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[ CAS No. 21988-87-4 ] {[proInfo.proName]}

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Chemical Structure| 21988-87-4
Chemical Structure| 21988-87-4
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Product Details of [ 21988-87-4 ]

CAS No. :21988-87-4 MDL No. :MFCD00192554
Formula : C12H15Br3 Boiling Point : -
Linear Structure Formula :- InChI Key :BHIFXIATEXVOQA-UHFFFAOYSA-N
M.W :398.96 Pubchem ID :89140
Synonyms :

Calculated chemistry of [ 21988-87-4 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 3
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 79.85
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.22
Log Po/w (XLOGP3) : 4.69
Log Po/w (WLOGP) : 4.84
Log Po/w (MLOGP) : 5.3
Log Po/w (SILICOS-IT) : 6.35
Consensus Log Po/w : 4.88

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.37
Solubility : 0.00172 mg/ml ; 0.0000043 mol/l
Class : Moderately soluble
Log S (Ali) : -4.42
Solubility : 0.0152 mg/ml ; 0.0000382 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.25
Solubility : 0.0000223 mg/ml ; 0.000000056 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.12

Safety of [ 21988-87-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 21988-87-4 ]

* 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.

  • Upstream synthesis route of [ 21988-87-4 ]
  • Downstream synthetic route of [ 21988-87-4 ]

[ 21988-87-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 50-00-0 ]
  • [ 108-67-8 ]
  • [ 21988-87-4 ]
YieldReaction ConditionsOperation in experiment
99% at 95℃; for 12 h; Inert atmosphere To aame-driedask, under N2, mesitylene (0.7 ml, 5 mmol) was added, followed by acetic acid (2.6 ml) and HBr in AcOH (33percent wt solution) (3.5 ml). Then para- formaldehyde (570 mg, 18.8 mmol, 3.7 equiv) was added. The solution was stirred for at 95 °C. After 3h solids started to develop. The mixture was stirred for another 9h, after which het mixture was cooled to rt. After crashing the mixture onto ice, the solids were filtered and dried. The solid was recrystallized from CH2Cl2: P.E. to yield the desired bromomethylated product as white needles (1.99 g, 5 mmol, 99percent). 1H NMR (500 MHz, Chloroform-d) 8 4.61 (s, 6H), 2.50 (s, 9H). 130 NMR (126 MHZ, CDC13)8 137.84, 133.18, 29.93, 15.38.
97% at 90℃; for 16.5 h; The compound was prepared by literature method. To a mixture of paraformaldehyde (2 g; 0.066 mol), and trimethylbenzene(1.0 g; 0.01 mol) in 100 mL of HBr/AcOH (30 wt percent) zinc bromide (2.25 g; 0.01mol) was slowly added at room temperature. The mixture was heated to 90 °C for 16.5 h, during which time white crystals were formed. The reaction was cooled to room temperature, and the white solid was filtered off, washed with water, and dried under vacuum overnight to give 1 as a white solid. Yield 3.9 g (97percent). Mp =185-187°C; 1H NMR (400 MHz, CDCl3): δ 2.46 (s, 9H, -CH3), 4.57(s, 6H, -CH2Br).
93% at 95℃; for 12 h; To a stirred mixture of mesitylene (0.1 mol), paraformaldehyde (0.33 mol) and 50.0 mL ofglacial acetic acid was added 40 mL of 31percent HBr in acetic acid rapidly. The mixture wasstirred for 12 hours at 95C and the reaction mixture was poured into 100 mL of water. Thewhite solid product thus separated was filtered under vacuum and was dried. The crudeproduct was crystallized from glacial acetic acid to give pure product 37.1 g (93percent yield);M.P.: 185 C.
92% at 95℃; for 12 h; 31 wtpercent HBr/acetic acid solution (5 cm3) was added to a mixture of mesitylene (0.86 g, 7.14mmol), paraformaldehyde (0.71 g, 23.57 mmol, 3.3 eq) and glacial acetic acid (3.6 cm3). Themixture was heated at 95 C for 12 hours and then poured onto water (10 cm3). The productwas then filtered off and dried overnight in a dessicator to give the title compound 6 as a whitesolid (2.57 g, 91percent).M.p. 190-191 C; Observed C, 36.43percent, H, 3.91percent, C12H16Br3 requires C, 36.13percent, H, 3.81percent;max (nujol)/cm-1: 2921, s, (C-H); 1564, s, (C=C, aryl); 1455, s, (C=C, aryl); H (400 MHz,CDCl3), 2.41 (9H, s, 3 x CH3), 4.60 (6H, s, 3 x CH2Br); C (100MHz, CDCl3), 138.29 (3 xring-C-CH2), 133.68 (3 x ring-C-CH3), 30.22 (3 x CH2Br), 15.76 (3 x CH3); m/z (CI, +ve,NH3), 418 ([M+NH4]+, 30percent), 319 ([M]+-Br, 30percent), 239 ([M]+-2Br, 30percent), 152 ([M]+-3Br,100percent); Found [M+NH4]+, 413.90684, C12H19NBr3 requires 413.90677.
90% at 95℃; for 12 h; To a mixture of mesitylene (12.0 g; 0.10 mol), paraformaldehyde (10.26 g; 0.34 mol), and 75 mL ofglacial acetic acid, 75 mL of a 33 wtpercent HBr/acetic acid solution was added rapidly. The mixture waskept for 12 h at 95 C and then poured into 100 mL of water. The product was filtered off on a Buchnerfunnel and dried. Flash column chromatography (hexane: ethyl acetate = 98.5:1.5) gave the desiredproduct as colorless needles. 90percent yield. mp 186° C (lit. [30] mp 183–186 °C); 1H-NMR (δH; CDCl3,400 MHz) δ 4.58 (s, 6H), 2.46 (s, 9H).
89% With hydrogen bromide In acetic acid at 95℃; for 24 h; To mesitylene 24 (44.5 g, 0.37 mol) and ^-formaldehyde (36.6 g, 1.22 mol) was added glacial acetic acid (185 mL) and hydrobromic acid (33percent in acetic acid, 260 mL). The suspension was stirred under argon atmosphere and heated at 95 0C. After 24 h the reaction mixture was crashed into water (150 mL) and stirred vigorously. The formed precipitate was filtered off and washed thoroughly with water to give compound 25 as a white powder (131.2 g, 89percent).

Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 5, p. 1262 - 1263
[2] Patent: WO2018/106112, 2018, A1, . Location in patent: Page/Page column 70
[3] Synthesis, 1994, # 11, p. 1132 - 1132
[4] Organic Letters, 2009, vol. 11, # 11, p. 2229 - 2232
[5] Tetrahedron Letters, 2013, vol. 54, # 8, p. 771 - 774
[6] CrystEngComm, 2016, vol. 18, # 15, p. 2735 - 2741
[7] Synlett, 2016, vol. 27, # 2, p. 294 - 300
[8] Organic and Biomolecular Chemistry, 2018, vol. 16, # 45, p. 8769 - 8782
[9] European Journal of Organic Chemistry, 2010, # 33, p. 6359 - 6365
[10] European Journal of Organic Chemistry, 2015, vol. 2015, # 9, p. 2012 - 2022
[11] Synlett, 2016, vol. 27, # 1, p. 141 - 145
[12] Journal of Materials Chemistry A, 2015, vol. 3, # 6, p. 3051 - 3058
[13] RSC Advances, 2014, vol. 4, # 106, p. 61884 - 61890
[14] Molecules, 2018, vol. 23, # 1,
[15] Patent: WO2007/64227, 2007, A1, . Location in patent: Page/Page column 58
[16] Tetrahedron, 1998, vol. 54, # 5-6, p. 949 - 968
[17] Dyes and Pigments, 2012, vol. 92, # 1, p. 696 - 704
[18] Arkivoc, 2012, vol. 2012, # 8, p. 187 - 197
[19] Inorganic Chemistry, 2013, vol. 52, # 3, p. 1161 - 1163
[20] Dalton Transactions, 2011, vol. 40, # 34, p. 8630 - 8642
[21] Journal of Chemical Crystallography, 2012, vol. 42, # 2, p. 165 - 172
[22] Journal of the Chemical Society, Chemical Communications, 1988, # 16, p. 1081 - 1083
[23] Organic and Biomolecular Chemistry, 2013, vol. 11, # 38, p. 6569 - 6579
[24] Synthesis, 1999, # 6, p. 993 - 998
[25] Collection of Czechoslovak Chemical Communications, 1976, vol. 41, p. 1777 - 1790
[26] Tetrahedron Letters, 2001, vol. 42, # 33, p. 5777 - 5779
[27] Journal of the American Chemical Society, 2002, vol. 124, # 49, p. 14510 - 14511
[28] Tetrahedron Letters, 2004, vol. 45, # 4, p. 723 - 727
[29] Journal of Molecular Structure, 2012, vol. 1019, p. 174 - 182
[30] Photochemical and Photobiological Sciences, 2013, vol. 12, # 2, p. 330 - 338
[31] RSC Advances, 2016, vol. 6, # 23, p. 19612 - 19619
[32] Journal of Chemical Sciences, 2015, vol. 127, # 2, p. 337 - 342
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  • [ 21988-87-4 ]
Reference: [1] Journal of Materials Chemistry A, 2013, vol. 1, # 46, p. 14666 - 14674
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