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[ CAS No. 1875-88-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1875-88-3
Chemical Structure| 1875-88-3
Chemical Structure| 1875-88-3
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Product Details of [ 1875-88-3 ]

CAS No. :1875-88-3 MDL No. :MFCD00002899
Formula : C8H9ClO Boiling Point : -
Linear Structure Formula :- InChI Key :HZFRKZWBVUJYDA-UHFFFAOYSA-N
M.W : 156.61 Pubchem ID :74647
Synonyms :

Calculated chemistry of [ 1875-88-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.39
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 1.41
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 2.46
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.08

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.01
Solubility : 1.53 mg/ml ; 0.00974 mol/l
Class : Soluble
Log S (Ali) : -1.44
Solubility : 5.7 mg/ml ; 0.0364 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.23
Solubility : 0.0916 mg/ml ; 0.000585 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 1875-88-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1875-88-3 ]

* 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 [ 1875-88-3 ]
  • Downstream synthetic route of [ 1875-88-3 ]

[ 1875-88-3 ] Synthesis Path-Upstream   1~3

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  • [ 1875-88-3 ]
  • [ 95-54-5 ]
  • [ 5468-66-6 ]
Reference: [1] Catalysis Science and Technology, 2016, vol. 6, # 6, p. 1677 - 1684
  • 2
  • [ 1875-88-3 ]
  • [ 6529-53-9 ]
YieldReaction ConditionsOperation in experiment
94.9% With phosphorus tribromide In cyclohexane at -10 - 80℃; for 3.75 - 8.25 h; The volume efficiency was 1.76 L per Kg of 2-(4'-chlorophenyl)ethanol starting material or 758 g of 2-(4'-chlorophenyl)ethyl bromide product (assay corrected) per liter.Process DescriptionTo a reactor affixed with a vent to a caustic scrubber to capture HBr gas that might evolve during the reaction was added 2-(4'-chlorophenyl)ethanol (1.00 Kg, 6.39 moles, 1.00 equiv.). The reactor contents were cooled to 0° C. The feed pump and line were rinsed with cyclohexane (0.019 Kg), and the rinses were directed to waste disposal. To the cooled solution was added phosphorous tribromide (0.869 Kg, 3.21 moles, 0.503 equiv.) while the stirred reactor contents were maintained at 0-10° C. The resulting reaction was highly exothermic and was controlled by the addition rate with a jacket temperature of -5° C. to -10° C. The feed pump and line was rinsed with cyclohexane (0.019 Kg), and the rinses were directed to waste disposal. The resulting reaction mixture was heated to 25° C. (20° C. to 30° C.), and stirring was continued at this temperature for 2 hours (1 to 3 hours). After this time, the reaction mixture was slowly heated to 80° C. (75 to 85° C.) over 60 minutes (45 to 75 minutes), and stirring at that temperature was continued for 3 hours (2 to 4 hours). A slightly turbid emulsion was formed upon heating. The reactor contents were cooled to 22° C. and then a sample of the reaction mixture was analyzed for reaction completion (>99percent by HPLC peak area). The reaction mixture was a thick but easily stirred emulsion. A receiver vented to a caustic scrubber was charged with purified water (0.514 Kg). The receiver contents were cooled to 5-20° C. The reaction mixture was transferred from the reactor to the receiver at a rate sufficiently slow to maintain the stirred receiver contents at about 15° C. The receiver contents were warmed to 35-40° C. and filtered through a polishing filter. The reactor was washed with additional purified water (0.085 Kg), and the washings were passed through the filter into the aqueous product mixture. The phases were allowed to separate at 35-40° C. The lower phase was drained from the upper phase. The lower phase weighed about 1.39 Kg and was about 96percent pure 2-(4'-chlorophenyl)ethyl bromide, which was therefore obtained in about 94.9percent yield (assay corrected).
94.9% at 0 - 30℃; for 3 h; The present invention uses SM-A and LCS-1 condensation to prepare Impurity F.Specific operations are as follows: 40g of p-chlorophenylacetic acid was added to 400ml of tetrahydrofuran,Stirring at room temperature dissolved; lithium aluminum hydride in batches, temperature control at 25 ~ 30 ,After the reaction was stirred for 20 hours, 200 ml of water was added slowly and the addition was completed.Add ethyl acetate 400ml stirred 30min, liquid separation, organic phase plus 200ml saturated brine and dried over 20g anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure 40 ~ 45 ,36.7 g of oil (S2) was obtained; S2 was added to the reaction flask, the temperature was lowered to 0 to 5 ° C in ice water,Slowly dropping phosphorus tribromide, dropping temperature during the course of 0 ~ 5 , the dropwise addition is completed,Heated to 25 ~ 30 , incubated for 3h,Add water 80ml, stirred 30min, liquid separation, the aqueous phase was extracted with dichloromethane 100ml × 2,The organic phases were combined and concentrated under reduced pressure to give an oil (S3): 48.8 g. Yield: 94.9percent.
65.2% With pyridine; dibromo sulfoxide In water; toluene EXAMPLE 5
Preparation of 4-chlorophenethyl bromide
A 500 ml. 3 neck round bottomed flask under nitrogen was charged 15.65 g. of 4-chlorophenethanol (1.0 eq., 0.10 moles) in 60 ml. toluene.
To the reaction was added dropwise 41.6 g of thionyl bromide (2.0 eq., 0.20 moles) in 15 ml. of toluene maintaining the temp. below 25 C. Finally, 8.7 g. pyridine (1.1 eq., 0.11 moles) in 20 ml. toluene was added dropwise again keeping the temperature below 30° C. with an external ice bath.
The reaction was monitored by GLC and after 1 hr. an additional 14.0 g of thionyl bromide (0.67 eq. 0.067 moles) was added followed three hours later by 9.7 gms. (1.1 eq., 0.11 moles).
Subsequently 4.3 g. of pyridine was added (0.55 eq., 0.055 moles) after which GLC indicated all the alcohol was consumed.
The reaction was quenched by the addition of 300 ml of water while cooling with an ice bath after which 400 ml. of ether was added.
The ether was washed water three times with 250 ml.), dried over MgSO4 and concentrated to give 14.4 g of product as an oil (65.2percent yield).
NMR (60 MHz): 2.9-3.7 (m, 4H) and 7.0-7.4 (ABq, 4H).
Reference: [1] Patent: US2009/143576, 2009, A1, . Location in patent: Page/Page column 2; 9-10
[2] Patent: CN106478506, 2017, A, . Location in patent: Paragraph 0122; 0123
[3] Patent: US5397793, 1995, A,
[4] Patent: US2002/19531, 2002, A1,
[5] Journal of the American Chemical Society, 1957, vol. 79, p. 3712,3715
[6] Journal of the American Chemical Society, 1977, vol. 99, # 9, p. 3059 - 3067
[7] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1979, p. 1128 - 1132
[8] Tetrahedron Asymmetry, 1998, vol. 9, # 15, p. 2725 - 2737
[9] Journal of the Chemical Society, 1964, p. 1548 - 1553
[10] Journal of Organic Chemistry, 1964, vol. 29, # 8, p. 2109 - 2116
[11] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4752 - 4756
[12] Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 404 - 408
[13] Patent: US5219871, 1993, A,
[14] Patent: WO2004/52851, 2004, A1, . Location in patent: Page 49
[15] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 386 - 393
[16] Advanced Synthesis and Catalysis, 2015, vol. 357, # 6, p. 1136 - 1142
[17] Chemical Communications, 2016, vol. 52, # 84, p. 12521 - 12524
[18] Patent: WO2009/111004, 2009, A1, . Location in patent: Page/Page column 9
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  • [ 66230-04-4 ]
  • [ 1745-18-2 ]
  • [ 622-98-0 ]
  • [ 1875-88-3 ]
  • [ 2012-74-0 ]
  • [ 23853-78-3 ]
  • [ 3739-38-6 ]
  • [ 938-95-4 ]
  • [ 39515-51-0 ]
  • [ 873-76-7 ]
Reference: [1] Journal of the Brazilian Chemical Society, 2015, vol. 26, # 9, p. 1831 - 1837
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