Structure of 54211-46-0
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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A method for the determination of 60 liquid crystal monomers in biotic and abiotic samples
Yuan Liu ; Wen-Long Li ; Zhong-Min Li ; Kurunthachalam Kannan ;
Abstract: Liquid crystal monomers (LCMs) are synthetic organic chemicals widely used in the manufacture of liquid crystal displays (LCDs) of digital electronic devices. As human interactions with digital electronics such as computers and smartphones intensify, exposure to LCMs is a public health concern. Nevertheless, there is limited research on the occurrence of LCMs in biological and non-biological matrices. We developed a method to determine 60 LCMs in electronic-waste panels (i.e., computer monitors), indoor dust, feces, and urine using gas chromatography–mass spectrometry (GC–MS). Solid matrices (i.e., dust and feces) were extracted using a solid-liquid extraction (SLE) procedure whereas liquid matrices (i.e., urine) were extracted using solid phase extraction (SPE). Indoor dust and feces extracts were purified by passage through silica gel packed gravity columns. The method limits of detection (LODs) and quantification (LOQs) were in the ranges of 0.05–13.0 and 0.18–39.1 ng/mL, respectively. Recoveries of all target analytes fortified at concentrations of 10 and 100 ng/mL on LCD panels, dust, feces, and urine were in the range of 71–130%, with standard deviations of 0.01–33%. Repeated analyses of similarly fortified samples yielded intra-day and inter-day variations (CV) of 0.32–12.6% and 0.76–14.3%, respectively. Matrix effects, calculated from fortified matrices, ranged from −28.5% to 28.5%. The method was applied in the analysis of LCD panels, indoor dust, dog feces and urine, which were found to contain 22, 42, 46, and 18 of the 60 targeted LCMs, respectively. LCMs were found in LCD panels (∑LCM = 1780 ± 165 ng/cm2 for desktop computer monitors; and 166,900 ± 80,100 ng/cm2 for smartphone screens), indoor dust (∑LCM = 2030 ± 1260 ng/g), dog feces (∑LCM = 1990 ± 2000 ng/g dw), and urine (∑LCM = 24.0 ± 14.6 ng/mL). The developed method can be applied in the analysis of LCMs in a wide range of environmental and biological samples.
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Keywords: Liquid crystal monomers ; Electronic-waste ; Dust ; Feces ; Urine ; Monitoring
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CAS No. : | 54211-46-0 |
Formula : | C24H23N |
M.W : | 325.45 |
SMILES Code : | N#CC1=CC=C(C2=CC=C(C3=CC=C(CCCCC)C=C3)C=C2)C=C1 |
MDL No. : | MFCD00799423 |
InChI Key : | AITQOXOBSMXBRV-UHFFFAOYSA-N |
Pubchem ID : | 104707 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 25 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.21 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 106.22 |
TPSA ? Topological Polar Surface Area: Calculated from |
23.79 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
4.07 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
7.04 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
6.62 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.35 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
7.16 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
6.05 |
Log S (ESOL):? ESOL: Topological method implemented from |
-6.43 |
Solubility | 0.000121 mg/ml ; 0.000000372 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (Ali)? Ali: Topological method implemented from |
-7.36 |
Solubility | 0.0000143 mg/ml ; 0.000000044 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-9.5 |
Solubility | 0.000000103 mg/ml ; 0.0000000003 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-3.29 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
1.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.59 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step (ii) Preparation of 4-Cyano-4§-n-pentyl-p-terphenyl The product from Step (i) 4-bromobenzonitrile (0.0275 m), tetrakis(triphenylphosphine) palladium (0.64 g), sodium carbonate (32 ml of a 2 m), toluene solution (64 ml) and methylated spirits (20 ml) are heated under reflux with vigorous stirring for 5 h. After cooling, the organic layer is separated, washed with water, dried over sodium sulphate and evaporated to dryness. The crude product is purified by passing through a short chromatography column (15 g silica) using a 1:1 mixture of petroleum spirit and dichloromethan, and crystallized from ethyl acetate with C 130 N 239 I. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride; In diethyl ether; at 72.0℃; | Step 1, in accordance with an aromatic nitrile (V): LiAlH4= 1: (1 to 3) Weigh the molar ratio of aromatic nitriles (V) with LiAlH4According to according aromatic nitriles (V): diethyl ether = 1: 3 (in a ratio mol: L) amount of diethyl ether, to take a good aromatic nitriles (V) with LiAlH4Was dissolved in diethyl ether; then by heating under reflux Reactions were carried out at 1 to 5 hours at 72 , and then follow the V (NaOH) / V (diethyl ether) volume = 2/1 ratio of ice was added an aqueous solution containing sodium hydroxide of 20wt% The reaction was continued to give the product an aromatic amine (VI); | |
With lithium aluminium tetrahydride; In tetrahydrofuran; water; at 72.0℃; | measuring aromatic nitrile (IV) and LiA1H4 with a mole ratio of 1 :(1.-3), measuring tetrahydrofuran (THF) with a ratio of 3:1 in mol:L compared with aromatic nitrile (IV), dissolving the measured aromatic nitrile (IV) and LiA1H4 in tetrahydrofuran; reacting at 72 C. by heating and refluxing for 1-5 hours, then adding ice water solution including 20 wt % sodium hydroxide with a volume ratio of V(NaOH)N(THF)2/1 in the reaction, aromatic nitrile (IV) prepared; a reaction equation of the step 1 is as follows: |