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2-Bromo-5-nitrothiophene is a heteroaryl halide derived from thiophene through a process of bromination followed by nitration. It is characterized by its white to light yellow crystal powder appearance and is utilized in the synthesis of various organic compounds, particularly oligothiophene precursors. These precursors are essential in the generation of (porphinato)zinc(II)-based chromophores, which have potential applications in the field of chemistry and materials science.

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  • 13195-50-1 Structure
  • Basic information

    1. Product Name: 2-Bromo-5-nitrothiophene
    2. Synonyms: LABOTEST-BB LT00455100;2-BROMO-5-NITROTHIOPHENE;2-Bromo-5-nitrothiophene ,98%;2-Nitro-5-bromothiophene;5-Nitro-2-bromothiophene;2-Bromo-5-Nitrothiophene 99%
    3. CAS NO:13195-50-1
    4. Molecular Formula: C4H2BrNO2S
    5. Molecular Weight: 208.03
    6. EINECS: 236-155-8
    7. Product Categories: Heterocycles;Thiophene&Benzothiophene;Miscellaneous;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiophenes;ThiophenesBuilding Blocks
    8. Mol File: 13195-50-1.mol
    9. Article Data: 6
  • Chemical Properties

    1. Melting Point: 44-48 °C(lit.)
    2. Boiling Point: 235-237°C
    3. Flash Point: 235-237°C
    4. Appearance: white to light yellow crystal powder
    5. Density: 1.945 g/cm3
    6. Vapor Pressure: 0.0295mmHg at 25°C
    7. Refractive Index: 1.647
    8. Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. BRN: 120955
    11. CAS DataBase Reference: 2-Bromo-5-nitrothiophene(CAS DataBase Reference)
    12. NIST Chemistry Reference: 2-Bromo-5-nitrothiophene(13195-50-1)
    13. EPA Substance Registry System: 2-Bromo-5-nitrothiophene(13195-50-1)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 13195-50-1(Hazardous Substances Data)

13195-50-1 Usage

Uses

Used in Chemical Synthesis:
2-Bromo-5-nitrothiophene is used as a key intermediate in the synthesis of various organic compounds, including:
1. 3-bromo-4-(5-nitro-2-thienyl)-6-ethoxypyridine
2. 5-chloro-2-methoxy-4-(5-nitrothien-2-yl)-pyridine
3. 5-(5-nitrothien-2-yl)pyrimidine
4. 2-methoxy-5-(5-nitrothien-2-yl)pyrimidine
These synthesized compounds can be further utilized in the development of pharmaceuticals, dyes, and other specialty chemicals.
Used in the Preparation of Oligothiophene Precursors:
2-Bromo-5-nitrothiophene is used as a building block for the preparation of oligothiophene precursors, which are essential in the synthesis of (porphinato)zinc(II)-based chromophores. These chromophores have potential applications in the field of chemistry and materials science, particularly in the development of advanced materials with unique optical and electronic properties.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 2-Bromo-5-nitrothiophene is also used in research and development for exploring new synthetic pathways, understanding its reactivity with various reagents, and discovering novel applications in different industries.

Check Digit Verification of cas no

The CAS Registry Mumber 13195-50-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,1,9 and 5 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 13195-50:
(7*1)+(6*3)+(5*1)+(4*9)+(3*5)+(2*5)+(1*0)=91
91 % 10 = 1
So 13195-50-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H2BrNO2S/c5-3-1-2-4(9-3)6(7)8/h1-2H

13195-50-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A15866)  2-Bromo-5-nitrothiophene, 97%   

  • 13195-50-1

  • 1g

  • 411.0CNY

  • Detail
  • Alfa Aesar

  • (A15866)  2-Bromo-5-nitrothiophene, 97%   

  • 13195-50-1

  • 5g

  • 1590.0CNY

  • Detail
  • Alfa Aesar

  • (A15866)  2-Bromo-5-nitrothiophene, 97%   

  • 13195-50-1

  • 25g

  • 7146.0CNY

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  • Aldrich

  • (544531)  2-Bromo-5-nitrothiophene  97%

  • 13195-50-1

  • 544531-1G

  • 479.70CNY

  • Detail
  • Aldrich

  • (544531)  2-Bromo-5-nitrothiophene  97%

  • 13195-50-1

  • 544531-5G

  • 1,726.92CNY

  • Detail

13195-50-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Bromo-5-nitrothiophene

1.2 Other means of identification

Product number -
Other names 2-Bromo-5-nitrothiophen

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13195-50-1 SDS

13195-50-1Relevant articles and documents

Studies on the biological activity of some nitrothiophenes

Morley, John O.,Matthews, Thomas P.

, p. 359 - 366 (2006)

The biological activity of nineteen substituted thiophenes (3) have been assessed by evaluating the minimum inhibitory concentration required to inhibit the growth of E. coli, M. luteus and A. niger. The series displays a wide range of activities with 2-chloro-3,5-dinitrothiophene (3a) or 2-bromo-3,5- dinitrothiophene (3c) showing the highest activity against all three organisms, while the simplest compound of the series, 2-nitrothiophene (3s) shows the smallest activity in each case. The mode of action of 3a and 3c is thought to involve nucleophilic attack by intracellular thiols at the 2-position of the heterocyclic ring leading to displacement of halogen, but other active derivatives, such as 2,4-dinitrothiophene (3h) and 5-nitrothiophene-2- carbaldehyde (3d) which have no displaceable halogen or leaving group are thought to act by forming Meisenheimer complexes. The Royal Society of Chemistry 2006.

INVESTIGATION OF THE KINETICS OF THE NITRATION OF THIOPHENE DERIVATIVES

Freidlin, G. N.,Glushkova, A. A.,Solop, K. A.

, p. 127 - 130 (1982)

The kinetics of the nitration of thiophene derivatives with nitric acid in acetic anhydride were investigated.The nitration of 2-substituted thiophenes is a second-order reaction.The rate constants and activation parameters of the reaction were calculated.The possibility of the Hammett and Yukawa-Tsuno equations for this reaction series is demonstrated.An isokinetic dependence is observed.

Synthesis, transition temperatures, and optical properties of various 2,6-disubstituted naphthalenes and related 1-benzothiophenes with butylsulfanyl and cyano or isothiocyanato terminal groups

Seed,Toyne,Goodby,Hird

, p. 2069 - 2080 (2007/10/03)

Fourteen compounds based on 2,6-disubstituted naphthalenes or related 1-benzothiophene moieties with butylsulfanyl and cyano or isothiocyanato terminal groups have been synthesised. The transition temperatures of the compounds and their refractive indices have been determined and the derived values for the optical anisotropies, polarisabilities and order parameters have been calculated. With one exception (which also shows a smectic A phase), all the compounds with naphthyl and phenyl groups are solely nematogenic; for these compounds the naphthyl unit gives an average increase in T(N-I) value and melting point of 72 and 20°C respectively compared to the values for the compounds with a phenyl in place of the naphthyl unit. The incorporation of a 2,5-thiophene unit in place of phenyl lowers T(N-I) and when it is part of a 1-benzothiophene unit the depression is even greater. The naphthalene compounds increase the values of optical anisotropy by approximately 0.04, compared to the phenyl systems, mainly because they increase the refractive index of the e-ray (n values); compound 12 has an exceptionally high optical anisotropy (Δn value) of 0.54.

Anisotropic organic compounds

-

, (2008/06/13)

STR1 The invention describes liquid crystalline compounds or formula (I), where A, D and G are independently selected from phenyl, thiophene, hydrogenated phenyl, chlorinated phenyl and fluorinated phenyl, B and E are independently selected from a single bond C= C. C C.C00, azoxy and diazo, k and m are independently selected from 1 and 0, such that m+n is 1 or 2, and R1 and R2 are independently selected from R, R0, alkynyl, thioalkyl, hydrogen, CN, NCS and SCN; provided that at least one of R1 and R2 is selected from CN, NCS and SCN and that at least one of A, D and G is phenyl; and excluding where at least one of R1 and R2 is independently selected as CN and one of A, D or G is not thiophene, and where m is 0, A, and D are phenyl, B is a single bond and only one of R1 or R2 is NCS. Also described are compounds suitable for inclusion in a device utilizing pretransitional characteristics of liquid crystalline materials in the isotropic phase, of general formula (II) where J and Y are independently selected from phenyl, thiophene, hydrogenated phenyl, chlorinated phenyl and fluorinated phenyl, X is selected from C= C. C C.COO azoxy and diazo, k is 1 or 0 and R3 and R4 are independently selected from R, RO, alkynyl, thioalkyl, hydrogen, CN, NCS and SCN; provided that at least one of R3 and R4 is selected from CN, NCS and SCN and that at least one of J and Y is phenyl.

Naphthyl organic compounds

-

, (2008/06/13)

Liquid crystal compounds of formula (I) are described, where formula (I) is given as R1 --A--(Xm --(B)n --R2 where A is selected from nathyl, flourinated naphthyl, brominated naphthyl, B is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine, R1 and R2 are independently selected from alkyl, alkoxy, alkynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and hydrogen, X is selected from C C, COO and C C, m is 0 or 1, n is 0 or 1 where m is 1 and n is 0 where m is 0; provided that where A is naphthyl, n is 1 and m is 0 then B is selected from methylated phenyl, brominated phenyl, thiophene, pyrimidine and pyridine; and further provided that where A is naphthyl, X is C C, m is 1 and n is 1, then B is selected from thiophene, pyrimidine and pyridine. Also described are liquid crystal compounds suitable for inclusion in devices utilizing pretransitional characteristics of liquid crystalline materials in the isotropic phase and described by formula (II): R3 --J--(Y)p --(Z)q --R 4, where J is selected from nathyl, fluorinated naphthyl, brominated naphthyl, Z is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine, R1 and R2 are independently selected from alkyl, alkoxy, alkynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and hydrogen, Y is selected from C=C, COO and C=C, p is 0 or 1, q is 0 or 1 where p is 1 and q is 0 where p is 0.

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