[ CAS No. 916578-53-5 ]

Name: 916578-53-5|tert-Butyl (4-(chloromethyl)phenyl)carbamate|97%
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SKU: A204416
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Quality Control of [ 916578-53-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 916578-53-5 ]

SDS Specification

Alternatived Products of [ 916578-53-5 ]

Product Details of [ 916578-53-5 ]

CAS No. :	916578-53-5	MDL No. :	MFCD14156082
Formula :	C₁₂H₁₆ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FRHLNTUJMCHWBT-UHFFFAOYSA-N
M.W :	241.71 g/mol	Pubchem ID :	46835249
Synonyms :

Calculated chemistry of [ 916578-53-5 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	5
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	66.45
TPSA :	38.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.86
Log Po/w (XLOGP3) :	2.88
Log Po/w (WLOGP) :	3.43
Log Po/w (MLOGP) :	2.92
Log Po/w (SILICOS-IT) :	2.69
Consensus Log Po/w :	2.96

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.1
Solubility :	0.192 mg/ml ; 0.000793 mol/l
Class :	Soluble
Log S (Ali) :	-3.34
Solubility :	0.109 mg/ml ; 0.000452 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.38
Solubility :	0.0102 mg/ml ; 0.0000421 mol/l
Class :	Moderately soluble

Medicinal Chemistry

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

Safety of [ 916578-53-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501	UN#:	2811
Hazard Statements:	H301-H311-H331-H341	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 916578-53-5 ]

* 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 [ 916578-53-5 ]
Downstream synthetic route of [ 916578-53-5 ]

[ 916578-53-5 ] Synthesis Path-Upstream 1~1

1
[ 916578-53-5 ]
[ 220298-96-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 16, p. 4879 - 4883

[ 916578-53-5 ] Synthesis Path-Downstream 1~20

1
[ 916578-52-4 ]
[ 916578-53-5 ]
[ 916578-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile for 5h;	120 5ML of acetonitrile solution was added to 345mg of 3,4-dihydro-[741] 6,7-dimethoxy-l-undecylisoquinoline-6-amine and 242mg of -t - butyl-S-chloromethy^phenylcabamate. Then, the resulting mixture was heated and stirred for 5 hours. The solvent was concentrated under reduced pressure, and the reaction mixture was separated through silica-gel column chromatography eluting with dichloromethane and methanol(10:l), to give 0.4Og of solid compound, 2-{A-t - butylalcohol carbonyl- [742] aminophenyl)methyl-3,4-dihydro-6,7-dimethoxy-l-undecylisoquinolinium chloride(m.p.l42°C). [743] 1H-NMR (CDCl , 300MHz):δ 0.84(t, 3H), 1.20(b, 14H), 1.45(s, 9H), 1.62(b, 4H),3.10(t, 2H), 3.26(t, 2H), 3.92(s, 3H), 3.97(s, 3H), 4.01(t, 2H), 5.34(s, 2H), 6.82(s, IH),7.27(s, IH), 7.60(d, IH), 7.67(s, IH), 7.96(s, IH)

Reference： [1]Current Patent Assignee: HANWHA SOLUTIONS CORPORATION - WO2006/129978, 2006, A1 Location in patent: Page/Page column 68

2
[ 144072-29-7 ]
[ 916578-53-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	With pyridine; thionyl chloride; In dichloromethane; for 0.5h;	B. To a stirred solution of /<?/-/-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g. 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL. 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL). and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford /<?/7-butyl 4-(chloromethyl)- phenylcarbamate as an orange solid in 50% yield (0.27 g. 50%): 1H NMR (300 MHz. CDCl3) delta 7.38-7.28 (m. 4H). 6.51 (br s. I H). 4.55 (s. 2H). 1.52 (s. 9H).
	With methanesulfonyl chloride; triethylamine; In tetrahydrofuran; at 0 - 25℃; for 16h;	To a mixture of <strong>[144072-29-7]tert-butyl (4-(hydroxymethyl)phenyl)carbamate</strong> (2.00 g, 8.96 mmol), TEA (1.81 g, 17.9 mmol) in THF (30 mL) was added MsCl (1.33 g, 11.6 mmol) dropwise at O C and stirred for 0.5 hour. Then warmed to 25 C and stirred for another 15.5 hours to give a yellow suspension. TLC (PE/EtOAc = 5: 1) showed the reaction was completed. The mixture was quenched with ice water (80 mL) slowly, then extracted with EtOAc (60 mL x2), the combined extracts were washed with brine (80 mL x2), dried over Na2S04, filtered and concentrated under reduced pressure to give tert-butyl (4- (chloromethyl)phenyl)carbamate (2.16 g, crude) as a pale yellow gum

Reference： [1]Patent: WO2008/127349,2008,A2 .Location in patent: Page/Page column 103
[2]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3434 - 3436
[3]Journal of Organic Chemistry,2020,vol. 85,p. 2752 - 2758
[4]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4879 - 4883
[5]Patent: WO2019/126730,2019,A1 .Location in patent: Paragraph 0645

3
[ 916578-53-5 ]
[ 866005-62-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium azide; tetrabutylammomium bromide / acetone / 0.5 h 2.1: triphenylphosphine / tetrahydrofuran; water / 5 h 3.1: dichloromethane / 0.02 h 4.1: triethylamine / 0.17 h 4.2: 0.17 h / 0 °C