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1,4-Butane sultone

1,4-Butane sultone structure

CAS No:
1633-83-6
Formula:
C4H8O3S
Chemical 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
Categories:
Chemical Reagents > Organic Reagents

Description

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.

Liquid

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 Brnsted 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].

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

1,4-Butane sultone Basic Attributes

Molecular Weight：

136.17

Exact Mass：

136.17

BRN：

110588

EC Number：

216-647-9

UNII：

4E0C1CLI2C

NSC Number：

71999

TSCA：

TSCA listed

DSSTox ID：

DTXSID4061836

Color/Form：

Clear colorless to yellow

HScode：

29349990

Characteristics

PSA：

51.8

Chemical Properties：

The reactivity of 1,4-butane sultone:Under conditions involving an excess of diol, the reaction of 1,4-butanesultone (BS) with 1,4-butanediol (BD) yields only a negligible amount of (4-hydroxybutoxy)butane-1-sulfonic acid (BDSA), and the formation of tetrahydrofuran (THF) (accounting for 30 mol% of the initial BD) is observed. BD was reacted with Na₂CO₃, used as the base, at a molar ratio of 10:1 for 1 hour at room temperature. After distilling off the unreacted BD, BS was added. The resulting BDSS was purified by precipitation, yielding a 45% yield[3].

XLogP3：

0.1

Appearance：

Clear colorless to yellow Liquid

Density：

1.331 g/mL at 25 °C (lit.)

Melting Point：

12-15 °C (lit.)

Boiling Point：

>165 °C/25 mmHg (lit.)

Flash Point：

>230 °F

Refractive Index：

n20/D1.464(lit.)

Water Solubility：

54 g/L (20 ºC) decomposes

Storage Conditions：

Store below +30°C.

Vapor Pressure：

0.00206mmHg at 25°C

Toxicity：

LD50 orally in Rabbit: 500 mg/kg

Flammability characteristics：

Thermal decomposition to emit toxic sulfur oxide fumes

Critical Temperature & Pressure：

Store below +30°C.

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

2810

wgk germany：

hazard class code：

safety instructions：

22-36/37-45-36

RTECS Number：

RP4300000

Marks：

Storage features：

The warehouse is ventilated, low temperature and dry; stored separately from food raw materials

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

22-40-68-20/21/22

Special Reports：

THIS IS A REVIEW OF THE HOST MEDIATED ASSAY AND BODY FLUID ASSAY AS REPORTED FOR 208 CHEMICALS. 1,4-BUTANE SULTONE WAS POSITIVE FOR AN UNSPECIFIED STRAIN OF SALMONELLA TYPHIMURIUM.[LEGATOR MS ET AL; AN EVALUATION OF THE HOST MEDIATED ASSAY AND BODY FLUID ANALYSIS A REPORT OF THE USA ENVIRONMENTAL PROTECTION AGENCY GENE-TOX PROGRAM; MUTAT RES 98 (3): 319-74 (1982)]

RIDADR：

2810

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 147 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

highly toxic

Drug Information

MeSH Entry Terms：

1,4-butane sultone

1,4-Butane sultone Use and Manufacturing

Methods of Manufacturing

By reacting tetrahydrofuran with acetyl chloride to obtain chlorobutyl acetate, then reacting with sodium sulfite to obtain hydroxybutanesulfonic acid, and finally dehydrating to obtain the product. The total yield is about 40%.

Uses

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

Intermediates

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.

Production

(1979) NOT PRODUCED COMMERCIALLY IN U.S.|(1981) NOT PRODUCED COMMERCIALLY IN U.S.

Manufacturing Info：

All other basic organic chemical manufacturing|1,2-Oxathiane, 2,2-dioxide: ACTIVE

Computed Properties

Molecular Weight:136.17
XLogP3:0.1
Hydrogen Bond Acceptor Count:3
Exact Mass:136.01941529
Monoisotopic Mass:136.01941529
Topological Polar Surface Area:51.8
Heavy Atom Count:8
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Butyl chloride

Tetrahydrofuran

1-Butanol

Sodium sulfite

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