3-Bromothiophene Property

Melting point:

<-10°C

Boiling point:

150 °C (lit.)

Density 

1.74 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.591(lit.)

Flash point:

140 °F

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

Specific Gravity

1.740

color 

Clear colorless to slightly yellow

Water Solubility 

IMMISCIBLE

Sensitive 

Light Sensitive/Stench

BRN 

105338

CAS DataBase Reference

872-31-1(CAS DataBase Reference)

NIST Chemistry Reference

Thiophene, 3-bromo-(872-31-1)

EPA Substance Registry System

3-Bromothiophene (872-31-1)

Safety

Hazard Codes 

T,Xi,N,Xn

Risk Statements 

10-25-41-51/53-36/37/38-23/24/25-20/21/22-43-36/37

Safety Statements 

26-36/37/39-45-61-38-28A-16-24/25-23-36-36/37-24/35

RIDADR 

UN 2929 6.1/PG 2

WGK Germany 

3

F 

8

Hazard Note 

Irritant

TSCA 

T

HazardClass 

6.1

PackingGroup 

II

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H301Toxic if swalloed

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Bromothiophene Chemical Properties,Usage,Production

Chemical Properties

clear colourless to slightly yellow liquid. It is not soluble in water, but can dissolve in common organic solvents such as chloroform, benzene, ether, and tetrahydrofuran.

Uses

3-Bromothiophene is used in the preparation of derivatives such as thienylenic alpha, μ-diformyl-alpha-oligothiophenes and 3-lithiothiophene. It is also used in the synthesis of 3-lithiothiophene by reacting with n-butyllithium.

Uses

3-Bromothiophene can be used as a reactant to synthesize:
3,3-Bithiophene via borylation followed by Suzuki coupling.
3-Alkylthiophenes by NiDPPP++ catalyzed cross-coupling with Grignard reagents.
3-Lithiothiophene by treating with n-butyllithium in hexane.
Derivatives of thienylenic α, ω?diformyl?α?oligothiophenes.
N-(2-(3-bromothiophen-2-yl)phenyl)methanesulfonamides by coupling at the 2-position with N-arylmethanesulfonamides, mediated by iodobenzene diacetate (178721).

Preparation

Preparation of 3-bromothiophene using 2,5-dibromothiophene
2,5-Dibromothiophene (121g, 0.5 moles), tris (3,6-dioxaheptyl) amine (1.0g, 0.003 mole), thiophene (500 cm3) and sodium amide (58.5g, 1.5 mole) were successively charged to a flask which had previously been purged with nitrogen. The reaction mixture was stirred and heated under nitrogen at 50-60°C for 6 hours. The product, after work up as described in Example 3, was found to contain 138.5g 3-bromothiophene and 2.6g 2-bromothiophene. The yield of 3-bromothiophene was 85% and the monobromothiophenes were in the ratio of 2 parts 2-bromothiophene to 98 parts 3-bromothiophene.

Reactions

3-Bromothiophene is an electron-rich aromatic hydrocarbon bromide. The bromine atom in it has good electrophilicity. It can perform a Suzuki coupling reaction under the catalysis of metal palladium, and react with different aryl or alkenyl borates. The corresponding substitution products are generated. This reaction is one of the very important methods in organic synthesis, which can build C-C bonds and form complex organic molecular structures.

Synthesis Reference(s)

Journal of the American Chemical Society, 74, p. 2965, 1952 DOI: 10.1021/ja01132a004
Synthetic Communications, 11, p. 25, 1981 DOI: 10.1080/00397918108064278