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124664

Sigma-Aldrich

4-Bromophenylacetonitrile

98%

Synonym(s):

4-Bromobenzyl cyanide

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About This Item

Linear Formula:
BrC6H4CH2CN
CAS Number:
16532-79-9
Molecular Weight:
196.04
EC Number:
240-602-2
MDL number:
MFCD00001916
UNSPSC Code:
12352100
PubChem Substance ID:
24847621
NACRES:
NA.22

Assay

98%

form

solid

mp

47-49 °C (lit.)

functional group

bromo
nitrile

SMILES string

Brc1ccc(CC#N)cc1

InChI

1S/C8H6BrN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2

InChI key

MFHFWRBXPQDZSA-UHFFFAOYSA-N

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General description

4-Bromophenylacetonitrile undergoes reduction using 1,1,3,3-tetramethyldisiloxane activated by a non-toxic titanium(IV) isopropoxide to yield 4-bromophenylethylamine[1].

Application

4-Bromophenylacetonitrile has been used in the synthesis of :
  • new fluorene-based alternating polymers[2]
  • light-emitting copolymer, poly(N 4,N 4-bis-(4-phenyl)-N 4,N 4′-bis-[4-(2-ethylhexyloxy)phenyl]-biphenyl-4,4′-diamine-co-1,2-bis(4′-phenyl)-1-(9′′,9′′-dihexyl-3-fluorenyl)ethane) using a Yamamoto coupling reaction[3]
  • N-methyl-3,4-bis(4-(N-(1-naphthyl)phenylamino)phenyl)maleimide, a novel non-doped red organic light-emitting diode (OLED) material[4]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

JAN Code

124664-BULK:
124664-VAR:
124664-100G:4548173103846
124664-25G:4548173103853

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Certificates of Analysis (COA)

Lot/Batch Number
WXBC6784V
WXBC6783V
WXBC6782V
S87844V
S87844

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Synthesis and device performance of new efficient blue copolymers containing biphenylenevinylene and triphenyldiamine.
Oh DH, et al.
Macromolecular Research, 19(6), 629-634 (2011)
Hsiu-Chih Yeh et al.
Chemical communications (Cambridge, England), (20)(20), 2632-2633 (2003-11-05)
Bright (maximum 10034 cd m(-2), 455 cd m(-2) at 20 mA cm(-2)) and efficient (maximum 2.4% at 4 mA cm(-2)) red (lambda(max)el 634-636 nm) organic light-emitting diodes employ arylamino-substituted fumaronitrile as the novel host emitter, which is readily prepared and
Polymeric light emitting properties and structural relationships of fluorene-based conjugated copolymers containing various hole transporting derivatives.
Park JH, et al.
Organic Electronics, 8(2), 272-285 (2007)
A mild and efficient method for the reduction of nitriles.
Laval S, et al.
Tetrahedron Letters, 50(50), 7005-7007 (2009)
Bocheng Wu et al.
Bioorganic & medicinal chemistry, 28(6), 115345-115345 (2020-02-18)
Signal transducer and activator of transcription 3 (STAT3) is an oncogenic transcription factor which has been recognized as a promising cancer therapeutic target. Small molecule pyrimethamine (PYM) is a known direct inhibitor of activated STAT3 and it is currently under
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