesulfonic acid sultone
CAS:
1633-83-6
MF:
C4H8O3S
MW:
136.17
EINECS:
216-647-9
Product Categories:
  • Building Blocks
  • Chemical Synthesis
  • Heterocycles
  • Heterocyclic Building Blocks
  • Others
  • S-Containing
Mol File:
1633-83-6.mol
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1,4-Butane sultone Chemical Properties

Melting point:
12-15 °C (lit.)
Boiling point:
>165 °C/25 mmHg (lit.)
Density 
1.331 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.464(lit.)
Flash point:
>230 °F
storage temp. 
Store below +30°C.
solubility 
54g/l (decomposition)
form 
Liquid
color 
Clear colorless to yellow
Water Solubility 
54 g/L (20 ºC) decomposes
Sensitive 
Moisture Sensitive
BRN 
110588
InChIKey
MHYFEEDKONKGEB-UHFFFAOYSA-N
CAS DataBase Reference
1633-83-6(CAS DataBase Reference)
EPA Substance Registry System
1,2-Oxathiane, 2,2-dioxide (1633-83-6)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-40-68-20/21/22
Safety Statements 
22-36/37-45-36
RIDADR 
2810
WGK Germany 
3
RTECS 
RP4300000
TSCA 
Yes
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29349990
Hazardous Substances Data
1633-83-6(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 500 mg/kg

MSDS

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1,4-Butane sultone Usage And Synthesis

Description

1,4-Butane sultone is an impurity in sulfobutyl ether β-cyclodextrin (SBE-β-CD), and has been reported to be a weak carcinogen. 1,4-Butane sultone can be used for preparation of Br?nsted acidic ionic liquids and the ionic liquid is green, highly water soluble, thermally stable, specific and catalytically stable, and can be used for the preparation of symmetrical 3,3'-diaryloxyoctanone compounds[1-2].

Chemical Properties

Butanesultone is a viscous, clear, colourless – or yellowish/brown – and odourless liquid. When heated, vapours of butanesultone are known to form explosive mixtures with air and are reported to cause explosion hazards.

Uses

1,4-Butane Sultone is an alkylating agent with weak carcinogenic activity.

Uses

1,4-Butane sultone can be employed as a reactant in the preparation of conjugated polymers which include polybetaine, poly[2-ethynyl-N-(4-sulfobutyl)pyridinium betaine] (PESPB).
It can also be used in the preparation of Bronsted acid catalysts such as 4-(succinimido)-1-butane sulfonic acid and poly(4-vinylpyridinium butane sulfonic acid) hydrogen sulfate. These catalysts facilitate the synthesis of 1-amidoalkyl-2-naphthols, substituted quinolines, and pyrano[4,3-b]pyran derivatives.

Application

1,4-Butane sultone is an intermediate widely used for sulfonated surfactants.It is also applied in photo development and electroplating.It is used as the Intermediate for the production of APIs.It used in sulfobutylether-β-cyclodextrin(SEBCD).

Safety Profile

Suspected carcinogen with experimental tumorigenic data. Poison by subcutaneous, intravenous, and intraperitoneal routes. Moderately toxic by ingestion. Experimental reproductive effects. Human mutation data reported. See also SULFONATES. When heated to decomposition it emits toxic fumes of SOx

Synthesis

Performing sulfonation on 3-butylene-1-alcohol or 3-butylene-1-chlorine serving as a raw material and a sulfonating agent under the oxidation-reduction of an initiator;performing acidification after the reaction is finished;performing lactonization by high vacuum dehydration cyclization and azeotropic dehydration cyclization;and finally refining to obtain a 1,4-butane sultone finished product.

References

[1] LAYLA A. TAIB; Mosadegh K. Introduction of novel br?nsted acidic ionic liquids with perchlorate counter-anion for one-pot synthesis of symmetric 3,3′-diaryloxindoles[J]. Research on Chemical Intermediates, 2021. DOI:10.1007/s11164-021-04419-5.
[2] MENG WANG. Determination of Low-ppm Levels of 1,4-Butane Sultone in Sulfobutyl Ether β-Cyclodextrin Using Liquid–Liquid Extraction and GC–MS[J]. Chromatographia, 2012. DOI:10.1007/s10337-012-2275-8.

1,4-Butane sultone Preparation Products And Raw materials

Raw materials

1,4-Butane sultoneSupplier

Changshu Hopax Chemical Co., Ltd. Gold
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